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

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Take a leisurely stroll through beautiful Bridgetown

Grenadines & Windwards Yachting

8 Days from $7,990
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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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 $8,220
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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Bright blue waters of the Caribbean

Pearls of the Caribbean

8 Days from $9,440
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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Soufriere bay, St Lucia

Pearls of the Caribbean

9 Days from $6,830
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

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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Relax on the shores of the Caribbean

Cruising the Caribbean's Windward Islands – with Smithsonian Journeys

9 Days from $6,800
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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St. George's, Grenada's charming capital city known for having the most beautiful harbor in the Caribbean.

Grenada to Grenada

12 Days from $3,090
Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.
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Enjoy the beautiful blue Caribbean

Grenada to Grenada

11 Days from $2,820
Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.
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Top Tobago Cays Deals

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

Trip Name From Days Summary
Grenadine Islands $2,030 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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Grenada to Grenada $3,090 12 Set sail on a 12-day cruise aboard the Star Clipper, exploring stunning islands like Tobago and Martinique, with highlights including the Tobago Cays and St. Lucia's waterfalls. Experience the Caribbean's serene beauty and rich culture while enjoying activities like snorkeling and history.
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Grenada to Grenada $2,820 11 Set sail on an 11-day cruise from St. George aboard the Star Clipper, featuring Grenada, Tobago, the Grenadines, Martinique, and St. Lucia while exploring picturesque villages and stunning beaches. Enjoy swimming, snorkeling, and local culture, concluding with a visit to Mayreau's serene Saline Bay.
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Grenada to Antigua $2,820 11 Take an 11-day cruise on the Star Clipper from St. George's, Grenada to St. John's, Antigua, exploring secluded bays and historic towns in Tobago and the Grenadines. Enjoy highlights like snorkeling in Tobago Cays and relaxing on beautiful beaches, while immersing yourself in vibrant local cultures.
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Aruba to Grenada $2,880 11 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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Grenada Roundtrip $3,150 12 Embark on a 12-day cruise through the Southern Caribbean aboard the Star Clipper, starting in St. George’s, Grenada. Experience stunning beaches, vibrant local culture, and historical sites across Tobago, the Grenadines, Martinique, and Barbados.
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Grenada to Antigua $2,010 8 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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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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