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Loading Travel Forecast…Departing Lisbon, Portugal on November 5, 2027, the Windstar Cruises ship Wind Surf runs this 15-night Ocean Crossing sailing. It's a classic Caribbean cruise. Travelers sailing in November can generally expect warm, sunny weather with gentle trade winds. Ports of call include Lisbon, Portugal, Funchal, Madeira, Jost Van Dyke, British Virgin Islands, with 1 more along the way. Scroll the daily outlook below to pack smart for every port of call.
Lisbon, Portugal is a scheduled port of call on day 1 of the 15-night Ocean Crossing cruise on Wind Surf. Expected weather: partially cloudy with highs near 67°F.
Day 2 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 3 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Funchal, Madeira is a scheduled port of call on day 4 of the 15-night Ocean Crossing cruise on Wind Surf. Expected weather: partially cloudy with highs near 76°F.
Day 5 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 6 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 7 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 8 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 9 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 10 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 11 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 12 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 13 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Day 14 of 16 is a day at sea aboard Wind Surf, cruising between ports on the Ocean Crossing itinerary.
Jost Van Dyke, British Virgin Islands is a scheduled port of call on day 15 of the 15-night Ocean Crossing cruise on Wind Surf. Expected weather: partially cloudy with highs near 82°F.
Philipsburg, St. Maarten is a scheduled port of call on day 16 of the 15-night Ocean Crossing cruise on Wind Surf.
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