Popular May Caribbean Cruises

Fancy a sunny break before summer gets busy? A Caribbean cruise in May is a brilliant way to enjoy warm weather, great value and a more relaxed pace.

Find our fantastic range of handpicked May Caribbean cruises below. Plus, book today & earn Cruise Miles®.

Why Book a Caribbean Cruise in May?

May is a fantastic month for a Caribbean cruise if you’re looking for that sweet spot between peak season and summer.

The weather is still beautifully warm, the seas are calm, and the islands feel a little less crowded - which means more space on the beaches, shorter queues at popular attractions, and an overall more laid-back atmosphere. It’s a great time to explore without feeling rushed, and you’ll often find sailings that offer excellent value compared to the winter months.

It’s also a month where variety really shines. You might find yourself exploring St Lucia, with its famous Pitons and lush scenery, then heading to Martinique, where French-Caribbean culture, local markets and beach cafés give the island a totally different feel.

Why Book with ROL Cruise?

When you book your Caribbean cruise with ROL Cruise, you’ll have the reassurance of booking with the UK’s No.1 Independent Cruise Specialist. We’re ABTA and ATOL protected, and our award-winning team has more than 1,000 years of combined experience - so you’ll always get expert advice from people who know cruising inside out.

We’ll help you find the right sailing based on your preferences, whether that’s the best-value itinerary, the ideal cruise line, or the right balance of sea days and island time. Plus, every booking earns rewards through our exclusive Cruise Miles® programme, which has already helped customers save over £12 million on their cruise holidays - alongside any loyalty points offered by your chosen cruise line, making your May Caribbean cruise even more rewarding.