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Caribbean Urban Exploration Tours

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Discover the vibrant urban landscapes of the Caribbean on our 9 captivating city tours for 2026. Surrounded by crystal-clear waters and lush tropical scenery, our Caribbean city tours offer a journey that seamlessly blends culture, history, and adventure, providing an in-depth understanding of this remarkable destination. Over 5 to 15 days, you will explore the Hidden Charms of the Caribbean, from the charming streets of San Juan to the French flair of Gustavia and the serene beaches of St. John. Indulge in village visits, urban exploration, and wildlife viewing, immersing yourself in the rich heritage of these vibrant cities. With prices starting at $2,245 to $37,570, embark on a Caribbean adventure that unveils the magic of the region's diverse landscapes and urban environments. Contact us to start planning your tropical getaway today!
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City of Basseterre and Frigate Bay from the Timothy Hill viewpoint in St. Kitts.
from $12,690
EXPLORE

Discover the Pearls of the Caribbean

Bridgetown - Sint Maarten - 15 Day Itinerary aboard Emerald Sakara
  • Visit Soufriere mud baths
  • Tour Iles des Saintes Fort Napoleon
  • See St. John's Nelson’s Dockyard
  • Observe Anguilla beaches
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Set sail on a 15-day Caribbean cruise from Barbados aboard the Emerald Sakara, visiting Saint Lucia for its mud baths, Antigua's historic dockyard, and Anguilla's vibrant coral reefs. Conclude your journey in Philipsburg, Sint Maarten, enjoying the region's rich culture and cuisine.
Cruise Details
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Enjoy the beautiful blue Caribbean
from $12,690
EXPLORE

Discover the Pearls of the Caribbean

Sint Maarten - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Experience Soufriere mud baths
  • See St. John's Nelson’s Dockyard
  • Discover Charlestown beaches
  • Visit Gustavia painted houses
Starts / Ends
Philipsburg / Bridgetown
Activities
Village Visits
Activity Level
Variable
Set sail on a 15-day Caribbean cruise aboard the Emerald Sakara, visiting islands like Anguilla for snorkeling and Virgin Gorda for stunning rock formations. Explore vibrant Gustavia in Saint Barthelemy, enjoy the charm of the Iles des Saintes, relax in Saint Lucia's hot springs, and experience the colonial beauty of Barbados.
Cruise Details
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Explore the famous rock formations of the baths
from $9,190
EXPLORE

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
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.
Cruise Details
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Explore colorful Bridgetown, Barbados
from $7,195
EXPLORE

Beaches of the Grenadines

Roundtrip Bridgetown - 9 Day Itinerary aboard Emerald Azzurra
  • Tour Soufriere pair of lava domes
  • Experience Bequia Island beaches
  • Enjoy Union Island beaches
  • Visit Tobago Cays to spot turtles
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Set sail on a 9-day Caribbean cruise from Bridgetown on the Emerald Azzurra, exploring charming locations like Speightstown, Kingstown, and Bequia Island. Discover stunning beaches, marine life, and local culture before returning to Bridgetown.
Cruise Details
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Stroll along the beaches of Puerto Rico
from $9,295
EXPLORE

Paradise Beaches from the U.S. Virgin Islands to The Bahamas

San Juan - Miami - 10 Day Itinerary aboard Emerald Kaia
  • Tour Grand Turk lighthouse
  • Wander Gordon's Beach
  • Walk Nassau bustling Straw Market
  • Dive San Salvador Island
Starts / Ends
San Juan / Miami
Activities
Urban Exploration, Local Market Visits, Snorkeling, Archaeological Site Visits
Activity Level
Variable
Set sail on a 10-day Caribbean cruise aboard the Emerald Kaia from San Juan, Puerto Rico, exploring the beautiful Turks and Caicos Islands and vibrant marine life in The Bahamas. Enjoy fresh local seafood and conclude your journey in the lively metropolis of Miami, blending cultural discovery with natural beauty.
Cruise Details
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Relax on the shores of the Caribbean
from $12,295
EXPLORE

Grenadines, Colombia & Panama Canal Transit

Bridgetown - Panama City - 12 Day Itinerary aboard Emerald Azzurra
  • Explore Bequia Caribbean lifestyle
  • Admire Cartagena Old Town
  • See San Blas Islands nature
  • Navigate the Panama Canal
Starts / Ends
Bridgetown / Panama City
Activity Level
Variable
Set sail on a 12-day Caribbean cruise from Bridgetown aboard the Emerald Azzurra, exploring islands like Bequia and Mayreau. Conclude your journey in Panama City after traversing the historic Panama Canal and enjoying vibrant local cultures and stunning coastal views.
Cruise Details
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Sunset over Cartagena, Colombia
from $12,295
EXPLORE

Panama Canal Transit, Colombia & the Grenadines

Panama City - Bridgetown - 12 Day Itinerary aboard Emerald Azzurra
  • Explore Cartagena walled Old Town
  • Discover Santa Marta oldest city
  • Tour Willemstad Queen Emma Bridge
  • See Mayreau Island Station Hill
Starts / Ends
Panama City / Bridgetown
Activity Level
Variable
Set sail on a 12-day Caribbean cruise from Bridgetown aboard the Emerald Azzurra, exploring islands like Bequia and Mayreau. Conclude your journey in Panama City after traversing the historic Panama Canal and enjoying vibrant local cultures and stunning coastal views.
Cruise Details
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Havana Musicians
from $2,245
EXPLORE

Classic Cuba

Cars, Rum, and Cigars - 5 Day Itinerary
  • 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
Activities
Hiking, Homestays
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.
Tour Details
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Farmer harvests his crop in Cuba
from $3,590
EXPLORE

Cuba Walking Tour

8 Day Itinerary
  • 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
Starts / Ends
Havana / Havana
Activities
Wildlife Viewing
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.
Tour Details
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