Top Caribbean Tours & Cruises in 2027

Join an 8-day Caribbean cruise from St. John's, Antigua, on the Star Clipper, exploring destinations like St. Barts, St. Kitts, and Martinique. Experience snorkeling, historic tours, and diverse beaches while enjoying the beauty of the French and British West Indies.

Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua.

Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua.

Embark on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Visit Anguilla's beaches, explore the British Virgin Islands, hike Jost Van Dyke, and enjoy shopping in St. Barts while uncovering historical sites and natural beauty.

Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.

Embark on an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, visiting beautiful locations like Anguilla, Tortola, and Virgin Gorda. Enjoy duty-free shopping in St. Barts and explore the colonial history of St. Kitts before returning to St. Maarten.

Embark on an 8-day Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring charming towns, lush rainforests, and beautiful beaches. Enjoy duty-free shopping in Gustavia before returning to St. Maarten.

Sail 8 days aboard Sea Cloud Spirit on a Caribbean round-trip from Philipsburg, St. Maarten. Explore Gustavia, St. John’s, Virgin Gorda, Jost van Dyke, and Norman Island with beaches, sailing, and historic sights.

Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.

Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.

Explore Guadeloupe and the Southern Caribbean aboard Le Ponant on an 8-day cruise. Swim in Tobago Cays, snorkel at Sandy Island, discover Grande Anse d’Arlet, visit Portsmouth, sail past The Pitons, and experience Creole culture, beaches, reefs, and island towns across multiple Caribbean destinations.

Set sail on an 11-day cruise through Panaman, Colombia and Caribbean Islands aboard Le Bellot. Visit Cartagena and Santa Marta with guided historic and cultural excursions. Explore the San Blas Islands for beaches, snorkeling, and Kuna culture. The voyage combines nature, culture, and Caribbean island experiences.