Caribbean Tours in 2026

from $3,090

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Jamaica to Antigua

12 Day Itinerary aboard Star Clipper

Starts / Ends

Port Antonio / St. John's

Activities

Spa Relaxation

Activity Level

Variable

Explore a paradise of vibrant coral reefs, powder-soft sand, and warm island hospitality on this 12-day cruise from Jamaica to Antigua aboard Star Clipper. Experience crystal-clear water, bright skies, and gentle breezes. Relish in the beauty of untouched beaches and become enchanted by seductive scents and rhythms.

• Swim in Montego Bay's waters
• Explore Santo Domingo
• Visit the Treasure Island
• Hike Virgin Gorda trails

Cruise Details

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from $8,050

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Grenada to Antigua

St. George - St. John - 11 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. John's

Activities

Snorkeling, Village Visits

Activity Level

Variable

Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.

• Explore St. George’s harbor
• Experience Charlotteville coast
• Relax at Englishman’s Bay
• Wander through Admiralty Bay

Cruise Details

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from $22,140

2for1

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

Starts / Ends

Marigot / Bridgetown

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

• Explore Anguilla’s turquoise waters
• Stroll through Gustavia
• Admire Nevis’ tranquil shores
• Visit Antigua’s Falmouth Bay

Cruise Details

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from $15,980

2for1

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

Starts / Ends

Bridgetown / Marigot

Activity Level

Variable

Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.

• Explore Bridgetown’s capital
• Wander Speightstown’s streets
• Discover Kingstown’s gardens
• Unwind on Bequia Island

Cruise Details

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from $3,090

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Grenada to Grenada

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. Georges

Activity Level

Variable

Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.

• Explore St. George’s Fort George
• Discover Charlotteville’s Tobago
• Unwind on Carriacou beach
• Visit Martinique ruins

Cruise Details

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from $8,050

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Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper

Starts / Ends

St. Georges / St. Georges

Activity Level

Variable

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 St. George’s panoramic view
• Discover Charlotteville coastline
• Unwind at Englishman’s Bay
• Visit Martinique ruins

Cruise Details

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from $7,590

2for1

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Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara

Starts / Ends

San Juan / Miami

Activities

Kayaking

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.

• Explore the pristine beaches
• Snorkel in crystal-clear waters
• Relax on secluded Gordon’s Beach
• Explore Grand Turk’s beaches

Cruise Details

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from $6,800

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Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Roundtrip Vieux Fort - 9 Day Itinerary aboard Le Bellot

Starts / Ends

Les Saintes / Bridgetown

Activities

Hiking

Activity Level

Variable

From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.

• Visit UNESCO World Heritage sites
• Visit Portsmouth, Dominica
• Explore Les Saintes, Guadeloupe
• See Mayreau's fishes and corals

Cruise Details

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from $8,370

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Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant

Starts / Ends

Dominica / Anses d'Arlet

Activities

Scuba Diving

Activity Level

Variable

Explore the Caribbean on an 8-day cruise aboard Le Ponant. Visit Dominica to explore mangroves and meet the Kalinago people. Cruise through Saint Vincent and the Grenadines, snorkeling in Tobago Cays' clear waters. Experience sunsets, local culture, and beaches in Marie-Galante. This cruise combines relaxation and adventure in the Caribbean.

• Enjoy iconic pitons of Saint Lucia
• Learn about Kalinago culture
• Explore Tobago Cays' coral reefs
• Relax on Marie-Galante's beaches

Cruise Details

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from $3,200

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Eastbound Atlantic Ocean Crossing

Bridgetown - Lisbon - 17 Day Itinerary aboard Royal Clipper

Starts / Ends

Bridgetown / Lisbon

Activity Level

Variable

Embark on this 17-day Eastbound Atlantic Ocean Crossing cruise aboard Royal Clipper, starting from the port of Bridgetown. Experience the allure of the Azores, and play host to transatlantic yachtsmen, traders, and explorers. It stands on the green and fertile island of Sao Miguel. Finally, conclude your cruise in the city of Lisbon, Portugal.

• Explore the east coast of Barbados
• Discover the Azores history
• Visit the Alfama

Cruise Details

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from $3,420

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Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer

Starts / Ends

Philipsburg / Malaga

Activities

Small Ship Sailing, Archaeological Site Visits, Local Market Visits

Activity Level

Variable

Set sail on a 21-day cruise aboard the Star Flyer, starting in Philipsburg and visiting Ponta Delgada in the Azores. End your journey in Malaga, Spain, exploring its Moorish heritage while enjoying 18 days at sea.

• Explore Philipsburg’s Dutch side
• Experience Marigot’s markets
• Unwind while crossing the Atlantic
• Visit Ponta Delgada’s churches

Cruise Details

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from $5,180

$100 Dep.

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West Caribbean Cruise

Belize - Fort Lauderdale - 11 Day Itinerary aboard SH Vega

Starts / Ends

Belize City / Fort Lauderdale

Activities

Wildlife Viewing, Rainforest Exploration

Activity Level

Variable

Embark on an 11-day SH Vega cruise through the Western Caribbean. Explore Mayan ruins in Belize, relax on Grand Cayman's beaches, snorkel Montego Bay’s reefs, and visit Jamaica’s mountains. Enjoy birdwatching at Great Inagua, swim with sharks in the Exumas, and marvel at Nassau’s beauty.

• Witness Bahama's pinkest flamingo
• Swim with nurse sharks in Exuma
• Snorkel vibrant coral reefs
• Visit Cockscomb wildlife sanctuary

Cruise Details

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from $5,610

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Eastbound Atlantic Ocean Crossing

Barbados to France - 29 Day Itinerary aboard Royal Clipper

Starts / Ends

Bridgetown / Nice

Activity Level

Variable

Set sail on a 29-day Eastbound Atlantic Ocean cruise aboard Royal Clipper. Enjoy sailing, historic ports, and scenic coastal landscapes.

• See Ponta Delgada, Azores scenery
• See Malaga, Spain's architecture
• Visit Mallorca’s Gothic cathedral
• Visit Calvi’s coastal citadel

Cruise Details

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from $2,940

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Westbound Atlantic Ocean Crossing

Lisbon - Barbados - 16 Day Itinerary aboard Royal Clipper

Starts / Ends

Lisbon / Bridgetown

Activity Level

Variable

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.

• Explore Lisbon’s vibrant streets
• Discover Portimão’s historic charm
• Wander Funchal’s lush landscapes
• Cruise Barbados’ stunning shores

Cruise Details

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from $8,490

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Panama, Colombia & Caribbean Islands

Colon to Fort-de-France - 13 Day Itinerary aboard Le Champlain

Starts / Ends

Colon / Fort de France

Activities

Land & Sea Exploration

Activity Level

Variable

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.

• Sail through the Central America.
• See San Blas, Bonaire & Grenadines
• Experience swim and snorkel.
• Learn traditions of the Kuna people
• Dive with an experienced instructor

Cruise Details

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