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Top Tobago Cays Trips & Tours in January 2026

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Discover Tobago Cays in January 2026 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during January 2026 as you enjoy Snorkeling, Kayaking, Village Visits, Archaeological Site Visits, and Small Ship Sailing. Prices for trips in January 2026 range from $2,030 to $62,480 for a vacation of 8 to 15 days. Choose any of the below 6 itineraries in January 2026 and customize it when you contact one of Adventure Life's expert Tobago Cays trip planners.
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    • Tobago Cays
Take a leisurely stroll through beautiful Bridgetown
from $8,790
OBC
EXPLORE

Grenadines & Windwards Yachting

Roundtrip Bridgetown - 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
Activity Level
Variable
Embark on an 8-day cruise aboard the Emerald Sakara, starting and ending in Bridgetown, Barbados. Explore historic towns, relax on stunning beaches, and enjoy snorkeling and water activities in the picturesque Saint Vincent and the Grenadines.
Cruise Details
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Beautiful beach in Dominica
from $9,870
EXPLORE

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip - 8 Day Itinerary aboard Le Ponant
  • Enjoy iconic pitons of Saint Lucia
  • Learn about Kalinago culture
  • Explore Tobago Cays' coral reefs
  • Relax on Marie-Galante's beaches
Starts / Ends
Dominica / Anses d'Arlet
Activities
Small Ship Sailing, 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.
Cruise Details
0
The crystal blue water of Jost van Dyke
from $2,820
EXPLORE

Antigua to Grenada

Antigua to Grenada - 11 Day Itinerary aboard Star Clipper
  • Explore Gustavia boutiques
  • Swim Norman Island coves
  • Visit Jost van Dyke beaches
  • Relax in St. Kitts landscapes
Starts / Ends
St. John's / St. Georges
Activities
Snorkeling, Hiking
Activity Level
Variable
Set sail on an 11-day Caribbean cruise aboard Star Clipper. Depart from Antigua and explore St. Barts, the British Virgin Islands, St. Kitts, Martinique, Bequia, and Grenada. Discover historic harbors, swim in crystal waters, and relax on world-class beaches.
Cruise Details
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White Sand Beach in Barbados
from $2,030
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
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.
Cruise Details
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Variety of boats and yachts on of Bequia's harbors in the Grenadines.
from $22,140
OBC
EXPLORE

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Explore Anguilla’s turquoise waters
  • Stroll through Gustavia
  • Admire Nevis’ tranquil shores
  • Visit Antigua’s Falmouth Bay
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.
Cruise Details
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Visit beautiful St. Vincent
from $22,140
OBC
EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Marigot - 15 Day Itinerary aboard Emerald Sakara
  • Explore Bridgetown’s capital
  • Wander Speightstown’s streets
  • Discover Kingstown’s gardens
  • Unwind on Bequia Island
Starts / Ends
Bridgetown / Marigot
Activities
Kayaking, Village Visits, Archaeological Site Visits, Local Market Visits
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.
Cruise Details
0
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