Destination Sailing Vacations


Harbor Sailboats is a proud partner with the Moorings, Sunsail and Footloose yacht charters offering sailing vacations of a lifetime. Take some stress out of the planing process by working with a team you know, and a team that knows you. When you book your trip, we will help coordinate boat choice, meal planing, water toys, flights and anything else related to your vacation.

Harbor Sailboats can now help plan your trip to the Caribbean, Far East, Indian Ocean, Mediterranean, South Pacific, United Kingdom, Asia, and of course here in North America. Our services are available at no additional cost and at times are offered specials not released to the general public.


Join us every spring for the annual Harbor Sailboats Club Flotilla in one of the tropical destinations. During these flotillas members will be skippering their own yachts and may choose to follow the loose float plan set by Harbor Sailboats or venture on their own. Again take some stress away knowing a Harbor Sailboats team member will be on the water helping with daily task and offering assistance to flotillas members.

This years flotilla will take place in May of 2017 in the British Virgin Islands. Contact for private yacht charters options or “per cabin” charters on the group boat skippered by a Harbor Sailboats USCG Captain.


Taken during the 2015 Flotilla at Sandy Cay