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Cruise itinerary

32 night ultimate caribbean leeward islands holiday

Ask your friends: Should I go?

  • Departure date: Tuesday, December 23, 2025
  • Return date: Saturday, January 24, 2026
  • Departure port: Miami
  • Ports of call: Philipsburg, St. John, Castries, Roseau, Basseterre, Charlotte Amalie, Half Moon Cay, Amber Cove, San Juan, Road Town, Ft. De France, Bridgetown, St. George's, Scarborough, Willemstad
  • Return port: Miami

Prices:

  • Inside $4,298
  • Outside $5,912
  • Balcony $6,112
  • Suite $10,758

Cruiseable's travel advisors can often find you additional savings & lower fares than the public prices listed here.

Day Location
Visitors jumping from rocks to the sea in St. Maarten.
Want an adrenaline rush? Head to Loterie Farm for a zipline adventure on St. Maarten.
The New World's oldest governor's mansion is still in use. Some 150 consecutive governors have served over the past 300 years. It's at the west end of Calle Fortaleza in Old San Juan, Puerto Rico.
West of San Cristóbal along the coastline is the neighborhood of La Perla in Old San Juan, Puerto Rico. It's part of the area's UNESCO World Heritage Site.
The sun sets on a catamaran on a quiet bay on Barbados.
Rent a bike and take to the road on St. Maarten.
Grab a towel and hit the beautiful beaches of St. Maarten.
Fort San Felipe del Morro in Old San Juan, Puerto Rico, a UNESCO World Heritage Site.
Selling textiles in St. Maarten in the Caribbean.
One of the beautiful beaches in Basse-Terre, Guadeloupe.
Near Cupecoy Beach, St. Maarten.
Guard bunks at historic Castillo de San Cristóbal in Old San Juan, Puerto Rico. Completed by Spanish forces in 1783, it was the largest fortification built by Spain in the New World.
Catedral Santiago Apóstol in Fajardo, along the northeast coast of Puerto Rico.
This bronze fountain "Raíces" (for "Roots") in Old San Juan celebrates Puerto Rico’s rich cultural diversity and historical heritage.
On the beach at the Hilton in Bridgetown on Barbados.
A dramatic landscape on St. Maarten.
Avocado gazpacho at Toro Salao on Calle Tetuan in Old San Juan, Puerto Rico.
Colorful al fresco dining in Old San Juan, Puerto Rico.
Balconies on Calle San Sebastian in Old San Juan, Puerto Rico, a UNESCO World Heritage Site.
The harbor at Bridgetown, capital of Barbados.

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