Classic Live-Aboard Sailboat Experiences

Discover the beauty of the waters around Key West and the lower Keys in Florida aboard a choice of character-filled sailboats.

Reef sailing, fishing, snorkeling, or an overnight (or longer) excursion further afield… We offer a range of charter options that can be designed around your personal preferences. Share your trip with friends or family to celebrate a special occasion, or simply cruise the ocean to expand your horizons and meet with nature at its most splendid. Whether you want to take the helm and pull up our sails with the crew or just relax, our dedicated and professional team will ensure you have a fantastic and memorable experience on one of the world’s most beautiful ocean waterways.

Private Stay & Sail for up to 4 Passengers

• Overnight Stay Onboard (One or More Nights)

• Stay safely docked at the Perry Hotel & Marina, one of the most beautiful 5-Star Marinas in Key West with full use of the many amazing amenities.

• Fall Asleep to the Sound of Gentle Lapping Waves

• Options to Combine With Day Sail or Excursions

• Onboard Kitchen Facilities

• 2 comfortable Cabins with en-suite bathrooms

• Cozy salon

• Plenty of deck space for relaxing and suntanning