Cruising the Caribbean - Your Sun-Soaked Guide to Tropical Island-Hopping

Everything you need to know before booking your dream Caribbean cruise – from best islands and cruise lines to what to pack and when to go.

So you’re thinking about taking a cruise to the Caribbean? Excellent choice! Whether you’re dreaming of white-sand beaches, rum punch in hand, or jungle adventures and coral reef snorkelling, the Caribbean really does have it all. Here’s everything you need to know, using some of the most frequently asked questions when planning a Caribbean cruise.

What is the best time to cruise the Caribbean?

The Caribbean is a year-round destination, but the most popular time to cruise is from December to April—hello, winter sun! This is the dry season, with warm temperatures, less rain, and calmer seas. It’s also peak season, so expect higher prices and busier ports. If you’re after a bargain and don’t mind the odd tropical shower, May to early June or September to early November can offer great deals. Just keep in mind: hurricane season runs from June to November - most cruises still sail safely, but travel insurance is a must.

Do I need a passport for a Caribbean cruise?

Yes… and sometimes no. For UK cruisers, a passport is essential. However, If you’re joining the cruise from the US on what’s called a closed-loop cruise (departing and returning to the same US port) and you are a US citizen, you may not need a passport - just a government-issued photo ID and a birth certificate will often do. But I highly recommend bringing a passport anyway. It makes disembarking easier, especially if you have a medical emergency or miss the ship and need to fly home from a foreign port.

What should I pack for a Caribbean cruise?

Think light, breezy, and beach-ready! Pack swimsuits, flip-flops, light layers, a sun hat, sunglasses, and high-factor sunscreen. Don’t forget a few smarter outfits for formal nights or speciality restaurants -cruise lines often have dress codes in the evening. Also handy: a reusable water bottle, insect repellent, motion sickness tablets (just in case), and a small day bag for excursions. Oh, and leave space for souvenirs—Caribbean rum and spices are hard to resist!

Which Caribbean islands are best to visit on a cruise?

That’s like asking which dessert is best - it depends on your taste! Here are a few favourites:

St. Maarten – Dutch and French culture, duty-free shopping, and the famous Maho Beach (where planes fly frighteningly low).
St. Thomas (USVI) – Stunning beaches, world-class snorkelling, and easy access to the neighbouring island of St. John.
Barbados – Vibrant nightlife, historic Bridgetown, and perfect surfing beaches.
Aruba – Desert-like landscapes, flamingo-dotted beaches, and year-round sunshine.
Jamaica – Think reggae, waterfalls, jerk chicken, and laid-back vibes.

Each island has its own personality—some are ideal for beach bums, others for adventure-seekers or culture lovers.

Are Caribbean cruises all-inclusive?

Not quite. Your cruise fare typically includes accommodation, main dining, snacks, entertainment, and transport between ports. But extras—like speciality dining, alcoholic drinks, shore excursions, Wi-Fi, spa treatments, and tips—often cost more. Some lines (like Virgin Voyages, Marella, or MSC Yacht Club) include more perks in their fares. If you’re a cocktail-in-hand-all-day sort of cruiser, look for packages that bundle drinks and Wi-Fi to save money.

Do Caribbean Cruises include Flights?

Caribbean Cruises are often sold as cruise only by brands such as Royal Caribbean, Norwegian Cruise Lines, Celebrity and Princess Cruises, with the option of adding on flights. UK travel agents can create a bespoke package, or choose a fly cruise with Marella, P&O Cruises or, from late 2025, Ambassador Cruise Line.

What is a typical Caribbean cruise itinerary?

A standard Caribbean cruise lasts 7 to 10 nights, though shorter and longer ones are available. Cruises usually sail from Florida (Miami, Fort Lauderdale, or Port Canaveral), San Juan, or even Barbados. Itineraries are often split into:

Eastern Caribbean – St. Thomas, St. Maarten, Puerto Rico, the British Virgin Islands
Western Caribbean – Cozumel (Mexico), Grand Cayman, Jamaica, Belize
Southern Caribbean – Aruba, Curaçao, Bonaire, Barbados, Grenada

You’ll often get a mix of beach days, historic towns, and active excursions like zip-lining or reef diving.

Is it safe to cruise the Caribbean?

Absolutely—but like any holiday, it’s wise to stay alert. Stick to reputable excursions, avoid isolated areas, and keep an eye on your belongings in busy markets. Most cruise lines also have their own private islands (like Royal Caribbean’s CocoCay or MSC’s Ocean Cay), which are ultra-safe, clean, and set up for a perfect beach day.

Will I get seasick on a Caribbean cruise?

Modern cruise ships are massive and have stabilisers to reduce motion. If you’re prone to motion sickness, pick a midship cabin on a lower deck, bring some sea bands or ginger tablets, and avoid heavy meals or alcohol on rough days. But honestly? Most Caribbean waters are pretty calm—especially during dry season—so chances are you won’t even notice the ship moving.

What are the best cruise lines for the Caribbean?

Some of the many brands that offer Caribbean Cruising

There’s something for everyone:

Royal Caribbean & Carnival – Great for families and first-timers, with fun activities and lively onboard vibes.
Celebrity Cruises & Princess – More refined, ideal for couples or grown-up getaways.
Virgin Voyages – Adults-only, trendy, and packed with perks (and no buffets!).
Marella Cruises – All-inclusive, British-style cruising with a more relaxed feel.
P&O Cruises & Ambassador Cruise Lines - Both British favourites offering a familiar, comfortable environment.
Windstar & SeaDream – Smaller ships for off-the-beaten-path islands and luxury without the fuss.
MSC Cruises & Disney Cruise Line - Family cruising to the Caribbean.

Final Thoughts: Is a Caribbean cruise worth it?

100% yes. Whether you’re in it for the island-hopping, the food, the culture, or just total relaxation, cruising is one of the easiest and most enjoyable ways to explore the Caribbean. You unpack once, wake up somewhere new every day, and everything’s organised for you. Sun, sea, and maybe a piña colada or two—what’s not to love?

Ready to book your Caribbean cruise? Start by thinking about what kind of trip you want—beaches, culture, adventure—and pick a cruise line and itinerary that ticks your boxes. Happy sailing!

Need more detail? See my Ultimate Guide to Caribbean Cruising

Caribbean Cruising- Everything You Need to Know Before You Set Sail