Trips to Local Caribbean Markets

from $2,020

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Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper

Starts / Ends

St. John's / Bridgetown

Activity Level

Variable

Set sail on an 8-day cruise aboard the Royal Clipper, starting in Antigua. Highlights include snorkeling in Les Saintes, Dominica’s lush rainforests, Grenada’s spice markets, and Barbados’ rich heritage.

• Explore Antigua’s vibrant dockyards
• Discover Les Saintes’ beaches
• Relax on Martinique’s white sands
• Stroll Grenada’s aromatic markets

Cruise Details

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from $8,390

2for1

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Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra

Starts / Ends

San Juan / St. John's

Activities

Hiking

Activity Level

Variable

Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.

• Discover Culebra Island’s shores
• Explore Vieques Island waterfront
• Tour St. John’s Annaberg ruins
• Relax on Jost Van Dyke’s White Bay

Cruise Details

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from $7,590

2for1

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Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara

Starts / Ends

St. Thomas / St. Thomas

Activity Level

Variable

Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty. Philipsburg’s lively port, Gustavia’s charming streets, and tranquil Saint John Island round out this cruise.

• Explore Saint John's pristine beach
• Stroll Philipsburg's lively markets
• Snorkel Norman Island's caves
• Visit 'The Baths' in Virgin Gorda

Cruise Details

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from $7,990

2for1

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Quintessential Caribbean

8 Day Itinerary aboard Emerald Sakara

Starts / Ends

San Juan / St. Thomas

Activities

Urban Exploration

Activity Level

Variable

Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbour, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays. Enjoy unique experiences and stunning landscapes throughout your cruise.

• Relax on Prickly Pear Cays' beaches
• Visit Guadeloupe’s fishing village
• Visit port of Falmouth Harbour
• Wander through lively Cruz Bay

Cruise Details

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from $4,800

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Bridgetown to Bridgetown

8 Day Itinerary aboard Silver Spirit

Starts / Ends

Bridgetown / Bridgetown

Activities

Wildlife Viewing, Spa Relaxation, Small Ship Sailing, Archaeological Site Visits, Local Market Visits

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.

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

Cruise Details

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from $3,090

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Jamaica to Antigua

12 Day Itinerary aboard Star Clipper

Starts / Ends

Port Antonio / St. John's

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 $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 $3,237

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Dominican Republic: North Coast Expedition

8 Day Itinerary

Starts / Ends

Puerto Plata / Puerto Plata

Activities

Ziplining, Rainforest Exploration

Activity Level

Easy Active

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

• 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

Tour Details

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from $3,125

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Dominican Republic: Culture and Cocktails

8 Day Itinerary

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.

• 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

Tour Details

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from $2,612

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Best of Dominican Republic

8 Day Itinerary

Starts / Ends

Punta Cana / Punta Cana

Activities

Volunteering, Hacienda Visits

Activity Level

Relaxed

Discover the best of the Dominican Republic's highlights on this 8-day adventure, from the idyllic beaches of Punta Cana to the historic charm of Santo Domingo, the lush landscapes of Jarabacoa, the cultural richness of Santiago de los Caballeros, the bustling streets of San Francisco de Macoris, and the coastal allure of Las Terrenas.

• 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

Tour Details

0

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

Activities

Snorkeling, Village Visits

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 $4,240

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Barbados to Panama

Bridgetown - Balboa - 15 Day Itinerary aboard Star Clipper

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.

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

Cruise Details

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from $4,350

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Panama to Antigua

15 Day Itinerary aboard Royal Clipper

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.

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

Cruise Details

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from $2,245

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Classic Cuba

Cars, Rum, and Cigars - 5 Day Itinerary

Activity Level

Relaxed

Rolled cigars, rum spiked with sugarcane juice, and colorful vintage cars - these are the icons of Cuba that await you on this 5-day People-to-People classic Cuba tour. Find yourself immersed in legendary Cuban culture as you explore legendary Havana, the tobacco mecca Vuelta Abajo, and breathtaking Valle de Viñales.

• Walk the vibrant streets of Havana
• Sample rum and local delicacies
• Tour cigar-rolling factories
• Explore stunning Valley de Vinales
• View Hemingway's former estate

Tour 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 $3,590

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Cuba Walking Tour

8 Day Itinerary

Starts / Ends

Havana / Havana

Activities

Homestays

Activity Level

Moderate

Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, Vinales, Havana, and five parks & reserves. Explore by foot and encounter local experts, farmers, and artists as you gain insight into their history, traditions & vibrant culture on this highlights Cuba trip.

• Explore Cuba on foot
• Snorkel in Zapata National Park
• Learn about the tobacco industry
• Hike to waterfalls and caves
• Be immersed in Cuba's culture
• Experience Cuban hospitality

Tour Details

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from $4,610

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Westbound Atlantic Ocean Crossing

Malaga - Bridgetown - 25 Day Itinerary aboard Star Clipper

Starts / Ends

Malaga / Bridgetown

Activity Level

Variable

Embark on a 25-day cruise aboard the Star Clipper, exploring Spain, Morocco, and the Canary Islands before heading to Barbados. Experience diverse cultures, stunning landscapes, and relaxation at sea on this unforgettable journey.

• Explore Malaga’s Moorish Alcazaba
• Discover Tangier’s culture
• Wander Cadiz’s palm-lined streets
• Visit Safi’s old town

Cruise Details

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from $7,120

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Westbound Atlantic Ocean Crossing

Civitavecchia - Bridgetown - 29 Day Itinerary aboard Royal Clipper

Starts / Ends

Civitavecchia / Bridgetown

Activity Level

Variable

Set sail on a 29-day cruise aboard the Royal Clipper, traveling from Civitavecchia to the Caribbean while exploring historic and vibrant locations like Bonifacio, Ibiza, and Malaga. Enjoy days at sea, classic sailing experiences, and onboard activities before reaching Barbados.

• Explore Bonifacio’s scenic harbor
• Discover Mahon’s Georgian charm
• Wander Palma’s markets
• Unwind on Ibiza’s beaches

Cruise Details

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