Sailing Vacations
Join us for a week long adventure staying aboard a
40ft-50ft cruising sailboat! Choose between two premium sailing locations: The Chesapeake Bay (offered May through September) or Abaco, Bahamas (offered November through April)
Perfect for families with children. Learn to sail as a family or group with a professional captain and have the boat to yourself each evening*. A fun, interactive, learning vacation that will have everyone involved and create lasting memories!
Chesapeake Bay
Chesapeake Family Sailing Adventure
The Chesapeake Bay has some breath-taking views and premiere sailing spots! We have a variety of destinations that are frequently visited during our charter itineraries including St Michaels, Annapolis, and more!
Weekend Adventure
Friday 4pm to Sunday at 4pm
Five Day Adventure
Monday Noon to Friday Noon
Boarding is at noon on Monday, arrive back at our base by noon on Friday.
Abacos, Bahamas
Bahamas Family Sailing Adventure
Embark as a family crew to sail and explore the Bahamian islands with an experienced Captain! This is a unique experience that enables the whole family to participate in the cruising lifestyle in one of the most popular sailing destinations in the world.
6 Day Adventure
Sunday afternoon to Friday afternoon
Cost: $9500
Includes lodging for up to 6 aboard, Drinking water, Breakfasts aboard & Captain for the duration of trip,
The Sailing Academy
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