Sailing Vacations
A learn-to-sail adventure that includes all ages for your family or friend group.
Abaco, Bahamas
Sailing Vacations in
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
Offered: February through April, 2026
Cost: $9500
Includes lodging for up to 6 aboard, adventure itinerary, drinking water, breakfasts aboard & Captain's instruction for the duration of trip.
It was the perfect blend of learning and having family fun. Captain Phin gave us an amazing personalized experience.
Annmarie S.
If you want to learn to sail this is the way to do it. Our family of 5 learned to sail in the Bahamas with Captain Jeff. It was hard work, rewarding and fun. He was patient, kind and thoughtful with our kids. On top of teaching us all how to sail we swam with the wild pigs, snorkeled in sunken ships, fed sting rays, and played on white sand beaches.
Tiffany E.
We had a wonderful time with The Sailing Academy in Green Turtle Cay, Bahamas. We not only learned the sailing basics from a great teacher (Captain Phin), but also really were really treated as family and got to experience lots of local fun and adventures. Local easts, walks through town during Junkanoo, spear fishing for lobsters and tasty fish, fed manta rays on the beach, sailed to a tiny island bar / restaurant with wild, swimming pigs and much more. We left with a new appreciation for the local culture and just how talented our captain was ranging from sailing / navigating, to the local adventures and great spirit and host.
Dan B.
It was the perfect blend of learning and having family fun. Captain Phin gave us an amazing personalized experience.
Annmarie S.
Chesapeake Bay, MD
Sailing Vacations in
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.
Offered: May through October
Weekend Adventure - $4900
Friday 1pm to Sunday at 4pm
3 Days, 2 Nights
Five Day Adventure - $7900
Monday 10a to Friday 4p
5 Days, 4 Nights
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I have some sailing experience; do I need to take ‘Sailing Basics’ before ‘ASA 101’?Have you trained on a sailboat with wheel steering, inboard engine, roller furling and know proper sheet winch techniques? All these skills are learned in our Sailing Basics course. These “big boat” skills are not covered in dinghy and small boat sailing courses. The Sailing Academy is unique in that we train on sailboats in the 26-30’ range with these features, and a working knowledge of such vessels is important prior to progressing to ASA 101. Please keep in mind, we only certify students who can perform all the required sailing skills confidently by the end of ASA 101. Since we do not automatically pass students, we recommend that beginners, or those new to larger keelboats start with Sailing Basics.
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What’s the weather policy?A smooth sea never made a skilled sailor! Unless conditions are extreme (ie: named storms), we do not reschedule courses. Our captains structure the schedule around the best forecasted conditions. Check the forecast and come prepared with appropriate gear.
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What is provided by The Sailing Academy?All scheduled classes include study materials, tests, life vests, classroom instruction, premium boats, top-notch instructors, and ASA certification fees.
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I'm coming from out of town, where should I stay?Contact our office about liveaboard options or stay at a local inn for a discounted rate. Places nearby include:
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What's the cancellation policy?Cancellations up to 7 days prior to your course can be rescheduled or refunded. Past this point, there are no refunds. If contacted within 7 days of your course, we will reschedule for a $100 fee. Cancellations or no-shows on the day of your course will not be rescheduled.