Skip to main content

Sailaway Vacations

Leeward Islands Sailing

Sophisticated sailing through luxury resorts, pristine beaches, and French Caribbean culture. The Leeward Islands offer upscale amenities with perfect trade wind sailing.

8 Major Islands

Luxury Marinas

Nov – May

Island Highlights

Antigua

365 beaches and historic English Harbour

Nelson's Dockyard

Shirley Heights

Deep Bay Beach

St. Barts

French sophistication in the Caribbean

Gustavia Harbor

Shell Beach

Luxury Shopping

St. Martin/Sint Maarten

Two cultures, one island paradise

Marigot Bay

Orient Beach

Maho Beach

Anguilla

Pristine beaches and world-class resorts

Shoal Bay

Meads Bay

Sandy Island

7-Day Leeward Islands Itinerary

Daily Schedule

1

Antigua - English Harbour

Charter base departure, explore historic dockyard

2

Barbuda

Pink sand beaches and frigate bird sanctuary

3

St. Barts - Gustavia

French culture and duty-free shopping

4

St. Martin - Marigot

French side cuisine and markets

5

BequiaAnguilla - Road Bay

Pristine beaches and luxury resorts

6

St. Kitts

Volcanic peaks and colonial history

7

Antigua - English Harbour

Return to base via Falmouth Harbour

Luxury Sailing

High-end marinas and world-class resorts. Premium dining, shopping, and spa facilities on every island.

 

French Culture

Experience French Caribbean cuisine, duty-free shopping, and European sophistication in a tropical setting.

Perfect Beaches

Some of the Caribbean’s most beautiful beaches with white sand, crystal-clear water, and excellent snorkeling