14-Night Cruise on Star LegendOcean Crossing - Weather

Departing Lisbon, Portugal on December 6, 2027, the Windstar Cruises ship Star Legend runs this 14-night Ocean Crossing sailing. It's a classic Caribbean cruise. Travelers sailing in December 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 — Monday, Dec 6, 2027 — Lisbon, Portugal

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

2. Day 2 — Thursday, Dec 9, 2027 — Funchal, Madeira

   Funchal, Madeira is a scheduled port of call on day 2 of the 14-night Ocean Crossing cruise on Star Legend. Expected weather: partially cloudy with highs near 72°F.

3. Day 3 — Sunday, Dec 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 14-night Ocean Crossing cruise on Star Legend. Expected weather: partially cloudy with highs near 80°F.

4. Day 4 — Monday, Dec 20, 2027 — San Juan, Puerto Rico

   San Juan, Puerto Rico is a scheduled port of call on day 4 of the 14-night Ocean Crossing cruise on Star Legend. Expected weather: partially cloudy with highs near 80°F.