• Sign up
  • Log in
Sailsquare
      • All Greece 0€
      • Ionian Islands 0€
      • Cyclades 0€
      • Dodecanese 0€
      • Saronic Islands and Athens area 0€
      • All Italy 0€
      • Northern Sardinia 0€
      • Aeolian Islands 0€
      • Aegadian islands 0€
      • Tuscany 0€
      • Liguria 0€
      • Pontine Islands 0€
      • Amalfi Coast 0€
      • All Spain 0€
      • The Balearic Islands 0€
      • Andalusia 0€
      • Catalunya 0€
      • Galicia 0€
      • Valencia 0€
      • All Caribbean 0€
      • BVI - British Virgin Islands 0€
      • Antigua and Barbuda 0€
      • Grenadines & Martinique 0€
      • Guadeloupe 0€
      • Bahamas 0€
      • Belize 0€
      • All Indian Ocean 0€
      • Bali 0€
      • The Maldives 0€
      • Mauritius 0€
      • Seychelles 0€
      • Corsica 0€
      • French Riviera and Porquerolles 0€
      • Brittany and Normandy 0€
      • Split Archipelago 0€
      • Kornati Islands 0€
      • Turkey 0€
      • French Polynesia 0€
      • Adventure 0€
      • Courses & regatta 0€
      • Day trips 0€
      • Flotilla 0€
      • Offshore 0€
      • Sport & wellness 0€
      • Whole boat with skipper 0€
      • All inclusive 0€
      • Premium 0€
      • Catamaran 0€
      • Gulet 0€
      • Monohull 0€
      • Families 0€
      • Solo Travellers 0€
      • Weekend 0€
      • Couples 0€
      • Mediterranean 0€
  • Rent a boat
  • Call us
    +44 20351 44220
    • ITA
    • FRA
    • DEU
    • ESP
  • You have 0 messages! 0€
  • 0 new alerts for you! 0€
  • Message area 0€
  • Holiday wishlist 0€
  • My profile 0€
  • Edit account 0€
  • Earn vouchers 0€
  • Log out
      • All Greece 0€
      • Ionian Islands 0€
      • Cyclades 0€
      • Dodecanese 0€
      • Saronic Islands and Athens area 0€
      • All Italy 0€
      • Northern Sardinia 0€
      • Aeolian Islands 0€
      • Aegadian islands 0€
      • Tuscany 0€
      • Liguria 0€
      • Pontine Islands 0€
      • Amalfi Coast 0€
      • All Spain 0€
      • The Balearic Islands 0€
      • Andalusia 0€
      • Catalunya 0€
      • Galicia 0€
      • Valencia 0€
      • All Caribbean 0€
      • BVI - British Virgin Islands 0€
      • Antigua and Barbuda 0€
      • Grenadines & Martinique 0€
      • Guadeloupe 0€
      • Bahamas 0€
      • Belize 0€
      • All Indian Ocean 0€
      • Bali 0€
      • The Maldives 0€
      • Mauritius 0€
      • Seychelles 0€
      • Corsica 0€
      • French Riviera and Porquerolles 0€
      • Brittany and Normandy 0€
      • Split Archipelago 0€
      • Kornati Islands 0€
      • Turkey 0€
      • French Polynesia 0€
      • Adventure 0€
      • Courses & regatta 0€
      • Day trips 0€
      • Flotilla 0€
      • Offshore 0€
      • Sport & wellness 0€
      • Whole boat with skipper 0€
      • All inclusive 0€
      • Premium 0€
      • Catamaran 0€
      • Gulet 0€
      • Monohull 0€
      • Families 0€
      • Solo Travellers 0€
      • Weekend 0€
      • Couples 0€
      • Mediterranean 0€
  • Rent a boat
  • Call us
    +44 20351 44220
    • ITA
    • FRA
    • DEU
    • ESP
  • ITA
  • FRA
  • DEU
  • ESP
Sailing holidays in the BVI with Skipper

Sailing holidays in the BVI with Skipper

Explore the beauty of the British Virgin Islands (BVI), “a sailor’s paradise”, with an unforgettable sailing holiday experience. The BVI are home to some of the most beautiful beaches and rarest wildlife ecosystems in the world.

  • Sailing Holidays
  • Caribbean
  • BVI - British Virgin Islands

COVID‑19

Book without stress paying a small deposit, cancellation is free!.

A boat with an X above it

No holiday found.

Currently there are no listed holidays matching your search.
How about widening your search?

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Sailing holidays in the BVI with Skipper

2 reviews
20 / 10
Fabian M.

Fabian M.

review about 7 Days Sailing Cruise around St. Maarten and the BVI's incl. breakfast and lunch on board January 2021

10 / 10
First-class sailoring, first-class company, first-class sailing boat, first-class experience. Rob is an exceedingly competent skipper of a superb sailing yacht. On the human level, Rob and Jacky are absolutely delightful people who go out of their way to make you feel welcome and comfortable in every way. Cannot recommend more highly!
Eleonora M.

Eleonora M.

review about Yoga on a sailboat, surrounded by sailor's paradise: the BVI March 2016

10 / 10
La vacanza trascorsa a bordo in compagnia di Giovanni è stata veramente un toccasana per me e sotto ogni aspetto, dalle meravigliose navigazioni sia lunghe che brevi con Giovanni sempre attentissimo ad ogni particolare riguardante la sicurezza e lo stare bene a bordo, alla bellezza dei luoghi visitati ed alla gustosissima e soprattutto sana cucina propiziatami, sempre tutto ad opera di Giovanni che quindi oltre ad essere espertissimo skipper e' anche un eccellente cuoco ed un piacevolissimo compagno di viaggio. Non saprei cos'altro aggiungere alle tre settimane trascorse in sua compagnia, una vacanza cosi' posso solo consigliarla a tutti coloro che amano le infinite e meravigliose sfaccettature del re mare e di tutto ciò che lo contraddistingue e lo rende il più bel luogo del pianeta! Mi auguro di poter ripetere l'esperienza il prossimo anno in qualsiasi oceano Giovanni navigherà! Grazie di cuore. Eleonora.
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

Why you should visit the BVI

The best destinations:

Tortola, Jost Van Dyke, Anegada, and Virgin Gorda are home to some of the most beautiful beaches in the world - including Cow Wreck Beach, Long Bay Beach, and The Baths. On each island natural wonder comes in a slightly different form, meaning that there is much to explore when on a sailing holiday in the BVI. Tortola, the capital island, and described by many as the Caribbean’s sailing capital, holds many of the main cultural centres and landmarks. Where as, Anegada, is a utopia for wildlife and nature - with a great number of rare species of plants and animals to see. Then, the island of Virgin Gorda, named by Christopher Columbus, is a popular island for its pretty bays and beaches - and has a very unique blend of different cultures, with numerous influences present still today.

Learn more about the different destinations within the BVI and about travelling by catamaran

.

Other travel ideas

  • Whole boat with skipper (2734)
  • Monohull (2633)
  • All inclusive (532)
  • Premium (377)
  • Day trips (294)
  • Catamaran (268)
  • Courses & regatta (156)
  • Offshore (101)
  • Sport & wellness (85)
  • Gulet (74)

Let's talk Sailsquare

Huffpost Sailing Today Yahoo!
Sailsquare press center

Sailsquare

  • Team
  • Careers
  • Press Room
  • Press Releases
  • Sustainable Tourism
  • General Terms & Conditions
  • Privacy

Travellers

  • Contact & Support
  • Blog
  • Customer Reviews
  • Sailsquare Concept
  • Reward Program
  • Ambassador Program
  • Traveller policy

Skippers & Businesses

  • List a holiday
  • Contact & Support
  • Crew Leader policy
  • Code of Conduct

Follow us on

Facebook Instagram Youtube Sailsquare blog

Secure online payments

Mastercard Visa America Express Apple Pay

Top Destinations

  • Italy
  • Greece
  • Northern Sardinia
  • Aeolian Islands
  • Tuscany
  • Pontine Islands
  • Liguria
  • France
  • Ionian Islands
  • Aegadian islands
  • Croatia
  • Cyclades
  • Spain
  • The Balearic Islands
  • Corsica
  • Split Archipelago
  • Saronic Islands and Athens area
  • French Riviera and Porquerolles
  • Caribbean
  • Sporades
  • Brittany and Normandy
  • Gulf of Naples
  • Dodecanese
  • Grenadines & Martinique
  • Istrian peninsula
  • Amalfi Coast
  • Atlantic islands
  • Guadeloupe
  • French Polynesia
  • Seychelles

Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Premium
© 2021 Sailsquare srl • All rights reserved - VAT 07860990964