Top Windward Islands Tours & Cruises in 2025

Join the Royal Clipper on this 8-day cruise through the Grenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts, Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day. From the horseshoe-shaped Carenage at St. …

Embark on an 8-day cruise aboard the Royal Clipper, starting in Antigua, the vibrant hub of yachting culture. Explore the pristine beaches and underwater wonders of Les Saintes, followed by Dominica’s lush rainforests, Trafalgar Falls, and a bubbling lake. Bask on Martinique’s idyllic …

Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Set sail from Bridgetown, Barbados, and discover stunning destinations across the Caribbean Sea. Visit Port St. Charles in Barbados, where glassy blue waters invite swimming, sailing, and snorkeling. Explore Kingstown, the capital of …

Join the Royal Clipper on a 15-day cruise departing from Bridgetown, Barbados. Experience the vibrant contrasts of this coastal town, with its red-sand beaches and lively streets. Explore the British-influenced heritage through landmarks like Trafalgar Square and discover traditions like cricket …

Experience an 8-day Caribbean cruise aboard Le Ponant. Explore the wild landscapes of Dominica and navigate the mangroves of the Indian River on a local boat, surrounded by green herons and pelicans. Meet the Kalinago people, who share their history and local cuisine, offering insight into their …

Join this 15-day cruise starting in Marigot aboard the Emerald Sakara. Discover Anguilla, a low-lying paradise renowned for its pristine white-sand beaches and vibrant coral reefs. Marvel at the historic UNESCO-listed Nelson’s Dockyard in Falmouth Harbor and uncover the charm of Bequia …

Set sail on a 15-day Caribbean cruise, beginning in Bridgetown aboard the Emerald Sakara. Explore Port St. Charles, a picturesque marina with breathtaking views of the aquamarine Caribbean Sea, and savor the tranquility of Bequia Island, a serene haven untouched by bustling tourism. Journey through …

Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Bellot on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its garrison. Visit …

Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …

Embark on an 8-day cruise aboard the Royal Clipper, exploring vibrant islands, pristine beaches, and cultural treasures. Begin in Bridgetown, Barbados, where British heritage meets laid-back island charm. Relax in Rodney Bay, St. Lucia, with its turquoise waters and lively marina. Sail to …

Embark on a 15-day cruise aboard the Star Clipper. This Caribbean and Panama Canal cruise begins in Bridgetown, Barbados, and explores the Caribbean's diverse cultures, landscapes, and history before concluding in Balboa, Panama. Visit the remote Tobago Cays, the spice island of Grenada, and …

Embark on this 8-day Caribbean cruise aboard the Emerald Sakara, beginning in Barbados. Relax with a rejuvenating mud bath or soak in the therapeutic hot springs of Soufriere. Explore the UNESCO-listed Nelson’s Dockyard in Falmouth Harbor and unwind on the serene beaches of Iles des Saintes. …

Embark on a 21-day cruise aboard SH Vega and explore the Atlantic coastline of South America. The adventure takes you from Barbados to Brazil, where you discover the wonders of this diverse region. During the trip, you encounter the rich biodiversity of the Amazon Rainforest, explore the colonial …

Embark on an 8-day cruise aboard the Star Flyer. With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this unique region, …

Experience an 8-day Caribbean cruise aboard the Emerald Sakara, exploring the best of the Caribbean. Sail from Marigot, Saint Martin, to Anguilla, known for its stunning white-sand beaches and vibrant coral reefs. Continue to Gustavia in Saint Barthélemy, where French and Caribbean cultures …

Embark on a 15-day cruise aboard the Royal Clipper, starting in Balboa, Panama—the gateway to the majestic Panama Canal. Experience a complete transit through its remarkable locks. Next, visit the remote San Blas Islands, known for the vibrant culture of the Kuna people. After a day at sea, …

Embark on a 25-day cruise aboard the Star Clipper. This 25-day voyage explores Spain, Morocco, and the Canary Islands before crossing the Atlantic to Barbados. Begin in Malaga, admiring Moorish landmarks, then visit Gibraltar’s Rock and Barbary macaques. Discover Tangier’s multicultural …

Crossing the mighty Atlantic Ocean provides the time to truly appreciate the pure pleasure of the sea. Imagine sailing the Atlantic in the footsteps of legendary explorers, enjoying the Old World family charm and the wonders of the New World. Admire Gran Canaria's exotic vegetation and magical …