Your Cruise, Your Weather
Plan Your Cruise With Free Weather Forecasts
Loading Travel Forecast…Loading Travel Forecast…Loading Travel Forecast…Join Windstar Cruises's Star Pride for a 11-night voyage on the Masterpieces at Sea: Gems of the Leeward Islands route, setting out from San Juan, Puerto Rico on October 28, 2026. It's a classic Caribbean cruise. Travelers sailing in October can generally expect warm, sunny weather with gentle trade winds. Ports of call include San Juan, Puerto Rico, St John, US Virgin Islands, St Barthelemy, with 8 more along the way. The forecasts below break the weather down port by port.
San Juan, Puerto Rico is a scheduled port of call on day 1 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 83°F.
St John, US Virgin Islands is a scheduled port of call on day 2 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 81°F.
St Barthelemy is a scheduled port of call on day 3 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.
Basseterre, St. Kitts is a scheduled port of call on day 4 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 83°F.
Falmouth, Antigua is a scheduled port of call on day 5 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.
Iles Des Saintes, Guadeloupe is a scheduled port of call on day 6 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 81°F.
Pigeon Island, St Lucia is a scheduled port of call on day 7 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 83°F.
St Georges, Grenada is a scheduled port of call on day 8 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 81°F.
Jost Van Dyke, British Virgin Islands is a scheduled port of call on day 9 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.
Virgin Gorda, British Virgin Islands is a scheduled port of call on day 10 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.
San Juan, Puerto Rico is a scheduled port of call on day 11 of the 11-night Masterpieces at Sea: Gems of the Leeward Islands cruise on Star Pride. Expected weather: partially cloudy with highs near 82°F.
Compare rates and find your next sailing.