Windward Islands Cruises

Experience an 11-day Caribbean sailing itinerary from and to Philipsburg, St. Maarten aboard Sea Cloud II. Visit St. Lucia, Martinique, Îles des Saintes, St. Barths, and the British Virgin Islands, with time at sea focused on hands-on sailing and relaxed days ashore.

Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin Islands.

Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean.

Sail across the Atlantic on this 16-day cruise aboard the Royal Clipper, blending culture and adventure. Discover Lisbon’s charm, Portimao’s historical treasures, Madeira’s vibrant nightlife, and Barbados’ stunning shores, with serene days at sea in between.

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage all the way to the stunningly beautiful Caribbean Islands.

Join Le Bellot for an exceptional 13-day cruise sailing from Colón to Fort-de-France. This itinerary gives you the opportunity to appreciate the richness and diversity of Afro-Caribbean cultures, an azure blue sky, and white-sand beaches. Visit stunning ports, including Portobelo, Cartagena, Santa Marta, Mayreau Island, and Soufriére.

Sit back and take in the smell of the fresh ocean breeze up on deck on this extraordinary 16-day cruise that takes you across the Northern Atlantic Ocean. Start at the famous and charming city of Las Palmas, Gran Canaria, and voyage to the stunningly beautiful Caribbean Islands.

Take part in an 18-day transatlantic cruise aboard Sea Cloud II from Las Palmas, Gran Canaria to Bridgetown, Barbados. Relax under full sails, explore Gran Canaria’s landscapes, and discover Bridgetown’s UNESCO World Heritage colonial architecture and beaches.

Set sail on a 23-day transatlantic cruise from Malaga to Barbados on the Star Clipper, exploring stunning sites like the Alhambra in Spain, the Hassan II Mosque in Morocco, and the volcanic landscapes of the Canary Islands. Conclude your journey in Bridgetown, Barbados, visiting historic landmarks.

Cruise from Halifax, Nova Scotia to Bridgetown, Barbados aboard the Seabourn Venture on a 9-day Southern Caribbean Yacht Harbors cruise. Enjoy relaxing days at sea and explore scenic Caribbean islands like Saint Kitts, Montserrat, and Saint Lucia. Visit UNESCO World Heritage Sites, snorkel in clear waters, and experience rich history and culture.