Private Charters

Cast off with Danger Charters for the best Key West private charters. Sail away aboard one of our custom-built 65ft sailing schooners on the adventure of a lifetime.


Go sailing in Key West and explore the turquoise and emerald waters of one of the world’s most renowned boating destinations on your own Key West private sailing charter from Danger Charters. Our expert captains and crews can help you and your guests make the memories of a lifetime aboard one of the beautiful sailing vessels that have made Danger Charters a local legend – custom-built 65-foot replicas of the classic 19th-century Florida Keys skipjack schooner. Book a private Key West sailing charter from Danger Charters and learn why Key West is a magnet destination for sailors from the USA and around the world.

Key West earns its reputation as a sailor’s delight with pleasant weather most days of the year, gentle breezes, and awesome scenery in the pristine natural setting of the Florida Keys Backcountry. Now, Danger Charters invites you to come aboard a Key West private sailing charter and live the dream of cruising tropical waters on a graceful tall ship. You can glide before the warm wind under creaking rigging and billowing white sails to experience the sublime pleasure of looking out over blue water from the deck of a fine sailing vessel.

Danger Charters – Top-Rated Key West Sailing Charters
Danger Charters has earned top ratings and accolades on the Internet and in the island community for the grace of our sailing ships and the customer service orientation of our captains and crews. Sail away on one of America’s best sunset cruises and toast family and friends with a glass of fine wine as the sky fills with color. Venture into the clear waters of the Florida Keys National Marine Sanctuary for a day of eco-touring and watersports fun. Or let Danger Charters help you put together a custom charter that will be the highlight of your Key West visit. When you book a private charter with us, your group will be treated to the ultimate sailing experience.

Book your Danger Charters Key West private sailing charter now and let’s sail together

Private Wind & Wine Sunset Sail for up to 30 Guests

Leave Key West in the cool of the early evening and have our top-rated Wind & Wine Sunset Sail all to yourself. Get an unobstructed view of the amazing Key West sunset while enjoying a glass of fine wine or premium beer and some delicious hors d’oeuvres.

A private charter sunset cruise is an unforgettable way to celebrate a honeymoon, anniversary, family reunion, career or business milestone, or any other very special occasion. And be sure to ask us here at Danger Charters if you have something in mind for a custom-designed trip or celebration at sea.

Private Charter Sail, Snorkel & Kayak for up to 20 guests

Go on sailing safari into the amazing Key West Backcountry where shallow, gin-clear water over white sand and seagrass flats, winding coral-lined channels, and lush green mangrove islands make a beautiful marine playground. Swim, snorkel, kayak, get some sun, and enjoy lunch and beverages on deck on a Private Charter Sail, Snorkel, and Kayak Trip.

With a sleek, graceful schooner reserved solely for the use of your group, you can enjoy watersports, play in the sun on pristine sandbars, or simply relax with a beer or glass of wine as the boat heels before the wind and the bow cuts the sparkling water. Go out for a half-day trip or ask about a full day charter if you like – Nothing compares to gliding on the peaceful waters of the Key West Backcountry under a cloud of canvas with the breeze in your face and incredible scenery all around.

  • Private sailing charters from Key West’s favorite sailing fleet
  • Top-rated by Coastal Living Magazine and Trip Advisor
  • Elegant 65ft skipjack sailing schooners
  • Family watersports fun or sophisticated sunset happy hour sails
  • Water, soft drinks, wine, beer, snacks or hors d’oeuvres included
  • Eight fine wines served on the Private Key West Sunset Sail
  • Custom-designed cruises or celebrations available on request


Current Specials

Use code ALLABOARD and save 10% off all day trips during January when you book online! (Excludes all Private Charters)

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