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.
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