14-Night Cruise on Wind SurfStar Collector: Caribbean Explorations - Weather

Join Windstar Cruises's Wind Surf for a 14-night voyage on the Star Collector: Caribbean Explorations route, setting out from Philipsburg, St. Maarten on January 16, 2027. It's a classic Caribbean cruise. Travelers sailing in January can generally expect warm, sunny weather with gentle trade winds. Ports of call include Philipsburg, St. Maarten, Anguilla, Tortola, British Virgin Islands, with 11 more along the way. The forecasts below break the weather down port by port.

1. Day 1 — Saturday, Jan 16, 2027 — Philipsburg, St. Maarten

   Philipsburg, St. Maarten is a scheduled port of call on day 1 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

2. Day 2 — Sunday, Jan 17, 2027 — Anguilla

   Anguilla is a scheduled port of call on day 2 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

3. Day 3 — Monday, Jan 18, 2027 — Tortola, British Virgin Islands

   Tortola, British Virgin Islands is a scheduled port of call on day 3 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

4. Day 4 — Wednesday, Jan 20, 2027 — Virgin Gorda, British Virgin Islands

   Virgin Gorda, British Virgin Islands is a scheduled port of call on day 4 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

5. Day 5 — Thursday, Jan 21, 2027 — St Barthelemy

   St Barthelemy is a scheduled port of call on day 5 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

6. Day 6 — Friday, Jan 22, 2027 — Falmouth, Antigua

   Falmouth, Antigua is a scheduled port of call on day 6 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 79°F.

7. Day 7 — Saturday, Jan 23, 2027 — Philipsburg, St. Maarten

   Philipsburg, St. Maarten is a scheduled port of call on day 7 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

8. Day 8 — Sunday, Jan 24, 2027 — Nevis, St Kitts and Nevis

   Nevis, St Kitts and Nevis is a scheduled port of call on day 8 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 74°F.

9. Day 9 — Monday, Jan 25, 2027 — Roseau, Dominica

   Roseau, Dominica is a scheduled port of call on day 9 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 76°F.

10. Day 10 — Tuesday, Jan 26, 2027 — Mayreau, Grenadines

    Mayreau, Grenadines is a scheduled port of call on day 10 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 80°F.

11. Day 11 — Wednesday, Jan 27, 2027 — Iles Des Saintes, Guadeloupe

    Iles Des Saintes, Guadeloupe is a scheduled port of call on day 11 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 77°F.

12. Day 12 — Thursday, Jan 28, 2027 — Basseterre, St. Kitts

    Basseterre, St. Kitts is a scheduled port of call on day 12 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 79°F.

13. Day 13 — Friday, Jan 29, 2027 — St Barthelemy

    St Barthelemy is a scheduled port of call on day 13 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.

14. Day 14 — Saturday, Jan 30, 2027 — Philipsburg, St. Maarten

    Philipsburg, St. Maarten is a scheduled port of call on day 14 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf. Expected weather: partially cloudy with highs near 78°F.