Caribbean Cultural Tours

from $9,190

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Splendours of the Caribbean

San Juan - St. Thomas - 7 Day Itinerary aboard Emerald Sakara

• Tour Nelson’s Dockyard
• Explore Nevis Island plantations
• Walk through Gustavia
• Swim Prickly Pear Cays

Starts / Ends

San Juan / St. Thomas

Activities

Village Visits, Urban Exploration

Activity Level

Variable

Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.

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from $4,800

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Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit

• Hike to Saint Lucia’s Pitons
• Snorkel Martinique’s colorful reefs
• Explore Gustavia’s historic harbor
• Stroll Bequia’s scenic shores

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Embark on an 8-day Caribbean round-trip cruise from Bridgetown aboard the Silver Spirit. Explore some of the most iconic and lesser-known islands in the region, including Saint Lucia, Martinique, Saint Barthelemy, Dominica, Grenada, and Bequia. Each destination offers unique cultural experiences, breathtaking natural beauty, and vibrant local life.

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from $21,340

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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.

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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

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.

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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.

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from $11,600

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Bridgetown to Bridgetown

22 Day Itinerary aboard Silver Spirit

• Explore top Caribbean islands
• Visit Bequia and Iles des Saintes
• Explore Gustavia’s historic harbor
• Experience the Caribbean culture

Starts / Ends

Bridgetown / Bridgetown

Activity Level

Variable

Sail round-trip from Bridgetown aboard Silver Spirit on a 22-day Caribbean cruise. Explore top islands like St. Lucia, Martinique, and Barbados, plus hidden gems like Bequia and Iles des Saintes. Enjoy beach days, island tours, and cultural stops with long port calls.

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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.

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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, Ziplining

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.

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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.

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from $4,330

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Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper

• Explore Bridgetown’s heritage
• Discover St. George’s coastal views
• Admire Kralendijk’s marine life
• Wander Willemstad’s streets

Starts / Ends

Bridgetown / Balboa

Activity Level

Variable

Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.

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from $3,420

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Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer

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

Starts / Ends

Philipsburg / Malaga

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.

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from $4,450

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Panama to Antigua

15 Day Itinerary aboard Royal Clipper

• Explore Balboa’s colonial charm
• Transit Panama’s iconic canal
• Discover San Blas culture
• Enjoy Aruba’s clear waters

Starts / Ends

Balboa / St. John's

Activity Level

Variable

Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.

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from $5,175

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West Caribbean Cruise

Belize - Fort Lauderdale - 10 Day Itinerary aboard SH Vega

• Explore Belize City
• Sail toward Grand Cayman
• Swim with stingrays
• Discover Montego Bay

Starts / Ends

Belize City / Fort Lauderdale

Activities

Rainforest Exploration, Helicopter Tours

Activity Level

Variable

Embark on an 10-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.

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from $5,610

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Eastbound Atlantic Ocean Crossing

Barbados to France - 29 Day Itinerary aboard Royal Clipper

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

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.

Cruise Details

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from $3,150

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Panama to Aruba

12 Day Itinerary aboard Star Clipper

• Transit the Panama Canal locks
• Walk colonial Balboa streets
• Explore forts in Portobelo
• Visit San Blas and Guna villages
• See Cartagena and Santa Marta

Starts / Ends

Balboa / Oranjestad

Activities

Archaeological Site Visits, Small Ship Sailing, Local Market Visits, Snorkeling

Activity Level

Variable

Sail the Panama Canal on a 10-day Star Clippers cruise through Central America. Begin in Balboa, then transit the Panama Canal and see the locks in action. Explore Spanish forts in Portobelo, meet the Guna people in the San Blas Islands, and discover Colombia’s coastal cities of Cartagena and Santa Marta. Enjoy scenic days under sail.

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from $24,990

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Pristine Islands of the Bahamas & the Panama Canal

Nassau - Panama City - 11 Day Itinerary aboard Scenic Eclipse

• Explore Nassau’s colonial streets
• Visit Staniel Cay’s beaches
• Discover San Salvador’s coral reefs
• Meet Cabo de La Vela’s Wayuu people

Starts / Ends

Nassau / Panama City

Activities

Wildlife Viewing

Activity Level

Variable

Join an 11-day cruise from Nassau to Panama City on the Scenic Eclipse, exploring the Bahamas' clear waters and vibrant island cultures. Experience highlights like Pig Beach and the Panama Canal, blending leisure with cultural discovery.

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from $3,199

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Southern Caribbean Yacht Harbors

Halifax - Bridgetown - 9 Day Itinerary aboard Seabourn Venture

• Tour Citadel Hill
• Visit Brimstone Hill Fortress
• Snorkel at Pigeon Island
• Visit Saint Lucia’s famous Pitons

Starts / Ends

Halifax / Bridgetown

Activities

Kayaking, Spa Relaxation, Photography Seminars

Activity Level

Variable

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.

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

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

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.

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