Wind Surf — 14-Night Star Collector: Caribbean Explorations Cruise Weather

The Wind Surf sails a 14-night Star Collector: Caribbean Explorations itinerary with Windstar Cruises, departing Philipsburg, St. Maarten on January 2, 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, Falmouth, Antigua, Anguilla, with 11 more along the way. Use the day-by-day forecast below to plan what to pack for each stop.

1. Day 1 — Saturday, Jan 2, 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.

2. Day 2 — Sunday, Jan 3, 2027 — Falmouth, Antigua

   Falmouth, Antigua is a scheduled port of call on day 2 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

3. Day 3 — Monday, Jan 4, 2027 — Anguilla

   Anguilla is a scheduled port of call on day 3 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

4. Day 4 — Tuesday, Jan 5, 2027 — Tortola, British Virgin Islands

   Tortola, British Virgin Islands is a scheduled port of call on day 4 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

5. Day 5 — Thursday, Jan 7, 2027 — Virgin Gorda, British Virgin Islands

   Virgin Gorda, British Virgin Islands is a scheduled port of call on day 5 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

6. Day 6 — Friday, Jan 8, 2027 — St Barthelemy

   St Barthelemy is a scheduled port of call on day 6 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

7. Day 7 — Saturday, Jan 9, 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.

8. Day 8 — Sunday, Jan 10, 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.

9. Day 9 — Monday, Jan 11, 2027 — Iles Des Saintes, Guadeloupe

   Iles Des Saintes, Guadeloupe is a scheduled port of call on day 9 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

10. Day 10 — Tuesday, Jan 12, 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.

11. Day 11 — Wednesday, Jan 13, 2027 — Roseau, Dominica

    Roseau, Dominica is a scheduled port of call on day 11 of the 14-night Star Collector: Caribbean Explorations cruise on Wind Surf.

12. Day 12 — Thursday, Jan 14, 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.

13. Day 13 — Friday, Jan 15, 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.

14. Day 14 — Saturday, Jan 16, 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.