CARIBBEAN SAILING DESTINATIONS
Islands worth sailing to — and routes worth taking your time for
The Caribbean is not one destination. It is a chain of very different islands, anchorages, cultures and sailing conditions. We use this page as a practical overview of the places that fit naturally into an Aurelia Blue voyage.
Crystal-clear water and steady trade winds are only part of the picture. What makes a route memorable is contrast: a quiet anchorage after a longer passage, a market morning after days at sea, dramatic volcanic scenery followed by a tiny Grenadine island, or a place that simply feels worth staying one more night.
Our routes vary with weather, season and local opportunities. The islands below are therefore best read as building blocks for real voyages, not as a fixed checklist.
Table of Contents
Martinique — French Caribbean Elegance
Martinique combines Caribbean scenery with French culture, excellent provisioning and useful international connections. Le Marin and Sainte-Anne make it one of the most practical gateways into the Windward Islands.
- Le Marin
- Sainte-Anne
- Fort-de-France
- Anse Mitan
- Rainforest and waterfalls
St. Lucia — The Island of the Pitons
Saint Lucia is immediately recognisable from the water. The Pitons, Soufrière, Marigot Bay and Rodney Bay give the island a mix of dramatic landscape, comfortable anchorages and lively stops ashore.
- The Pitons
- Soufrière
- Marigot Bay
- Rodney Bay
- Sulphur Springs
Bequia — Caribbean Charm at Its Best
Bequia is one of the places where sailing tradition and island life still sit naturally together. Admiralty Bay, the waterfront, small local businesses and the relaxed pace make it an easy place to slow down.
- Admiralty Bay
- Princess Margaret Beach
- Local markets
- Waterfront cafés
- Relaxed island atmosphere
St. Vincent — Adventure and Nature
Saint Vincent feels greener, steeper and less polished than many better-known Caribbean stops. Its west coast brings waterfalls, black-sand beaches, rainforest and anchorages with a strong sense of place.
- La Soufrière
- Wallilabou Bay
- Black-sand beaches
- Rainforest
- Young Island
Tobago Cays — A Caribbean Paradise
The Tobago Cays are one of the defining sailing landscapes of the Grenadines: reef-protected water, small islands, turtles, bright shallows and evenings that often become the visual memory of the whole voyage.
- Sea turtles
- Snorkelling
- Reef-protected lagoons
- White-sand beaches
- Sunsets
FROM ISLAND LIST TO REAL ROUTE
See how these islands connect under sail
The best route is rarely the one with the most stops. It is the one that gives each island enough space to feel different from the last.
Grenada — The Spice Island
Grenada combines protected southern bays with markets, rainforest, local food culture and one of the Caribbean’s most attractive harbour approaches at St. George’s.
- St. George’s
- Grand Anse
- Woburn Bay
- Spice markets
- Underwater Sculpture Park
Tobago — Relaxed and Authentic
Tobago remains outside the busiest Caribbean charter circuits. Charlotteville, Pirates Bay and the island’s quieter coastline offer a slower atmosphere and excellent opportunities for swimming and snorkelling.
- Charlotteville
- Pirates Bay
- Englishman’s Bay
- Buccoo Reef
- Quiet anchorages
Dominica — Nature Island of the Caribbean
Dominica is shaped by rainforest, rivers and volcanic terrain rather than resort development. Portsmouth and the Indian River provide a very different stop from the beach-focused islands farther south.
- Indian River
- Boiling Lake
- Trafalgar Falls
- Rainforest
- Whale watching
Guadeloupe — French Caribbean Diversity
Guadeloupe and its surrounding islands bring together French-Caribbean food culture, national-park landscapes and a useful series of anchorages for voyages moving north through the island chain.
- Deshaies
- Les Saintes
- Bouillante
- National Park
- French-Caribbean culture
Antigua — The Sailor’s Island
Antigua adds a different northern Caribbean character: historic harbours, strong sailing culture, English Harbour, Shirley Heights and a coastline full of beaches and protected bays.
- Nelson’s Dockyard
- English Harbour
- Shirley Heights
- Deep Bay
- Great Bird Island
The ABC Islands — Aruba, Bonaire and Curaçao
The ABC Islands sit outside the main Windward chain and feel different immediately: drier landscapes, Dutch-Caribbean culture, colourful waterfronts and outstanding diving.
- Aruba beaches
- Bonaire Marine Park
- Curaçao waterfront
- Diving
- Drier climate
San Blas Islands — A World Apart
The San Blas Islands belong to a very different kind of voyage. Hundreds of small islands and cays, remote anchorages and Guna communities create an experience far removed from conventional Caribbean tourism.
- Guna culture
- Remote anchorages
- Small islands and cays
- Snorkelling
- Long-range cruising
NO BROCHURE VERSION
Which Caribbean sailing destination is right for you?
There is no single best island. Martinique works brilliantly as a gateway, the Grenadines reward compact island-hopping, Dominica brings dramatic nature, Tobago offers a quieter southern rhythm and Antigua adds a distinct northern sailing culture. The best choice depends on season, available time and the kind of travel you want.
Compare routes before choosing islands
Once you have shortlisted destinations, use our Caribbean sailing itinerary guide to connect them realistically, compare Caribbean sailing seasons, or look at Grenadines vs BVI sailing and Windward Islands vs BVI sailing.
Caribbean sailing destinations: frequently asked questions
What are the best Caribbean islands for sailing?
For varied island-hopping, the Windward Islands and Grenadines are especially strong. Northern routes through Dominica, Guadeloupe and Antigua offer a very different character.
How many islands should a one-week route include?
Usually fewer than first-time planners expect. Real sailing time and time ashore matter more than the number of stops.
Do seasons change the best route?
Yes. Wind, swell and tropical weather patterns influence which island chains make the most sense at different times of year.
YOUR CARIBBEAN ADVENTURE STARTS HERE
Turn the island list into a real voyage
Browse the departures we are actually sailing, or talk to us about shaping a private route around the islands that matter most to you.
See the islands on real routes
