17-Night Cruise on Star PrideStar Collector: Bermuda & Caribbean Island Explorer - Weather

Departing Boston, Massachusetts on October 22, 2027, the Windstar Cruises ship Star Pride runs this 17-night Star Collector: Bermuda & Caribbean Island Explorer sailing. It's a classic Caribbean cruise. Travelers sailing in October can generally expect warm, sunny weather with gentle trade winds. Ports of call include Boston, Massachusetts, Hamilton, Bermuda, Hamilton, Bermuda, with 11 more along the way. Scroll the daily outlook below to pack smart for every port of call.

1. Day 1 — Friday, Oct 22, 2027 — Boston, Massachusetts

   Boston, Massachusetts is a scheduled port of call on day 1 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 60°F.

2. Day 2 — Saturday, Oct 23, 2027 — At Sea

   Day 2 of 18 is a day at sea aboard Star Pride, cruising between ports on the Star Collector: Bermuda & Caribbean Island Explorer itinerary.

3. Day 3 — Sunday, Oct 24, 2027 — At Sea

   Day 3 of 18 is a day at sea aboard Star Pride, cruising between ports on the Star Collector: Bermuda & Caribbean Island Explorer itinerary.

4. Day 4 — Monday, Oct 25, 2027 — Hamilton, Bermuda

   Hamilton, Bermuda is a scheduled port of call on day 4 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 76°F.

5. Day 5 — Tuesday, Oct 26, 2027 — Hamilton, Bermuda

   Hamilton, Bermuda is a scheduled port of call on day 5 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 76°F.

6. Day 6 — Wednesday, Oct 27, 2027 — St George, Bermuda

   St George, Bermuda is a scheduled port of call on day 6 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 76°F.

7. Day 7 — Thursday, Oct 28, 2027 — At Sea

   Day 7 of 18 is a day at sea aboard Star Pride, cruising between ports on the Star Collector: Bermuda & Caribbean Island Explorer itinerary.

8. Day 8 — Friday, Oct 29, 2027 — At Sea

   Day 8 of 18 is a day at sea aboard Star Pride, cruising between ports on the Star Collector: Bermuda & Caribbean Island Explorer itinerary.

9. Day 9 — Saturday, Oct 30, 2027 — St Barthelemy

   St Barthelemy is a scheduled port of call on day 9 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.

10. Day 10 — Sunday, Oct 31, 2027 — Virgin Gorda, British Virgin Islands

    Virgin Gorda, British Virgin Islands is a scheduled port of call on day 10 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.

11. Day 11 — Monday, Nov 1, 2027 — San Juan, Puerto Rico

    San Juan, Puerto Rico is a scheduled port of call on day 11 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 83°F.

12. Day 12 — Tuesday, Nov 2, 2027 — St John, US Virgin Islands

    St John, US Virgin Islands is a scheduled port of call on day 12 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 80°F.

13. Day 13 — Wednesday, Nov 3, 2027 — Basseterre, St. Kitts

    Basseterre, St. Kitts is a scheduled port of call on day 13 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 83°F.

14. Day 14 — Thursday, Nov 4, 2027 — St Barthelemy

    St Barthelemy is a scheduled port of call on day 14 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.

15. Day 15 — Friday, Nov 5, 2027 — Philipsburg, St. Maarten

    Philipsburg, St. Maarten is a scheduled port of call on day 15 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.

16. Day 16 — Saturday, Nov 6, 2027 — Jost Van Dyke, British Virgin Islands

    Jost Van Dyke, British Virgin Islands is a scheduled port of call on day 16 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride.

17. Day 17 — Sunday, Nov 7, 2027 — Virgin Gorda, British Virgin Islands

    Virgin Gorda, British Virgin Islands is a scheduled port of call on day 17 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride.

18. Day 18 — Monday, Nov 8, 2027 — San Juan, Puerto Rico

    San Juan, Puerto Rico is a scheduled port of call on day 18 of the 17-night Star Collector: Bermuda & Caribbean Island Explorer cruise on Star Pride.