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St. Kitts Small Ship Cruises

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Cruise to the picturesque island of Saint Kitts located directly South of the island of Gustavia and West of the islands of St John and Barbuda. This island and its neighbor Nevis constitute the Federation of Saint Kitts and Nevis with the official language of English and its currency being the East Caribbean Dollar. Actively adventure through St. Kitts by touring through the UNESCO-awarded Brimstone Hill Fortress National Park or zipline, have off-road adventures, hike, or even golf at Royal St. Kitts. Or, you could take a break from the hustle and bustle of everyday life and relax, swim, snorkel, or dive on the well-known Cockleshell Beach. Travel to the Caribbean on a small ship cruise and reap the benefits of being able to reach smaller reefs, coves, and beaches. Contact our travel experts to start planning your ideal trip today!
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10 Best St. Kitts Small Ship Cruises for 2026-2027

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Relax on the beaches of St. Maarten

Cruising the Leeward Islands

8 Days from $6,395
Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.
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Tropical waterfall and turquoise pool in lush forest of Dominica

Treasure Islands

8 Days from $2,010
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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City of Basseterre and Frigate Bay from the Timothy Hill viewpoint in St. Kitts.

Discover the Pearls of the Caribbean

15 Days from $12,690
Set sail on a 15-day Caribbean cruise from Barbados aboard the Emerald Sakara, visiting Saint Lucia for its mud baths, Antigua's historic dockyard, and Anguilla's vibrant coral reefs. Conclude your journey in Philipsburg, Sint Maarten, enjoying the region's rich culture and cuisine.
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Enjoy the beautiful blue Caribbean

Discover the Pearls of the Caribbean

15 Days from $12,690
Set sail on a 15-day Caribbean cruise aboard the Emerald Sakara, visiting islands like Anguilla for snorkeling and Virgin Gorda for stunning rock formations. Explore vibrant Gustavia in Saint Barthelemy, enjoy the charm of the Iles des Saintes, relax in Saint Lucia's hot springs, and experience the colonial beauty of Barbados.
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Learn about Spanish colonial history in Old San Juan

Caribbean Yachting Discovery

8 Days from $6,745
Set sail on an 8-day Caribbean cruise aboard the Emerald Kaia from Antigua, visiting St. Kitts, Guadeloupe, and Saint-Barthelemy, before exploring the British Virgin Islands' iconic sites. End your journey in San Juan, Puerto Rico, the oldest European settlement in the Americas.
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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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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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The crystal blue water of Jost van Dyke

Antigua to Antigua

8 Days from $2,060
8-day itinerary from St John's Antigua aboard Star Clipper calling at St Barts, BVI islands including Norman Island, Virgin Gorda, Jost van Dyke, Anguilla and St Kitts. Route includes historic harbors, small towns, beaches and sailing passages across the Caribbean.
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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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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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All St Kitts Tours & Small Ship Cruise Deals

3 Best St. Kitts Small Ship Cruise Deals for 2026-2027

Trip Name From Days Summary
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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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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San Juan to San Juan $5,000 8 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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St. Kitts & Leeward Islands Travel Guide

Colorful flowers and bright blue sea in the Caribbean

Leeward Islands Overview

Caribbean cruise vacationing to the Leeward Islands. Explore more details about the Leeward Islands including modern history and cuisine in the region as you prepare for your Caribbean cruise.
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Best Time to Visit St. Kitts and Nevis

Between December and April is the most popular time to visit St. Kitts and Nevis but this is also the most expensive time. Hotels prices, airfare, and crowds will be at their absolute height during these months, especially surrounding winter holidays. You should make sure to book your trip at least four months in advance if you want to come during these months and if you want to be in St. Kitts and/or Nevis for the winter carnival, it's highly recommended you book at least six months in advance.

Between May and June is the best time to visit St. Kitts and Nevis. It's a shoulder season between the high season and hurricane season so lodging and airfare prices will drop significantly along with a lot of the crowds. Rainfall is still rare in this season so there's not much of a downside.

Between July and November is not the best time to visit St. Kitts and Nevis- but it's not a terrible time to. You'll find the lowest rates during this time of year but some attractions, restaurants, and hotels will be closed during these months. Being hurricane season in St. Kitts and Nevis, this is also the rainiest time of the year by a landslide. That being said the foliage will look absolutely gorgeous during this time and it's unlikely that it will rain every day, throughout the day, on your trip.

 

Best St. Kitts, Leeward Islands Caribbean Small Ship Cruise Lines for 2026-2027

  • Star Clippers Americas - has introduced passengers to the excitement of an authentic tall ship sailing in several of the Caribbean's most stunning sites, including St. Kitts, the British West Indies' first thriving colony. Shopping in vibrant Basseterre, golfing, touring historic plantation mansions, or taking a short stroll through the rainforest are worthwhile activities. Fourteen deluxe suites on Royal Clipper have private verandas, minibars, whirlpool tubs, and 24-hour room service. All but six of the ship’s 114 cabins are outside, and the two 430-square-foot Owner's Suites may accommodate up to eight people.
  • Emerald Cruises - a leading operator of luxury yacht and river cruises, offering modern comfort and immersive travel experiences. Emerald Sakara sails to St. Kitts, a volcanic island with fine sandy beaches and rich colonial heritage. 
Enjoy the natural beauty of the Caribbean

Leeward Islands Geography

Along with the Windward Islands, the small Leeward Islands form the Lesser Antilles on the eastern border of the Caribbean Sea. The geography of the Leeward Islands is comprised primarily by coral and volcanic islands. The soil on the coral islands is not well suited to agriculture, making these countries' primary economic engine tourism.
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St. Kitts: Sailing the Caribbean on a small ship cruise with Adventure Life Video

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