BlueFoot Travel
Navigation menu
  • Home
  • Sailing Trips
  • Yachts
  • Destinations
  • Reviews
  • More Info
    • About Us
    • FAQ
    • Pack for a Purpose
    • The Environment
    • Yacht Charter Guest Course
    • Yacht Menu & Bar
  • Blog
  • Contact Us
  • Instagram
  • Facebook
COVID-19 Notice: Advice for booking your next yacht charter with BlueFoot Travel

Caribbean Sailing Destinations

Explore Paradise From The Sea

  • Overview
  • Map

Why the Caribbean is the perfect sailing destination

The diversity of the Caribbean makes it a wonderful region to explore from the sea. Colourful landscape, seascape, rooftops, boats, clothes, and even the language! There are thousands of beaches, rum stocked bars, turquoise waters and wonderful people. The beauty of the islands is that for all the things the islands have in common, there’s also much that makes them different.

The Leeward Islands

The Leeward Islands of the Caribbean span some 200 miles and include ten main islands. As you will see anchorages vary from sophisticated harbours to deserted white-sand beaches, and sailing conditions vary throughout. Up in the northeast from Anguilla to Saint Martin and onto St. Barts passages take a few hours, making for easy and leisurely cruising. Further south, the passages become longer, so you can really experience trade winds and ocean swells.

Travelling south, the next island group includes Saba, Statia, St. Kitts & Nevis, and Montserrat. These are the newest of the islands, with Montserrat still growing! The final group of Leeward Islands includes Barbuda, Antigua, Guadeloupe and Dominica. These islands’ landscapes vary tremendously, ranging from pink beaches to mountainous and jungle-like terrain, all of which are great when exploring from the sea and ashore. 

The Windward Islands

From the French island of Martinique, the Windward Islands stretch southward almost 200 miles to the island of Grenada. Fortunately, they lie almost exactly across the easterly trade wind, which makes for fairly easy passages up and down this part of the island chain. They are just far enough apart to allow for some wonderful sailing in the open water before being able to dive into a secluded bay.

There are four main islands – Martinique, St. Lucia, St. Vincent and Grenada. Between St. Vincent and Grenada lie the Grenadines – a group of tantalisingly beautiful islands with picture-perfect white beaches, crystal clear waters and colourful reefs, all waiting to be explored from the sea and ashore.

Sailing Holidays in Style

If you have not been to the Caribbean before, you really must come. And if you have been before, then you know you want to come back! Whether you are travelling solo, as a couple or a group, you will have an unforgettable sailing holiday with BlueFoot Travel. So select a sailing destination and yacht and experience an unforgettable yacht charter.

Sailing Holidays in The Caribbean

View Sailing Trips

Our Sailing Destinations

We offer crewed charters around these Caribbean islands!

Need Assistance?

Contact us

Caribbean Sailing Destinations

A beach in Anguilla in the Caribbean
Anguilla
English and Falmouth Harbour as seen from Shirley Heights in Antigua & Barbuda
Antigua & Barbuda
Trellis Bay in the British Virgin Islands
British Virgin Islands
The luscious hills of Dominica
Dominica
Caribbean Cabin Charters from St Vincent to Grenada
Grenada
Aerial view of the Saintes in Guadeloupe - cropped
Guadeloupe
Baie de St Pierre by David Giral2A.JPG
Martinique
Montserrat as seen from Nemo when anchored in Antigua 500
Montserrat
The coast of Sint Martin
Sint Maarten & St Martin
A stunning view of St Barths
St Barts
Sailing along St Kitts, viewing Brimstone Hill Fortress
St Kitts & Nevis
The Caribbean Island of St Lucia with Pitons and Palm Trees
St Lucia
Tobago Cays group of islands, St. Vincent and the Grenadines
St Vincent & The Grenadines
US Virgin Islands
Sailing Trips
Destinations
Reviews
BlueFoot Travel
FAQ
Blog
Yachts
  • Holidays
  • Guest Reviews
  • Sailing Trips
  • Sailing Destinations
  • Yachts
  • More info
  • About Us
  • Blog
  • Coronavirus (COVID-19)
  • Environment
  • FAQ
  • Pack for a Purpose
  • Sign-up to Sail in Style
  • Bookings
  • Sailing Holiday Consultation
  • Booking A Cabin Charter
  • Booking A Crewed Yacht Charter
  • Contact Us
  • Website
  • Our Cookie Policy
  • BlueFoot Travel’s Privacy Policy
  • Website Terms & Conditions
  • Social
  • Facebook
  • Google Business
  • Instagram
  • LinkedIn
  • TripAdvisor
  • Twitter
  • YouTube

Book your yacht charter today

Sign-up to Sailing in Style

© 2022 BlueFoot Travel. All rights reserved.

BlueFoot Travel