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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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5 Best St. Kitts 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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Discover the Pearls of the Caribbean $15,980 15 Embark on a 15-day Caribbean cruise aboard Emerald Azzurra, exploring stunning coral reefs, granite pools, and picturesque landscapes across destinations like Anguilla and Virgin Gorda. Enjoy snorkeling, hiking, and vibrant local culture while visiting Saint Barthelemy and the British Virgin 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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St. Kitts & Leeward Islands Travel Guide

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. 
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St. Kitts: Sailing the Caribbean on a small ship cruise with Adventure Life Video

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