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Charleston Sailboat Charters

Sailing is more than just wind hitting cloth – it’s a dream with no boundaries. Experience an activity that is over 3,000 years old and captures the awe and passion of so many people. Enjoy yourself and relax on the bow as the ocean breeze propels the sailboat through gentle rolling waves – or take the wheel and feel the currents running underneath the keel.

Captain Jay Keeney turned his passion for being on the water into his career, and he was made for it. The Mental Heeling is a beautiful 1988 30ft Catalina MKII sailboat with ample deck space for you to move around. This vessel can carry groups of up to 6 people with seating below that includes a saloon (dining area) and a head (toilet). Options for this party vessel are plentiful! You can choose to embark on the “Sunset Sail” to enjoy gorgeous views, or if you’re more of the adventurous type the “Learn to Sail” charter, where Captain Keeney teaches you and your friends the basics of sailing, terminology, tactics, charting, and the rules of the water! One thing is for certain, every charter is customized to YOU! As we like to say, “You’re the captain, we’re the guides!”

Why the Sail Knot
843.732.6266

Harborage at Ashley River Marina • 33 Lockwood Drive • Charleston, SC

Sailing is more than just wind hitting cloth – it’s a dream with no boundaries. Experience an activity that is over 3,000 years old and captures the awe and passion of so many people. Enjoy yourself and relax on the bow as the ocean breeze propels the sailboat through gentle rolling waves – or take the wheel and feel the currents running underneath the keel.

Captain Jay Keeney turned his passion for being on the water into his career, and he was made for it. The Mental Heeling is a beautiful 1988 30ft Catalina MKII sailboat with ample deck space for you to move around. This vessel can carry groups of up to 6 people with seating below that includes a saloon (dining area) and a head (toilet). Options for this party vessel are plentiful! You can choose to embark on the “Sunset Sail” to enjoy gorgeous views, or if you’re more of the adventurous type the “Learn to Sail” charter, where Captain Keeney teaches you and your friends the basics of sailing, terminology, tactics, charting, and the rules of the water! One thing is for certain, every charter is customized to YOU! As we like to say, “You’re the captain, we’re the guides!”

  • Sunset Tours
  • History & Ghost Stories
  • Brunch
  • Sunrise
  • Private Couples Cruises
  • Unique Engagements
  • Sailing Lessons
  • Racing
  • Corporate Events
  • Fireworks Cruises