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Top Caribbean Trips & Tours in January 2026

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Discover Caribbean in January 2026 on one of these 20 tours hand-selected by the travel experts at Adventure Life. Explore the best of during January 2026 as you enjoy Snorkeling, Small Ship Sailing, Village Visits, Wildlife Viewing, and Hiking. Prices for trips in January 2026 range from $1,960 to $62,480 for a vacation of 5 to 15 days. Choose any of the below 20 itineraries in January 2026 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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Pink beach huts in the Caribbean
from $2,020
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Windward Islands

Roundtrip Barbados - 8 Day Itinerary aboard Royal Clipper
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Cruise Details
0
White Sand Beach in Barbados
from $2,020
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Grenadine Islands

8 Day Itinerary aboard Royal Clipper
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of nature on this Caribbean adventure.
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,960
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Treasure Islands

8 Day Itinerary aboard Star Flyer
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Cruise Details
0
St Barts harbor view
from $8,390
2for1
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Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
St. John's / San Juan
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Cruise Details
0
Explore the famous rock formations of the baths
from $5,245
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A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
Starts / Ends
San Juan / San Juan
Activity Level
Variable
Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Cruise Details
0
Relax on the beaches of St. Maarten
from $1,960
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Leeward Islands

8 Day Itinerary aboard Star Flyer
Starts / Ends
Philipsburg / Philipsburg
Activity Level
Variable
The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Cruise Details
0
Enjoy the beautiful blue Caribbean
from $22,140
2for1
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Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
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.
  • Experience Falmouth's historic port
  • Discover Soufriere's Sulfur Spring
  • Visit Falmouth Harbour in Antigua
  • Explore Nelson’s Dockyard
Cruise Details
0
Relax on the sunny beaches of the Caribbean
from $7,990
2for1
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Eastern Caribbean with St. Barths

Marigot - Bridgetown - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
Marigot / Bridgetown
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbour’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise
  • Experience Falmouth's historic port
  • Discover Soufriere's Sulphur Spring
  • Visit Falmouth Harbour in Antigua
  • Explore Nelson’s Dockyard
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
from $8,790
2for1
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Grenadines & Windwards Yachting

8 Day Itinerary aboard Emerald Sakara
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Set sail on an 8-day extraordinary Caribbean cruise, discovering pristine beaches and vibrant coral reefs while hopping between culturally rich islands aboard Emerald Sakara. Enjoy pristine beaches, vibrant local cultures, and water activities like swimming and snorkeling.
  • Discover Bequia’s secluded beaches
  • Savor Caribbean dining experiences
  • Snorkel Tobago Cays' waters
  • Admire panoramic views from Mayreau
Cruise Details
0
Explore colorful Gustavia
from $11,390
2for1
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Eastern Caribbean with St. Barths

Bridgetown - Marigot - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
Bridgetown / Marigot
Activity Level
Variable
Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
  • Explore Bridgetown's culture
  • Stroll Gustavia's colorful streets
  • Admire Marigot’s scenic coastline
  • Savor Soufriere's delicious cuisine
Cruise Details
0
Explore beautiful Jost van Dyke
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, Village Visits
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
0
Explore colorful Bridgetown, Barbados
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
0
The crystal blue water of Jost van Dyke
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
0
Relax on the shores of the Caribbean
from $22,140
2for1
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Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara
Starts / Ends
Bridgetown / Marigot
Activities
Snorkeling
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.
  • Experience Falmouth's historic port
  • Discover Soufriere's Sulfur Spring
  • Visit Falmouth Harbour in Antigua
  • Explore Nelson’s Dockyard
Cruise Details
0
Kayaking in Cuba
from $3,590
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Cuba Kayaking West Tour

8 Day Itinerary
Activities
Kayaking
Activity Level
Easy Active
Experience Cuba on a unique land and kayaking program. Discover three of Cuba’s greatest resources: its people, colorful culture, and natural wonders. In Havana, meet the artists, musicians, and historians who are preserving tradition. Explore great colonial cities and pristine marine & terrestrial habitats.
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Tour Details
0
Bicycle on Cuban street
from $4,390
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Cuba Cycling Tour

Quintessential Cuba - 8 Day Itinerary
Activity Level
Moderate
A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where Cuba’s history may not have been made, but where it was lived every day. It reveals to you to Cuba’s true resource, its true legend: its people.
  • Cycle through western Cuba
  • Visit Hemingway's former home
  • Ride through Cuba's tobacco fields
  • Explore Havana on foot
Tour Details
0
Beautiful beach in Dominica
from $8,370
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Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
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.
  • Enjoy iconic pitons of Saint Lucia
  • Learn about Kalinago culture
  • Explore Tobago Cays' coral reefs
  • Relax on Marie-Galante's beaches
Cruise Details
0
Cycling through the revolutionary landscape of Cuba
from $3,890
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Cuba Multisport

8 Day Itinerary
Starts / Ends
Havana / Havana
Activities
Biking, Homestays
Activity Level
Moderate
Explore the intriguing island of Cuba on this active 8-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil countryside. Experience great colonial cities including Havana, Cienfuegos, Trinidad, and Sancti Spiritus. Discover Cuba's history, rich traditions, and dynamic present on this Cuba multisport trip.
  • Bike, kayak, snorkel, and hike Cuba
  • Appreciate Cuba's colonial past
  • Be immersed in Cuba's culture
  • Enjoy excellent wildlife viewing
  • Experience Cuban hospitality
Tour Details
0
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