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Top Caribbean Trips & Tours in February 2026

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Discover Caribbean in February 2026 on one of these 9 tours hand-selected by the travel experts at Adventure Life. Explore the best of Bridgetown, Tobago Cays, Havana, Basseterre, and Falmouth during February 2026 as you enjoy snorkeling, cruises, small ship cruises, homestays, and small ship sailing. Prices for trips in February 2026 range from $1,640 to $32,040 for a vacation of 5 to 9 days. Choose any of the below 9 itineraries in February 2026 and customize it when you contact one of Adventure Life's expert Caribbean trip planners.
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White Sand Beach in Barbados
$1,700
EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Variable
Join the Royal Clipper on this 8-day cruise through the Grenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts, Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day. From the horseshoe-shaped Carenage at St. …
Cruise Details
0
Pink beach huts in the Caribbean
$1,700
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest
$1,640
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
0
Relax on the beaches of St. Maarten
$1,640
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on an 8-day cruise aboard the Star Flyer. With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this unique region, …
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
$7,590
EXPLORE

Grenadines & Windwards Yachting

8 Day Itinerary aboard Emerald Sakara
  • Discover Bequia’s secluded beaches
  • Savor Caribbean dining experiences
  • Snorkel Tobago Cays' waters
  • Admire panoramic views from Mayreau
Starts / Ends:
Bridgetown / Bridgetown
Activities:
Snorkeling
Activity Level:
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Set sail from Bridgetown, Barbados, and discover stunning destinations across the Caribbean Sea. Visit Port St. Charles in Barbados, where glassy blue waters invite swimming, sailing, and snorkeling. Explore Kingstown, the capital of …
Cruise Details
0
Kayaking in Cuba
$3,390
EXPLORE

Cuba Kayaking West Tour

8 Day Itinerary
  • See Cuba's great cities
  • Visit the Bay of Pigs
  • Kayak and snorkel in Cuba
  • Enjoy unique architecture & cuisine
Activities:
Homestays, Kayaking, Snorkeling
Activity Level:
Easy Active
The world’s fascination with Cuba has lasted for many generations, and for good reason. Cuba is a cultural hub, with a mix of descendants of indigenous people, European immigrants, and slaves. The country's music and art draw from these diverse influences. Cuba has also exerted an …
Tour Details
0
Relax on the shores of the Caribbean
$6,320
EXPLORE

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Vieux Fort - Fort-de-France - 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
Activities:
Land & Sea Exploration, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Embark on a 9-day cruise through the Caribbean aboard Le Bellot, tailored for travelers seeking cultural immersion. Start in Vieux Fort, St. Lucia, and see the UNESCO-listed Gros and Petit Pitons. Sail to Portsmouth, Dominica, to explore landscapes and local chocolate. Continue to Les Saintes, …
Cruise Details
0
Farmer harvests his crop in Cuba
$3,390
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
Activities:
Hiking, Homestays, Local Market Visits, Snorkeling, Urban Exploration, Wildlife Viewing
Activity Level:
Moderate
Experience the diversity of Cuba on an 8-day guided Cuba tour. This People-to-People tour explores the diverse urban cities of Cienfuegos, Trinidad, and Havana and provides visitors incredible opportunities to delve into the rich traditions and heritage of Cuban culture. Hike pristine landscapes, …
Tour 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 …
Tour Details
0
1-9 of 9 Results
TrustScore 4.8 | 344 reviews
TrustScore 4.8 of 5
total score
Based on 344 reviews on
review score
5 hours ago
Arvin has been very responsive and professional.
Carlotta Diaz
review score
1 day ago
Claudia Corona was very helpful and professional. She answered all my many questions in a very timely manner and really worked with me to taylor-make my trip. Very good experience.
Katie Dahlman
review score
3 days ago
We had such a great experience with Adventure Life when we booked the Galapagos trip a few years ago. Mary Curry helped us then, and again now. She is very knowledgeable, prompt in communication back and forth, and makes it so easy. Thank you, Mary! P.S. Your chat room person, Jo, was also wonderful.
MTPhil
review score
4 days ago
The entire experience was great. Erin really knows her stuff and provided me with a lot of great insight and advice.
MARGARET CINCOTTA
review score
5 days ago
Mary Curry is the BEST! I have worked with her for multiple family trips for over 10 years, and she is responsive, works within your preferences and budget, has great suggestions and has personal travel experience at many of the locations. We prefer active family vacations and Adventure Life and Mary Curry make sure that is what we get!
Heather Spanbauer

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