Sailing Trips in the Caribbean

Island-hop this stunning tropical archipelago, basking and splashing every nautical mile of the way. Typically the reserve of the rich and famous, this tract of oceanic paradise is now open and awaiting the Intrepid explorer. Snorkel or hike around the fascinating small islands, or simply relax with a concoction of rum and fruit juice while taking in the Caribbean sun.

Fast Facts

  • Our boat is generally a 50+ foot monohull (see below - same boat used for European and Caribbean sailing adventures)
  • • Passengers contribute to a food kitty at the beginning of the trip, which they then manage themselves to buy and prepare breakfast and lunch for the group
  • • Evenings are spent dining at local restaurants
  • • During the day, island-hop from one gorgeous location to the next, swimming, snorkelling, exploring the islands and basking in the sun

Featured Trips

British Virgin Islands Sailing

7 days, Norman Island to Tortola


  • • Anchor at Dead Man’s Bay for a laze on the beach
  • • Navigate the amazing rock formations at The Baths
  • • Hike around the island of Jost Van Dyke
  • • Relax and sip cocktails in a beach hammock

» View full trip details


Martinique & St Lucia Sailing

7 days, Anse d'Arlet to Le Marin


  • • Explore a sleepy fishing village in southern Martinique
  • • Admire the historical beauty of Fort de France
  • • Enjoy the lush tropical climate of sunny Rodney Bay
  • • Don a snorkel and mask to get acquainted with the Caribbean's colourful marine life
  • • Hike to the World Heritage-listed Pitons
  • • Stroll the local markets of St-Anne

» View full trip details



View all Sailing Trips in the Caribbean