Alumni Flotillas Schedule

Adventure awaits — but spots are limited! Don’t miss your chance to level up your sailing skills and create memories and friendships that will last a lifetime. These unique voyages only happen once a year — secure your spot before it sails away!
To reserve a full boat or a cabin for a future Alumni Flotilla, a $500 non-refundable deposit is required. A $2,500 down payment is due six months before departure to secure the boats and trip. The remaining balance must be paid 100 days before departure.
If you cancel a reserved cabin, the $500 deposit is forfeited and cannot be applied to other trips or activities.

May 28 - June 5, 2025

British Virgin Islands | 1 Alumni Boat | 4 Cabins | 0 Cabins Available | 0 Waitlisted
Join our first Outbound Sailing Alumni Flotilla Boat! You will be on an OS Alumni skippered and crewed boat sailing alongside our Adventure Learning program in the British Virgin Islands! With over 60 islands and cays to explore, each offering its unique charm and beauty, the BVI provide endless opportunities for adventure. Iconic spots like the Baths on Virgin Gorda, the famous Willy T floating bar, and the tranquil anchorages at Jost Van Dyke ensure that your sailing itinerary will be filled with breathtaking sights and unforgettable experiences.
British Virgin Islands
St. Vincent

June 2026

Greece | 3 Alumni Boats | 10 Cabins | 10 Cabins Available | 0 Waitlisted
The Greek Islands offer a spectacular destination for bareboat chartering, combining stunning natural beauty, rich history, and vibrant culture. With over 6,000 islands and islets scattered across the Aegean and Ionian Seas, the diversity of landscapes and experiences is unparalleled. The Cyclades, Dodecanese, and Ionian Islands each have their unique charm, with pristine beaches, crystal-clear waters, and picturesque villages.
Reserve Flotilla ($500)

February / March 2027

Whitsunday Islands - Australia | 3 Alumni Boats | 10 Cabins | 8 Cabins Available | 0 Waitlisted
The Whitsunday Islands, located off the coast of Queensland, Australia, are an exceptional destination for bareboat chartering, offering some of the world's most spectacular sailing conditions. This stunning archipelago of 74 islands is renowned for its crystal-clear turquoise waters, pristine white sand beaches, and vibrant coral reefs.
Reserve Flotilla ($500)
Bahamas