Set Sail for Adventure: Embrace the Majesty of Tall Ship Cruising!

Experience the Caribbean the Way Sailors Dream About

7 Night Caribbean "Treasure Islands" Sailing

November 28 – December 5, 2026

Roundtrip from St. Maarten, this itinerary explores some of the most beautiful islands in the Caribbean, including Anguilla, St. Barts, St. Kitts and the British Virgin Islands.

Star Flyer is a beautiful 4 masted tall ship carrying just 166 guests, offering an experience that feels far more like travelling aboard a private yacht than a large cruise ship. Powered significantly by the wind whenever conditions allow, she sails through the Caribbean with towering masts and billowing white sails, visiting smaller ports and secluded anchorages that larger ships simply cannot access.

Life onboard is as active or as relaxed as you choose. Guests can help hoist the sails, take a turn at the helm, climb the mast for incredible views, relax on the famous bowsprit nets suspended above the sea, or simply enjoy the ocean breeze from the open decks. Complimentary water sports equipment including kayaks, paddleboards and snorkeling gear are brought ashore for guests to enjoy throughout the voyage.

Add exceptional dining, a relaxed atmosphere, and a community of like minded travellers, and you have a sailing experience that many guests describe as truly unforgettable.

Click HERE for more information & Pricing

Roundtrip from St. Maarten, this itinerary explores some of the most beautiful islands in the Caribbean, including Anguilla, St. Barts, St. Kitts and the British Virgin Islands.

Unlike large cruise ships that spend much of their time in busy commercial ports, Star Flyer visits intimate harbours and anchorages where guests can step ashore and experience the Caribbean at a slower, more authentic pace.

Each day offers a new island to explore, world class snorkeling opportunities, beautiful beaches, charming waterfront towns and spectacular sailing between destinations. Staterooms start at $2375 per person - PLUS $100 on-board credit and prepaid gratuities.

Discover the Thrills of a Tall Ship Cruise: Sail into Adventure and Maritime History!

Experience the excitement of a tall ship cruise, a journey aboard a traditional sailing vessel renowned for its towering masts and billowing sails. From scenic coastal voyages to epic ocean crossings, these cruises offer an immersive experience, highlighting sailing adventures, hands-on engagement, and exploration of remote destinations. Perfect for adventure seekers and maritime enthusiasts, a tall ship cruise ensures an indelible voyage across the high seas

intimate entertainment Star Clippers Cruise

Tall ship cruises stand out for their:

Historical Charm: Embracing the romantic nostalgia of traditional sailing vessels, tall ship cruises offer a unique blend of maritime heritage and adventure.

Hands-On Experience: Unlike conventional cruises, passengers actively participate in sailing tasks, fostering a sense of camaraderie and adventure as they work alongside the crew.

Remote Exploration: With their smaller size, tall ships can access secluded ports and off-the-beaten-path destinations, offering passengers the opportunity to discover hidden gems and untouched landscapes.

Guests on Board:

The number of passengers on a tall ship cruise can vary depending on the size and design of the vessel. Generally, tall ships are smaller in scale compared to modern cruise ships, accommodating anywhere from tens to a few hundred passengers. This smaller size contributes to a more intimate and personalized experience, allowing passengers to forge closer connections with fellow travellers and the crew, and facilitating access to smaller ports and more remote destinations along the journey.