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U.S. Virgin Islands Small Ship Cruises

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U.S. Virgin Islands
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Visit the United States Virgin Islands, located just south of the British Virgin Islands. This lovely archipelago is technically an unincorporated but organized territory of the United States, meaning if you're an American Citizen then you won't need a passport to enter the country. Take a walk on the white sanded beaches or snorkel in the crystal clear waters of the many beaches including Salomon Beach, Scott Bay Beach, and Trunk Bay. Travel on a small ship cruise with the benefits of a small ship cruise that allows access to smaller coves, reefs, and ports. Afterward, read your favorite book on a picture-perfect deserted island or take a hike up the mountain tops to enjoy the gorgeous view of the US Virgin Islands. You could even make Puerto Rico a stop on your personalized cruise. Contact our travel experts to start planning your dream Caribbean trip today!
Best Small Ship Caribbean Cruises

10 Top U.S. Virgin Islands Small Ship Cruises for 2026-2027

Best Small Ship Caribbean Cruises
The Southeast Peninsula of Saint Kitts with Nevis in the Background

Quintessential Caribbean

8 Days from $9,990
Explore the Caribbean on an 8-day cruise from Saint Thomas to San Juan aboard Emerald Sakara. Visit Saint John, Nevis, Guadeloupe, Antigua, Saint Barthélemy, and the British Virgin Islands. Discover UNESCO-listed landmarks, swim in clear waters, and experience regional architecture, food, and history throughout the journey.
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Lush green forests and clear blue waters of the Caribbean

San Juan to San Juan

8 Days from $5,000
Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views.
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Visit beautiful Norman Island

Vibes of the Virgin Islands

8 Days from $9,990
Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty.
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Islands of the Caribbean

Quintessential Caribbean

8 Days from $7,990
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.
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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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Tropical Caribbean Beach in Martinique

Antigua Roundtrip

8 Days from $2,010
Join an 8-day Caribbean cruise from St. John's, Antigua, on the Star Clipper, exploring destinations like St. Barts, St. Kitts, and Martinique. Experience snorkeling, historic tours, and diverse beaches while enjoying the beauty of the French and British West Indies.
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Explore the famous rock formations of the baths

Splendours of the Caribbean

7 Days from $9,190
Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.
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Gustavia Harbor in St. Barths

Cruising the Leeward Islands

8 Days from $9,990
Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
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Panoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape

Pirate Islands With A Yachtie Vibe

8 Days from $6,995
Sail 8 days aboard Sea Cloud Spirit on a Caribbean round-trip from Philipsburg, St. Maarten. Explore Gustavia, St. John’s, Virgin Gorda, Jost van Dyke, and Norman Island with beaches, sailing, and historic sights.
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Relax on the white sandy beaches of the Caribbean

Treasure Islands

8 Days from $2,010
Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.
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All Caribbean Deals

8 Top U.S. Virgin Island Small Ship Cruise Deals for 2026-2027

Trip Name From Days Summary
Leeward Islands $2,010 8 Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.
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Treasure Islands $2,010 8 Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
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Windward Islands $2,080 8 Sail aboard the Royal Clipper on an 8-day journey through vibrant Caribbean islands, pristine beaches, and rich history. Highlights include Dominica’s lush Cabrits National Park, Antigua’s Falmouth Harbor, and Martinique’s stunning shores.
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Panama to Antigua $4,450 15 Set sail on a 15-day Royal Clipper cruise from Balboa, Panama, featuring a full Panama Canal transit and visits to the San Blas Islands, Cartagena, and the Caribbean gems of Aruba, Curacao, and Bonaire. Experience lush Grenada and volcanic St. Lucia, and finish your journey in Antigua, all while enjoying elegant sailing and stunning island views.
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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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Leeward Islands $2,010 8 Embark on an 8-day roundtrip cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring St. Maarten, Nevis, Dominica, Antigua, and St. Barts. Experience stunning beaches, vibrant culture, and unique natural landscapes across the Leeward Islands.
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Treasure Islands $2,010 8 Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.
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Sun-Drenched Sailing Days $6,995 8 Sail 8 days aboard Sea Cloud Spirit through the Caribbean, Lesser Antilles & Grenadines. You explore St. Maarten, Martinique, St. Lucia, Dominica, Nevis, and Anguilla, combining colonial towns, volcanic peaks, rainforests, and white-sand beaches with authentic sailing experiences at sea.
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All Caribbean Articles

U.S. Virgin Islands Travel Guide

Best Time to Visit the U.S Virgin Islands

The best time to visit the U.S. Virgin Islands is between April and June. This is because there's very little rainfall, the temperatures are comfortable in the mid-70's to 80's (Between 21-27 degrees Celsius), and it's not the peak tourism season resulting in less expensive lodging and activities along with fewer crowds.

Between December and March is also a good time to go but this is the peak tourism season so hotel and activity prices can raise as much as 50 percent.

Between July and November you'll find unbelievable deals but these months are during hurricane season so it's not recommended that you go during this time.
Huahine

Cuisine of the Virgin Islands

The Virgin Islands have an unusual cuisine, that's been influenced by Europeans, Indians, Americans, and traditional African recipes.
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Pacific Explorer

Virgin Islands Politics

A trip to the U.S. Virgin Islands has very tricky and confusing politics surrounding it. For example, The U.S. Virgin Islands are an unincorporated U.S. territory which means they have a say in Congress, but only in committees. It's both important and enlightening to understand the politics around the U.S. Islands, especially if you're from the U.S.
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Snorkel and dive in the clear waters of the Caribbean

Caribbean Island Guide

Explore the best Caribbean islands for luxury travel, pristine beaches, culture, adventure, and exclusive experiences. From St. Lucia to Turks & Caicos, the Bahamas and even Aruba, find your perfect island getaway.
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