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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!
All Tobago Tours

Top 10 Tobago Cays Small Ship Cruises, Trips, and Tours for 2026-2027

All Tobago Tours
Take a leisurely stroll through beautiful Bridgetown

Grenadines & Windwards Yachting

8 Days from $11,990
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.
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White Sand Beach in Barbados

Grenadine Islands

8 Days from $2,080
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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Explore colorful Bridgetown, Barbados

Grenadines & Windwards Yachting

8 Days from $9,990
Embark on an 8-day Caribbean cruise from Bridgetown, Barbados aboard Emerald Azzurra. Visit Kingstown, Bequia, Mayreau, Union Island, and Tobago Cays. Discover small island communities, historical landmarks, coral reefs, and quiet beaches. Enjoy daily opportunities for swimming, snorkeling, and local exploration in Saint Vincent and the Grenadines.
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Beautiful beach in Dominica

Gliding the Waters of the Windward Islands

8 Days from $8,370
Explore Guadeloupe and the Southern Caribbean aboard Le Ponant on an 8-day cruise. Swim in Tobago Cays, snorkel at Sandy Island, discover Grande Anse d’Arlet, visit Portsmouth, sail past The Pitons, and experience Creole culture, beaches, reefs, and island towns across multiple Caribbean destinations.
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Soufriere bay, St Lucia

Relax The Caribbean Way

8 Days from $6,495
Experience an 8-day voyage aboard Sea Cloud II roundtrip from Bridgetown, Barbados, through the Lesser Antilles & Grenadines. You snorkel in the Tobago Cays, explore spice-rich Grenada, visit Saint-Pierre in Martinique, admire St. Lucia’s Pitons, and enjoy Caribbean sunsets at sea.
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Bright blue waters of the Caribbean

Pearls of the Caribbean

8 Days from $5,360
Embark on an 8-day Caribbean cruise from Martinique through the Grenadines aboard Le Bougainville. Explore vibrant towns, secluded beaches, coral reefs, tropical islands, and volcanic landscapes. Snorkel, swim, stroll along scenic shores, and enjoy historic sites.
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Magnificent sailing ship moored in the Soufrière Bay, on the southwest coast of Saint Lucia.

Grenada to Antigua

8 Days from $2,010
Embark on an 8-day cruise from St. George’s, Grenada, aboard the Star Clipper, visiting highlights like Fort George and the Tobago Cays for snorkeling. The journey wraps up in St. Kitts after exploring St. Lucia's Pitons, Martinique's beaches, and Dominica's rainforests.
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Boats Moored to the Quay at Bridgetown Harbour

Barbados to Panama

15 Days from $4,450
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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Explore colorful Bridgetown, Barbados

Beaches of the Grenadines

9 Days from $7,195
Set sail on a 9-day Caribbean cruise from Bridgetown on the Emerald Azzurra, exploring charming locations like Speightstown, Kingstown, and Bequia Island. Discover stunning beaches, marine life, and local culture before returning to Bridgetown.
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Bright blue waters of the Caribbean

Aruba to Grenada

11 Days from $2,880
Set sail on an 11-day Caribbean cruise aboard the Star Clipper from Aruba to Grenada, exploring vibrant destinations like Oranjestad and Willemstad. Enjoy highlights such as snorkeling in Tobago Cays and visiting St. George’s and its historic sites in Grenada.
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Top Tobago Cays Deals

Top 8 Tobago Cays Small Ship Cruise Deals for 2026-2027

Trip Name From Days Summary
Grenadines & Windwards Yachting $11,990 8 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.
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Discover Eastern Caribbean & Grenadines $15,980 15 Set sail on a 15-day Caribbean journey, where pristine beaches, vibrant coral reefs, and island-hopping adventures immerse you in diverse cultures. Experience the genuine warmth of local hospitality as you explore tropical paradises aboard the Emerald Azzurra.
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Discover Eastern Caribbean & Grenadines $13,340 15 Set sail on a 15-day Caribbean cruise from Philipsburg on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Visit charming islands like Virgin Gorda, Saint Barthelemy, and Bequia for stunning beaches, local cuisine, and water activities amidst breathtaking views.
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Discover Eastern Caribbean & Grenadines $13,390 15 Join a 15-day Caribbean cruise from Bridgetown on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Experience local culture in Speightstown, enjoy water sports in Kingstown, and relax in natural hot springs in Soufriere before returning to Barbados.
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Grenadines & Windwards Yachting $9,990 8 Embark on an 8-day Caribbean cruise from Bridgetown, Barbados aboard Emerald Azzurra. Visit Kingstown, Bequia, Mayreau, Union Island, and Tobago Cays. Discover small island communities, historical landmarks, coral reefs, and quiet beaches. Enjoy daily opportunities for swimming, snorkeling, and local exploration in Saint Vincent and the Grenadines.
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Beaches of the Grenadines $7,195 9 Set sail on a 9-day Caribbean cruise from Bridgetown on the Emerald Azzurra, exploring charming locations like Speightstown, Kingstown, and Bequia Island. Discover stunning beaches, marine life, and local culture before returning to Bridgetown.
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Grenadine Islands $2,080 8 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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Barbados to Panama $4,330 15 Set sail on a 15-day cruise with Star Clipper from Bridgetown, Barbados, exploring the Caribbean’s rich culture and history, ending in Balboa, Panama. Visit stunning destinations like Tobago Cays, Grenada, and the San Blas Islands, and experience the Panama Canal.
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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

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