14-Night Cruise on Wind SurfOcean Crossings - Weather

The Wind Surf sails a 14-night Ocean Crossings itinerary with Windstar Cruises, departing Lisbon, Portugal on December 5, 2026. It's a classic Caribbean cruise. Travelers sailing in December can generally expect warm, sunny weather with gentle trade winds. Ports of call: Lisbon, Portugal, St Johns, Antigua, Philipsburg, St. Maarten. Use the day-by-day forecast below to plan what to pack for each stop.

1. Day 1 — Saturday, Dec 5, 2026 — Lisbon, Portugal

   Lisbon, Portugal is a scheduled port of call on day 1 of the 14-night Ocean Crossings cruise on Wind Surf. Expected weather: partially cloudy with highs near 61°F.

2. Day 2 — Friday, Dec 18, 2026 — St Johns, Antigua

   St Johns, Antigua is a scheduled port of call on day 2 of the 14-night Ocean Crossings cruise on Wind Surf. Expected weather: partially cloudy with highs near 79°F.

3. Day 3 — Saturday, Dec 19, 2026 — Philipsburg, St. Maarten

   Philipsburg, St. Maarten is a scheduled port of call on day 3 of the 14-night Ocean Crossings cruise on Wind Surf. Expected weather: partially cloudy with highs near 80°F.