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Top Caribbean Trips & Tours

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Select one of the below 3 best Caribbean trips for 2025 and 2026. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Iles des Saintes, Gustavia, Marigot, Virgin Gorda, and Norman Island. Our Caribbean trips for 2025 feature hiking, urban exploration, cruises, and local market visits, and start from $2,245 for trips of 5 to 7 days. Contact Adventure Life's Caribbean trip planning experts to start planning your next seamless trip.
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Panorama of Les Saintes
$7,190
EXPLORE

Caribbean Sojourn

Bridgetown - Marigot - 7 Day Itinerary aboard Emerald Azzurra
  • Visit UNESCO-listed Nelson's dock
  • Discover quaint island towns
  • Stroll Gustavia’s colorful street
  • Dip into a therapeutic mud bath
Starts / Ends:
Bridgetown / Marigot
Activities:
Archaeological Site Visits
Activity Level:
Variable
Set sail on a 7-day Caribbean cruise aboard the luxurious Emerald Azzurra. Begin in Barbados, soaking in vibrant culture and stunning beaches. In Soufrière, indulge in volcanic mud baths and explore scenic volcanic landscapes. At Falmouth Harbour, visit Nelson’s Dockyard, a UNESCO …
Cruise Details
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Explore colorful Gustavia
$6,340
EXPLORE

Caribbean Enchantment

7 Day Itinerary aboard Emerald Azzurra
  • Visit Botanical Garden in Deshaies
  • Visit Fort Napoleon on Les Saintes
  • Visit The Baths on Virgin Gorda
  • Explore St. Barts’ vibrant streets
Starts / Ends:
St. John's / Marigot
Activities:
Adventure Options, Hiking, Local Market Visits, Snorkeling, Urban Exploration
Activity Level:
Variable
Embark on a 7-day Caribbean cruise aboard Emerald Azzurra. Start in Antigua and sail to Les Saintes, a French-Caribbean archipelago with picturesque towns and the historic Fort Napoleon. Discover Deshaies in Guadeloupe, known for its colorful Creole architecture and beautiful beaches. Visit Virgin …
Cruise Details
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Havana Musicians
$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, Local Market Visits, Urban Exploration
Activity Level:
Relaxed
Experience Classic Cuba on this 5-day Cars, Rum, and Cigars highlights tour. Encounter Hemingway's Havana as you visit his favorite bars and his former estate. Get a taste of Cuba's revolutionary spirit and contemporary culture with visits to Havana's Tropicana and Fábrica de …
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