The Caribbean is one of most visited cruise destinations in the world, and for good reasons: the pristine beaches, diverse culture, and proximity to the US make these islands a year-round vacation spot. But booking a Caribbean cruise doesn’t have to mean getting on a megaship with thousands of passengers. In fact, Star Clippers tall sailing ships offer a very different experience.

Star Flyer, one of three clipper ships in Star Clippers’ fleet, offers a small ship sailing experience that is oceans apart from your typical cruises. Two itineraries—Leeward Islands and Treasure Islands—sail round-trip from St. Maarten between November and March each year, calling on lesser-known islands such as Dominica; Anguilla; Iles de Saintes; and Virgin Gorda and Jost van Dyke in the BVI. 

Reasons Why A Star Flyer Sailing Is Perfect Caribbean Sailing

Keep it Small: Not all Caribbean cruise ships are massive: Star Flyer carries a maximum of just 166 passengers. And with the expansive teak decks (featuring two pools), guests have no trouble finding a private spot to relax with a good book, watch the nautical team lower and raise the sails, or to simply enjoy some personal space. The bow sprit net—located at the front of the ship—is a prime spot where guests can lay suspended over the ocean watching the dolphins frolic below.

Explore Remote Island and Secluded Harbors: While larger cruise ships disembark their thousands of passengers into busy ports filled with loud tourist shops, Star Flyer ships cast anchor in remote harbors populated with local businesses and private yachts. Small tender boats take guests to and from shore—often to visit charming towns or off-the-beaten-path beaches where it’s not unusual to be one of only a handful of snorkelers or sunbathers taking advantage of Star Clippers’ complimentary water sports activities. 

Let the Wind Carry You: Star Flyer is a true sailing vessel, using wind power whenever possible to navigate between islands. In fact, all Star Clippers itineraries are created using tide charts and wind maps to ensure the ships can sail under wind power as much as possible—up to 80% of the time in the Caribbean. Gliding into port under full sail—all 36,000 square feet of billowing canvas—is a thrilling experience, and one that allows guests to imagine what it must have been like for the early explorers who arrived in this exotic region on board very similar vessels (minus, of course, the onboard luxuries like multiple swimming pools, massage services, and a full range of great dining).

Extend Your Stay in St. Maarten: Guests booking select Star Flyer Treasure Island sailings during the 2024-2025 season can take advantage of Star Clippers’ Complimentary Two-Night Stay at the beautiful Holland House Beach Hotel in Phillipsburg, St. Maarten. Guests choose when they want to stay—before or after the sailing, or one night on each end.

Star Clippers’ Caribbean sailings are available for booking through Spring 2026, with rates starting at $1,875USD or $2,320CAD per person, single occupancy.

For more than 25 years, Star Clippers has been introducing travelers to the thrill of modern tall ship sailing to remote ports in the Caribbean, Mediterranean, and Central America. The company operates three of the world’s largest and tallest sailing vessels: Star Clipper and Star Flyer are traditional clipper ships with modern amenities carrying 166 guests, while the 227-guest Royal Clipper holds the Guinness World Record for being the largest and only five-masted, full-rigged sailing ship in service today. All three ships have expansive teak decks, swimming pools, informal dining, convivial tropical bars on deck, and piano lounges.

For more information, applicable restrictions and to make a booking, contact your travel agent, or call 800-442-0551 or visit www.starclippers.com.