Florida Keys Yacht Charter

Florida Keys Yacht Charter Guide

A spectacular archipelago of over a thousand palm-fringed islands, Florida Keys are a natural paradise for exquisite sailing vacations. Boasting breathtaking coral reefs, azure waters, and gentle breezes, this is one of the world’s most captivating sailing destinations, making a Florida Keys yacht charter an adventure to remember.

From stunning beaches and snorkeling sites to abandoned sea fortresses, mysterious shipwrecks, and iconic bars once frequented by Ernest Hemingway himself, each Florida Keys island holds its own distinct charm and allure.

Reasons to Charter a Yacht in the Florida Keys

Home to bohemian artists, shipwrights of New England, wealthy merchants, and Cuban rum smugglers at one time, the Florida Keys still possess an atmosphere of irreverence and laidback island living – along with exclusive high-end resorts and premier marinas hosting luxury yachts.

Whether it’s enjoying a Rum Runner during the happy hour at Sloppy Joe’s or relaxing at the elite Palm Island resort, Florida Keys has got it all. Add incredible scenery, rich marine life, colorful reefs and fish, amazing beaches, and an array of excellent diving and snorkeling sites, and it’s no wonder why Florida Keys yacht charter experiences have few rivals.

Below, we share our top three reasons to charter a yacht in the Florida Keys:

Gorgeous Scenery

Pristine palm-dotted beaches, powdery white sand, and crystal-clear waters shimmering in hues of turquoise and aquamarine are Florida Keys’ signature scenery worthy of a postcard.

Tropical islands, the magical underwater world of coral reefs, and remote nature preserves matching the allure of the Everglades National Park set Florida Keys apart as a truly remarkable sailing destination boasting dreamy landscapes resembling Tahiti and the Caribbean.

Scuba Diving Heaven

Thanks to its proximity to the Florida Reef and numerous shipwreck sites, the Keys are a treasure chest for scuba divers.

From thrilling deep-sea diving to exploring artificial reefs of sunken warships to family fun snorkeling above the corals, no Florida Keys sailing vacation would be complete without experiencing its enchanting riches under the sea.

Colorful History

The Florida Keys has a unique cultural heritage stamped with Caribbean and Cuban influences, a colorful history of pirates, salvagers, and Prohibition-era smugglers, and the legacy of Ernest Hemingway, giving the islands an artsy, bohemian aura.

Whether it's visiting the famous novelist’s favorite watering holes in Key West or exploring abandoned ghost towns and sea fortresses dating back to the Civil War years, Florida Keys offer a glimpse into a different world of nostalgic Americana.

Featured Florida Keys Yacht Charter Destinations

While it’s easy to cruise along the Florida Keys chain, taking in the views and stepping ashore to explore the island lifestyle improvising the route as you go along, several Keys stand out as exceptional.

Below, we list some of the most iconic destinations for Florida Keys yacht charters:

Key West

Known for its vibrant atmosphere, historical significance, and artistic community, Key West has a character of its own. Sunset celebrations at Mallory Square, a pilgrimage to the Ernest Hemingway Home and Museum, and a night out on Duval Street are par for the course in Key West.

Unlike the glitzy, high-energy Miami Beach, Key West's South Beach and Higgs Beach are more laidback boasting soft white sands and crystal-clear waters perfect for snorkeling.

The island’s proximity to both the Gulf of Mexico and the Atlantic Ocean means excellent fishing opportunities.

Key West is also the end point of the Atlantic Intracoastal Waterway, a 1000-mile sailing route connecting New England and Florida famous for its beautiful scenery and spots few land-bound tourists get to see.

Marathon Key

Situated in the middle of the Keys, Marathon is perfect for nature lovers and water enthusiasts. The Dolphin Research Center, beautiful snorkeling sites, and stunning views from the Seven Mile Bridge are ideal for family fun, while adventure seekers will enjoy fishing for mahi-mahi and tuna.

Key Largo

Located just eighteen miles from the glittering Miami skyline and Biscayne Bay and home to the John Pennekamp Coral Reef State Park, Key Largo is a natural paradise for scuba divers. Located near the Florida Reef – the third-largest barrier reef in the world - Key Largo is a gateway into an extraordinary world of underwater wonders.

Natural coral and fish diversity aside, experienced divers flock to Key Largo to explore the shipwreck of USS Spiegel Grove, a warship purposely scuttled just off the coast of the island. Comparable to the world’s largest artificial reef, the USS Oriskany warship sunk in the Gulf of Mexico just off the coast of Pensacola, the USS Spiegel Grove shipwreck is a treasure trove for dedicated divers.

In addition to diving, snorkeling, and glass-bottom boat tours, Key Largo is known for its relaxed atmosphere and casual charm, along with cozy local bars and great seafood cuisine.

Indian Key

A bustling community in the early 1800s, Indian Key served as a thriving hub for shipwreck salvaging. During that period, ships would often run aground on the reefs around the island, and ingenious salvagers would come to the rescue of the crews and passengers – and claim the wrecked vessels for themselves.

Now, the island is uninhabited, lending it an eerie ghost town feel. History buffs will appreciate the opportunity to explore the ruins of the old settlement.

Accessible by boat or kayak only, Indian Key offers seclusion and tranquility, and its shallow waters, corals, and rich marine wildlife are ideal for snorkeling.

Plantation Key

Beloved by luxury yacht guests seeking authentic experiences, Plantation Key has a laidback atmosphere and is largely untouched by the hustle and bustle of the more tourist-saturated spots in the Florida Keys.

With easy access to Key Largo and Islamorada, Plantation Key is a great launchpad for water-based activities from kayaking and paddleboarding to scuba diving and fishing. The island’s Anne’s Beach is a popular highlight boasting shallow blue waters and a boardwalk stretching over seagrass beds.

Windley Key

A small but beautiful island with a charming marina, Windley Key is best known for its Fossil Reef Geological State Park, showcasing an ancient coral reef that dates back over sixty million years.

For nature lovers, Windley Key offers a network of scenic hiking trails, and its peaceful ambience provides a welcome break.

Bahia Honda Key

Home to the Bahia Honda State Park, Bahia Honda Key is renowned for its picturesque white-sand beaches, clear blue waters, and opportunities for snorkeling, hiking, and wildlife watching.

A virtually uninhabited tropical paradise, Bahia Honda is a perfect getaway in unspoiled nature and spectacular sunset views over the Gulf of Mexico.

Dry Tortugas

The westernmost island chain of the Florida Keys, Dry Tortugas hides unique treasures above and below the sea.

The Seven Dry Tortugas islands are home to the most pristine coral reefs in the region, abundant marine life, and sunken shipwrecks.

The island’s natural beauty aside, its key feature is the historic Fort Jefferson, a colossal fortress that served as a prison during the Civil War years.

When to Visit: Florida Keys Weather

Florida Keys is a year-round sailing destination thanks to its tropical climate. The best weather is between March and May, while the winter months and early spring are favored by sailing yacht enthusiasts due to stronger winds.

The only period to avoid is June through to November -hurricane season in the Atlantic Ocean.

The Cost of a Florida Keys Yacht Rentals

Yacht rentals in the Florida Keys have different price points depending on the charter boat’s type, size, and amenities on board.

A motor yacht with the capacity for 2-6 guests can cost between $25,000 - $45,000 per week. For charter yachts with larger capacity, expect to spend $60,000 and upward, whereas a luxury yacht charter with a professional crew (unlike bareboat charter) can cost anywhere between $100,000 - $200,000 per week or more.

Find Florida Yacht Charters That Offer the Right Features

Choosing a private yacht for that unforgettable sailing holiday is all about personal preferences.

Whether you hope to set sail and relax on the deck, jump into the water for action and adventure, or entertain a group of guests, it’s important to look for yacht charters with specific features to cater to your individual needs.

Here are some of the key luxury yacht features to consider:

Water Toys

Florida Keys is a paradise for swimming, snorkeling, diving, kayaking, and just about any other water sport. If you’re looking to experience the best of those azure blue waters, charter a yacht with jet skis, paddleboards, kayaks, foils, or snorkeling equipment on board.

Spacious Decks and Cabins

Comfortable, well-appointed cabins and spacious decks are a must on a luxury yacht, especially if you’re embarking on a longer voyage and expect comfort and easy access to the water.

Jacuzzi

A hot tub or a jacuzzi on deck enhances the sailing experience, especially on those breezy Florida Keys evenings when enjoying a sunset with a cocktail in hand.