Caribbean Travel Guides: Turquoise Water and Timeless Streets
Classic cars rolling through Havana, palm trees leaning over a Dominican beach, salsa drifting out of an open doorway. The Caribbean does not rush, and honestly, neither should you once you get there. Pick a country below and start planning.
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Where the Sea Actually Looks Like the Postcard
Here is the thing about the Caribbean. You have seen the turquoise water in a hundred adverts and you still won't quite believe it when you're standing in it. Havana feels like stepping into a film set, all crumbling colonial facades and 1950s Chevrolets rattling past. The Dominican Republic swings between all-inclusive resort stretches and jungle waterfalls you'd never guess were twenty minutes away. This hub is your jumping-off point. Real routes, honest costs, and the little lessons that keep a trip running smooth.
- 2 countriesCovered on this hub
- Tourist card or visa-freeDepends where you're from
- £35 / $47 / €41Budget daily, from
- Nov to AprDry-season sweet spot
- Sun all yearWarm whenever you go
Best Time to Visit the Caribbean
Warm year-round, but there is a proper wet season worth dodging. Here's the honest breakdown.
Dry Season
Nov to AprThe big one. Blue skies, lower humidity, and postcard-perfect beach days across both islands. Also peak season and peak prices, so book ahead if you're travelling around the holidays.
Shoulder Season
May & NovOur favourite window. Weather is still lovely either side of the wet months, crowds thin out, and prices dip noticeably from the December to April rush.
Rainy Season
Jun to OctShort, heavy afternoon downpours rather than all-day washouts, and it's also hurricane season, so keep an eye on forecasts. Prices drop and the islands are much quieter.
Carnival Season
FebBoth Cuba and the Dominican Republic throw serious Carnival celebrations through February. Streets fill with music and colour, book accommodation early if you want to catch it.
What to Expect, Country by Country
Two very different Caribbean experiences. We currently cover Cuba and the Dominican Republic in depth, with more islands on the way.
Cuba
Classic cars, crumbling colonial grandeur, and a music scene that spills out onto every street corner. Old Havana alone is worth the trip, and Vinales and Trinidad round it out beautifully.
Dominican Republic
Way more than the resort strip. Sixteen national parks, waterfalls, mountains, and a responsible tourism scene that is gaining real ground beyond Punta Cana.
The Greater Antilles
Jamaica's reggae-soaked mountains, Puerto Rico's rainforests, and Haiti's rich, complicated history. All firmly on our list to cover next.
The Lesser Antilles
Sailor's paradise territory. The British Virgin Islands, Barbados, St Lucia's twin peaks, and a string of islands built for slow, sun-soaked days.
Guides by Country
The Caribbean destinations we cover so far, with more islands on the way. Each card opens that country's full hub of guides, itineraries, and budgets.
Ready to Book the Big Stuff?
Two searches sort most of any Caribbean trip: where you'll sleep and how you'll get there.
Find Your Stay
Casas particulares from £15 / $20 / €18 a night in Cuba, all-inclusive resorts in the DR, and everywhere in between. Compare thousands of places in one search.
Search Hotels on Booking.comGrab a Flight Deal
Flights into Havana and Punta Cana from around £300 / $400 / €350 return in shoulder season. Compare routes before prices climb.
Compare Flight DealsTop 5 Things to See and Do in the Caribbean
Famous for a reason. Here's our honest take on five experiences that live up to every bit of the hype.
Old Havana, Cuba
A UNESCO World Heritage site where 1950s Chevrolets still rattle past crumbling colonial plazas. Wander the cobbled streets, grab a mojito, and stay out for a night of salsa. It genuinely feels like stepping back sixty years.
Explore our Cuba guides →Punta Cana Beaches, Dominican Republic
Powder-white sand and water so clear it looks touched up. Great for an all-inclusive reset, but venture beyond the resort strip for waterfalls, cenotes, and mountains few visitors bother with.
Explore our DR guides →Salsa in Havana
Music is not background noise here, it is the whole atmosphere. Find a local club, not a tourist show, and let someone drag you onto the floor. You will be terrible at it and it will not matter one bit.
Explore our Cuba guides →Diving & Snorkelling
Coral reefs, shipwrecks, and warm, clear water most of the year. Both Cuba's Jardines de la Reina and the DR's northern coast offer proper world-class dive sites without the crowds of bigger destinations.
Plan a diving trip →Vinales Valley, Cuba
Cuba's tobacco country, all limestone cliffs and bright green fields. Tour a family-run farm, watch cigars rolled by hand, and stay for the sunset over the mogotes. Slower pace, huge payoff.
Explore our Cuba guides →Latest Caribbean Guides
Our newest articles, itineraries, and city guides from across the region.
Caribbean Travel Resources
The booking sites and tools we actually use on our own trips. No filler, just what works.
Casas & Hostels
Cuban casas particulares and Dominican hostels, with millions of traveller reviews.
Search Hostelworld →Hotels & Resorts
Our go-to for everything from £15 / $20 / €18 casas to Punta Cana all-inclusives.
Search Booking.com →Car Hire
Compare rental prices across the Dominican Republic. Handy for exploring beyond the resort strip.
Compare with DiscoverCars →Tours & Activities
Havana walking tours, Vinales cigar farms, and DR waterfall trips in one search.
Browse GetYourGuide →eSIM Data
Land connected. One eSIM covers the Dominican Republic from about £4 / $5.50 / €4.70. Cuba's network is more limited, so check coverage first.
Get an Airalo eSIM →Travel Insurance
Non-negotiable for either island. Good cover costs less than a night out and saves you a fortune if things go wrong.
Compare with VisitorsCoverage →Flight Compensation
Delayed or cancelled flight? You might be owed money. Takes a couple of minutes to check.
Check with CompensAIR →Airport Transfers
Pre-book a driver and skip the taxi haggle after a long flight into Havana or Punta Cana.
Book a Transfer →When Travel Goes Sideways
Lost passports, pickpockets, cancelled flights. It happens to the best of us. Here's how to handle it like a pro.
Travel Problems Hub
From missed connections to lost luggage, the fixes for travel's most common headaches.
Visit the Hub
Robbed Abroad?
The exact steps to take in the first 24 hours after a theft, from police reports to emergency cash.
Read the Guide
Health & Wellbeing
Sun safety, dodgy tummies, and staying healthy on the road. The stuff that keeps a trip on track.
Stay WellCaribbean Travel FAQs
The questions we get asked most, answered honestly.
Do I need a visa to visit the Caribbean?
For Cuba, most nationalities need a tourist card, easily sorted online or through your airline before you fly. US citizens face extra restrictions and generally need to travel under an approved category. The Dominican Republic is visa-free for most UK, EU, US, and Canadian passport holders for tourist stays, with a tourist card cost usually built into your flight or resolved on arrival. Always check current official advice before booking, since Cuba's rules shift more often than most.
When is the best time to visit the Caribbean?
November to April is the classic dry season for both Cuba and the Dominican Republic, with the best weather and, naturally, the biggest crowds and prices. May and November are excellent shoulder months, still warm, noticeably cheaper, and quieter. June to October is hurricane season, so keep half an eye on forecasts if you're travelling then, though it also brings the lowest prices of the year.
How much does a Caribbean trip cost per day?
Cuba is genuinely great value if you stay in casas particulares and eat where locals eat, budget around £35 / $47 / €41 a day. The Dominican Republic swings a lot depending on style, an all-inclusive resort can run £80 to 150 / $107 to 200 / €93 to 175 a day, while independent budget travel outside the resorts is closer to Cuba's numbers. Flights tend to be the biggest single cost for both.
Is the Caribbean safe for travellers?
Broadly yes, and Cuba in particular has a reputation for low violent crime. The everyday risk in both countries is petty theft, pickpocketing and bag snatching, especially around Old Havana and busy Dominican tourist areas. Keep valuables out of sight, use official taxis, and you'll most likely have zero issues. Always check current government travel advice before you go, especially for the Dominican Republic's off-resort regions.
Can I use my card in Cuba?
This one catches people out. US-issued credit and debit cards do not work in Cuba at all, including for ATM withdrawals. Cards issued elsewhere, UK, EU, Canada, generally work but often carry a 3% surcharge per transaction. Bring more cash than you think you'll need as a backup, since connectivity and card systems can be unreliable outside Havana.
Can I drink the tap water in the Caribbean?
No, stick to bottled or filtered water in both Cuba and the Dominican Republic. It's technically drinkable in some spots but not worth the risk for visitors. Bring a reusable bottle with a built-in filter, be cautious with ice away from hotels and resorts, and you'll sidestep the stomach issues that catch out a lot of first-timers.
Not Sure Where to Start?
Take the pressure off. Our Start Here page walks you through planning step by step, or browse every destination we cover and see what grabs you.