Casco Bay Custom Charters

Casco Bay Custom Charters

Embark on an unforgettable journey: customizable private boat charters & tours of casco bay, celebrating a decade on the water.

Experience Casco Bay’s Splendor with Our Private Boat Charters & Tours. 

At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. For the past decade, we’ve shared more than just boat tours. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. 

With a focus on customization, each voyage with us is tailored to uncover the genuine essence of Casco Bay, enhanced by our commitment to exceptional service. Led by experienced crews passionate about sharing their knowledge and love for Maine, we ensure your journey is not only enjoyable but truly memorable.

SEARCH CHARTERS BY GROUP SIZE

Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.

Small Groups aboard MONHEGAN

Intimate cruises for up to 6 on a vintage lobster boat

Learn More »

Large Groups aboard MARIE L

Classic coastal tours for up to 16

DINING CHARTERS

The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef’s dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter!

Private Sunset Dinner Cruise

Small Groups (up to 6 guests) aboard MONHEGAN

Bottomless Mimosas & Croissant Brunch

Large Groups (7-16 guests) aboard MARIE L

ELOPE ON A PRIVATE ISLAND

Experience the magic of saying ‘I do’ on a private island with our Fortland Elopement Package. Escape to Fortland for an intimate, and unique wedding ceremony set against the backdrop of a stunning coastal landscape. An unforgettable way to share your vows and begin your new adventure in love

FORTLAND ISLAND ELOPEMENT PACKAGE

Unique, intimate wedding ceremonies on Fortland.

SAIL WITH GLEAM

For a limited-time, we’re partnering with GLEAM to offer sailing charters off the coast of Maine. GLEAM is a fully restored vintage 12 meter yacht that hosts up to 13 guests. Each captivating sailing excursion includes captain and crew for an effortless Maine summer sail.

GLEAM Private Sailing Charters

Sailing Excursions along Maine's Coast

CREATE YOUR OWN CUSTOM CHARTER

Tailor any of our curated tours and experiences for your group’s needs, from corporate bleisure to family-friendly outings and celebrations. Collaborate with our team to craft your perfect day, selecting from diverse food, beverage, and tour itinerary options. Your bespoke Maine adventure awaits.

Unforgettable 5-Star Maine Experiences ⭐⭐⭐⭐⭐

Embrace authentic maine with casco bay custom charters.

Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages. Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories.

Eager for an unparalleled experience? Book your private boat charters and coastal tours to navigate the beautiful waters of Casco Bay!

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Southern Maine

June - October 

Offering 2 hour group sails, and 3-6 hour private excursions out of Saco, ME.  Sail along the rocky Maine coastline while spotting minke and humpback whales, porpoises, seals, bald eagles and Atlantic sunfish. Host your own private cocktail party!  Feel like a kid again and jump off of the bows of the boat into the warm Saco river and float with pool noodles.

Saco is perfectly located 20 minutes from Kennebunkport and 20 minutes from Portland.

2 hour sail:  $125 pp

Sail out of the mouth of the Saco river, past the historic Wood Island lighthouse and through Biddeford pool.  Look for seals, porpoises, sturgeon and minke whales.  If it is windy or wavy that day, no problem!  We will cruise up the gorgeous Saco river instead, where you can view bald eagles, sturgeon, osprey, blue herons, and egrets.

Private sails: starting at $750

Rent the boat privately for your excursion!  We cater the day specifically to your desires, including time of day, how long we sail, and the activities.  Trip options include sailing along the beautiful rocky coast of Maine, cruising down the lush marshland of the Saco river, or a mixture of both. Incorporate a swim stop in the river, or just cocktail and cruise with the sun on your face.  The day and boat are yours to enjoy!  Private sails include a captain and crew, so you can enjoy every moment in luxury.

You can book online here through the "book now" button or call or email for private bookings and special events and inquiries.  Private sail start times are typically 10am, 1pm, and 5pm but can be adjusted per your request.

We are located at the Camp Ellis Pier, at 5 Bay Ave, Saco, ME 04072.  Before your charter, park in the Camp Ellis pier parking lot.  You will have to purchase a parking permit at the machine in the center of the lot.  Look for our sign, walk down the dock and the S/V Liberty will be waiting for you!  We board 5 minutes prior to departure.

Bimini Sailing Charters in Southern Maine and Key West

To book a trip, ask for a price or for other inquiries, please

call  +1-571-334-7885 , or send us an email to  [email protected]

Welcome to Bucks Harbor Marina!

Bucks Harbor Marina is under new ownership and preparing for its next chapter in the life of Penobscot Bay. The Marina will open June 29, 2024, but its services and hours will be limited due to the work that needs to be done.

Fuel - The Marina will be unable to dispense fuel this summer. The fuel tanks must be replaced, and the new tanks won't be delivered until the fall. We know this is a huge inconvenience, but rest assured that we're working on it!

Memberships - We will have moorings for rent as well as accommodations for dinghies and parking. Call Ari at 207-326-8839 or email [email protected]

Visiting Yachts - There are moorings available for the night and the dock will be open as a place to land, explore the town of Brooksville, and take advantage of the other Marina services and facilities such as laundry, showers, bathrooms, etc.

Boat Rentals - There are a limited number of outboard motor boats that are available for rent this summer. Call Ari at 207-326-8839 or email [email protected]

Market - The market will be open for ice cream, snacks, gifts, and beverages, including beer and wine.

We appreciate everyone's patience as we try to get back up and running!

Happy Summer, Andrew, Millie, Colin and Ari

You make the memories. We make the arrangements.

maine yacht charters

North America

Maine Yacht Charters | Scenic Adventures

Maine is the northernmost state in the northeastern United States. It is famous for its scenic, jagged, mostly rocky coastline, low, rolling mountains, heavily forested interior, and picturesque waterways. Here you’ll find the freshest seafood, such as fish, lobsters, and clams. On Maine yacht charters, you can experience all this area has to offer.

maine yacht charters

The Maine coast juts out to sea and curves inland with hundreds of harbors, inlets, and rivers. With over 5,000 miles of coast, including islands, the best way to explore is on a Maine yacht charter.

Climate and Weather

Located in New England, Maine has a humid continental climate with warm summers and cold winters. The summer months have an average high temperature of 70°F (21.1°C) in the peak of July. Nights are comfortable during the summer season.

5 Can’t-Miss Stops | Maine Yacht Charters

Maine is an idyllic spot for a luxury yacht charter. It has some of the most beautiful natural scenery in the United States. Here are five memorable stops on your Maine Yacht Charter.

Portland Head Light

If you’re looking for the most iconic stop on your luxury yacht charter in Maine, look no further than Portland Head Light. This historic lighthouse, which dates back to 1791, is at the entrance of Casco Bay. Wander through its grounds, take pictures of the stunning view, and even tour the lighthouse.

The views from here are simply breathtaking. The surrounding area has many places to explore, including Fort Williams Park and Two Lights State Park.

Acadia National Park

Acadia National Park is a must-see destination on your luxury yacht charter in Maine. It is on Mount Desert Island and has more than forty miles of rugged, rocky coastline. There’s something for everyone to explore. Start your journey at the mouth of the Somes Sound, home to some of the deepest fjords in the US.

At the center is Cadillac Mountain, the highest point on the east coast. Make sure you take time to admire the panoramic views from the top. As you sail around the park, you can also see whales, porpoises, and seals.

The Bold Coast

For a truly unique experience, no Maine yacht charter would be complete without a trip along the Bold Coast . The Bold Coast has a beautiful, rugged shoreline. You might even spot some seals or whales along your journey if you’re lucky.

The Bold Coast is in the extreme northeastern corner of Maine, with Lubec to the west and Cutler to the east. The coastline stretches along Machias Bay, making it a great place to sail or drop anchor overnight.

Monhegan Island

Nestled off the coast of Maine, Monhegan Island is a nature-lovers paradise. This unspoiled island offers miles of rugged shoreline, picturesque harbors, and charming village streets.

Monhegan Island is a great destination for outdoor enthusiasts. Enjoy ocean views from the rocky bluffs, hike the Nature Conservancy preserve, or explore the island’s many lighthouses. Try kayaking, whale watching, or fishing if you’re feeling adventurous.

Portland Harbor

Portland Harbor in Casco Bay is a stunning spot to visit while sailing on a yacht in Maine.

It has a rich culture, fantastic restaurants, and natural beauty. Portland Harbor is a great place for an afternoon of exploration or resting after a long day on the open sea.

The waterfront is also home to many attractions. One is the Maine Narrow Gauge Railroad Co. & Museum, which features authentic trains from 1866 to the present day. There are also lots of galleries and museums to explore.

Things to See and Do on Maine Yacht Charters

  • Visit Baxter State Park . For outdoor enthusiasts, spend a night watching stars and listening to the quiet wilderness at this park.
  • Go white-water rafting on the Kennebec River.
  • Explore the Maine Maritime Museum on the banks of the Kennebec River in historic Bath.
  • Walk with your dog on one of Maine’s many pet-friendly beaches.
  • Boost your well-being at a luxurious spa or wellness retreat.
  • Sail the coast and enjoy secluded bays, fresh fish, and lobster.
  • Visit the quaint, historic towns of Belfast , Boothbay , Castine , Rockland , and Southwest Harbor , Portland .

Maine Marinas

Some popular marinas in Maine include:

  • Fore Points Marina in Portland
  • Harborside Hotel, Spa & Marina in Bar Harbor
  • Landings Marina in Rockland
  • Boothbay Harbor Marina in Boothbay.

Sample Sailing Schedule | Maine Yacht Charters

Let us help you arrange your Maine yacht charter vacation. For more information, see our Yacht Charter Guide .

Let us deliver on your dream vacation.

Contact us to start a conversation about your dream vacation, and let us show you how we can help bring your vision to life through our exceptional yacht charter services.

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maine catamaran charter

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Coastal Maine Yacht Charter

Coastal Maine Yacht Charter

Luxury Yacht Charter Through Coastal Maine

Camden to bar harbor.

Home to stunning coastlines, breathtaking scenery, and enduring maritime tradition

With its iconic rocky beaches, historic lighthouses, and postcard-perfect towns lining the shores, coastal Maine is known as one of the most naturally-beautiful destinations in the United States. It’s also home to more than 3,000 offshore islands, most of which are uninhabited and pristine, making yacht exploration a stellar choice. From secluded coves and awe-inspiring inlets to charming communities and historical sites, this majestic seafaring respite offers a chance to relax, unwind, and discover the region’s unique beauty.

Nature views during a coastal Maine yacht charter

As you peruse the seaside mansions of Kennebunkport, sample the local fare in cosmopolitan  Portland , explore Acadia National Park, and venture ashore at Bar Harbor, you’ll discover the essence of the “Down East” region. Explore a world of lobster pots stacked on old, wooden docks, serene, isolated anchorages, and towns cloaked in nautical history.  From beachside lobster bakes and clam boils to historic museums and quaint island villages, true maritime traditions endure.

maine catamaran charter

CAMDEN, MAINE

Meet your charter in the picturesque town of Camden, just a 20-minute drive from Knox County Regional Airport. One of Maine’s busiest and most interesting tourist stops, it’s worth setting out on foot to explore the intriguing town before settling in on board. Peruse the eclectic boutiques, art galleries, and cafés, or hike to the top of Mount Battie for gorgeous views of Camden Harbor and Penobscot Bay. Then return to the respite of your yacht and enjoy a celebratory cocktail on deck.

View of Acadia National Park on coastal Maine yacht charter

CAMDEN TO CASTINE

Your captain will cruise through further into Penobscot Bay to the quaint harbor town of Castine.  Rich in nautical history and home to the Maine Maritime Academy, Castine is considered one of the oldest towns in  New England , boasting historic buildings, charming inns, and beautiful homes with characteristic New England architecture. Grab a lobster roll at one of the fabulous local eateries, stroll along a pebbled beach, and tour historical sites such as Fort Madison at the mouth of the harbor, offering incredible panoramic views of the ocean.

Lighthouse in Castine on a Coastal Maine yacht charter

CASTINE TO PULPIT HARBOR ON NORTH HAVEN

As you cruise the bay towards Pulpit Harbor, make sure you’re up on deck, as the views along the way are absolutely stunning. Arrive in Pulpit Harbor, a gorgeous protected anchorage on the island of North Haven, marked by Pulpit Rock and a generations-old osprey nest greeting you at the entrance. The town itself is quaint and tranquil, perfect for a quiet stroll before returning to the haven of your yacht for an expertly-prepared meal on board.

Bird nest in Pulpit Harbor during Coastal Maine yacht charter

Depart Pulpit Harbor and head south, cruising through the Fox Islands archipelago to Seal Bay on Vinalhaven. Along the magnificent rugged coastline, you’ll find a spectacular protected anchorage surrounded by a panorama of scenic beauty, abundant wildlife, and a leisurely island community. It’s the perfect spot to make use of your yacht’s kayak or paddleboard for up-close exploration of the rocky shores and hidden coves, most likely spotting a friendly group of resident seals, and maybe even a majestic bald eagle during your travels.

Seals on a coastal Maine yacht charter

MERCHANTS ROW TO EGGEMOGGIN REACH

From Seal Bay, your captain will motor through Merchants Row, a breathtaking archipelago of eight Maine Coast Heritage Trust island preserves open for exploration.  Each island is like a jewel, with lush emerald flora, jagged-topped landscapes, and the glistening blue-green sea stretching far ahead. Choosing which of these splendid isles to explore will be your only concern. Continue on to Eggemoggin Reach, home to the Eggemoggin Reach Regatta, an annual classic boat event that celebrates the spirit of traditional wooden vessels in an environment that matches its authentic nautical history. Anchor off at WoodenBoat School in Brooklin, and head ashore to explore the grounds, learn about the history of traditional wooden boats, and enjoy some souvenir shopping. Return to your home on the water for a personalized meal prepared by your chef.

Merchants Row view on a coastal Maine yacht charter

EGGEMOGGIN REACH TO BLUE HILL

Nestled on a large peninsula that extends south into Penobscot Bay, Blue Hill offers an unspoiled landscape luring travelers with its forested hikes and pristine waters for canoeing, kayaking, paddle boarding, and sailing. The quaint seaside town is rich with artists and craftspeople, excellent food, charming art galleries, and local shops, all waiting for your unhurried enjoyment.

Stunning Blue Hill view on coastal Maine yacht charter

BLUE HILL TO LONG ISLAND

Depart Blue Hill and make way towards Isle de Haut, where you can stop-off to dine at one of many local eateries offering the freshest of Maine’s iconic seafood.  Continue to Frenchboro, a small town located on Long Island, where the primary industry is lobster fishing. Once anchored, venture ashore to explore gorgeous forested hiking trails, tour old-world fishing ports, and possibly enjoy the iconic “Lobsters in the Rough” dinner, a no-frills lobster feast held right on the shore.

Lobster is essential on a coastal Maine yacht charter

LONG ISLAND TO ROQUE ISLAND

If time permits, take a quick jaunt to Roque Island, as it boasts one of the most beautiful beaches in Maine, with a crescent-shaped expanse of pristine white sand, which is rarely seen in this region. A nature-lovers paradise, bird life is abundant and the scenic sweeping landscape offers breathtaking views as far as the eye can see.

Roque Island beach coastal Maine yacht charter

ROQUE ISLAND TO MOUNT DESERT ISLAND

Home to Acadia National Park, Mount Desert Island (pronounced as “dessert” by locals) is home to stunning beaches, sweeping cliffs, and towering mountains, offering a plethora of recreational activities amidst a backdrop of scenic wonder. From hiking, biking, and nature trails to swimming, sailing, and kayaking, there truly is something for everyone. The Northeast Harbor is smaller and quiet, with a few shops, art galleries, and quaint local cafés to enjoy, while the Southwest Harbor is a bit livelier, with unique shops, local eateries, and several historic museums, all worth a visit.

Kayaks in Acadia National Park on coastal Maine yacht charter

A visit to Maine simply isn’t complete without a stop at renowned Bar Harbor, a quintessential Down East seashore community that blends New England character with stunning coastal beauty. With its many yachts and lobster boats, and its view of the offshore islands and glistening ocean, it’s the perfect setting as your journey comes to an end. Bid your yacht and crew farewell, and fly out of Bar Harbor airport, returning with memories that will last a lifetime.

View from Bar Harbor on coastal Maine yacht charter

yachts for charter

BELLA VITA

ASPEN ALTERNATIVE

OCEAN CLUB

SAFARI EXPLORER

AQUASITION

FAR FROM IT

JUST ENOUGH

JUST ENOUGH

MISS STEPHANIE

MISS STEPHANIE

ROCK 13

NO BADA BEES

ODIN

DESTINATIONS

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MAINE YACHT CHARTERS

IDEAL TIME TO CHARTER: June – September

Maine yacht charter itineraries boasts rocky coastline, quaint hidden harbors, fishing villages that support a thriving lobster industry, spectacular coastal cliffs, and million-dollar views at every turn. Discover why the reliable prevailing wind from the West gave this downwind region the nickname “Down East”. Plan your summer vacation around this popular event in Camden-Rockland:  MAINE LOBSTER FESTIVAL . Popular boarding ports are Portland, Rockland and Camden Harbor.

maine catamaran charter

SUGGESTED ITINERARY

For best results, tell us your desired travel dates and itinerary ideas to our complimentary planning service. 

Maine Coastal Yacht Cruise Map

Rockland, Isleboro, (Lobster Feast) – You are greeted in Rockland at noon (which is the usual charter time for meeting your yacht and crew). Enjoy your first of many incredible food feasts while underway. Set sail for Islesboro to anchor for the evening. Go for a leisurely walk ashore while your talented crew prepares a traditional Down East lobster feast.

Eggemoggin Reach to Buck’s Harbor – After breakfast, sail along the coast of Islesboro, where you can view the lovely Dark Harbor estates. Anchor off one of the East Bay islands for lunch and a possible walk ashore, depending on the tides. From there, sail to the head of famous Eggemoggin Reach and anchor in Buck’s Harbor. You are likely to see a variety of Maine schooners at anchor. You may go ashore here and return in time for appetizers and dinner onboard.

Bar Harbor, Acadia National Park – Once breakfast is finished and the boat is secure, the captain hoists sail and heads down Eggemoggin Reach under the Deer Isle Bridge. Continue through Casco Passage, past Bass Harbor Bar and into Northeast Harbor. Lunch is served either under sail or at a favorite anchorage. You may enjoy exploring Northeast Harbor. The Mount Desert Island Carriage Trails are close by, as are Bar Harbor and Acadia National Park on Mount Desert Island, where the first light of morning touches the US. Dinner is served onboard, unless you prefer to eat ashore in famous Bar Harbor at one of the many fine restaurants.

Swans Island (Water Sports) – You can choose to explore more of the area or get underway after breakfast and sail up Somes Sound, the only fjord in the Northeastern US. Continue up to Somesville and eat lunch while sailing out of the Sound. You may anchor in Southwest Harbor for the evening or sail on to Swans Island, whichever you prefer.  You also may enjoy the paddleboard, kayaks, or sailing/rowing dinghy as often as you like.  Fishing may also be an option while under sail or at anchor.

Outer Islands, (Lobster Quest) – From the anchorage either in Southwest Harbor or Swan’s Island, set sail for either Isle au Haut or even possibly Matinicus, if the winds were favorable. Both islands offer you the opportunity to experience what life on one of the outermost islands is like. On Matinicus you can go out in a traditional Maine lobster boat for a few hours if you chose.

Vinalhaven, North Haven – After a leisurely breakfast, set sail for Vinalhaven and possibly anchor off of Brimstone Island, where you can go ashore. Pause for lunch and then sail through Fox Island Thorofare, between Vinalhaven and North Haven, anchoring in one of their pristine harbors. You may enjoy wandering through the small town of North Haven and visiting some of the art galleries.

Vinalhaven islands, Pulpit Harbor, (Nature Sights) – After breakfast, sail through the myriad of islands around Vinalhaven, feasting on the breathtaking beauty. You are sure to see seals, porpoises, osprey, loons and maybe even bald eagles. Your days of sailing can stretch far into the evening. Anchor in Pulpit Harbor, North Haven, for the last evening on board. You are welcome to go ashore for a walk, or perhaps the little sailing dinghy to explore the harbor.

Rockland Return – After your last breakfast aboard, we get underway and sail back to Rockland where it all began. Saying good-bye is always difficult for us, but our charter guests often become friends and we’ll meet again.

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TIMELESS Offshore Motor Yacht 62 62' 62‘

from $28,500 /wk

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Capricia (Crewed) Alden 54 with Captain 54‘

TBD/ Includes Captain

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Breezing Up J-46 46‘

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Wind Dancer Gulfstar 44.5 45‘

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Defiant Morgan 43 43‘

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Pax Sceptre 41 41‘

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Coconut Grand Banks 40 40‘

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Elan J-40 40‘

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Nefer Nubi NO LONGER AVAILABLE Hans Christian 38 38‘

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Lucky Dog Sabre 36 36‘

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Osprey Hinckley Pilot 35 36‘

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Sweetness Cape Dory 36 36‘

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Tailwind Sabre 36 36‘

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Presence J/35 35‘

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Curve of Time Morris Ocean 32 32‘

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Andromeda Sabre 30 30‘

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Thira Catalina 30 30‘

Get in touch with us.

NorthPoint Yacht Charters arranges sailing and power boat cruising charters, we offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

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An insider’s sailing guide to yacht charter in Maine & Newport

Oyster Yacht Sailing In Maine

Sailing in Newport is perfect if you seek stunning sunsets over beautiful yet understated harbours, exhilarating cruising and ultra-friendly locals. And what better way to see it all than on an Oyster Newport Boat Charter? A quintessential American summer destination, Newport is a must-visit spot for New England yacht charters, with a race calendar to entice every level of sailor, from beginners to experienced old hands. The salty air provides the perfect backdrop to explore its eclectic range of monuments, festivals and architecture on a Newport sailboat charter. Meanwhile, sailing in Maine is ideal for explorers, with 3,500 miles of glorious coastline to discover. Historic lighthouses invite you to the horizon, whilst over 6,000 lakes and ponds mean this is one region you will never tire of cruising on a Maine yacht charter.

CRUISING AREA

Sailing in Maine and Newport on a luxury yacht charter

Those sailing in Maine, Newport and the rest of New England in the US summer season can expect warm and humid weather. In July, nearly 15 hours of daylight will mean endless hours spent out on the boat or soaking up the sun ashore, while temperatures rise to around 24°C/71.6°F and wind speeds reach up to 5 mph. And as the summer continues, so does the good weather, making it a reliable destination that as good as guarantees a good tan and lots of lasting memories. One of the world’s favourite sailing destinations, the light winds that blow all year round here will give novice sailors on Newport yacht charters and Maine yacht charters a taste of the freedom and exhilaration a sailing charter provides. New England is most popular in July and August, when the seaside towns and cities come alive with culture and all the best lobster bars are open for business. The area is big enough to escape the crowds on your yacht but the crowds make for vibrant and bustling holiday that will have you dreaming of returning the following year.

Sailing New England on an Oyster Yacht

New England is best experienced by sailing yacht, with countless coves and stunning harbours that motorboats simply can’t reach. An Oyster Newport Boat Charter offers an unmatched on-the-water vacation, in comfort and privacy with a knowledgeable crew who will guide you through the area and cater to your every desire. It is the perfect place to enjoy watersports – snorkelling and diving, water skiing and boarding, as well as surfing. Your perfect US yacht charter awaits.

You can sail on Newport yacht charters and Maine yacht charters on one of our  Oyster sailing yachts for charter , such as the stunning Oyster 625 Black Lion. The Oyster 625 offers spacious interiors for a sailing yacht, with a generously proportioned galley, a full-beam owner’s suite, two en-suite cabins forward and a fourth guest cabin a guest cabin. Designed for outdoor living, with safe navigation and easy sailing facilitated by a large cockpit, flat aft deck and forward sundeck, it is made for yacht charters.

CRUISING DESTINATIONS

Sailing in Newport 

A Newport sailboat charter offers the chance to discover historic sites hailing back to Newport’s Colonial history, alongside musical and arts festivals that light up the city and incredible beaches for sunbathing and watersports and impressive architecture. All this makes Newport the destination that keeps on giving. Start by taking a walking tour of Newport’s Old Quarter and view the magnificent mansions in the Bellevue Avenue Historic District – it’s not hard to imagine how life was here in the past. If you’re a surfer, you will want to catch some waves at Easton's Beach before enjoying a relaxed BBQ on its golden sands. If you are an art lover, you are in for a treat – Newport is home to over 30 private art galleries offering everything from contemporary artworks to the more traditional. Whatever your taste, there is something for everyone. No Newport Boat Charter holiday would be complete without a visit to the famous Martha’s Vineyard. This picture perfect island is home to around 16,000 people but the population swells to more than 100,000 people during the summer months. Drink in the brightly-painted seaside cottages and cobblestone streets, and marvel at the pristine beaches at Chappaquiddick Point. After lunch at an elegant dockside bistro, head back to the yacht for some adrenaline-fuelled watersports.

Craving an island escape? Cruise over to Nantucket on your Newport sailboat charter, where the rich and famous go to while away the long hot summer months. Drop anchor and spend the day drinking in its one-of-a-kind history and make sure to stop by the whaling museum where you will discover how hard life used to be in this relaxing and entertaining destination. Designated as a National Historic Landmark District, it is the finest surviving architectural and environmental example of a late 18th- and early 19th-century New England seaport town. When you’ve enjoyed your fill of history, why not take a good book and enjoy some downtime on one of the delightfully uncrowded stretches of sandy beach? And when you’ve recharged your batteries, you’ll be ready for the evening. The island really comes to life at night, with vibrant harbourside nightlife which is perfect for an evening of bar-hopping and enjoying locally-caught seafood. All this gives just a taste of all there is to explore for those onboard New England yacht charters.

On land or on water, the best time to take a Newport Boat Charter is during the months of July and August, when the city bustles with activity and the weather is reliably and gloriously sunny. Don’t miss the Newport Folk Festival in July and Jazz Festival in August, both of which were established in the 1950s and have been a draw to the city ever since. (The Newport Folk Festival is infamous as the event where Bob Dylan famously ‘went electric’, much to the fury of the audience of traditionalist folkies.)

Sailing in Maine

Maine  is renowned for its dramatic lighthouses, rugged mountains and enchanting sea life, found just 20 miles from the coast. With a coastline just shy of 3,500 miles, there is a lot to discover. But the joy of the area is that once you are there, you don’t need to waste time on long passages between ports – it is possible to enjoy Maine in bite-sized chunks and cruise at your leisure. The whale-watching season runs from mid-April to September and captivates thousands on crewed sailing yacht charters with the prospect of sighting humpback whales, pilot whales, minke whales and finback whales, as well as rarer visitors like sei whales, sperm whales, orcas and right whales. When you’ve had your fill of wildlife spotting, sail in Maine’s MidCoast and islands. This is a veritable paradise, with its many secluded coves, inviting harbour villages with a view and some of the best lobster you’ll ever taste especially in Swan's Island. Maine is renowned for its seafood restaurants, ranging from the local lobster shacks to five star restaurants. You can discover plenty of great places to eat and drink at in our  Maine Insider Sailing Guide. 

Sailing in Maine in July and August guarantees the best weather as temperatures reach up to 25°C/77°F and wildflowers and blueberries shoot out from the bushes, adorning the landscape. These months are typically warm and mild - the perfect climate for outdoor activities and watersports. (Don’t be put off by Maine’s famous fog – it is a truly atmospheric experience that is as much part of any trip as sun-filled days.) You can hike, camp, swim, water ski, cycle, white water raft and kayak the summer away on board a luxury New England yacht charter with Oyster.

GET IN CONTACT

Learn more about how to charter a sailing yacht in New England with Oyster by taking a look at our Maine sailing guide  here . Discover  Oyster luxury sailing yachts for charter  or contact Oyster Charter Manager, Fiona McCarthy to begin planning your trip.

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Winner of European Yacht of the Year 2023. She sets a new 50 foot bluewater benchmark, offering a stunning combination of sailing performance, comfort, safety and luxurious living space.

Oyster 495 sailing yacht with man at helm

Heralding a new generation of Oysters, this 60 foot bluewater cruiser is a sailing yacht for all oceans. Practical and well-provisioned for long distance sailing or cruising in coastal waters.

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The much-anticipated Oyster 595 is well-proportioned and extremely versatile. Offering exciting, customised build options with no compromise, she is capable of great things.

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A versatile sub-70 foot sailboat offering the perfect balance of size and practicality. She can be sailed shorthanded effortlessly or take a full crew and up to eight friends and family.

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This long range 75 foot cruising yacht is designed for very big adventures. A joy to sail yourself, she also boasts dedicated crew quarters.

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An exhilarating 90 foot sailing yacht, delivering comfort and safety with uncompromising performance. She is capable of taking you anywhere in the world effortlessly, in luxury and style.

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Maine Yacht Charters

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New England Lighthouse In Late Afternoon The Portland Head Light At Portland Maine USA

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MAINE (USA)

The USA’s Maine coastline is best explored by yacht; and a Maine yacht charter is the most convenient way to achieve this. It extends for more than 3,400 miles making it larger than the Californian coast. There are more than 4,613 islands along the coastline just waiting to be explored. A mega yacht charter vacation off the coast of Maine, offers the perfect combination of tranquility and adventure. There are picturesque coastal towns and quaint lighthouses dotted along the shore. During your voyage keep an eye out for seals, migrating whales and porpoises. 

Why not begin your itinerary from DiMillo’s Marina in Portland? It’s a great city for entertainment, nightlife and shopping as well as having a fully serviced marina. There are many restaurants here to dine in before setting off on your superyacht journey. Set sail for Monhegan Island which is 1.4 miles long and 0.7 miles wide. Only ten miles out to sea, the island has several hiking trails, exquisite “fairy houses” not far from Penobscot Bay. Ask your captain to drop anchor off Hurricane Island which once had a thriving community due to quarrying. Visit Castine, home of Maine’s Maritime Academy and other marine related industries. 

Relaxing on charter

Maine has an intriguing rocky coastline, lots of maritime history and nature areas such as the Acadia National Park. No trip to this park is complete without seeing Thunder Hole. It’s a landmark with stunning views, high rocks and a small cavern at the bottom of the inlet. When waves hit the rocks and release air, thunderous booms can be heard. It shows how powerful the ocean can be with the waves reaching 40 feet in height, nature at its best. You’re sure to get wet so remember to take a waterproof. In Baxter State Park, there’s Mount Katahdin and the Appalachian Trail along with plenty of wild moose. You will also see beautiful sandy beaches and lobster shacks.

Take a cruise to Butter Island, a firm favourite with superyacht charter guests for its spectacular beaches. Anchor in Penobscot Bay before setting off to Nubble Beach to enjoy a swim. If you’ve got the energy, climb up to the top of Montserrat Hill where you can take in magnificent views of the Camden Hills and Mount Megunticcok.

Blue Hill Bay lying to the west of Mount Desert Island in Hancock County, Maine, is very popular with recreational boaters. Here you can also tuck into local delicacies like crab, lobster, salmon and mussels. The town of Blue Hill at the far end of the island offers a great chance to buy local handicrafts and souvenirs. Maine is gaining in popularity with luxury yacht charter enthusiasts so do include it as part of your vacation itinerary.

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Yachting Destinations In and Around Maine

In close proximity to Maine are a number of exciting sailing destination.

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Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Ellis Boat Charters

Maine bareboat charters & boat rentals – midcoast & downeast maine, ellis charter boats.

Your charter starts with an Ellis Boat Company representative giving a full tutorial on the operation of the vessel out of Southwest Harbor, Maine. All Charter vessels include a tender and proper cruising/safety equipment. Additionally, the entire Ellis Charter Fleet is properly insured, well-maintained, and thoroughly cleaned between each charter.

  • Jericho Bunker&Ellis
  • Nena Wilbur42
  • Freyja B.Cove41
  • Timbuktu Hinckley40
  • A. Song Wilbur38
  • Elsie Ellis36
  • All That Jazz Ellis36
  • Marengo Ellis36
  • Liberty Ellis36
  • Emily Ellis36
  • Exit Strategy Ellis36
  • DownEaster Ellis36
  • Lab Adore Hinckley36
  • NoAltitude Ellis28

Jericho - Bunker and Ellis for Rent or Chartering

CHARTER BOAT DETAILS

“Nena” is a comfortable and spacious cruiser that sleeps 4 people and has ample space for guests (up to 12). The generous galley is located up in the shelter. Operational helms and comfortable settees are located both in the shelter and up on the flybridge. 

maine catamaran charter

Fast and Nimble - The Hinckley T40 "Timbuktu" provides a fun boating experience while avoiding the prolific lobster trap lines that populate the Maine coast. Timbuktu is outfitted for day-cruising and/or overnighting, with or without a Captain.

Hinckley Talaria

Added to the fleet in 2020, this Wilbur 38 flybridge Cruiser is ready for cruising the Downeast Maine coast. A tender and outboard will be included. This vessel will be fully equipped for overnighting and lengthy cruising. 

maine catamaran charter

New to the fleet in 2024, this Ellis 36 Flybridge Cruiser sleeps four down below with a full galley topside. Loaded with systems and easy to operate with bow & stern thrusters, this vessel will be fully equipped for overnighting and extended cruising. 

maine catamaran charter

2023 Ellis 36 Express Cruiser "All That Jazz". Includes: Ellis Cantilevered seats & Ellis fold-out tables, a Davit system with tender, diesel heating & cooking, solar charging, and a DC-AC inverter. Sleep 2 in the cabin and 2 in the salon. Ample seating for up to twelve people.

maine catamaran charter

The Ellis 36 Bowrider Express "Marengo" is arguably the prettiest boat in Maine's waters. It is a premier yacht - available to clients who are planning to hire a Captain. The seating is comfortable and the galley is well-equipped - this is the perfect yacht for hosting cocktail cruises for up to 12 people.

maine catamaran charter

Custom Designed and built by Ellis Boat Company, this beautiful Ellis 36 Express Cruiser features a custom top design, 465 hp Yanmar diesel engine, Garmin electronics, generator, and more. 

maine catamaran charter

This Ellis 36 Express Cruiser is built with an extra long cabin allowing for a settee and extra sleeping accommodations below. Charter features include a large mounted grill in the cockpit and a big tender with 9hp Yamaha outboard. Additional information and photos here. 

Maine's Ellis 36 Express Cruiser - Boat for Charter

Formerly "Too Priceless" this Ellis 36 has seen quite a few upgrades from Ellis Boat Company recently, including a new Garmin plotter, generator, heat and air conditioning, induction cooktop, built-in grill, and a full shelter enclosure.

maine catamaran charter

The Hinckley Picnic Boat EP is a classic and fun-to-drive Maine yacht. This boat has a Yanmar 400 Engine with a single Hamilton Jet Drive. Hire a Captain or bareboat this vessel yourself. 

maine catamaran charter

This Ellis 28 Express Cruiser, fully restored in 2017, features a 225 hp Volvo Diesel engine, bow thruster, Garmin plotter/radar, v-berth, heating system, head, hot water, salt/fresh water, anchor, small galley, and tender on davits.

maine catamaran charter

CURRENT ELLIS CHARTER BOATS BELOW

EVENING STAR YACHT CHARTERS

Maine Bareboat Yacht Charters

maine catamaran charter

Sail the Coast of Maine on a Beautiful Classic Sailboat

Looking to charter a bareboat yacht on the coast of Maine?   Evening Star   is a 45' traditional sailboat available for bareboat charter from Belfast Harbor in the heart of Penobscot Bay!   The yacht Evening Star is equipped with Hood Stowaway roller furling masts and has two double staterooms, each with its own head and shower.  

Now Taking Reservations for 2024      Available Bareboat or with Captain

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Treat yourself to the best Portland, Maine boat charters with Sail Portland Maine. There is no better way to experience our vibrant city’s coastline!

Relax aboard our sailing vessel the Eleanor Hawkes, or our newly acquired picnic boat, the Calista Ann, as we cruise through tranquil waters of Portland Harbor sailing Casco Bay. Bring along any beverages and snacks you want, there are a myriad of eateries, breweries, and food trucks in Portland. Come enjoy the sights and sounds of our lovely Casco Bay and the Portland skyline and working waterfront.

Flappy Hour at Crown Jewel

Experience the ultimate Flappy Hour celebration on a chartered cruise to Crown Jewel, nestled on the picturesque shores of Great Diamond Island in Casco Bay. Click the image below to book your experience with Crown Jewel today!

island cruise portland maine

Our Custom Day and Sunset Charter Cruises

Every day we offer two-hour public or private charters that might have you cruising past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained and crewed excursions aboard our vessels, the Eleanor Hawkes or the Calista Ann. 

We provide multiple trip options to ensure that your Portland, Maine boat cruise fits into your schedule or the ability to customize times for a private charter. You can choose from three different charter times throughout the day:

Eleanor Hawkes (Sailboat) → Book a Sail on the Eleanor Hawkes

Public and Custom Private Charters Available. You’re welcome to bring your own food and beverages aboard.

  • 12:00 PM – 2:00 PM (Fall hours vary)
  •   3:00 PM – 5:00 PM (Fall hours vary)
  •   6:00 PM – 8:00 PM ( Fall hours vary )

Calista Ann (Classic Motor Yacht) → Book a Cruise on the Calista Ann

Public and Custom Private Charters Available. You’re welcome to bring your own food and beverage aboard.

  •   6:00 PM – 8:00 PM (Fall hours vary)

Private Charters → Book Your Private Charter

Private charters are based on availability..

Our private cruises are perfect for a group of up to 6 guests on the Eleanor Hawkes and up to 12 passengers on the Calista Ann . For even more space, book the Calista Ann – she is the newest addition to the company, keeping with the style and intimacy that our brand represents. She is a classic Downeast Picnic boat and is a comfortable cocktail cruiser. 

Private charters could be anything from a couple wanting to cruise to one of the nearby island restaurants for an anniversary dinner and then a cruise back under the stars, or a couple who wants to elope and get married by the captain with a few friends to witness – your imagination is the limit! We can recommend catering as well. 

Some of the many incredible island restaurants we can take you to by boat are Crown Jewel on Great Diamond Island, The Dolphin Marina & Restaurant or Iris Eats in Harpswell, and Island Lobster Company on Peaks Island.

Book Your Portland Maine Boat Tour!

When you book your ticket for one of our private chartered boat trips at Sail Portland Maine, it can be anything you want it to be! There are so many beautiful and unique factors about our beloved Casco Bay – from diverse wildlife like seals and porpoise to the historic Fort Gorges and the sun setting over coastal islands, soak in the beauty that is Portland’s harbor. For an incredible adventure you’ll talk about for years to come, reserve your trip with us below!

Book Your Sailing or Cruising Trip on the Waters of Casco Bay Now

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Boat Charters in Portland, Maine

Casco Bay | Portland | Maine

Public and private charters aboard an authentic lobster boat

Cruise the islands of Casco Bay, enjoying wildlife, stunning views of Portland Harbor, the famous Portland Headlight, and more. We can accommodate up to 21 guests and are perfect for reunions, birthdays, bachelor/bachelorette parties, intimate weddings or whatever you are celebrating. Complimentary beverages on all charters!

Search for your preferred date and time in our booking system. Our calendar is always up to date!

Book your preferred date and time within our reservation tool online. Once booked, you will receive an email confirmation.

Sit back, relax & enjoy the ride. Our captain will be happy to accommodate you, together with 1 additional crew member.

DISCOVER YOUR NEXT ON-THE-WATER ADVENTURE

Aboard brianna marie.

Hop on board M|V Brianna Marie, a Young Brothers 38' Flybridge model, built in 1983. Designed by Earnest Libby in Beals, Maine, Young Brothers lobster boats are known for their high quality construction while being seaworthy, spacious, and stable.

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Say Hello to Our Team

Owen and Brianna are both originally from Maine. They met while working in the yachting industry. They have sailed many miles together on different types of boats. Several years ago, they returned to their home state of Maine, where they got married and live happily now, together with their dog! These boomerangers have gone there and back again - and look forward to doing the same with you in Casco Bay!

CRUISE WITH US THERE AND BACK AGAIN!

14 Ocean Street, South Portland, ME 04106

(207) 321-8954

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  3. The Cat makes noise departing Portland

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  5. The Cat as seen from Portland Head Lighthouse, Maine

  6. BoatSmith Delivers and Assembles Dex's Ariki Hulls and Beams

COMMENTS

  1. Maine Boat Charters & Rentals

    Welcome to the 2024 Charter Season. NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine, Northern New England and the Canadian Maritimes. We offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet. Both bareboat and crewed charters are available.

  2. Bimini Charters

    Luxury Sailing Catamaran Charters. One of the only sailing catamarans in Maine! Sail, swim, & sunset with Bimini Charters. ... so that your trip is as memorable and fun as possible. We are one of the only sailing catamaran charters in Maine, offering much more space and comfort than monohull sailboats. Snorkel at the best reef, paddle board ...

  3. Ellis Boat Charters

    Our charter fleet currently includes a number of Ellis 36s, a Hinckley Talaria, and a Wilbur 38 Flybridge Cruiser. All Charter vessels include a small tender on davits and proper cruising/safety equipment. Explore Maine and New England's offshore islands and diverse coastal harbors with a classic Maine-built boat - available through Ellis ...

  4. Casco Bay Custom Charters

    The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef's dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter! ... GLEAM is a fully restored vintage 12 meter yacht ...

  5. 2024 Luxury Catamaran Sailing Charters in Maine

    Luxury Catamaran Sailing Charters in Maine. By Bimini Charters. 47 reviews. Recommended by 95% of travelers. See all photos. About. from. $135.00. per adult.

  6. Saco Small-Group Catamaran Sailing Charter 2024

    Luxury Catamaran Sailing Charters in Maine. 61. 2 hours. Free Cancellation. From. $135.00. Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion. 10. 2 hours. Free Cancellation. From. $150.00. Discover Maine's Coastal Charms: Half-Day Scenic Sail. 2. 4 hours. Free Cancellation. From. $270.00.

  7. Southern Maine Sailing Catamaran Charters

    Private sail start times are typically 10am, 1pm, and 5pm but can be adjusted per your request. We are located at the Camp Ellis Pier, at 5 Bay Ave, Saco, ME 04072. Before your charter, park in the Camp Ellis pier parking lot. You will have to purchase a parking permit at the machine in the center of the lot.

  8. Maine Yacht Charter Boats & Boat Rentals

    Small full service marina offering bareboat charters, sail and power. Also supplies, fuel dock, mooring rentals, reservations and directions by land, sea or air. located in Brooksville.

  9. Maine Yacht Charters

    On Maine yacht charters, you can experience all this area has to offer. The Maine coast juts out to sea and curves inland with hundreds of harbors, inlets, and rivers. With over 5,000 miles of coast, including islands, the best way to explore is on a Maine yacht charter. Climate and Weather.

  10. Coastal Maine Yacht Charter

    Luxury Yacht Charter Through Coastal Maine Camden to Bar Harbor. Home to stunning coastlines, breathtaking scenery, and enduring maritime tradition. With its iconic rocky beaches, historic lighthouses, and postcard-perfect towns lining the shores, coastal Maine is known as one of the most naturally-beautiful destinations in the United States.

  11. THE TOP 10 Maine Catamaran Cruises (w/Prices)

    60. Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for... Read More. 2 hoursFree CancellationInstant Confirmation. from$135.

  12. Sailing in Maine

    You can hike, camp, swim, water ski, cycle, white water raft and kayak the summer away on board a luxury New England yacht charter with Oyster. The region has a continental climate with warm, humid but dry summers and very cold winters. The season runs from April to October, with temperatures reaching up to 25 o C in June and July, with gentle ...

  13. Maine Coastal Cruise Charter at Carol Kent Yacht Charters

    Maine yacht charter itineraries boasts rocky coastline, quaint hidden harbors, fishing villages that support a thriving lobster industry, spectacular coastal cliffs, and million-dollar views at every turn. Discover why the reliable prevailing wind from the West gave this downwind region the nickname "Down East".

  14. Charter Gallery

    TIMELESS Offshore Motor Yacht 62. 62'. 62'. from $28,500 /wk. Capricia (Crewed) Alden 54 with Captain. 54'.

  15. Maine Yacht Charters

    It is the perfect place to enjoy watersports - snorkelling and diving, water skiing and boarding, as well as surfing. Your perfect US yacht charter awaits. You can sail on Newport yacht charters and Maine yacht charters on one of our Oyster sailing yachts for charter, such as the stunning Oyster 625 Black Lion. The Oyster 625 offers spacious ...

  16. THE TOP Maine Catamaran Cruises (UPDATED 2024)

    A: The best Catamaran Cruises in Maine according to Viator travelers are: Windjammer Classic Sunset Sail from Camden, Maine. Luxury Catamaran Sailing Charters in Maine. Portland Tall Ship Cruise on Casco Bay.

  17. Maine Boat Charter

    Midcoast Maine Boat Tours. From Portland to Belfast and the Acadia Mountains, we can't wait to show you the breathtaking coast of Maine. All of our charter Charters are private. Our crew will create an unforgettable experience for you. Learn More.

  18. Crowd-Free Boat Charter in Portland, Maine

    Meet Our Boats. Eleanor Hawkes (Sailboat) → Book a Trip on the Eleanor Hawkes. The Eleanor Hawkes has space for a group of up to 6 people, making it one of the smallest chartered cruises in Portland - and thus, one of the most crowd-free and intimate experiences on the harbor! 12:00 PM - 2:00 PM: $85 per Person/$500 Private Charter.

  19. Maine Yacht Charters

    The USA's Maine coastline is best explored by yacht; and a Maine yacht charter is the most convenient way to achieve this. It extends for more than 3,400 miles making it larger than the Californian coast. There are more than 4,613 islands along the coastline just waiting to be explored.

  20. Ellis Charter Boats

    Your charter starts with an Ellis Boat Company representative giving a full tutorial on the operation of the vessel out of Southwest Harbor, Maine. All Charter vessels include a tender and proper cruising/safety equipment. ... The Hinckley Picnic Boat EP is a classic and fun-to-drive Maine yacht. This boat has a Yanmar 400 Engine with a single ...

  21. Home

    Evening Star Yacht Charters offers a beautiful traditional 45' sailboat for bareboat charter on Penobscot Bay and the coast of Maine. Evening Star has two separate sleeping cabins, each with its own head & shower. She equipped with Hood Stowaway masts and sail furling systems to make sail handling easy. Her electronics include networked Raymarine chartplotters with 48 mile color radar and AIS ...

  22. Portland, Maine Boat Tours, Sails, and Public & Private Charters

    Calista Ann (Classic Motor Yacht) → Book a Cruise on the Calista Ann. Public and Custom Private Charters Available. You're welcome to bring your own food and beverage aboard. 12:00 PM - 2:00 PM (Fall hours vary) 3:00 PM - 5:00 PM (Fall hours vary) 6:00 PM - 8:00 PM (Fall hours vary) Private Charters → Book Your Private Charter

  23. Boomerang Yacht Charters

    Public and private charters aboard an authentic lobster boat. Cruise the islands of Casco Bay, enjoying wildlife, stunning views of Portland Harbor, the famous Portland Headlight, and more. We can accommodate up to 21 guests and are perfect for reunions, birthdays, bachelor/bachelorette parties, intimate weddings or whatever you are celebrating.