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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 2024-2025

Dock going out into the crystal blue ocean

Classic Yachtsman Caribbean

Antigua to Barbados
8 Days from $1,700
Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing journey is unforgettable, with destinations including Barbados, St. Lucia, Dominica, Antigua, Martinique, and more!
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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 $5,430
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 Christmas Cruise

Bridgetown to Balboa
15 Days from $3,540
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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Boats Moored to the Quay at Bridgetown Harbour

Barbados to Panama

Bridgetown to Balboa
15 Days from $4,440
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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Nassau Lighthouse

Island Odyssey: Bahamas to the Grenadines

Nassau - Bridgetown
13 Days from $23,390
Sail on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Begin the trip in Nassau then sail to Compass Cay and explore its pristine beaches, snorkel in crystal-clear waters, or spot marine life from the marina. Explore Long Island on foot or by bike and more!
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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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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 2024-2025

Trip NameSaveFromDaysNext DepartureSummary
Barbados to PanamaSavings$444015Nov 2, 2024Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to …
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Classic Yachtsman CaribbeanSavings$17008Nov 30, 2024Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
0
Grenadine IslandsSavings$17008Dec 7, 2024On this 8-day expedition cruise, the Royal Clipper explores the Grenadine Islands. Enjoy blissful, laid-back beach days and appreciate the beauty of …
0
Island Odyssey: Bahamas to the GrenadinesCustom Label$2339013Oct 24, 2024Sail on this 13-day Island Odyssey: Bahamas to the Grenadines cruise from Nassau to Bridgetown aboard Scenic Eclipse. Begin the trip in Nassau then …
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Barbados to Panama Christmas CruiseSavings$354015Dec 14, 2024Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Star Clipper sails through the turquoise Caribbean waters en route to the …
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TrustScore 4.8 | 207 reviews
TrustScore 4.8 of 5
total score
Based on 207 reviews on
review score
1 hour ago
I am a returning client to Adventure Life and am very pleased with their commitment to put together a great trip. Clara replied and clarified to any and all questions we had.
Claire Palmer
review score
2 days ago
Jessica was very responsive to my questions and never balked when I asked her to go back and find more options. She really worked hard to find the right cruise for us.
Amy Siegel
review score
2 days ago
Friendly, accommodating, knowledgeable, timely. They have made us feel very comfortable for our trip!
Gregg Chamberlain
review score
2 days ago
Adventure Life took care of a lot of details for me because I flew separately and met up with the group at the start of the trip. On the return they dropped me off in Cantania and flew back to the UK as one group. I was the only American on the Exodus trip which was not a problem. Communication between the two companies was good.
Happy Camper
review score
2 days ago
We loved our time aboard the Angel. Beautiful boat and crew. Naturalist Jose Luis was incredible-very knowledgeable and thoughtful. He adapted tours to our group and we all had an amazing trip. Love staying a the quaint hacienda and the recommended activities.
Christine

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