When youve worn out the Caribbean cruise itineraries leaving from Florida ports, it may be time to venture to the islands further south. Our editors have tracked down a more unusual 7-night cruise sailing from San Juan, Puerto Rico starting from just $599 thats just $86/night! Plus, the deluxe Celebrity Summit has three winter embarkation dates to choose from, including two during peak cruise season.After setting sail from San Juan, this ship makes its first stop in the Dutch city of Philipsburg, St. Maarten, an ideal location to pick up souvenirs thanks to its wealth of duty-free shopping. Next is Roseau, Dominica where visitors can pluck fresh mangos and star fruit right off the trees while taking life a bit slower for a while. Following Dominica is a visit to Grenada during which time the ship will dock in St. Georges the islands capital where pastel hues and red-tile roofed homes line the streets. Passengers will also experience Tobago, which offers a blend of vibrant beaches and tropical rainforests. Before returning to San Juan, the Summit will also call on Bridgetown in Barbados, a perfect place to go snorkeling, or wind down on the white-sand beaches. Sailing dates include December 12, January 9, and January 23. Those that book the December 12 sailing can upgrade to an oceanview stateroom starting from $648, or a balcony cabin from $697.