Best St. Kitts Small Ship Cruises for 2026-2027

All St Kitts Small Ship Cruises

10 Best St. Kitts Small Ship Cruises for 2026-2027

All St Kitts Small Ship Cruises

All St Kitts Luxury Tours & Small Ship Cruises

1 Best Luxury St. Kitts Small Ship Cruises for 2026-2027

Eastern Caribbean with St. Barths

8 Days from $7,990

Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbor’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise

All St Kitts Tours & Small Ship Cruise Deals

9 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. 0
Treasure Islands	$1,970	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! 0
Windward Islands	$2,030	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. 0
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. 0
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. 0
Antigua Roundtrip	$2,010	8	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. 0
Antigua Roundtrip	$2,010	8	Set sail on an 8-day round-trip cruise from St. John’s, Antigua, aboard the Star Clipper, exploring St. Barts, the British Virgin Islands, and Anguilla. Highlights include duty-free shopping, scenic hikes, and beautiful beaches before concluding in Antigua. 0
Antigua Roundtrip	$2,010	8	Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua. 0
Treasure Islands	$2,010	8	Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts. 0

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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.

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.