21 Night Transatlantic Cruise
This 21-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises sails from Lisbon to St. Maarten (Philipsburg), departing December 5, 2026, calling at Antigua (St. John's), St. Maarten (Philipsburg), Gustavia St Barths, and 4 more ports, and returns December 26, 2026. Cabin prices start from $5,399 per person.
Lisbon cruise port is one of the most atmospheric arrivals in Europe. Ships sail up the Tagus River past the 25 de Abril Bridge (a near-twin of San Francisco's Golden Gate) and the Christ the King statue, with the city rising up on seven hills to the north.
Read more →St. John's is the capital and main cruise port of Antigua, one of the Leeward Islands in the eastern Caribbean. The Heritage Quay and Redcliffe Quay cruise terminals sit in the heart of St. John's, directly adjacent to the duty-free shopping district.
Read more →St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →Falmouth's historic port was purpose-built for mega-ships and sits in a town known for its well-preserved Georgian colonial architecture. Popular excursions include Dunn's River Falls, bamboo rafting on the Martha Brae River, and Montego Bay beaches.
Read more →St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →Ocean View cabin
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Other Caribbean (Eastern) departures
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