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Tobago Cays Small Ship Cruises, & Tours

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Visit the stunning archipelago of Tobago Cays located in the Southern part of the St. Vincent des Grenadines. Take a long walk on the stunning white sand beaches that are picture perfect for snorkeling, swimming and scuba diving. Visit Baradal: a small island in the Tobago Cays that offers a getaway from crowds, fantastic beaches, and a beautiful tropical forest in the mid-section. Petit Tabac (also known as Jack Sparrow Island) is the most popular island to visit in the Cays, this is because it has a top notch beach, Pirates of the Caribbean was filmed here which offers cool tourist destinations, and it's crowded, which is a benefit for some. Travel on a luxury small ship cruise that allows access to smaller coves, reefs, and ports to improve your Caribbean experience. Contact our travel experts to start planning your personalized trip today!

Top Tobago Cays Small Ship Cruises, Trips, and Tours for 2025-2026

White Sand Beach in Barbados

Grenadine Islands

Bridgetown to Bridgetown
8 Days from $1,700
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.
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St George's Harbor - Grenada

Pearls of the Caribbean

Fort de France to Fort de France
9 Days from $6,620
Join the Le Champlain on its 9-day sailing expedition to explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, Bequia Island and tour the Grenadine Islands - one of the world’s most stunning archipelagos
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Boats Moored to the Quay at Bridgetown Harbour

Barbados to Panama

Bridgetown to Balboa
15 Days from $3,830
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Grenada, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, immerse yourself in tribal culture, and marvel at the Panama Canal.
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Take a leisurely stroll through beautiful Bridgetown

Grenadines & Windwards Yachting

Bridgetown to Bridgetown
8 Days from $7,990
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.
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Beautiful beach in Dominica

Gliding the Waters of the Windward Islands

Pointe-a-Pitre Roundtrip
8 Days from $8,200
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.
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Soufriere bay, St Lucia

Pearls of the Caribbean

Roundtrip Fort-de-France
9 Days from $5,200
Join Le Bellot on its 9-day sailing expedition roundtrip from Fort-de-France and explore the enchanting islands in the Caribbean Sea visiting Port Elizabeth, St. George's, Saint Lucia, Soufrière and many more!
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Boats Moored to the Quay at Bridgetown Harbour

Barbados to Panama

Bridgetown to Balboa
15 Days from $3,720
Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Star Clipper sails through the turquoise Caribbean waters en route to the Panama Canal, visiting Tobago Cays, Bonaire, Curacao, Aruba, and Colombia along the way. Explore the tropical jungles, snorkel in vibrant reefs, Experience tribal culture, and the Panama Canal.
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Relax on the shores of the Caribbean

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

Vieux Fort - Fort-de-France
9 Days from $6,320
From Vieux Fort, St. Lucia set sail aboard Le Bellot for a 9-day Caribbean Windward cruise to visit the heart of the most enchanting islands in the Caribbean Sea. Before disembarking in Vieux Fort, explore long stretches of white-sand beaches, idyllic turquoise waters, and the laid-back island way of life.
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Stroll along the beautiful beaches of the Caribbean

The Essential of the Caribbean

Fort-de-France Roundtrip
13 Days from $8,150
Sail the lovely seas of the Caribbean roundtrip from Fort-de-France to discover the stunning islands of Antigua, Jost van Dyke, Gustavia, and Portsmouth. Join this 13-day cruise onboard Le Champlain to the heart of the West Indies.
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Enjoy the beautiful blue Caribbean

Discover Eastern Caribbean & Grenadines

Marigot - Bridgetown
15 Days from $21,340
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.
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Tobago Cays & St. Vincent des Grenadines Travel Guide

Port Elizabeth, Bequia

Windward Islands Geography

The Windward Islands in the Lesser Antilles of the Caribbean Islands forms the easternmost boundary of the Caribbean Sea. The Windward Islands are unique because they usually have mountainous or volcanic origins.
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The Best Time to Visit the Tobago Cays

Just like most Caribbean islands, the best time to visit the Tobago Cays is during the shoulder months for the less expensive prices and considerably fewer crowds. The best time to visit St. Vincent des Grenadines is between May and June for just that reason.

Between July and October is the off-season in the Cays that corresponds with hurricane season in this area. Tropical storms are at their height in July and they'll last until October but the landscape of these islands is majestic and your trip will be considerably less expensive. 

November, at the tail end of hurricane season, is an excellent time to visit for those wanting to save some money but not sacrifice the sunny experience. This is a shoulder season as the Cays begin preparing for the upcoming busy high season.

Between December and April is the peak tourism season on these islands and can be a good time to go. Hotel rates and crowds will be at their height but the weather is perfect and this can be a nice break from the winter season depending on where you're coming from
Port Elizabeth, Bequia

Windward Islands Geography

The Windward Islands in the Lesser Antilles of the Caribbean Islands forms the easternmost boundary of the Caribbean Sea. The Windward Islands are unique because they usually have mountainous or volcanic origins.
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Top Tobago Cays Small Ship Cruise Deals for 2025-2026

Trip NameSaveFromDaysNext DepartureSummary
The Essential of the Caribbean$815013Dec 17, 2024Sail the lovely seas of the Caribbean roundtrip from Fort-de-France to discover the stunning islands of Antigua, Jost van Dyke, Gustavia, and …
0
Grenadines & Windwards YachtingCustom Label$79908Mar 8, 2025Set sail on an 8-day extraordinary Caribbean cruise, discovering pristine beaches and vibrant coral reefs while hopping between culturally rich …
0
Discover Eastern Caribbean & GrenadinesCustom Label$1598015Jan 16, 2027Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. …
0
Discover Eastern Caribbean & GrenadinesCustom Label$2134015Dec 6, 2025Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the …
0
Discover Eastern Caribbean & GrenadinesCustom Label$1518015Nov 15, 2025Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the …
0
TrustScore 4.8 | 405 reviews
TrustScore 4.8 of 5
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Based on 405 reviews on
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5 days ago
Wonderful personal attention to detail and very helpful suggestions by experienced travel experts
John K
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6 days ago
Franny has been such an amazing help with all my trip planning. This is our 3rd trip to plan with her and she is always so willing to assist and find the best deals for my family and friends.
Suzanne Turbyfill
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1 week ago
Our advisor at Adventure Life, Mary Curry, was knowledgable and quick to respond with answers to any questions we had. She made our booking efficiently and set up a time for us to make a secure payment through her directly. We’ve used Adventure Life repeatedly and would definitely recommend it.
Sarika FREY
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1 week ago
Very efficient and responsive.
Patricia
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1 week ago
I selected Adventure Travel as I was not satisfied with the responsiveness of the agent for the cruise I was trying to book and it had good recommendations. So far, I am quite happy with my agent, Betty, very responsive and accommodating.
charles

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