Star Clippers invites family travelers to experience an intimate Caribbean sailing aboard its Star Flyer ship.
Guests may choose from two itineraries: Leeward Islands and Treasure Islands. These itineraries sail round trip from St. Maarten between November and March, with stops in Anguilla and the British Virgin Islands. Family travelers booking the Treasure Island itinerary during the 2024/2025 season have the option to add a complimentary two-night stay at Holland House Beach Hotel in Phillipsburg, St. Maarten. The stay may be added before or after the sailing, or one night before and one night after.
© Star Clippers
Star Flyer carries a maximum of 166 passengers. As one of Star Clippers’ three clipper ships in its fleet, Star Flyer offers a small ship experience without compromising amenities. Lounge on its expansive teak decks, featuring two pools. Check out the bow spirit net at the front of the ship and lay suspended over the water, watching marine life below. Star Clippers also offers complimentary water sports activities.
An added benefit of a small-ship cruising, Star Clippers’ ships port at more remote and secluded spots, allowing passengers to enjoy an off-the-beaten-path experience.
Caribbean sailings are available to book through spring 2026. Rates start at $1,875 or $2,320 per person based on single occupancy.
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