florida keys yacht charter itinerary

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Florida Keys Yacht Charters

A classic florida experience: the florida keys.

Florida Keys yacht charters are one of the most popular yachting vacations in the continental US. Florida Keys are composed of more than 40 islands south of Miami and offer the best diving and snorkeling in the US. The 110 miles of Florida Keys chain are also the home to North America’s only living coral barrier reef.

Just off the southern tip of mainland Florida are the Florida Keys, a chain of tropical islands that stretch 120 miles from the Atlantic Ocean to the Gulf of Mexico. The islands — each with its own distinct personality — are a playground for all ages, whether snorkeling with schools of colorful fish, diving to explore a famous shipwreck, fishing for the perfect marlin, or simply enjoying an umbrella drink while watching a gorgeous sunset.

From laid back escapes to daily adventures, the best way to experience all that the Florida Keys have to offer with a custom yacht charter vacation.

Florida Keys Yacht Charter Highlights

• Over 1700 islands to explore
• World-class sportfishing
• Home to the only living coral barrier reef in the continental United States
• Warm temperatures and waters year-round
• Some of the world’s best sunsets

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Best Time to Charter a Yacht in the Florida Keys

The Florida Keys are the ideal year-round yacht charter destination. Average highs range from 75F/24C in January to 89F/32C in August. Winter months are the driest, and the Keys don’t experience the cold fronts that can bring frost to the mainland. When temperatures are at their peak, the ocean breezes will cool you down. From late May through October, thundershowers and rain can pop up, but wet weather rarely lasts the entire day. Best of all, the waters are warm and calm throughout most of the year.

Florida Keys Yacht Charters – Top 3 Places to Visit

The first and northernmost of the Florida Keys is Key Largo, a natural paradise both on land and under the sea. Referred to as the Diving Capital of the World, it is home to the John Pennekamp Coral Reef State Park and the Florida Keys National Marine Sanctuary which includes the world’s largest artificial reef, the 510-foot USS Spiegel Grove shipwreck.

Key Largo is also a sportfishing destination, with over 600 species of fish in the surrounding waters, including the popular yellowtail snapper. For a truly memorable experience, check out one of the island’s dolphin encounter programs where you can learn more about the mammals or even swim alongside them.

Located just 90 minutes south of Miami, between Everglades National Park and the Florida Strait, Islamorada is a village made up of six islands. Islamorada is known as the Sportfishing Capital of the World. For anglers, you can fly fish in the shallow backcountry waters for bonefish, redfish and tarpon in the morning, then head offshore and try to snag a sailfish that same day.

Divers will love exploring the area reefs and visiting the History of Diving Museum that includes intriguing finds, like a 16th-century treasure chest. Take a step back in time to Florida in the early 1800s at Indian Key Historic State Park and Lignumvitae Key Botanical State Park, or hike the tropical nature trails at Long Key State Park.

The southernmost key in the chain and the southernmost point in the United States, Key West is actually closer to Cuba than it is to Miami. Spanning just two by four miles and with a population of around 27,000 full-time residents, you’ll find its Bahamian and Cuban heritage all over the island.

Famed for its natural beauty, history, climate, art, architecture and abundance of activities for all ages, it’s a great option for family charters or couples charters. Visit the Ernest Hemingway Museum and discover why Key West captivated the acclaimed author. Snorkel or dive the area reefs and shipwrecks.

Florida Keys Week-Long Yacht Charter Itinerary

Day 1: Biscayne Bay & South Beach

When you arrive in the Sunshine State, you’ll be greeted by the crew of your South Florida yacht charter, who will assist you with your luggage and help you board your luxury yacht. You’ll get your sea legs with a cruise in Biscayne Bay and along the Intracoastal Waterway where the beautiful homes of the rich and famous can be seen on Fisher Island , Palm Island , Star Island , and Hibiscus Island . We’ll return to dock at South Beach , where you’ll experience the best of Miami nightlife. Enjoy a drink and the ocean breeze at a beach party or head indoors to one of the finest nightclubs in the country for a wild night of dancing.

Day 2: Head to the Florida Keys

While you recover from your night of partying in Miami, you can sip on fresh-brewed coffee as we head south towards the Florida Keys. You can enjoy a variety of water sports along the way – from diving to wakeboarding, waterskiing etc.

Day 3: Key Largo

Today you’ll certainly want to go snorkeling or diving, in this self-proclaimed Dive Capital of the World. On land, there is much to explore and plenty of activities to take part in, including dining, shopping, golfing, and much more! Key Largo is a wildlife haven with two state parks, a national park, and a national marine sanctuary. The John Pennekamp Coral Reef State Park is America’s first underwater park and offers an amazing array of fishes and colorful coral. As the sun sets, you can tender out to Indian Key , where you can watch the colors fade from the sky on this natural key.

Day 4: Key West

In the early morning, we’ll cruise to Key West , where you’ll have to opportunity to view the unique island culture that is world-famous. As the southernmost point in the continental U.S., Key West touts clear blue skies and beautiful weather. During the day, enjoy watersports, fishing, diving, golfing or shopping, because once the sun sets, you’ll be ready to truly begin your Key West experience. Head to Mallory Dock for the Sunset Celebrations, which is an impromptu occurrence every day of the week. You’ll see musicians, jugglers, and mimes as you walk to one of the sidewalk cafes, open-air bars, or elegant restaurants. This is what Key West is all about.

Yacht charters to Key West are like nothing else. This island breaks all stereotypes and all the rules to become a destination that is uniquely Key West.

Many people recognize Key West as a party town. This may be due to the fact that there are more bars per capita here than anywhere else in the country. The local bars know how to treat their patrons. The Schooner Warf Bar, for instance, meets the needs of its clients’ wild side by starting happy hour at 9:00 in the morning. However, one thing that people don’t realize about the island is that it also has more churches than anywhere else in the United States.

Key West yacht charters are popular because of the Caribbean-style atmosphere, the beautiful sandy beaches, and the stunning coral reef. The 160-mile-long reef is the third-largest in the world and the only one in the United States. Key West beaches are unlike any others in the Florida Keys because the sand was shipped from the Caribbean on barges.

Day 5: Marqueses Keys

We’ll head even further west to the Marqueses Keys , a group of uninhabited islands that are surrounded in mangroves. You may want to take out the kayak and explore the environment up close. Enjoy an afternoon of water sports and sunbathing before relaxing on the deck of your yacht with a cocktail in hand to watch one of the most beautiful sunsets in the world.

Day 6: Little Torch Key

As we make our return trip, you’ll enjoy a fabulous gourmet breakfast al fresco style so you don’t miss a second of the stunning scenery. We’ll take time to stop at any of the smaller Keys we may have missed along the way, such as Little Torch Key for dinner at the exclusive Little Palm Island Resort and Spa.

Day 7: Miami

Today will be your last day on your Florida yacht charter . You’ll enjoy a delicious brunch served by your personal chef before packing your things in preparation for reaching Miami. We look forward to seeing you again as you make a return trip to the beautiful Florida Keys!

Florida Keys Yacht Charters – What to See & Do

Florida Keys National Marine Sanctuary – Extending from south of Miami westward to the Dry Tortugas, The Florida Keys National Marine Sanctuary is the world’s third-largest barrier reef in the world and the only one in North America. Home to over 6000 species of marine life, it’s a popular destination for swimming, fishing, boating, ecotourism and more. It is also one of the most popular spots for diving, especially the Shipwreck Trail and the world’s largest artificial reef, the USS Spiegel Grove, a 510-foot retired Navy ship that was intentionally scuttled in 2002.

John Pennekamp Coral Reef State Park – Located in Key Largo, this is the first undersea park in the United States. Explore the reef on a snorkeling, scuba diving or glass-bottom boat tour. Rent a kayak, paddleboard or canoe and make your way through the mangrove trails. Or spend a day at Cannon Beach where you can swim to the remnants of an early Spanish shipwreck just 100 feet from shore.

History of Diving Museum – This museum on Islamorada is known for its dedication to preserving, collecting and displaying artifacts related to the history of diving around the world, and the role that the Florida Keys has played in this history. Exhibits include the Treasure Room with its 16th-century iron treasure chest and 70-pound silver bar, a display breaking down the evolution of underwater photography, and the collection of atmospheric diving suits.

The Ernest Hemingway Home and Museum – Located in the heart of Old Town Key West, Nobel Prize-winning author Ernest Hemingway lived and wrote here for over 10 years. Step back in time by taking a guided tour of the house and gardens, and be sure to look out for the world-famous six-toed cats that live on the property.

Key West Aquarium – Situated in Key West’s Mallory Square, the aquarium is a popular attraction for the entire family. Stroll through the shark, jellyfish, and alligator exhibits, learn about sea turtle conservation or watch one of the animal feedings throughout the day.

How much does it cost to charter a yacht in the Florida Keys?

Yacht charter rates in the Florida Keys start from approximately $20,000 US up to $170,000 US, depending on the size of the boat, the year it was built, the number of cabins, amenities, selection of water toys, and season. Contact Worldwide Boat and one of our yacht charter specialists will help you select the yacht that best fits your needs and budget.

Book Your Florida Keys Yacht Charter with Worldwide Boat

Take advantage of the convenience of chartering close to home with a Florida Keys yacht charter. The Keys are just a short flight away yet they feel like a different world completely. Enjoy the natural beauty and serenity on one of our Florida Keys yacht charters with endless exciting things to do and see !

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Florida Keys Sailing Itinerary

Chart your course with confidence and explore our handcrafted Florida Keys sailing itinerary.

Day 1: Travel day & Sleepaboard

Day 2: Head first for Boca Grande Key

Day 3: Arrive at the Dry Tortugas

Day 4: Daytrip to Loggerhead Key inside the Park

Day 5: Back east to the Marquesas Keys

Day 6: Night out on Duval Street

Day 7: checkout and travel day, florida keys charter planning.

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Sarah’s Magical Florida Keys Itinerary

7 days/8 nights.

The Florida Keys are a magical place that feels like an exotic country with the conveniences and accessibility of the US. The Keys are islands of mangroves with spectacular beaches and turquoise waters, rivaling those of the South Pacific. The gentle breezes keep mosquitos at bay and the relaxed atmosphere, along with comfortable temperatures, creates a true paradise. The Keys are renowned for excellent restaurants, eco-tourism, wildlife, live music and world-class fishing. This suggested itinerary will take you through the best that the Keys have to offer while traveling and relaxing on your private yacht.

Check out our Florida & The Keys Yacht Charter Specials

Embark in Miami and head for Key Largo (3 hours).

Have dinner at Skipper’s Dockside, a classic Keys outdoor dining experience. Enjoy local snapper and Key Lime pie as you become acquainted with the atmosphere of the Keys. Take in the sunset and the steel drum band and be transported into your vacation.

Enjoy the afternoon exploring John Pennekamp Coral Reef State Park , the first undersea park in the U.S.

Explore the extensive coral reefs, beautiful tropical fish and occasional sea turtle. The park’s crystal-clear waters are enjoyed by novice snorkelers and experienced divers, alike. On land, Pennekamp offers stunning beaches and boardwalk trails among the sprawling mangrove forest.

Pennekamp State Park

In the early evening, depart for Islamorada (2 hours) and drop anchor for dinner at Upper Matecumbe Key. Bask in the ambiance and sample gourmet fare at the Cheeca Lodge and Spa , a famous favorite of President George H.W. Bush while his family ran fishing tournaments in the Keys. Use your yacht’s tender to arrive in style at the Lodge’s dock, the longest in the Keys.

Islamorada is a series of islands and is known as the “fishing capital of the world.”

The islands are a destination for elite and casual fishing, specifically famous for the unique sport of bonefishing. Enjoy a day of fishing or a round of golf at the Cheeca. In the evening, head for beautiful outdoor dinner at Morada Bay and their famous fresh stone crab and calamari. Morada Bay is the best al fresco dining in Islamorada and is located on a bayside beach with iconic sunsets and local live music. This is also the place to be for the best full moon party in the Keys.

Islamorada’s ecotourism

Many of Islamorada’s islands are uninhabited, which makes for incredible ecotourism. We recommend spending the morning using your yacht’s tender to travel the winding canals and explore the various islands of pelicans, frigate birds and iguanas.

If you’re traveling with children, the Theater of the Sea is a famous destination for swimming with the dolphins and interacting with local sea life. Have an adventurous afternoon jet skiing then head to Pierre’s restaurant for dinner, the finest dining in the Keys. Enjoy the local catch of the day, fine wine and a Cuban cigar on the balcony at sunset.

As you head down the Keys (2 hours), spend the day at Bahia Honda State Park , one of the most beautiful beaches in North America.

A true island paradise, Bahia Honda has crystal-blue waters and soft, white sand. There are coral reefs to explore and this is the place to use the toys available on your yacht. Relax and take in the view from deck as you head for an evening at Hawk’s Cay Resort on Duck Key. This family-friendly, yet elegant, resort has many dining options and bustling nightlife.

Head to Key West, the cultural center of the Florida Keys.

There are countless dining and shopping options on Key West. Take a trolley tour  of the island and explore Hemingway’s house (with the famous Hemingway cats), the lighthouse, and have a wonderful dinner on Duval Street. Experience local flavor at the  Blue Heaven restaurant with its sand floors and Key West’s famous feral chickens clucking about.

Quick doses of joy can be had at the Key West Butterfly and Nature Conservatory. Walk among hundreds of “flowers of the sky”, tropical plants, and their celebrity flamingos, Rhett and Scarlett.

Enjoy the evening in the southernmost part of the continental US and catch a glimpse of the elusive “green flash” at the nightly sunset festival in Mallory Square .

Head back to Miami, enjoying the luxuries of the yacht along the way.

Take in the tranquility of the aquamarine seas as you end your beautiful vacation in the Keys.

Disembark in Miami.

Meet Sarah Nottage, our Florida Keys Expert

Charter Manager, Sarah Nottage, is also Carol Kent Yacht Charter International’s expert on the Florida Keys. Lucky Sarah has traveled to the Keys since she was a child and has deep local knowledge of this beautiful part of the world.

You can learn more about Sarah HERE. To find out all about all things about Florida Keys yacht vacations, you can contact Sarah by email or call +1 781 631 1800.

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Florida Keys

3-Hour Cruise

Depart Miami to Key Largo, AKA the Diving Capital of the World, and an ideal location for water sports as one can kayak through the mangroves or jet ski along the coast. Also, no trip to Key Largo is complete without a visit to Pennekamp Park, the most visited snorkel site in the Keys famous for its underwater Jesus Christ statue and surrounding reefs.

Marathon Key

Wake up to breakfast onboard, as you cruise to the heart of the Florida Keys, Marathon Key. Drop anchor to explore the turquoise waters by jet skis or by snorkel and swim with the dolphins before stepping ashore to visit Marathon City Marina, considered the prize-gem for those exploring the keys by yacht.

The Lower Keys

2-Hour Cruise

Welcome to the Lower Florida Keys, an archipelago of small islands lying in crystal blue waters within the Gulf of Mexico. Anchor in Big Pine Key and take the rest of the day to swim and snorkel within the region’s unique sites and natural attractions: coral reefs, sunken ships and 150+ species of fish.

Take an early morning cruise to the southernmost point of the USA, Key West. Spend the morning kayaking to the mangrove islands or visit the westernmost part of the Florida Keys: Dry Tortugas National Park. Snorkel through the archipelago’s undisturbed colorful coral reefs and explore 19-th century Fort Jefferson. In the afternoon, tender ashore to explore the Ernest Hemingway house and museum, and later enjoy a romantic dinner at Latitudes, located on Sunset Key, a private island only accessible by boat.

As you begin your cruise back to Miami, drop anchor in one of the Lower Keys: Duck Key. Spend the day exploring the warm gulf waters or tender ashore to the luxury Hawks Cay resort before enjoying evening drinks and a chef prepared meal aboard your yacht.

Halfway back to Miami drop anchor in Islamorada, featured in the Netflix series Bloodlines. Islamorada is known for hosting the largest fishing fleet per square mile in the world. Go ashore to the famous Cheeca Lodge & Resort where George H.W. Bush used to run a fishing tournament, which also features the longest pier in all of the Florida Keys. Make sure your chef prepares the catch of the day for a rewarding dinner on your yacht.

Biscayne Bay

For a last leisurely day on the water, cruise by Stiltsville and drop anchor off Key Biscayne. Drop the water toys into the water and enjoy a fun morning alongside other yachts in Biscayne Bay. Before you finish your charter, head up the Miami River and dock at Seaspice or Kiki on the River, two of Miami's hotspots for the in-crowd, for a final lunch or dinner in true Miami style.

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Florida Keys Itinerary

CHARTER IN FLORIDA KEYS

At the southernmost tip of the United States you’ll find Florida; home of oranges, Walt Disney World, and warm climates. Past throngs of tourists and citric associations lies Florida Keys, an archipelago off the coast of Florida where the weather is more tropical and the atmosphere decidedly different than it’s more popular mainland sibling. For yachters, another layer of the keys is opened up as this coral cay features some of the best diving in the Atlantic with an abundance of ship wrecks to explore and marine life to be fascinated by. In the north you’ll find John Pennekamp Coral Reef State Park in Key Largo which features a replica of Christ of the Abyss. Meanwhile, down south in Islamorada cast your line in the sport fishing capital of the world. With the motto “One Human Family”, in the southernmost point of this southernmost tip, Key West, you’ll encounter a welcoming, warm haven of people and life.

MIAMI BEACH MARINA & PUMPKIN KEY

Windley key, caesar creek channel, dinner key marina, miami beach marina, day 1 — miami beach marina & pumpkin key.

Embark the yacht at the Miami Beach Marina in South Beach, Miami. The crew will welcome you with a refreshing cocktail as you settle onboard thus with a drink in hand, head south to Biscayne Bay National Park. Dolphin sightings are abundant so keep your eyes peeled for a postcard perfect moment of dolphins leaping across the Keys sunset as you anchor off at Pumpkin Key.

DAY 2 — KEY LARGO

Home to some of the best diving in North America, strap on your scuba diving gear at John Pennekamp State Park and dive in to see the statue of Christ of the Abyss or the mesmerizing vibrancy of the coral reef. In the evening anchor off at Rodriguez Key and take a tender to Key Largo. From here a taxi or Uber ride to The Fish House restaurant will satisfy not only your hunger but your taste buds as it is one of the best seafood restaurants in the Keys. 02

DAY 3 — WINDLEY KEY

The diversity of coral reefs guarantees that you will never tire of visiting yet another. So don your scuba attire and visit one of the many reefs including: Molasses Reef, Pickles Reef, Conch Reef, and Davis Reef. After you resurface, make way for the marina in Windley Key. One of the more lively marinas in the Keys, enjoy the beaches, restaurant and boutiques by day and the animated bars and reggae music by night.

DAY 4 — DUCK KEY

True to its name Duck key is shaped like an upside down duck head. Ideal for watersports, take out your water skis, paddle boards and snorkeling gear for a day of fun in the sun. If you’re feeling less energetic, lounge on board or at the one the areas stunning beaches.

DAY 5 — TAVERNIER

Make way for Tavernier, where the yacht will drop the anchor for the night. While en route, make a snorkeling pit stop south of the Lower Matecumbe Key, facing the Caloosa Cove Marina.

DAY 6 — CAESAR CREEK CHANNEL

This channel has a colorful history as it used to be frequented by rum runners, drug smugglers and importers of illegal immigrants. Today it makes for an excellent snorkeling destination. If you’ve had your fill of snorkeling, enjoy a day of lounging on the sundeck admiring the crystalline waters.

DAY 7 — DINNER KEY MARINA

Cruise alongside Elliott Key and through the Biscayne Channel to enter into Biscayne Bay. Anchoring here for the evening will allow you to spend a final afternoon enjoying the yacht’s water toys. On your last night enjoy an alfresco dinner complete with a plate of oysters and conch fritters.

DAY 8 — MIAMI BEACH MARINA

Return to Miami Beach Marina to disembark.

LUXURY YACHTS AVAILABLE FOR CHARTER IN Florida

Little Castle

$19,000/wk 60.01ft /18.29m 4 Guests 2 Cabins 2 Crew

Cat And The Fiddle

$23,000/wk 62.01ft /18.9m 6 Guests 3 Cabins 2 Crew

$17,500/wk 63.98ft /19.5m 6 Guests 3 Cabins 2 Crew

$21,000/wk 64.01ft /19.51m 6 Guests 3 Cabins 1 Crew

Victoria 68

$15,000/wk 68ft /20.73m 6 Guests 3 Cabins 2 Crew

$32,000/wk 70ft /21.34m 6 Guests 4 Cabins 2 Crew

$20,000/wk 70.01ft /21.34m 6 Guests 3 Cabins 3 Crew

$18,000/wk 69.98ft /21.33m 6 Guests 3 Cabins 2 Crew

$35,000/wk 72ft /21.95m 6 Guests 3 Cabins Crew

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Florida Keys - 7 Day Yacht Charter Itinerary

Read the full Florida Charter Guide .

Embark in South Beach, get settled in and head out to Coconut Grove. Coconut Grove, Florida has been dubbed a “village with a rhythm all its own." Coconut Grove’s variety and originality are reflected in the dining choices offered by its eateries and in the jazz, salsa and reggae heard in its funky neighborhood bars. The waterfront parks of Coconut Grove, Florida offer some of the best vantage points for watching manatees and sailboats, while specialty Coconut Grove stores sell an exhilarating range of merchandise.

Today you are off to Key Largo. Kay Largo is at the top of the Florida Keys island chain and boasts natural wonders plus friendly locals who are ready to help you enjoy them. You could arrange an eco-tour or just stroll around checking out the beautiful parks and beaches or one of the numerous local art galleries.

Today you are off to Little Palm Island on Little Torch Key. This award winning tiny but luxurious resort is a 5 star couple’s haven. Dockage starts at $350 per night. Peter will need to book in advance.

Today you are off to Sunset Key or Stock Island. Sunset Key is a Private Island. The Westin Hotel has a great marina which is a favorite for yachts owners and charterers. At Stock Island you could visit the Botanical Gardens or for something more chilled out visit the Hogfish Bar and Grill. They claim their establishment allows guest to “Step back in time and experience the way the Florida Keys used to be – fresh seafood, strong drinks, panoramic waterfront views, outdoor dining and plenty of local characters”. Tucked away in Safe Harbor, Stock Island, the Hogfish Bar and Grill is a true "locals” spot that avoids the pretension and hype of more touristy areas.

Today you could be off to the Dry Tortugas. Almost 70 miles (112.9 km) west of Key West lies a cluster of seven islands, composed of coral reefs and sand, called the Dry Tortugas. Along with the surrounding shoals and waters, they make up Dry Tortugas National Park. The area is known for its famous bird and marine life and its legends of pirates and sunken gold. Fort Jefferson, one of the largest coastal forts ever built, is a central feature.

Day 6 & 7

Key West – You can either use the yacht as a base or book at the A&B Marina. Hang out and explore Key West or do some day trips to the surrounding Keys, returning to the A&B Marina in the evening.

Enjoy your last morning on board disembarking at 12 noon for your flight home.

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Florida Keys Itinerary

Charter yachts sample itinerary.

Please see below a Sample Miami to Key West, Florida Keys Itinerary. This itinerary shows highlights of attractions and activities available on your yacht charter. You may customize your trip to match your preferences. Contact Us for personal service and knowledge of this charter itinerary.

Florida Keys Sample Itinerary

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7-Night Itinerary Florida Keys | Songs In The Sails- Yacht Charter Vacation

Embark on a Magical Yacht Charter Journey with Songs in the Sails Yacht Charters: A Week-Long Harmony in the Florida Keys

Day 1: Biscayne Bay & South Beach – Prelude to Elegance Start your musical yacht charter adventure by arriving in Florida and stepping onto your opulent yacht at South Beach. Cruise through Biscayne Bay, where melodies meet luxury, as you admire the residences of the affluent. The day crescendos with a dock at South Beach, offering a taste of the vibrant Miami nightlife.

Day 2: Head to the Florida Keys – Sailing to Serenity Revel in water sports as you sail south towards the Florida Keys, recovering from the previous night’s festivities with a symphony of aquatic delights.

Day 3: Key Largo – Submerged Melodies and Coastal Charms Dive into Key Largo’s underwater wonders, where Songs in the Sails Yacht Charters invites you to explore the mesmerizing John Pennekamp Coral Reef State Park. Above water, discover the coastal charm and attractions that make Key Largo a harmonious stop on your itinerary.

Day 4: Key West – Cultural Crescendo at the Southernmost Point Arrive in Key West and immerse yourself in its unique cultural notes. Let the day’s activities compose a vibrant melody, and as the sun sets, experience the famous Sunset Celebrations at Mallory Dock—a crescendo to a perfect Key West day.

Day 5: Marqueses Keys – Western Waters and Sunset Sonatas Head west to the uninhabited Marqueses Keys, where the rhythm of water sports meets the breathtaking symphony of a Florida Keys sunset.

Day 6: Little Torch Key – Eastward Encore at Exclusive Oasis Return east, making melodic stops at smaller Keys like Little Torch Key. Indulge in an exquisite dinner at the exclusive Little Palm Island Resort and Spa—an enchanting encore to your musical yacht charter.

Day 7: Miami – Brunch Finale and Cherished Memories Conclude your week-long yacht charter with a delightful brunch on board, savoring the culinary crescendo crafted by your personal chef. As you return to Miami, cherish the memories of your Florida Keys adventure—a harmonious finale to a week filled with Songs in the Sails.

Come Sail Away with Songs In The Sails Yacht Charters. We offer crewed yacht charters all over the world, in the Caribbean and Mediterranean. Let us help you plan your next vacation!

Call us today at 706-901-7525 or email us at [email protected]

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• Florida Keys Itinerary

Florida Keys Yacht Itinerary

Things to Do From a Luxury Yacht in the Florida Keys

Florida keys itinerary day 1.

There is no better place to be in the United States than the Florida Keys. This beautiful chain of islands connects the US to the sunny Caribbean lifestyle.

Board your private charter at Galleon Marina, Key West or one of the other marinas in the Keys. Then, get ready to set sail! Get all set up on the boat and spend some time exploring the island. Visit the old house of Ernest Hemingway and enjoy dinner in the world famous Duvaal district. 

After enjoying an evening in Key West, wake up on the water and enjoy a freshly prepared breakfast.  As your charter pulls out to sea, soak in the beautiful scenery and sun. 

After a day of snorkeling and diving, enjoy a day of pampering. Schedule a tee time at one of many courses in the Keys. And if golfing is not your game, schedule a personal massage on the deck of your yacht.

A day does not get more relaxing than this! Finally, enjoy a sunset dinner on the boat with fresh caught fish and a bottle of white wine.

Spend your 4th day getting a little sporty. The Florida Keys are home to some of the best sport fishing in the world. And if fishing is not your style, grab a jet ski! Jet skis are a great way to spend a morning and have an exhilarating experience.

Spend your morning drinking freshly brewed coffee on the upper deck. Our chef will make your favorite pancakes while you enjoy the gorgeous views.

The Florida Keys are full of wildlife, both above and below the sea. So, spend the afternoon of your 5th day swimming with dolphins ! Dolphins are a staple of the Keys and swimming with them offers an unforgettable experience.

The 6th day of your charter will offer a story to tell for years to come. Come face to face with sharks! You will be cage diving with Tiger Sharks, Bull Sharks, Hammerheads, and more!

On your final day, the yacht will return to the Marina. Spend your last evening wandering the shops and restaurants of Key West. And enjoy your final evening in paradise.

Yacht Around the Florida Keys to See where the US meets the tropical sea.

If a week like this in the florida keys sounds like bliss, we can help. chat with the h2o luxury yachts team today to start planning your tropical getaway to the florida keys today. to learn more about the keys, click here . .

The Florida Keys

The Florida Keys sits along the third largest barrier reef in the world providing miles of pristine protected coral reefs teeming with colorful tropical fish. Dozens of uninhabited keys fringed by white sand beaches are ranked some of the best places in the U.S. for star gazing. Key West is only a three-hour drive from Miami on the Overseas Highway, rated one of the top scenic drives in America, or a direct flight via several major US airlines. Come explore one of the best kept secrets in America and sail the Florida Keys.

Dive into our unique itinerary destinations by exploring our interactive Florida Keys map.

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To view our florida keys destinations.

Welcome to the Southernmost City. Immerse yourself in the culture of the Florida Keys by setting off from Key West into beautiful tropical sailing grounds. Within a short sail from the marina lies several protected reef sanctuaries perfect for a day of snorkeling followed by dolphin watching and those famous southernmost island sunsets.

Things to do: marinas, food, fuel, provision, paddleboard, kayak

Stock Island

Our Key West base provides a unique starting point to set off into beautiful tropical sailing grounds with no passport required. Our vessels are located at resort marinas with access to resort amenities such as the pools, shopping, dining, and resort shuttles to downtown Key West. After you have enjoyed a relaxing start to your vacation you can easily set off on your easterly or westerly Florida Keys itinerary.

Things to do: marina, food, fuel, provision, paddleboard, kayak

Marquesas & Boca Grande

Spend a day anchored at the beaches of Boca Grande then head to the wild & isolated Marquesas which offers three beaches to swim & explore, and a night anchored under the stars in utter solitude.

Things to do: overnight anchorage, beach, paddleboard, kayak, stargazing

Dry Tortugas National Park

70 miles from Key West lies the Dry Tortugas National Park and magnificent Fort Jefferson. Expect the unexpected when you anchor up next to the largest brick masonry structure in the Western hemisphere set on an island in the middle of the Straits of Florida. The archipelago’s coral reefs are the least disturbed & healthiest in the US and the park is teaming with life. Get up close and personal with abundant sea life, playful dolphins, curious sea turtles and dozens of species of birds. The park is accessed only by one daily ferry, sea plane service or private vessel. The jewel in the crown is Loggerhead Key, the largest key in this isolated island group, accessible only by private vessels.

Things to do: snorkel, beach, paddleboard, kayaks, birding, stargazing, camping, historic tour

The Lower Keys

The Florida Keys sit along the third largest barrier reef in the world with miles of pristine protected coral reefs teaming with colorful tropical fish. One of our favorite snorkel sites in the Lower Florida Keys is Looe Key National Marine Sanctuary. Anchor in the Newfound Harbor for the evening or take a slip at Little Palm Island for a luxury experience.

Things to do: luxury marina, overnight anchorage, food, kayak

Bahia Honda

Known for iconic Florida scenery, the historic Flagler Trestle Train Bridge, palm-line beaches, clear waters and fun snorkeling make this a favorite destination for visitors to the Florida Keys. Beaches are rare in the Florida Keys, owing to the reef, but the sands at the 300-acree Bahia Honda State Park are some of the best.

Things to do: snorkel, kayak, beach, concessions

Take your time sailing past the iconic seven-mile bridge and make a stop at Sombrero Key for snorkeling at the historic lighthouse. Then set sail for the first -class Hawks Cay Resort at Duck Key for fine dining and a night at the marina.

Things to do: marina, snorkel, food, fuel, provision, ice, land activities

In the heart of the keys you will find this “village of islands.” Anchor off Indian Key, a Historic State Park open to the public and rich with history and nature activities. This island is only accessible by boat. Enjoy beautiful snorkeling at Hens & Chickens Reef or Alligator Reef Lighthouse.

Things to do: overnight anchorage, snorkeling, swimming, paddleboard, kayaking, hiking

Key Largo is the gateway to the Keys and home to the first underwater state park in the United States. John Pennicamp State Park, which encompasses 70 nautical square miles of protected reef. Whether you are heading to Key West from Miami or this is the last stop of your itinerary before heading back to Key West it is the perfect stop to take a slip for the night. Enjoy a nice land-based meal and activities before continuing on your Florida Keys journey.

Things to do: marina, snorkeling, land activities

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

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