BVI Flotilla 2026

Exciting news, sailors — we’ll be offering flotillas again in the beautiful British Virgin Islands this winter! After two successful flotillas last year, we’re thrilled to be offering more 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 7 to February 14, 2026 and the week of February 15 to February 22, 2026.

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.

Up to two people can be in a cabin, 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. Our early bird pricing, effective through June 1, per cabin is as follows:

$4,750 for a Monohull Cabin

+$200 for your choice of Monohull Cabin

$5,415 for a Catamaran Cabin

+$200 for your choice of Catamaran Cabin

**Single Occupancy Cabins Available**

+ $600 for ASA 104

+ $300 for ASA 114

Book Flotilla 

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 August 1st. Full payment is due by September 1st or upon booking. Additional fee for ASA certifications. Airfare not included.