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6643

British Virgin Islands

A Learn-To-Sail-Vacation

hosted by Annapolis Sailing School
  • 2026: Feb 7th - 14th & Feb 15th - 21st
  • 8 Days | 7 Nights
  • 104 / 114
Annapolis Sailing School BVI Flotilla

Destination

We will be sailing the British Virgin Islands, starting out in Tortola and traveling each day around the islands to explore their wonderful beaches and lagoons. We’ll discover the best watering holes for sailors and enjoy delicious Caribbean food when we dinghy ashore. All the while, you’ll be developing the skills and confidence to charter a vessel yourself. The BVIs are the perfect place for this, with a large number of islands within easy sailing distance of each other and consistent winds that make for excellent sailing.

School

Annapolis Sailing School has been teaching sailors since 1959, believing that sailing should be both serious and fun. Students are encouraged to put in the work while discovering the joy of the sport, leaving with confidence and a lasting love for sailing. This vacation embodies that philosophy, offering hands-on experience that allows participants to prove to themselves that they truly can do it.

CERTIFICATIONS

The Learn-to-Sail Vacation with Annapolis Sailing School  offers :

¤ ASA 104 | BAREBOAT CRUISING
¤ ASA 114 | CRUISING CATAMARAN

SAMPLE ITINERARY

Day 1
ARRIVAL

Arrive in Road Town, do some shopping, and enjoy dinner ashore.

Day 2
TRELLIS BAY

Complete the final yacht briefing, set sail, and arrive at Trellis Bay or another nearby anchorage.

Day 3
VIRGIN GORDA / NORTH SOUND

Sail to the Baths at Virgin Gorda in the morning, have lunch on shore, then continue to the North Sound, stopping at either the Bitter End Yacht Club or Leverick Bay.

Day 4
ANEGADA

Head to Anegada, swim on its beaches, explore this remarkable coral atoll, and enjoy a famous Anegada lobster dinner.

Day 5
CANE GARDEN BAY

Sail toward Cane Garden Bay or another anchorage north of Tortola, or spend the entire day in beautiful Anegada exploring the island, taking an excursion, or relaxing with a swim.

Day 6
JOST VAN DYKE

Continue on to Jost Van Dyke, where you can visit Foxy’s, enjoy the Soggy Dollar Bar, hike to the Bubbly Pool, or relax on Sandy Cay.

Day 7
INDIANS / NORMAN ISLAND

Snorkel at the Indians, then moor at Norman Island to explore its famous caves.

Day 8
TORTOLA

Return sail to Road Town, Tortola, arriving at the marina before 11 a.m.

Please Note. This itinerary is meant to serve as an example, however, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.

BOATS
  • 45'+ Catamaran(114 certification only available on the catamaran.)
  • 48' Monohull

PHOTOS

  • Learn-To-SailFeb 7 - 14 & Feb 15 - 21, 2026
  • from $2,500 USD per person
  • 104 / 114

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