BVI Flotilla 2027
Exciting news, sailors — we’ll be offering flotillas again in the beautiful British Virgin Islands this winter! After two years of successful flotillas, we’re thrilled to be able to keep offering unforgettable tropical experiences. You’ll sail through crystal clear waters, enjoy fresh warm breezes — a welcome escape from a chilly Maryland winter — and make new friends and memories to last a lifetime.
We have spots available for the week of February 6 to February 13, 2027 and the week of February 14 to February 21, 2027.
This flotilla gives participants to get experience chartering a boat with seasoned captains as well as spending the week with other adventurous people. This is an active trip and every cabin will be participating in running the boat both under sail and at anchor. In keeping with our ‘Seriously Fun’ philosophy, sailors will have the option to add ASA 104 for $600 and add ASA 114 for $300. Please note, if you want to do both ASA 104 and ASA 114, you’ll need to book the Catamaran cabin.
Cabins are priced for 2 people, so be sure to coordinate with family and friends to book a cabin together. Only one person needs to book if two people go together. There are a limited number of cabins available at a single occupency price. Choice of cabin is available at an additional charge, people who choose choice of cabin will have first pick of bow or stern cabins. The cabin price covers food and soft drinks aboard, all fees related to the boat (mooring balls, ice, trash, etc) , and a lobster dinner ashore on Anegada.
Don’t wait to book either — we’re offering exclusive discounts for early bookings and returning students!
Early bird pricing, effective through August 5th, per cabin:
Monohull Cabin $4,680
Catamaran Cabin $5,310
+$200 for your choice of Cabin on the catamaran
**Single Occupancy Cabins Available at 75% cost**
Returning Flotilla Sailor?
Book before August 5th and get an even greater discount!
Monohull Cabin$4,420
Catamaran Cabin $5,015
+$200 for your choice of Catamaran Cabin
Regular prices after August 5th
Monohull Cabin $5,200
Catamaran Cabin $5,900
+$200 for your choice of Catamaran Cabin
Certifications available
+ $600 for ASA 104
+ $300 for ASA 114 (only availabe on catamaran)
Book Flotilla
Sample Itinerary
Feel free to click below to watch our Q&A session about the Flotilla on our Youtube Page.
Have questions? Feel free to call our office or email us at info@annapolissailing.com
There is a $1,000 deposit due at time of booking. Deposits are 50% refundable until September 1st. Full payment is due by October 1st or upon booking whichever is later. Additional fee for ASA certifications. Airfare not included.