Welcome Aboard!

If you’re seeking an extraordinary experience, Key West Sailing Academy & Charter is definitely the right choice for you. Our aim is to provide the discerning client an elegant & exclusive boutique experience through our personalized service, unique style, and outstanding gourmet dining aboard exceptionally comfortable and well appointed vessels.


Our vessels are docked at Key West Harbor Marina Yacht Club, arguably the finest marina facility in the Florida Keys. Our guests and students have complimentary use of all the club’s amenities, including a fine dining restaurant, sunset bar, pool, private beach and gym. The crystal clear, warm, tropical waters off Key West make for the perfect sailing environment year round. Fantastic diving, snorkeling, fishing, and miles of white sand rimmed islets and islands offer idyllic day sails and magical overnight anchorages. And of course there’s historic Key West, with all the nightlife, shopping and restaurants our beautiful town has to offer when you’re at port. We add the perfect touch, consistently delivering the highest standards to our clientele by drawing on our years of experience in luxury hospitality domestically & internationally. No other charter company or sailing school in Key West can deliver this luxury package like we can.

Sailing Academy


We offer fully private learning experiences for the discerning client through our American Sailing Association certification programs. The tropical, clear waters around Key West make for the perfect sailing environment year round, with both inshore calm protected areas for the beginner to blue water offshore sailing for advanced courses. Obtaining a first-rate sailing education is an important step toward a lifetime of sailing enjoyment. The right choice in your instructor and the vessels you train on makes all the difference in the world. Whether your a beginner or seasoned sailor, we offer courses to meet all your needs. Visit our Sailing School page and take the next step

Private Sailboat Charter


Sunset Sail, Half Day, Full Day, Overnight Adventure or an Extended Sailing Vacation. Experience the magic of the Keys the way very few visitors do, on your own private sailing yacht. Whether you want to enjoy a perfect Key West sunset away from the crowds, spend the day snorkeling the reefs, fishing and combing the beach, or spend an intimate, perfect night under the stars anchored at a pristine deserted island. We'll make your time aboard the most memorable you'll spend in the Keys. Visit our Charters & Destinations pages to start your adventure.