15-Night Cruise on Wind SurfOcean Crossing - Weather

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.

1. Day 1 — Friday, Nov 5, 2027 — Lisbon, Portugal

   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.

2. Day 2 — Monday, Nov 8, 2027 — Funchal, Madeira

   Funchal, Madeira is a scheduled port of call on day 2 of the 15-night Ocean Crossing cruise on Wind Surf. Expected weather: partially cloudy with highs near 76°F.

3. Day 3 — Friday, Nov 19, 2027 — Jost Van Dyke, British Virgin Islands

   Jost Van Dyke, British Virgin Islands is a scheduled port of call on day 3 of the 15-night Ocean Crossing cruise on Wind Surf. Expected weather: partially cloudy with highs near 82°F.

4. Day 4 — Saturday, Nov 20, 2027 — Philipsburg, St. Maarten

   Philipsburg, St. Maarten 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 81°F.