The Caribbean sea has dozens of islands that range in size from large to tiny, and each island has its own vibe. Some islands have many different clusters or resorts and towns, while others only have a few hotels on the whole island. If you don’t yet have much experience with Caribbean vacations, it’s hard to know where you should be looking because some islands are much better than others depending on what you are after.
We have been keeping our list of Caribbean island destinations from cheapest to most expensive since 2011, and our list of Caribbean destinations for all-inclusive resorts from cheapest to most expensive since 2012, but cheapest obviously doesn’t always make the best choice.
After having spent time on all of the popular islands and most of the smaller ones as well, I have compiled my recommendations for the best Caribbean island destinations for different kinds of trips. Below we cover best, cheapest, islands where everyone speaks English, best party islands, and much more. We also have a separate list of the best Caribbean islands and resorts for honeymoon couples.
Last updated in October, 2023.
Find the best budget Caribbean destination for you
Below you’ll find our picks in a wide variety of categories, and it’s very likely that one of the categories will closely match your main goal. You might also want to look into Caribbean cruises, which combine several of these in one easy trip.
Best Caribbean destination for cheap and high-quality all inclusive resorts: Punta Cana, Dominican Republic

You can be in your gorgeous resort less than an hour after your plane touches down, as everything is built for efficiency on a big scale. That isn’t really true almost anywhere else in the Caribbean except for Cancun. Your big choice will be which of the European-based resort chains to spend your entire holiday at, because there is almost nothing interesting outside of the resort compounds. You can book a day trip to the large capital city of Santo Domingo from any resort and it’s worth it if you are interested in history and such, but most guests are better off just staying at their hotel.
Punta Cana also ranks tops for the best Caribbean island destination for families with kids, which is all explained in detail in this link.

The all-inclusive resorts all offer various off-site excursions for diving and fishing and zip-lines and whatnot, but aside from those you’ll want to stay in your own resort so it’s important to choose wisely. In the end, you won’t find better all-inclusive deals at well-run resorts anywhere.
My video showing all-inclusive resorts in Punta Cana and Cancun
If you are pretty sure you are interested in staying in an all-inclusive hotel in the Caribbean then most of the list below won’t be as interesting, but the video above should help you a lot. In it you’ll see lots of video footage of various all-inclusive resorts in Punta Cana and Cancun and their prices for a visit in January, which is high season.
These are the links to the resorts mentioned in the video:
>>>Emotions by Hodelpa Puerto Plata – US$176/night for two as of August, 2023 for January 2024 stays
>>>Barceló Bávaro Palace Punta Cana – US$290/night
>>>Occidental Costa Cancún – US$236/night
>>>Allegro Playacar Playa del Carmen – US$207/night
>>>Cozumel Hotel & Resort Trademark Collection by Wyndham – US$247/night
>>>Sandals all-inclusive resorts – The best premium resorts at US$500 and up
Best cheap Caribbean destination for all-inclusives where everyone speaks English: Montego Bay and Ocho Rios, Jamaica

The Montego Bay Airport is almost as large and busy as the Punta Cana Airport, but it’s nowhere near as efficient. Still, you can be at your resort about an hour after you land, if you get a bit lucky, and after that it should be smooth sailing. Montego Bay even has an amazing Sandals resort with overwater bungalows for those with larger budgets.

There are dozens of large hotels along the beaches of Jamaica’s northern coast between Montego Bay and Ocho Rios, mostly run by the same large European chains that own the resorts in Punta Cana. Read the reviews carefully and choose the resort that seems to suit you best, because you probably won’t be leaving the place except for a visit to the impressive Dunn’s River Falls near Ocho Rios.
It’s also worth noting that as of late 2023, the cheaper all-inclusive resorts in Jamaica seem to be suffering from mostly bad reviews. It’s very noticeable for someone who has been checking these reviews for 10 years now. It seems possible that the cheaper resorts aren’t able to get enough reliable and trained staff so standards are falling. If you can, stay at a Sandals resort and you’ll get the best service in Jamaica.
Best Caribbean destination for the absolute cheapest good all-inclusive resorts: Puerto Plata, Dominican Republic

We continue to find well-rated all-inclusives here that start at US$110 per night in low season, and only US$160 per night in high season. And to be clear, these are prices for two people sharing a room by the beach, including all taxes and gratuities, and including all the alcohol you can drink to go along with 3 buffet meals each day.

On the other hand, if you tend to be pretty easy to please and are forgiving when things go a bit wrong, you can have an amazing trip for almost nothing in Puerto Plata. Personally I’d be fine at resorts like these and some of my friends would as well, but my partner would be miserable the entire time so I won’t be taking her to one of them anytime soon.
Another factor to consider is the cost of the flights. Punta Cana has far more flights from more airports, so many people will still have a better experience going there. But flights into Puerto Plata are often around the same price, so if you can find a good connection then this is probably your best budget all-inclusive choice.
*Varadero, Cuba*
While citizens of the United States still aren’t able to book themselves into the all-inclusive resorts of Cuba, this has long been a popular budget destination for Canadians and Europeans. Varadero Beach resorts are even cheaper than those in the Dominican Republic because Cuban wages are famously almost zero. If you want to support this then you can save money at the same time.
Varadero has about 30 all-inclusive resorts out on its peninsula and if you are in Canada or Europe you should have an easy time finding them at travel agents or online travel sites. But if you are in the United States you’ll be shocked to find that it’s close to impossible to read about any of these places due to the ongoing travel ban.
Best Caribbean destination for a great long-weekend trip: Paraside Island/Nassau, Bahamas

These are NOT all-inclusive resorts, by the way, so you’ll be on the hook for all of your drinks and meals. But there are loads of restaurants, bars, and nightclubs in various price ranges to choose from, so at least you’ll have the exact variety that pleases you. There are about another dozen large hotels on the main island of New Providence, most of which are even closer to the airport, but those don’t have the same access to off-site choices as Paradise Island.

Overall, with many direct flights from major hubs and large cities in North America, you can get to Nassau faster than any other place on this list, saving at least an hour in each direction if not more. The shorter the trip, the more important it is to save time in flight, so this is the first destination to consider.
Long story short, if your time is limited and your budget is healthy then you can be enjoying the Bahamas more quickly from leaving your home than pretty much any other Caribbean destination. However, if your budget is too low for Paradise Island then you are probably better off flying an hour or so longer to Cancun, which is discussed below.
Best Caribbean destination for big nightlife and spring break: Cancun, Mexico

You’ll be paying a cover charge in the US$60 to US$80 neighborhood or even higher, but it will include your drinks so it’s not a bad deal for the right crowd. There are many high-rise beach hotels in the same area, and hundreds more in greater Cancun, ranging from incredibly cheap to insanely expensive. So as long as you are willing to pay the club admission, you can go to Cancun on almost any budget.
Cancun is so large and varied by itself that I recently wrote a guide to choosing where to stay in Cancun. There are 7 distinct areas including two offshore islands, and each has its own price range and vibe. If you want to go to the mega clubs then the Cancun Hotel Zone is your best bet, but you can still reach those clubs from other areas and many of them are cheaper and also nicer in some ways.

As expensive as the nightclubs can be, there are many cheap options for food and drinks in the exact same area. You can get a filling quesadilla for under US$2, and an ice-cold Corona for around US$2.50 if you look around. Or you can pay US$30 for a pasta dish at the restaurant of your hotel next door. Cancun has it all.
By the way, the nightclubs are all located in one small part of the Cancun Hotel Zone and if you think you’d like to visit the clubs each night it could be worth staying in one of the hotels within walking distance because cabs in the area can be expensive. If you look on a map you’ll see the the Cancun Hotel Zone is on a peninsula that is shaped like a 7 and connected to the mainland on both ends. The nightclubs are all located in the area in the top-right of the number 7, so out on the far point.
Best budget Caribbean destination for a wide variety of restaurants, bars, and activities: Playa del Carmen, Mexico

While the main tourist district (5th Avenue) in Playa del Carmen is no doubt “touristy,” it’s also quite charming and pleasant. There are scores of smaller hotels mixed within the town and a close walk from the beach, and all of them are surrounded by small restaurants, bars, nightclubs, and shops, with almost no chains in sight.

By the way, the restaurants scene in Playa del Carmen is fairly international, so you needn’t worry about having to choose from only Mexican joints. There is sushi and just about anything else you can imagine, so even those who aren’t fond of Mexican food will not go hungry. Hotels a bit off the beach are quite cheap as well, so this is a great value destination in general.
Best budget Caribbean destination for families with kids: Punta Cana, Dominican Republic

Here’s the thing: especially if your children are young but even if they are around 16 years old, you don’t want them exploring a foreign island on their own, particularly if they don’t speak the local language. If you stay at a normal beach hotel you’ll always be watching them or worrying about them, or both. One great feature about all-inclusive resorts is they have perimeter security checking who is leaving and arriving and many of them are on huge pieces of land as well.

>>>A full list of the best Caribbean islands for families with kids
Best budget Caribbean destination for an old-school chill-out beach holiday and 420-friendly: Negril, Jamaica

If that is you then you specifically want to stay somewhere along the pleasant 7-Mile Beach area, which runs north of the tiny (and disappointing) town of Negril itself. South of the town there are more small hotels and resorts, mostly perched on a cliff instead of on the beach. The cliff area is also where you’ll find the very touristy Rick’s Cafe, known for cliff diving, and pretty much a must-visit stop on any Negril trip.

Speaking of a chilled out holiday, if cheap Red Stripes and rum drinks aren’t enough to take the edge off, Negril is also a place where marijuana is sold and enjoyed out in the open. As of mid 2015, it has been officially decriminalized in Jamaica, so a US$4 fine is (in theory) the worst outcome. But in reality, the only police you will see are the Tourist Police, who are actually there to keep tourists safe, and they will otherwise ignore you. As always, you have to be aware of your surroundings, but this is the best place for 420 fans, and it’s all very cheap and easy.
Best Caribbean destination that is wonderful and everything is very cheap: Cartagena, Colombia

Cartagena is a cheapskate’s or backpacker’s dream because even little splurges are within anyone’s budget. A normal taxi ride from the airport to the beautiful walled historic city is about US$5, and still under US$10 to get from the airport to the newer beach area of Bocagrande just beyond the colonial area. In other words, the value is amazing, but there are some things to know.

Your main decision will be whether to stay in the walled historic city, where hotels are small and don’t have many exterior windows, or along Bocagrande where hotels are large if a bit generic. Whichever you choose, you’ll want to spend time in the other place on your trip, and a taxi between them is literally only about US$4 without any haggling needed.
Best affordable Caribbean destination with a gorgeous historic city next to excellent beaches: San Juan, Puerto Rico

Another difference is that similar things in San Juan will cost 2 to 3 times as much as in Cartegena, so there is obviously a price to pay for the additional luxury. You can also do a San Juan visit while speaking English the whole time, while in Cartagena knowing some Spanish will be very helpful.

Another benefit here is that the San Juan Airport is another of the busiest in the Caribbean, so flights are frequent and fares tend to be modest. It’s also part of the United States, so you can use US dollars and expect most services to be of good standard. And again, this is one of the few Spanish-native places in the Caribbean where most people that you encounter also speak fluent English, as many of them have lived in the mainland US at one time or another.
Best affordable Caribbean destination to stay for more than two weeks: San Juan, Puerto Rico

Whether you want to stay in historic Old San Juan, or in the nearby beach areas of Condado or Isla Verde, you’ll find loads of apartment buildings in between the tall hotels. As a result there is an active market for apartment rentals on AirBnB as well as services that normally only rent by the week or month. Outside of Christmas or New Year’s weeks, you should be able to get a pretty good deal on a longer-term apartment rental.

Longer term visitors will also be happy to know that there are movie theaters and a wide variety of international restaurants in the popular areas, so you can lead a pretty normal life while you are enjoying the sunny climate. Rental cars are also famously cheap here, so you can easily get out and see other parts of the island, as long as you are prepared to deal with some of the Caribbean’s most unpredictable drivers.
Best Caribbean destination for jewelry shopping: St. Thomas, US Virgin Islands

A short taxi or shuttle ride or a 30-minute walk from the cruise terminal, you’ll come to the island’s main city called Charlotte Amalie. It was founded in the 1600s so it’s quite a handsome town, but at some point in the mid 20th Century nearly every business in town was converted into a jewelry shop. So it’s actually a disappointing place for a non-jewelry visitor, while it’s an amazing place for those looking for jewelry.

Needless to say, you have to be careful when buying expensive goods when away from home, but most jewelry shoppers here do seem to be happy. Knowing typical prices before you arrive is obviously wise, and you’ll want to be prepared to bargain as well.
Photo credits: All photos by Roger Wade except Puerto Plata by Ichunt on Flickr and raunov on Flickr
Comment*can an american travel to cuba if they fly out of windsor ontario?
James,
It looks like it’s possible although maybe just a bit complicated. Here is some information I found. Good luck! -Roger
Comment*Single Senior wants 5-7 day
Fly, Hotel caribbean island under $900.00
Is that possible?
Sandy,
That price is a little tougher for a single than for each member of a couple staying in the same room, but it’s definitely possible. Obviously it depends on your starting airport to know how much the flight would be. You should be able to fly from most big cities in the east of the US to Punta Cana for around US$400. That leaves $500 for a hotel. You won’t get a beachfront all-inclusive for that, but there are definitely nice hotels on a few of those islands starting under US$100 per night and including breakfast. The cheapest option (meaning the place your money goes furthest) would probably be the Cancun area. Flights are usually reasonable and you can get a cool hotel in Playa del Carmen for under US$100 for sure. Let me know if you have any other questions. -Roger