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. Most of our staff has traveled the world for sailing vacation so we can share a little knowledge on the best ways to do it!

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. The annual flotilla consistently brings together an average of 10 boats and 50 people for an unforgettable sailing vacation.

2019 Flotilla Location and Dates Announced!

Tahiti is booked! Join us April 5th-April 12th for a 7 day cruise along the French Polynesia Islands aboard a fleet of catamarans from 40-50 feet. Tahiti offers some of the most amazing views inside the protected reef system while also introducing longer and more challenging sails between islands. Contact Flotilla Leader Keenan Hirsh for pricing and details!


Photo Taken During the 2017 Flotilla In The BVI's