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Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
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Cruises to the Caribbean

Caribbean cruise destinations

  • Jamaica: Montego Bay, Falmouth, and Ocho Rios are some of the most popular ports in Jamaica. Whether you explore the attractions at Aqua Sol Theme Park in Montego Bay or snorkel off the shore of Ocho Rios’ turtle beach, you’ll find an exciting vacation awaits you in Jamaica.
  • Puerto Rico: Stop in San Juan, Puerto Rico’s capital, and explore the area’s natural wonders and manmade marvels. Hike the rugged landscape of El Yunque Forest and snap some pictures of the colorful architecture in Old San Juan.
  • Virgin Islands: Looking for turquoise waters? Cruise to St. Thomas. St. Croix offers lush jungles and charming colonial towns to explore, while St. John is known for its massive mangrove trees and powder-soft sandy beaches.

How long do Caribbean cruises last?

There are several different lengths for Caribbean cruise deals. Here are the most popular options:

  • Short-term cruises: There are Caribbean cruises that last three to five days. They’re ideal for the traveler looking for a brief weekend getaway. Some cruise ships leave from Fort Lauderdale and travel through the Western Caribbean for a short, but fun-filled, getaway.
  • Weeklong cruises: The standard Caribbean cruise lasts around seven days. In this amount of time, you can expect to visit four to seven ports in various island locations.
  • Extended stay cruises: Hit the high seas for up to 21 days! During this trip, you’ll see multiple regions of the Caribbean, develop a deeper understanding of the area, and be able to stop at 8 to 15 ports of call.

Cheap Hotels

Estimated price for 1 night/2 adults

Hotel El Convento

Hotel El Convento

100 Cristo St, San Juan, 00901
  • Free Cancellation
  • Reserve now, pay when you stay
4.5 out of 5.0
 
 

Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, breakfast, and room service. Our guests praise the breakfast and the helpful staff in our reviews. ...

Hotel El Convento$208

May 23 - May 24

Sheraton Old San Juan Hotel

Sheraton Old San Juan Hotel

100 Brumbaugh Street, San Juan, 00901
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 

Stay at this 4-star business-friendly hotel in San Juan. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms ...

Sheraton Old San Juan Hotel$195

May 30 - May 31

The Reef at Atlantis

The Reef at Atlantis

Paradise Beach Drive, Paradise Island, New Providence
    4.5 out of 5.0
     
     

    Stay at this 4.5-star luxury resort in Paradise Island. Enjoy free WiFi, a private beach, and a marina. Our guests praise the helpful staff and the spacious ...

    The Reef at AtlantisGet Rates

    Boutique Hotel Palacio

    Boutique Hotel Palacio

    Calle Duarte 106, Santo Domingo, Distrito Nacional, 10211
    • Free Cancellation
    • Reserve now, pay when you stay
    3.5 out of 5.0
     
     

    Stay at this 3.5-star business-friendly hotel in Santo Domingo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the spacious rooms and the ...

    Boutique Hotel Palacio$67

    Jun 4 - Jun 5

    *Prices are cruise only, per person, double occupancy. Taxes, fees and port expenses not included. Rates are valid for US and Canadian residents only. Fuel supplement may apply. Savings advertised and Expedia Extras are based on specific cabin types and sailing dates, and may not be available for all cabin types/sailings.