Caribbean Cruises
Cruise around the idyllic islands and turquoise waters of the Caribbean uncovering the diverse treasures of Jamaica, Cuba, Puerto Rico, Barbados, the British Virgin Islands and more. Discover a patchwork of cultures across the region on a cruise ship or sailing yacht, or don a snorkel to discover the spectacular underwater world below.
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Popular Cruises
11 Days San Juan to San Juan
Operator: Viking Cruises
From
5,434pp
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1,395pp
15 Days San Juan to San Juan
Operator: Azamara Cruises
From
4,946pp
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73pp
Featured Caribbean Cruise Lines Featured Cruise Lines
Where superyacht design and your dream destinations meet. Welcome to how Virgin does cruise ships. With Richard Branson at the helm, Virgin Voyages is more redefining what a luxury cruise ship means by combining premium elements from favorites on land with the freedom and simplicity of a life well lived on the open ocean. With with cool interiors filled with chic bars, city styled eateries, clever accommodation and rock star suites Virgin offers Sailors a new onboard experience, from wellbeing activities, fresh to order eateries and original boundary breaking entertainment without the formalities and traditions of other contemporary cruise lines.
Here at Azamara, we continue our efforts to be the world's top up-market cruise line. As such, we are committed to providing you with unparalleled service; more the finest dining at sea; a glorious spa and wellness retreat, and innovations such as Destination Immersion® experiences. With our hallmark of stay longer, experience more, we'll not only take you to awe-inspiring destinations, but also give you more time to fall in love with them.
For 150 years, Holland America Line has been a recognized leader in cruising. If you are looking for some of the most spacious and comfortable ships at more sea, award-winning service, exquisite dining, extensive activities and enrichment programs and compelling worldwide itineraries, you've come to the right place. Balance. Depth. Authenticity. These are the elements we bring to more than 500 itineraries, stopping in 100 countries, the world over.
Discover
Must do experiences and highlights when cruising the Caribbean
Old Meets New in San Juan 
Captivating Jamaica 
Views from the British Virgin Islands 
Cuban Rhythms Latest Reviews
What our clients are saying about their journeys to the Caribbean
Cruising the Caribbean
Circle Caribbean From Fort Lauderdale
Christine and Rob, NSW, Australia, Nov 2025
We are now Platinum members with Princess and always find the cruise staff to be friendly and willing to help and please passengers. We cruised the Caribbean on the Island Princess which is a smaller ship compared with some of its sister ships. We did notice that the variety of food choices were not as wide as some other ships we have cruised with. read more Ports of call were fabulous, and we enjoyed not having to use a tender to reach ports. Georgie was great in handling our bookings and keeping us informed of changes to flights by United Airlines. We would recommend cruising with this company for a hassle free holiday. Thank you Georgie.
Cruising the Caribbean in Comfort and Style
West Indies Explorer
Julie & David, QLD, Australia, Mar 2018
As a first experience of ocean cruising, Viking has probably spoilt us for a number of other lines. While not a small ship (~900 passengers), we did not encounter the congestion that we imagine happens in much larger ships. The stateroom was lovely, the bathroom larger than expected and very functional, with plenty of storage for everything.
Dining read more options were varied and all very good. Most notably, the tasting menus at The Chef’s Table, which we booked three times, were absolutely exquisite. All the included extras (shore excursions, drinks and wifi) as well as the “no casino, no kids” policy made a positive difference.
The “Viking Sea” is only 2 years old and is decorated in sleek and simple Scandinavian style, featuring beautiful Scandinavian artworks. The ship is spotlessly clean, and one of the highlights was the exceptional quality of all the onboard staff, who were friendly, helpful, engaging, and always happy to have a chat. Viking must have an impressive staff training program.
Our itinerary for the 11 day cruise was a busy one and the included shore excursions were all excellent and very well organised. We visited 9 different islands, with different history, scenery and cultures, shown to us by excellent local guides, and all were both beautiful and fascinating.
The days when we did additional optional excursions were very busy, but we especially loved the French Cooking Class with a local chef in Saint Martin. We were sad to see the lingering devastation of cyclones going back a number of years on all the islands. I would recommend this cruise to others and I am sure that we will travel with Viking again in future.
Dining read more options were varied and all very good. Most notably, the tasting menus at The Chef’s Table, which we booked three times, were absolutely exquisite. All the included extras (shore excursions, drinks and wifi) as well as the “no casino, no kids” policy made a positive difference.
The “Viking Sea” is only 2 years old and is decorated in sleek and simple Scandinavian style, featuring beautiful Scandinavian artworks. The ship is spotlessly clean, and one of the highlights was the exceptional quality of all the onboard staff, who were friendly, helpful, engaging, and always happy to have a chat. Viking must have an impressive staff training program.
Our itinerary for the 11 day cruise was a busy one and the included shore excursions were all excellent and very well organised. We visited 9 different islands, with different history, scenery and cultures, shown to us by excellent local guides, and all were both beautiful and fascinating.
The days when we did additional optional excursions were very busy, but we especially loved the French Cooking Class with a local chef in Saint Martin. We were sad to see the lingering devastation of cyclones going back a number of years on all the islands. I would recommend this cruise to others and I am sure that we will travel with Viking again in future.
