Best St. Kitts Small Ship Cruises for 2025-2026

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!

All St Kitts Small Ship Cruises

10 Best St. Kitts Small Ship Cruises for 2025-2026

All St Kitts Small Ship Cruises

All St Kitts Tours & Small Ship Cruise Deals

5 Best St. Kitts Small Ship Cruise Deals for 2025-2026

Trip Name	From	Days	Summary
Eastern Caribbean with St. Barths	$7,990	8	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 0
Caribbean Sojourn	$11,990	7	Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town. 0
Eastern Caribbean with St. Barths	$7,990	8	Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience. 0
Discover the Pearls of the Caribbean	$21,780	15	Embark on a 15-day cruise aboard Emerald Azzurra from Barbados to Marigot, visiting highlights like Nelson’s Dockyard and the beaches of Iles des Saintes. Discover serene islands, snorkel vibrant reefs, and enjoy cultural experiences across the enchanting Caribbean. 0
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. 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 2025-2026

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.