Ocean Crossing
Indulge yourself in leisurely, unscheduled days where time suspends in the magic of the sea. Sleep late. Dine early. Establish your own rhythm in sync with the waves and the arc of...
Cruise only — prices from Solo cruise only — from
Ports of Call & Itinerary
15-night voyage departing Lisbon, arriving Philipsburg.
Printable Itinerary (PDF)Route Map
Ocean Crossing
4 ports plotted · click a marker for details
Day 1
Lisbon , Portugal
Friday, 05/11/2027
The rhythm of Lisbon invites you to join its captivating dance. This splendid capital city on the banks of the Rio Teja offers a warm welcome and an unparalleled blend of architectural styles. Elegant outdoor cafés line the cobbled sidewalks. Turn-of-the-century funiculars climb the scenic hills. Find the UNESCO sites of the Tower of Belem and the Monastery of the Hieronymites. And, everywhere, the city engages you with its easy style and remarkable charm.
Day 4
Funchal, Madeira , Portugal
Monday, 08/11/2027
Considered one of Portugal's main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty. Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there'll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.
Day 15
Great Harbour, Jost Van Dyke , British Virgin Islands
Friday, 19/11/2027
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.
Day 16
Philipsburg , Sint Maarten (Dutch part)
Saturday, 20/11/2027
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Category B
188 sqft · Up to 2 guests
Category BX Deluxe
188 sqft · Up to 2 guests
Category A
188 sqft · Up to 2 guests
Category AX Deluxe
188 sqft · Up to 2 guests
Category TX Deluxe
188 sqft · Up to 2 guests
Suite
376 sqft · Up to 3 guests
Broadmoor Suite/Sea Island Suite
495 sqft · Up to 3 guests
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Your Ship
Wind Surf
Windstar's Flagship Sailing Yacht
As part of our Wind Class, our 342-guest Wind Surf offers a sailing experience like no other — one with real working sails.
