Destination
Caribbean Islands
The Caribbean offers much more than postcard-perfect beaches and turquoise waters—it’s a region rich in history, culture, biodiversity, and hidden gems that are best experienced by small ship. While large cruise ships crowd the main ports, small ship cruises allow you to explore the Caribbean in a more intimate, immersive, and authentic way—visiting off-the-beaten-path islands, lesser-known bays, and charming coastal villages.
At Small Ship Travel, we specialize in expertly curated cruises aboard small ship vessels, with many itineraries on ships with just 100–250 passengers or fewer. We partner with top cruise lines that emphasize local connections, sustainability, and thoughtful exploration. Whether you’re seeking sun-soaked sailing, eco-focused expeditions, or culturally immersive voyages, we’ll help you find the perfect cruise for your Caribbean journey.
We work with a trusted portfolio of premium and luxury small ship cruise lines that offer thoughtfully designed itineraries throughout the Caribbean, emphasizing destination immersion, elevated service, and responsible travel.
With just 112 guests onboard, SeaDream’s twin yachts offer an ultra-relaxed, all-inclusive experience that feels more like private yachting than traditional cruising. Their itineraries visit yacht-accessible harbors like St. Barts, Jost Van Dyke, and Mayreau, with a focus on casual elegance, exceptional cuisine, and water sports from the ship’s onboard marina.
Windstar’s sailing and motor yachts carry 148–342 guests, calling on quieter Caribbean ports and hidden beaches. Their casual-luxury style combines fine dining, small-group excursions, and the opportunity to sail under the stars aboard iconic ships like Wind Surf and Star Breeze.
This French expedition line brings refined, boutique cruising to the Caribbean, with itineraries that include Guadeloupe, the Grenadines, Dominica, and more. Ponant’s elegant ships carry fewer than 200 guests and feature French gastronomy, cultural programming, and enrichment with naturalists and local experts.
Silversea offers ultra-luxury small ship cruising throughout the Caribbean, with all-suite accommodations, personalized butler service, and expertly curated itineraries that visit both popular islands and off-the-beaten-path gems. Guests enjoy fine dining, enrichment programs, and immersive excursions designed to reveal the region’s rich cultural and ecological diversity.
Bridging the worlds of private yachting and ultra-luxury cruising, The Ritz-Carlton Yacht Collection sails to intimate Caribbean ports, offering all-suite accommodations with private terraces, world-class dining, and immersive shore experiences. With just 298 guests aboard Evrima and upcoming sister ships, the experience is elevated, personalized, and entirely unique to the Ritz-Carlton brand.
Scenic brings its signature “ultra-luxury discovery yacht” experience to the Caribbean aboard Scenic Eclipse. With just 228 guests, Eclipse features submarines, helicopters, a Discovery Team of experts, and all-suite accommodations. Scenic’s Caribbean voyages focus on remote harbors, ecological wonders, and cultural depth, all delivered with exceptional attention to detail and all-inclusive service.
Set to debut with highly anticipated sailings in the Caribbean, Four Seasons Yachts will redefine luxury on the water. Designed for uncompromising privacy, space, and service, each voyage will feature suite-only accommodations, signature Four Seasons hospitality, and thoughtfully curated itineraries that highlight the best of the Caribbean’s culture, nature, and understated elegance.
The Caribbean cruise season is year-round, but the best time to sail is generally from December through April, when weather is dry and pleasant. Here's a breakdown:
High season with warm temperatures, low humidity, and calm seas. Ideal for beach time, snorkeling, and cultural exploration. This is the best time for consistent weather across the region.
Shoulder season offers fewer crowds, lush scenery, and great value. The weather remains warm, though occasional brief showers are possible.
The Caribbean’s low season includes the Atlantic hurricane season (June–November), but many southern islands (such as Grenada, St. Lucia, and Aruba) lie outside the hurricane belt and offer uncrowded, great-value experiences. Some lines reduce itineraries but maintain excellent service and flexible routing.
Small Ship Travel believes the Caribbean deserves more than a cruise—it deserves to be experienced with care, curiosity, and style. We handpick every cruise line and itinerary based on authenticity, guest experience, and access to lesser-known destinations.
As a Virtuoso affiliate through member agency Travel Experts, we offer exclusive benefits, such as onboard credits, upgrades, private excursions, and pre/post-cruise arrangements in gateways like San Juan, St. Martin, or Barbados. Our advisors help with every detail—from flights and travel insurance to local recommendations and personalized itinerary design.
Reach out to our travel concierges today to create your perfect journey.
Get in the mood for cruising by reading our travel guides, recommendations and cruise reviews.
River cruising offers a seamless and luxurious way to experience Europe’s most historic and scenic waterways, from the fairy-tale castles of the Rhine to the imperial capitals of the Danube and the artistic treasures of the Seine. Unlike ocean cruises, these intimate voyages bring travelers directly into the heart of medieval villages, grand cities, and world-renowned wine regions, allowing for deeper cultural immersion. Along the way, passengers can explore UNESCO-listed landmarks, savor locally inspired cuisine, and enjoy exclusive excursions, from private château tours to classical concerts in Vienna.
