Star Clippers’ 'Celebrate the Holiday Season at Sea' Special Offer

Discover the romance of tall ship sailing with Star Clippers for memorable Christmas and New Year's holidays. Trade winter weather for warm breezes, uncrowded natural beauty and the romance of true tall ship sailing with Star Clippers’ collection of holiday sailings for the 2026-2027 winter season. From Caribbean island hopping to tropical escapes along the coastlines of Costa Rica and Panama, Star Clippers offers a relaxed and intimate way to spend Christmas and ring in the New Year aboard authentic sailing vessels. 

The company’s three true clipper ships – Royal Clipper, Star Clipper and Star Flyer – will sail a variety of festive itineraries throughout December and early January, combining beachside celebrations, local holiday traditions and the unique atmosphere that only a sailing ship can provide. Guests can expect open-air deck parties, holiday dinners, island excursions, and the unforgettable sight of giant white sails unfurled against warm Caribbean skies.

Special Offer Details

• Book by June 30, 2026, and
• Get a USD 400 / CAD 500 per stateroom air or cruise fare credit and a bottle of Champagne!
• Applies to select Christmas and New Year’s 2026-2027 Star Clippers sailings

Featured Holiday Sailings

7-night Windward Islands Christmas Cruise aboard 227-guest Royal Clipper, departing round-trip from Barbados on December 19, 2026. 

Recognized by Guinness World Records as the world’s largest five-masted full-rigged sailing ship in service, the Royal Clipper will call on ports throughout the Grenadines and Windward Islands. On December 21, the charming four-masted Star Flyer joins the Royal Clipper to sail alongside each other towards Cabrits, where guests can visit orchid-festooned rainforests, waterfalls, and a bubbling lake. In St. Lucia, travelers can enjoy peaceful beaches, water sports, or cultural discoveries. A morning visit to St. Kitts allows guests to shop in colorful Basseterre, play golf, and tour old plantation houses. Guests can celebrate Christmas Day surrounded by the turquoise waters of Martinique while enjoying the spacious teak decks and elegant onboard atmosphere that define the Star Clippers experience. 

Rates begin at $2,080 (CAD $2,560) per person, double occupancy. 

7-night Leeward Islands Christmas Cruise offers a festive Caribbean escape departing round-trip from St. Maarten on December 19, 2026. 

Carrying just 166 guests, Star Flyer recreates the golden age of sailing while offering modern comforts and relaxed luxury. The itinerary includes stops in St. Barts, Dominica, Guadeloupe, and Martinique, blending French Caribbean charm with secluded beaches and colorful island culture. Chic boutiques and waterfront cafes lure the guests in St. Barts’ Gustavia while Antigua’s Falmouth Harbor evokes the ancient presence of Admiral Nelson, with marinas, old inns, venerable pubs and convivial crowds of sun-tanned yacht crews - the epicenter of the Caribbean yachting world. Evenings onboard feature sunset cocktails beneath the ship’s towering sails. 

Fares start at $2,010 (CAD $2,480).

7-night Panama-to-Costa Rica Christmas sailing departs on December 19, 2026.

Guests aboard the 166-passenger Star Clipper will visit destinations such as Isla Tortuga and the Pearl Islands, areas known for their lush rainforests, quiet beaches, and wildlife-rich waters. In Costa Rica’s Isla Tortuga, travelers can kayak through calm bays, snorkel among tropical fish or unwind on white-sand beaches shaded by palms. In Panama’s Pearl Islands, considered among the best deep-sea fishing grounds in the world, guests may spot dolphins and exotic birdlife while exploring secluded coves and untouched shorelines. 

Prices start at $2,010 (CAD $2,480).

In addition to holiday-specific departures, Star Clippers will also offer the same sailings for New Year’s: 

• Royal Clipper’s Grenadine Islands New Year’s Cruise sails round-trip from Barbados on December 26, 2026 (US $2,280 / CAD $2,760);
• Star Flyer’s Treasure Islands New Year’s Cruise departs from St. Maarten the same day (US $2,210 / CAD $2,680); and
• Star Clipper sails out of Panama on December 26 for a Central American New Year’s (US $2,210 / CAD $2,680). 

All itineraries feature festive onboard celebrations, island beach gatherings and relaxed sailing through some of the Caribbean’s most picturesque waters. 

More About Star Clippers

For more than 35 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. Its fleet of three authentic clipper ships—Star Clipper, Star Flyer, and Royal Clipper—offers a unique alternative to conventional cruising, combining the romance of the golden age of sailing with modern amenities and exceptional service. Carrying just 166 to 227 guests, the ships feature expansive teak decks, open-air dining, and a relaxed onboard atmosphere. 

Unlike traditional mega-ships, Star Clippers vessels are designed to deliver an authentic sailing experience with fewer passengers, open bridge policies, and itineraries focused on smaller ports and hidden harbors. Guests can climb the mast platform, help raise the sails, enjoy complimentary watersports directly from the marina platform, and experience the simple pleasures of sailing powered by the wind whenever possible.

*** Images courtesy of Star Clippers

*** Terms & Conditions apply; ask us for full offer, itinerary, date, and pricing details.