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Loading Travel Forecast…Loading Travel Forecast…Loading Travel Forecast…The Wind Surf sails a 7-night Classic Caribbean itinerary with Windstar Cruises, departing Philipsburg, St. Maarten on December 26, 2026. It's a classic Caribbean cruise. Travelers sailing in December can generally expect warm, sunny weather with gentle trade winds. Ports of call include Philipsburg, St. Maarten, St Barthelemy, Nevis, St Kitts and Nevis, with 5 more along the way. Use the day-by-day forecast below to plan what to pack for each stop.
Philipsburg, St. Maarten is a scheduled port of call on day 1 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 79°F.
St Barthelemy is a scheduled port of call on day 2 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 79°F.
Nevis, St Kitts and Nevis is a scheduled port of call on day 3 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 75°F.
Roseau, Dominica is a scheduled port of call on day 4 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 77°F.
Mayreau, Grenadines is a scheduled port of call on day 5 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 80°F.
Iles Des Saintes, Guadeloupe is a scheduled port of call on day 6 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.
Basseterre, St. Kitts is a scheduled port of call on day 7 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 80°F.
Philipsburg, St. Maarten is a scheduled port of call on day 8 of the 7-night Classic Caribbean cruise on Wind Surf. Expected weather: partially cloudy with highs near 79°F.
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