Key West Private Charters

Best on Key West knows that your reasons for visiting the Keys vary, but nonetheless it’s always a special time for you, your loved one, your family and your friends. That’s why we offer private charters of some of our best boats that sail the Atlantic Ocean, Caribbean Sea and Gulf of Mexico.

Sailing in the Lap of Luxury

Whatever your reason for being in the Keys, we want to help make it special. We provide private charters for a plethora of events — just tell us what you want to do while you have full control of our boat. We can set up a day of watersport activities, head to the living reef for snorkeling, tour the backcountry, set sail across the waters, and end it all with a romantic sunset and moonlit cruise. We can even include kayaking and parasailing.

Our private charter cruises can be completely customized, including delicious food and beverages from our catering kitchen. All of our catamarans are equipped with satellite radio, and we can even arrange for a DJ or live music (like a steel drum percussionist or 5-piece band).

Best on Key West also lets you charter our boats for our pre-packaged cruises and activities. The Island Ting and Power Adventure packages are perfect for corporate teams, family reunions, bachelor/bachelorette parties, spring break parties, quinceañera bashes and more.

Make Your Day Special

From a romantic two-person getaway to a full-out party with up to 125 guests, we can accommodate your Key West adventure on our amazing catamarans. For larger groups, you’re able to charter multiple boats so you can include everyone in your island adventure.

We want to ensure you have the time of your life, so we work with you to make every detail perfect. We can customize a menu of hors d’oeuvres, lunch buffet or the whole works with our catering kitchen staff. A privately chartered boat is the perfect way to say your wedding vows, spend time with loved ones or reward your team for all their hard work.

Our Boats

All of our boats are licensed by the State of Florida to serve beer and wine. Our largest boat, the Marquesa, is fully licensed and stocked with a full liquor bar.


Our largest catamaran, the Marquesa is 69-feet long and can carry up to 125 passengers. We often sail her at lower capacities for a more intimate sailing experience. With more than 2,300-square-feet of deck space, there’s plenty of room for all of your guests. The Marquesa features two bathrooms, freshwater shower, and a “Stairway to the Sea” for easy water access.


The Cubed is one of the fastest sailing commercial vessels you’ll find anywhere. At 60-feet long and capacity to carry 65 passengers, there’s lots of room to relax in the sun or the shade. The Cubed features two bathrooms, a freshwater shower, and a “Stairway to the Sea” for easy water access.


One of our newer catamarans, the Flyer is able to carry 68 passengers. The boat is 60-feet long and has ample seating in the sun and shade. There are two bathrooms aboard and a freshwater shower, as well as easy access to the water via the “Stairway to the Sea.”


At 41-feet long, and with spacious decks, the Pelican can comfortably carry 20 passengers. This swift vessel features a bathroom and freshwater shower.

Appledore II

Available seasonally, the Appledore II is an 86-feet long windjammer. With a capacity of 49 passengers, there’s adequate room for seating and roaming about. The Appledore II is a 2-masted tall ship and features a bathroom.

Appledore V

Perhaps the cream of the crop, the Appledore V is a beautiful 2-masted schooner that sits at 65-feet long and seats 24 passengers. This safe and swift schooner previously sailed the Great Lakes before touring the Keys. The boat features a bathroom.