Popular September Caribbean Cruises

Fancy a sunny escape as summer winds down? A Caribbean cruise in September is a brilliant way to enjoy warm weather and a more relaxed pace.

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

Why Book a Caribbean Cruise in September?

September is a great month for Caribbean cruising if you like the idea of a quieter, more laid-back escape.

With school holidays coming to an end, many sailings feel calmer, and you may even find better value compared to the peak summer months.

The Caribbean is still beautifully warm, the sea is ideal for swimming, and the overall pace in many ports feels wonderfully unhurried - perfect for travellers who want to recharge as much as explore.

It’s also a fantastic time to focus on destinations that feel colourful, cultural and full of character. Puerto Rico is a brilliant option if you like a mix of beach time and history, with its old town streets and lively atmosphere. St Martin is perfect for island-hopping vibes, with a blend of French and Dutch influence, while Guadeloupe offers a mix of rainforest, coastline and authentic Caribbean charm. For something a little different, Bonaire is a favourite for snorkelling and diving thanks to its crystal-clear waters and relaxed feel.

Why Book with ROL Cruise?

Booking your September Caribbean cruise with ROL Cruise means you’ll have peace of mind and expert support from start to finish. We’re ABTA and ATOL protected, and proud to be the UK’s No.1 Independent Cruise Specialist. With over 50 cruise industry awards and a team with more than 1,000 years of combined experience, you can trust us to help you find a sailing that suits you - whether you’re after the best itinerary, the best value, or a particular cruise line or ship.

You’ll also earn rewards every time you book 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. It’s all part of making your Caribbean escape feel even more rewarding - before you’ve even set sail.