Caribbean Tours

from $2,010

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Tour Basseterre colonial history
• Hike St. Kitts rainforests
• Swim South Friars Bay waters

Starts / Ends

St. John's / St. John's

Activity Level

Variable

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.

Cruise Details

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from $2,010

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Explore St. John's dockyards
• Sail Sir Francis Drake Channel
• Swim Virgin Gorda Baths
• Hike Jost van Dyke trails

Starts / Ends

St. John's / St. John's

Activity Level

Variable

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.

Cruise Details

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from $2,010

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Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper

• Hike St. Kitts rainforests
• Tour Basseterre colonial history
• Shop Philipsburg Dutch bargains
• Explore Tortola to see Soper's Hole

Starts / Ends

St. John's / St. John's

Activity Level

Variable

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.

Cruise Details

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from $2,010

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Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Anguilla's white sand coves
• Tour Tortola to see Soper's Hole
• Swim South Friars Bay waters
• Hike Jost Van Dyke trails

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

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.

Cruise Details

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from $2,010

Air Credit

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Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Anguilla's white sand coves
• Tour Tortola to see Soper's Hole
• Swim South Friars Bay waters
• Hike Jost Van Dyke trails

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

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.

Cruise Details

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from $2,010

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Treasure Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Visit Anguilla's white sand coves
• Tour Tortola to see Soper's Hole
• Swim South Friars Bay waters
• Hike Jost Van Dyke trails

Starts / Ends

Philipsburg / Philipsburg

Activity Level

Variable

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.

Cruise Details

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from $2,010

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Leeward Islands

Roundtrip St Maarten - 8 Day Itinerary aboard Star Flyer

• Swim Gustavia beaches
• Visit Nelson's Dockyard ruins
• Snorkel Terre-de-Haut waters
• Hike Dominica trails

Starts / Ends

Philipsburg / Philipsburg

Activities

Snorkeling, Small Ship Sailing

Activity Level

Variable

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.

Cruise Details

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from $22,140

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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara

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

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.

Cruise Details

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from $15,980

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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara

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

Starts / Ends

Bridgetown / Marigot

Activities

Archaeological Site Visits, Kayaking

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.

Cruise Details

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from $2,443

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Best of Dominican Republic

8 Day Itinerary

• Visit UNESCO site in Santo Domingo
• Taste the culture and local food
• Visit coffee factory in Jarabacoa
• Learn about tobacco production
• Visit cocoa & chocolate plantation
• See the beaches of Las Terrenas

Starts / Ends

Punta Cana / Punta Cana

Activities

Hacienda Visits, Volunteering

Activity Level

Relaxed

Visit Dominican Republic and uncover hidden gems, from Jarabacoa coffee farms and cigar factories to coastal escapes in Punta Cana. Our tours include top-rated attractions, immersive cultural visits, and unforgettable nature experiences. Discover the best things to do in the Dominican Republic, from the capital to the coast.

Tour Details

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from $2,820

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Grenada to Antigua

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

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

Starts / Ends

St. Georges / St. John's

Activities

Village Visits, Local Market 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.

Cruise Details

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from $7,590

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Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara

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

Starts / Ends

San Juan / Miami

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.

Cruise Details

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from $3,090

SS 25%

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Grenada to Grenada

Roundtrip St George - 12 Day Itinerary aboard Star Clipper

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

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.

Cruise Details

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from $3,793

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Dominican Republic: Culture and Cocktails

8 Day Itinerary

• Visit UNESCO site in Santo Domingo
• Visit coffee factory in Jarabacoa
• Visit Los Pepines murals
• Swim in azure waters of Cayo Arena
• Visit cocoa & chocolate plantation

Starts / Ends

Santo Domingo / Santo Domingo

Activity Level

Easy Active

This 8-day journey will give you a genuine taste of the Dominican Republic. From UNESCO World Heritage Sites to street art and local delicacies, immerse yourself in the diverse landscapes and cultures of this Caribbean gem. With optional beach extensions, savor every moment of your unforgettable journey.

Tour Details

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from $3,400

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Dominican Republic: North Coast Expedition

8 Day Itinerary

• Enjoy canyoning in Puerto Plata
• See the landscape using 4x4 buggy
• Visit the Los Pepines murals.
• Learn about tobacco production
• See the lovely bay of Rio San Juan
• Zip line over the Laguna Dudu

Starts / Ends

Puerto Plata / Puerto Plata

Activities

Hiking, Wildlife Viewing, Ziplining, Rainforest Exploration

Activity Level

Easy Active

Spend your week on the vibrant North Coast of the Dominican Republic. During this 8-day Dominican Republic trip, experience stunning landscapes, beautiful pristine beaches, and rich cultural traditions, and discover the beauty of this magical stretch of coast.

Tour Details

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from $2,820

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Grenada to Grenada

Roundtrip St George - 11 Day Itinerary aboard Star Clipper

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

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.

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

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

Starts / Ends

Les Saintes / Bridgetown

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.

Cruise Details

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from $8,220

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Gliding the Waters of the Windward Islands

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

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

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.

Cruise Details

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