Offer details

Blending freedom with support, flotilla holidays from Tortola offer a sailing holiday with a difference. During the day you’ll sail your own boat while expert crews guide you and your sailing group to some of the BVI’s best locations. Island-hop from one stunning anchorage to the next, walk along gorgeous stretches of beach, and snorkel with colourful fish. At night, enjoy the lively social scene. Sip a cocktail as the sun slips below the horizon—the BVI is the destination of choice for the social sailor.

BVI two-week flotilla

  • Leverick Bay Resort & Marina
  • Diving and snorkeling at The Indians
  • The Baths National Park
  • World-famous “Painkiller” cocktails
  • Searching for buried pirate treasure
  • Lobster dinner on Anegada
What’s included
  • Fully equipped cruising yacht for the duration of your holiday
  • Lead Crew: Skipper, Host and Technician
  • One tank of yacht fuel
  • Full cylinder of cooking gas and full tank of water
  • Guaranteed mooring at each stopover
  • Dinghy and outboard
  • All sailing, navigation and safety equipment onboard
  • Fully equipped galley/kitchen
  • All clean linen including bath and tea towels
  • Snorkelling Equipment
  • First Morning Breakfast
  • Flotilla Punch Party
  • End Cleaning
  • End of Week Regatta
What’s not included
  • Food and Drink
  • Mooring and marina Fees
  • Children’s life jackets (we recommend bringing your own)
  • Beach Towels
  • Security Deposit


*Price per yacht, based on 8 ppl on board


Day 1 At the base

Following a smooth 20-minute transfer from the airport, you’ll arrive at our base at Wickhams Cay II on the beautiful island of Tortola, BVI.

Day 2 Road Town to Norman Island

Push off from the dock and begin your flotilla adventure by sailing towards Norman Island, the southernmost region of the cruising grounds.

Day 3  Norman Island to Cooper Island

A best-kept secret among the Caribbean yachting community, Cooper Island is one of the smaller islands within the southern cluster that sits just below the Sir Francis Drake Channel.

Day 4 Cooper Island to Leverick Bay

On day four, cruise past granite boulders, turquoise cays and secluded grottos near The Baths while the flotilla makes its way towards the lovely Leverick Bay Resort and Marina.

Day 5  Leverick Bay to Anegada

After breakfast, say farewell to Leverick Bay, then sail 13nm to discover the low-lying coral-rich island of Anegada. Unlike other islands formed from volcanic rock, Anegada’s coral and limestone base feature vibrant reefs and abundant marine life below the surface.

Day 6  Anegada to Trellis Bay

Your next stop will be Beef Island, along the quaint shores of Trellis Bay. Pick up a mooring and refill provisions at the local market, or if the timing is right, sign yourself up for Trellis Bay’s monthly full moon party to enjoy live music and fun with new friends.

Day 7  Free day sailing

Today is your chance to go explore this fan-favorite cruising playground on your own schedule. Trellis Bay’s idyllic location allows you many options to go discover somewhere less familiar with new flotilla friends.

Day 8  Cane Garden Bay

Meet up with your flotilla again in beautiful Cane Garden Bay, which is tucked away on the north side of Tortola.

Day 9  Cane Garden Bay to Jost Van Dyke

Begin day nine with a westbound passage towards the picture perfect sands of Jost Van Dyke.

Day 10  Free day sailing

On the tenth day of your flotilla, you’re free to frolic wherever you want. So you can head down to Peter Island a day early or extend your stay at Jost Van Dyke to continue soaking up the sun in Great Harbour or venture up to Little Jost Van Dyke .

Day 11 Peter Island

After your day of freedom amongst the turquoise-blue Caribbean waters, plot a course for Peter Island, which is where you’ll find the infamous pirate-themed Willy T floating bar.

Day 12 Peter Island to Marina Cay

Known for its colorfully-painted buildings lining the shore, Marina Cay is one of the most distinctive landmarks in the BVI.

Day 13 Free day sailing

The last two days of your BVI flotilla adventure have arrived, and you get to spend them however you’d like. Divers may enjoy a visit to nearby Salt Island, where the underwater Wreck of the Rhone waits to be discovered.

Day 14 Back to Base

Today is the final day of flotilla fun and cruising freedom, so we make our way back to the  base, where this incredible sailing adventure began just two weeks ago.

*To be used as a guide only.

Area map

Don't see what you're looking for?

Tell us what you want and we will do the searching for you
  • Date Format: DD slash MM slash YYYY
  • Date Format: DD slash MM slash YYYY

Don’t See What You Want?

With so much choice available, why not get one of our charter experts to help?

Simply fill out the details below and we will get in touch.


  • :
Arrange a Callback