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Sailaway Vacations

Windward Islands Sailing

Experience the dramatic beauty of the southern Caribbean, where volcanic peaks, lush rainforests, and vibrant cultures create unforgettable sailing adventures.

Volcanic Islands

Trade Winds

Dec – Apr

Island Highlights

St. Lucia​

Dramatic volcanic peaks, lush rainforests, and world-class resorts

Pitons

Soufrière

Marigot Bay

Rodney Bay

Martinique

French Caribbean culture with sophisticated cuisine and rum distilleries

Fort-de-France

Mount Pelée

Les Salines

Saint-Pierre

Dominica

Nature island with pristine rainforests, waterfalls, and whale watching

Roseau

Whale watching

Waterfalls

Morne Trois Pitons

St. Vincent & Grenadines

Chain of islands with excellent sailing and exclusive resorts

Bequia

Mustique

Tobago Cays

Citadel Museum

7-Day Windward Islands Discovery

Daily Schedule

1

Rodney Bay, St. Lucia

Marina base with excellent facilities and dining

2

Marigot Bay

Most beautiful bay in the Caribbean with lush surroundings

3

Martinique

French Caribbean culture and sophisticated cuisine

4

Dominica

Nature island with whale watching and rainforest hikes

5

Bequia

Charming island with boat building traditions

6

Tobago Cays

Marine park with pristine reefs and sea turtles

7

Rodney Bay, St. Lucia

Return via the dramatic Pitons UNESCO site

Strong Trade Winds

Consistent 15-25 knot trade winds provide excellent sailing conditions. More challenging but rewarding for experienced sailors.

Rich Culture

Blend of French, British, and Caribbean cultures with local cuisine, rum distilleries, and vibrant music traditions.

Marine Paradise

Excellent diving and snorkeling with coral reefs, sea turtles, and humpback whale watching opportunities.