Private and Custom charters in the heart of Key West.

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Key West Sailing Adventures Video Brochure


Enjoy a Sailing Charter for your visit to Key West

Live the Life of an Island Sailor

Charter a sailboat in the Historic Seaport, downtown Key West The whole sailboat is yours to enjoy, sailing is included with all charter packages. We offer private and custom charters for up to 6 passengers. Sailing trips to the reef and beyond; Island hopping, Family and Romantic getaways, birthdays, anniversaries, engagements, weddings, 3 boat team building, bucket list.

We have federally documented sail vessels and USCG licensed captains who know the secret spots and qualified first mates who will outfit you with snorkel gear, swim with you and make sure you are comfortable. Families are our specialty. All sailboats are set up for local and long distance charters, with fully operating kitchenette, 2 cabins, 2 bathrooms with showers and a large main salon. To Book with a Visa, M/C, or Discover Call 305 304 4911 for Captain Albert or E Mail for questions and dates.

Charter Types to choose from or Mix and Match

1- Sailboat day charter up to 6 persons- Enjoy your own yacht; We do what you want when you want,suggestions a- 4 hour sail to the reef with snorkeling, up to 6 people gear included with captain, mate, fuel and wind- $585. b- 6 hour sail-wrap a sunset into your reef sail. Sail home with the spectacular Key West sunset to celebrate- $745 c- 2 hour sunset sail with fresh fruit and cheese - $345 2- Full nautical charter the whole boat is yours to spend quality time on; most people find 3 nights works out best but we will work with you on custom times. 3 night charter package includes sailing. A half day sail to the reef with snorkeling is the normal request but we will carry your wishes. These packages are suggestions only. All charters include sailing add more sailing or choose your time to go. Wildthing a 44’ Morgan sailboat is $475/night for 2 Moondance a 42’ Irwin sailboat is $475/night for 2 Obsession a 37’ O ‘Day sailboat is $375/night for 2 All vessels accommodate up to 4 in 2 cabins it is $45 per person per night over 2, young children for free. 6 will be considered for families, couches in main salon 3- Key West Sampler Charter- the name says it all, take in Key West and then sail off on the day of your choosing at noon for 24 hours with a captain, mate and all meals for a memorable adventure. Sailing to the barrier reef, lunch after a swim always tastes better. Then sail to an uninhabited island with a beach and a sandbar. Dinner served under the stars in a quiet lagoon. Usually 3 nights, 4 days. Based on 2 persons-$2200 add $300 per extra person 4- Overnight Excursions- A sailors delight- choose as many nights as you have time for, some folks go for a week end or a week. This is true relaxation. Every morning we ask what you would like to do and give you choices. Many great choices from the Atlantic Ocean side to the Gulf of Mexico ,$1400/night for 2 add $175 for each extra person/night 5- Sunset Weddings for up to 6 persons, just bring your license with have the rest at $1595.00 6- Wedding/Honeymoon Combo 2 nights, 3 days. Take the plunge and take a dip-Sail, snorkel, dine, beach, relax $2945

Video taken by guests on a Key West Sailing Adventure in 2011


Consider chartering one of our three sail-boats in Key West’s Historic Seaport for a truly memorable experience. We can accommodate up to 6 guests per boat. You can leave your car at home, Duval St is only 3 blocks way; while you wait for your charter rent a bicycle or walk into town. Watch the sunset at Mallory Square while local acts like "Dominique and his flying cats", fire-eaters, jugglers, and many others vie for your attention!

As the night arrives the music comes alive as only Key West can present. All this and much more only minutes away from our well-situated yachts three walking blocks from downtown Key West. This is a truly unique experience! If you can dream it we can sail it!

Since 1995, many have enjoyed designing their own private and custom charters or choosing one from our selection of charters; mix and match if you like. Family friendly, Mom, Dad & Kids help pull sails together and take the helm. Couples can enjoy the relaxed life style that is sailing. Also Corporations have chartered team-building outings with us for their employees; 2 or 3 boats sailing together, racing, snorkelling, exploring, and fishing. Weddings and honeymoons are popular to celebrate on a sail-boat with a Key West sunset in the background. We are well known for our Sailing Excursions. Let us take you on a sailing adventure with captain, mate and all meals. Explore the barrier reef; play on uninhabited beaches anchor in a quiet lagoon.

Why choose us? Great location! Great crew! Great times! Sail ho!

Please give us a call or send an email to the address below and we'll be in touch with you right away. As always, your privacy and security are of the highest priority.




201 William Street
Historic Seaport; E-Dock;
Slips: E-10, E-11, E-12
Key West, FL

Mailing Address:

PO Box 4165
Key West, FL


305-304-4911 or