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Loading Travel Forecast…Departing San Juan, Puerto Rico on January 23, 2027, the SeaDream Cruises ship SeaDream I runs this 7-night Leeward Islands Discovery sailing. It's a classic Caribbean cruise. Travelers sailing in January can generally expect warm, sunny weather with gentle trade winds. Ports of call include San Juan, Puerto Rico, St John, US Virgin Islands, Virgin Gorda, British Virgin Islands, with 5 more along the way. Scroll the daily outlook below to pack smart for every port of call.
San Juan, Puerto Rico is a scheduled port of call on day 1 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 79°F.
St John, US Virgin Islands is a scheduled port of call on day 2 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 77°F.
Virgin Gorda, British Virgin Islands is a scheduled port of call on day 3 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 78°F.
Nevis, St Kitts and Nevis is a scheduled port of call on day 4 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 74°F.
Anguilla is a scheduled port of call on day 5 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 78°F.
St Barthelemy is a scheduled port of call on day 6 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 78°F.
Jost Van Dyke, British Virgin Islands is a scheduled port of call on day 7 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 78°F.
San Juan, Puerto Rico is a scheduled port of call on day 8 of the 7-night Leeward Islands Discovery cruise on SeaDream I. Expected weather: partially cloudy with highs near 79°F.
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Most PopularHalf or Full-Day Private Boat Charter from St. John or St. Thomas
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Most PopularNevis Nice , Private Local and Historical Island Tour
From $130
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Most PopularTraditional Sailing Adventure to Anguilla's Prickly Pear Cays
From $644
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St John, US Virgin Islands
Most PopularHalf or Full-Day Private Boat Charter from St. John or St. Thomas
From $695
Book Now
Budget PickSt. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin
From $119
Book NowNevis, St Kitts and Nevis
Most PopularNevis Nice , Private Local and Historical Island Tour
From $130
Book NowAnguilla
Most PopularTraditional Sailing Adventure to Anguilla's Prickly Pear Cays
From $644
Book NowPowered by Viator/Tripadvisor. Booking through our links may earn us a commission keeping this site free at no cost to you.