Cheapest Caribbean Islands: 32 destinations by price in 2023
Extremely popular with both North Americans and Europeans during the winter months, the Caribbean is filled with islands and destinations that range from cheap & basic to posh & exclusive. You’ll also find islands where English dominates, but also where Spanish, French, or Dutch are far more common.
Ranking Caribbean islands and destinations by price is challenging for a variety of reasons, so we simplified it by including only a cheaper 3-star hotel room for a week and two cheap flights from New York City. Generally speaking, islands with cheaper hotels will also have cheaper meals and diving etc. Many of the best deals in the Caribbean are at its 400 or so all-inclusive resorts. If that sounds interesting also check out our list of the cheapest Caribbean islands for all-inclusive resorts, which lists 17 destinations from cheapest to most expensive.
Updates for 2022
COVID-19 situation
As of September, 2022, most Caribbean islands have no COVID or vaccination restrictions or require just a negative test or proof of vaccination. Mexico, Dominican Republic, and Jamaica have removed all restrictions so you can travel freely.
We have the COVID rules and guidelines for visitors for some countries in this article, and a more complete list can be found at the link below.
Updates for 2023
All hotels rates and airfares have been updated for the 2023 high season as of September, 2022.
The last time we updated this list it was for stays in the Omicron times. Airfares were low and hotel prices were pretty reasonable as well. Now for stays in January, 2023, airfares are up about 30% on average to the highest fares we have seen since we began tracking them in 2012. Booking early is usually the best way to get a good deal because last-minute bargains are pretty much a thing of the past.
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Below are the 32 most popular Caribbean destinations (some with a few per island, plus Mexico) ranked from cheapest to most expensive. Those not sure if they can afford a trip at all will obviously choose from the ones near the top, while those who would rather avoid people who aren’t sure if they can afford a trip or not will find better choices further down the list.
Criteria for the index below
- Hotel rates are the average of the 4-cheapest 3-star (and up) hotels in high season for two people, including all taxes and fees. Hotels that don’t get very good or better reviews are not counted.
- Airfare for the cheapest round-trip high-season flight available from NYC
- 7-nights + Flight Index is 7 nights hotel for two plus two round-trip airfares from NYC, including all taxes
Caribbean islands and destinations ranked by price
(prices are for high-season winter travel)
1 – Cancun/Playa del Carmen/Cozumel, Mexico
By far the busiest destination in the Caribbean, Cancun is obviously not an island so it might not count for some people. But Greater Cancun also consists of Playa del Carmen, the Riviera Maya area as well as the nearby island of Cozumel, so it’s a huge cluster of resort areas all served by one busy airport.
With cheap flights from almost everywhere and hotels starting at suspiciously low prices, Cancun is easily the cheapest Caribbean destination and a great choice for the Spring Break crowd as well. It’s worth noting that the cheapest hotels in Cancun won’t be within walking distance of the beach, although most will have a pool. The 3-star Cancun hotels in these low price ranges are located in the Downtown Cancun area and it’ll cost at least triple these prices to stay on the beach or in the Hotel Zone. The Downtown area still has great weather along with cheap restaurants and bars, so it’s a decent choice compared to staying home. There are 7 major areas around here so we have done a guide for choosing where to stay in the Cancun area.
>>>Best Cancun all-inclusive resorts for couples, families, spa lovers, and more
- Cheap 3-star hotel average: $39
- Cheapest RT airfare from NYC: $356
- 7-nights + Flight Index: $1,036 for two people
- Popular with: Americans, Canadians, budget travelers from all over Europe, Spring Breakers
Mexico COVID-19 rules: No vaccination or testing requirement at all.
2 – Punta Cana, Dominican Republic
Punta Cana has some modestly priced hotels that include breakfast, but it’s much better known as the best and cheapest place for luxury all-inclusive resorts at amazing rates. In fact, some of these all-inclusives only cost a bit more than the ones that only include breakfast. There are really good air+hotel packages available that can keep prices down and offer fantastic value for the Caribbean. The modern nearby airport is the busiest in the DR, and the roads in this area are in good shape as well.
As you might expect, the 3-star hotels in these price ranges will not be on the beach, but they are mostly quite close and also have their own pool. Again, if your options are staying home or staying in one of these places, it’s a pretty easy decision. That said, spending more for one of the cheapest all-inclusives on the beach is probably money well spent. Punta Cana is also our top pick for Caribbean islands for families with kids, by the way.
- Cheap 3-star hotel average: $44
- Cheapest RT airfare from NYC: $388
- 7-nights + Flight Index: $1,139
- Popular with: Americans, Canadians, Brits, French, Germans, Spanish, Belgians, Dutch, Swiss, Portuguese, Russians
3 – Samana, Dominican Republic
Samana has quite a few posh and expensive resorts, but it’s also got a nice mix of more affordable simple hotels near the beach. This is a newer resort area that is expanding at a fast clip, with a new airport with increasing services as well. Samaná is the whale-watching capital of the DR, with some very nice beaches to boot. They do have a small airport nearby, but most visitors fly into the large Santo Domingo Airport and take a one-hour taxi or shuttle ride.
Once again, the Samana hotels in this price range will not be beach resorts, but they do have excellent weather and provide very good value for those on smaller budgets.
- Cheap 3-star hotel average: $61
- Cheapest RT airfare from NYC: $325
- 7-nights + Flight Index: $1,152
- Popular with: Canadians, Brits, Italians, Portuguese, Swedish
4 – La Romana, Dominican Republic
La Romana does have just enough inexpensive hotels to make it this high on the list, but the area is mostly known for larger upscale resorts. The famous Casa de Campo Resort started the trend, and it’s still almost exclusively a package resort area for the upscale crowd. La Romana is often included in the Punta Cana market when you search for hotels, so you can fly into that airport if it’s cheaper, and take a shuttle to your resort on the brand-new highways between them. In fact, flights into Punta Cana Airport are almost always cheaper so that is what we used for this entry.
- Cheap 3-star hotel average: $74
- Cheapest RT airfare from NYC: $388
- 7-nights + Flight Index: $1,387
- Popular with: Americans, Canadians, Brits, French, Italians, Spanish
5A – Puerto Plata, Dominican Republic
Puerto Plata includes several clusters of resort beaches along the northern shore of the Dominican Republic. The hotels here are among the cheapest in the Caribbean, and this area is also known for very affordable all-inclusive packages. The diving and snorkeling aren’t top-notch, but at least it’s good value otherwise. Flights to the nearby airport aren’t as cheap as they used to be, and the Santiago Airport a bit further south is 90 minutes away by road. Those looking for a luxury all-inclusive at an appealing price would probably be happier in Punta Cana (see above).
- Cheap 3-star hotel average: $68
- Cheapest RT airfare from NYC: $415
- 7-nights + Flight Index: $1,392
- Popular with: Americans, Canadians, Irish, Brits, Northern Europeans
Dominican Republic COVID-19 rules: No vaccination or testing requirement at all.
5B – Varadero, Cuba
For a couple years Americans were allowed visits to Cuba for “cultural tourism”, and cruise ships started coming as well. But Americans still can’t legally sun themselves in Varadero or any other Cuban resort city and that doesn’t look ready to change in the coming months into 2023.
Still, Canadians and Europeans are very fond of this commercialized stretch of beach out on a restricted peninsula. You’ll find mostly larger all-inclusive resorts here built specifically for the package crowds. Varadero is relatively cheap and good value for the Caribbean, and quality in its beachfront resort hotels is fairly high. Once Americans can visit Cuba solely for leisure, things are bound to change quite a bit.
(included as a service to Canadians and Europeans who wonder where Cuba stacks up from a price standpoint)
- Cheap 3-star hotel average: *
- Cheapest RT airfare from Toronto: *
- 7-nights + Flight Index: US$1,469 for two people ALL INCLUSIVE!
- Popular with: Canadians, Europeans including Russians, almost no Americans…yet
6 – Curaçao
Officially part of the Kingdom of the Netherlands, Curaçao has excellent diving and some of the cheaper hotels in the southern part of the Caribbean. It also has a large and busy airport which helps keep airfares reasonable from North America and several key European cities.
Curaçao is also seldom in the path of hurricanes, so autumn trips are a great value here and come with greater peace of mind. Airfares aren’t quite as cheap as they were in early 2022, but they are still very good value compared to nearly all of the islands farther down this list.
- Cheap 3-star hotel average: $90
- Cheapest RT airfare from NYC: $373
- 7-nights + Flight Index: $1,494
- Popular with: Americans, Canadians, Dutch, Germans, Italians, scuba divers from all over
7 – San Juan, Puerto Rico
Cheap and direct flights from many cities help make San Juan a good budget choice, even if hotel prices here start higher than other destinations near the top of this list. The Old San Juan area is gorgeous and there are many surprisingly affordable eating and sleeping options there. Starting just next door you’ll find a long string of tourist-oriented areas with some of the best city beaches in the world.
There are virtually no all-inclusive resorts on Puerto Rico, so this is a pay-as-you-go destination. If you want a bit of culture and don’t need nonstop buffets, then San Juan might be the best option in the Caribbean at a modest price. San Juan can also be a great choice for trips of only a few days because airfares are low even if hotels aren’t quite so cheap.
- Cheap 3-star hotel average: $124
- Cheapest RT airfare from NYC: $296
- 7-nights + Flight Index: $1,534
- Popular with: Americans, Canadians, Brits, Germans, Spanish
8 – Negril, Jamaica
Negril, which is about 90-minutes from Montego Bay Airport by road, has a beautiful west-facing (sunset) beach and an abundance of cheaper 2-star and 3-star hotels, making it among the Caribbean’s best value destinations for hotels that are actually on the sand. In fact, Negril may have the cheapest actual beach hotels in the Caribbean because the cheaper ones in the places above tend to be at least a couple blocks from the water.
There are also many all-inclusives and upscale & pricey 4-stars, so it’s a good mix rather than just all down-market. The gorgeous area along 7-Mile Beach is lined with smaller hotels and a few larger ones plus a few all-inclusives. THIS is where you want to go in Jamaica if you want to visit the country rather than just visiting the grounds of a hotel.
- Cheap 3-star hotel average: $104
- Cheapest RT airfare from NYC: $383
- 7-nights + Flight Index: $1,569
- Popular with: Americans, Canadians, Brits, Germans, Dutch, Spanish, Portuguese, Italians
Jamaica COVID-19 rules: No vaccination or testing requirement at all.
9 – Montego Bay, Jamaica
Jamaica’s busiest airport is near the heart of Montego Bay so visitors can be checked-in sooner here than if they went to Negril or Ocho Rios nearby. This is a very well developed and touristy area along Jamaica’s north shore, with plenty of large all-inclusive resorts all the way up the price scale.
All along the north shore you’ll find a string of large hotels (many all-inclusive), and there are a few good activities as well. But the actual town of Montego Bay, centered along the so-called “Hip Strip” is disappointing. In other words, if you want to stay in an independent hotel and try many nearby restaurants and bars, go to Negril. Montego Bay is really only good for its larger resorts.
- Cheap 3-star hotel average: $124
- Cheapest RT airfare from NYC: $383
- 7-nights + Flight Index: $1,725
- Popular with: Americans, Canadians, Brits, Germans, Dutch, Spanish, Portuguese, Italians
10 – Rincon, Puerto Rico
If you are a serious surfer and want to give it a try in the Caribbean then come to Rincon, on Puerto Rico’s west coast. Others are probably better off in the more developed San Juan area, but surfers love it here and often rent local houses rather than staying in the somewhat pricey hotels. Flights to the local airport are reasonable, and the sometimes-cheaper San Juan airport is also an easy drive.
- Cheap 3-star hotel average: $153
- Cheapest RT airfare from NYC: $296
- 7-nights + Flight Index: $1,742
- Popular with: Americans, Spanish, surfers from everywhere
11 – St. Maarten/St. Martin
Famously divided with a French half in the north (Sint Martin) and a Dutch half in the south (Saint Maarten), this island otherwise treats itself as one destination.
Almost all (cheap) flights are into the airport in the Dutch area, and hotels are grouped together as well, with both halves being mid-range choices with almost nothing in the low-budget category. Unsurprisingly, the food tends to be better in the French part, but it’s quite easy to go back and forth. The island also has some casinos so if that is something you enjoy while on vacation this could be an even better choice.
- Cheap 3-star hotel average: $144
- Cheapest RT airfare from NYC: $377
- 7-nights + Flight Index: $1,835
- Popular with: Americans, Canadians, French, Dutch
12 – Barbados
While it’s a bit farther than other cheap Caribbean destinations, there are sometimes good airfares from the US to Barbados. This island has many good-value 3-star beach resorts towards the south, and a long line of exclusive and luxurious hotels and resorts in what might best be described as the Beverly Hills of the Caribbean.
Barbados has a well developed hotel scene so it won’t feel as exotic as some of the smaller islands nearby. Some of the diving here is excellent so it can be great value for the scuba set. Flights from the US are had become quite expensive in early 2021, but they are fairly reasonable again late in 2022 and into 2023. Since Barbados is also home to a huge chunk of the luxury market in the Caribbean, it’s also popular with rich Europeans and South Americans as well.
- Cheap 3-star hotel average: $138
- Cheapest RT airfare from NYC: $428
- 7-nights + Flight Index: $1,896
- Popular with: Americans, Canadians, Brits, Germans
13 – Guadeloupe
Still an official part of France, Guadeloupe is very unusual in that it’s sometimes actually cheaper to reach by air from Paris than from New York. During our tests for early 2023, we found very reasonable flights from New York to Guadeloupe, so that doesn’t always hold true.
In other words, this is a very French island that caters nicely to budget and mid-range Europeans, but it can be expensive and difficult to reach from North America if you aren’t starting in the right city. Hotels here can be good value if you can get an airfare bargain.
- Cheap 3-star hotel average: $185
- Cheapest RT airfare from NYC: $288
- 7-nights + Flight Index: $1,999
- Popular with: French Canadians, French
14 – Ocho Rios, Jamaica
About 90-minutes east of Montego Bay Airport on Jamaica’s northern shore, Ocho Rios is similar in price to Montego Bay and Negril (see above). It’s also a very popular cruise port, so the local waterfalls and other attractions can be jammed or nearly empty depending on the day.
There are large and impressive resorts all along the north shore between Montego Bay and Ocho Rios, including many all-inclusives. But similar to Montego Bay, the actual town of Ocho Rios is underdeveloped, unimpressive, and somewhat annoying, filled mostly with nearly identical souvenir shops and a few jewelry malls. If you want to stay in a small hotel and try different restaurants and bars along a beach, go to Negril and stay clear of Ocho Rios. Another way of saying it is that the only reason that Ocho Rios is lower on this list is that it has fewer cheap hotels than Montego Bay or Negril, not that it’s actually a nicer place to visit.
- Cheap 3-star hotel average: $163
- Cheapest RT airfare from NYC: $383
- 7-nights + Flight Index: $2,023
- Popular with: Americans, Canadians, Brits, Germans, Dutch, Spanish, Portuguese, Italians
15 – Grenada
Known for its beautiful volcanic views and for not being overly developed, Grenada is a good choice for English-speaking folks looking to get away from the package crowds. Prices at the resorts are mostly in the middle range, but a few top-end places are here as well. Flights can sometimes be cheap, though be sure to check hotel prices before you book the airfare.
The island of Grenada is not very well developed so don’t expect too much in the way of shopping or culture. The scenery here is some of the best in the Caribbean, but most visitors are happy to stay in their hotels for most or all of their visit.
- Cheap 3-star hotel average: $157
- Cheapest RT airfare from NYC: $422
- 7-nights + Flight Index: $2,139
- Popular with: Americans, Canadians, Brits
16 – Martinique
A favorite of French-speakers from Canada and Europe, Martinique has a relatively large population without a great number of resorts, so it doesn’t feel as touristy as many other islands. You’ll find great cuisine here, and quite a few budget hotel options as well.
Norwegian Air used to fly into Martinique as of a few years ago and their fares were as amazing as they were unsustainable. Flights in 2023 are much more expensive so this island isn’t a great choice for most people.
- Cheap 3-star hotel average: $109
- Cheapest RT airfare from NYC: $763
- 7-nights + Flight Index: $2,181
- Popular with: French Canadians, French
17 – Aruba
Almost completely flat, Aruba is another Dutch island without a striking volcano at its center. Still, it has a well developed tourist infrastructure and a busy airport with cheap flights from Europe, so it’s a popular choice for northern Europeans as well as Americans.
Most hotels on Aruba are in the mid-range and upper end, but there are enough affordable places that get good reviews to make it pretty high on this list. Aruba is another (along with Bonaire and Curacao) that is just north of Venezuela and hasn’t had a hurricane come near it in decades. This makes it one of the better choices for an autumn vacation when so many other islands are potentially in the crosshairs of storms.
- Cheap 3-star hotel average: $159
- Cheapest RT airfare from NYC: $400
- 7-nights + Flight Index: $2,193
- Popular with: Americans, Canadians, Brits, Dutch
Aruba COVID-19 rules: Aruba requires a negative test from any visitor over 15 years old, or a test upon arrival. Citizens from quite a few US states also require “additional testing” and information is on the website linked below. You must also purchase Aruba visitors insurance from them, which runs about US$10 per day for most people.
18 – Trinidad and Tobago
About 95% of the population lives on Trinidad, but about half the resorts are on Tobago and usually people just visit one island or the other since they aren’t close together. Slightly cheaper flights go into Trinidad, but we are using data for Tobago here since it’s more popular with resort-goers.
The hotel markets are listed separately as well, but prices and the overall range are quite similar and both offer good value. In other words, if you are considering a first visit, it’s probably best to book on Tobago unless you want to specifically explore the culture (and oil fields) of Trinidad.
- Cheap 3-star hotel average: $179
- Cheapest RT airfare from NYC: $540
- 7-nights + Flight Index: $2,460
- Popular with: Americans, Brits, Germans
19 – Antigua & Barbuda
Antigua is one of the more accessible Caribbean islands that is known as a playground for the rich and famous. It’s a beautiful place and flight deals are often available, but resorts here range from moderate on up to shockingly expensive.
Several celebrities have homes on the island, which tells you something about the crowd that books here. Still, there are some modestly priced hotels that get very good reviews, so it’s a possibility for budget visitors. Similar to Trinidad and Tobago, these islands aren’t close together so you’ll want to choose just one. And in the 2017 hurricanes, almost all of the hotels on Barbuda were wiped out, so at this point it’s all about Antigua itself.
- Cheap 3-star hotel average: $208
- Cheapest RT airfare from NYC: $342
- 7-nights + Flight Index: $2,462
- Popular with: Americans, Canadians, Brits, Germans, Italians
20 – St. Lucia
Arguably the most beautiful island in the Caribbean, St. Lucia is an interesting mix of options with some surprisingly good deals at hotels combined with rather expensive airfares. Flights aren’t always expensive though, so this is a good island to put in an airfare alert and pounce when a bargain appears.
This is a popular stop for cruise ships and there is also a great mix of upscale resorts, so St. Lucia is justifiably popular for many different groups. If you’ve seen a photo of gorgeous twin mountains on St. Lucia they are called the Pitons are are located on the western coast towards the south. Not many hotels have a view of them, but there are ways to explore and even climb them for those with enough energy. St. Lucia also makes our list of the best Caribbean islands for honeymooners, by the way.
- Cheap 3-star hotel average: $201
- Cheapest RT airfare from NYC: $452
- 7-nights + Flight Index: $2,590
- Popular with: Americans, Canadians, Brits, Germans
21 – Bonaire
You wouldn’t come to Bonaire for the beaches, because this small and mostly-flat island isn’t blessed with sandy shores like most of the Caribbean, but it does have excellent diving and wind surfing as well. This all contributes to more of an informal atmosphere on Bonaire, with a nice selection of cheap hotels available.
Flights to Bonaire are rarely cheap, especially when compared to nearby Aruba and Curaçao, so those tend to be more popular among the budget travel crowd. And once again, the three ABC islands are in the far south of the Caribbean and haven’t had a hurricane come anywhere near them in decades, so they could be a good choice during the season (June through December) if that is something that worries you.
- Cheap 3-star hotel average: $188
- Cheapest RT airfare from NYC: $614
- 7-nights + Flight Index: $2,743
- Popular with: Americans, Dutch, scuba divers, wind-surfers
22 – Nassau, Bahamas
Nassau is another very popular stop for cruise passengers, and it’s also well known for Paradise Island just over the bridge, which is home to the famous Atlantis Resort and Casino complex. Flights are cheap from most places, but hotels in the Nassau area start in the mid range and go way up from there. There’s great shopping and nightlife here, at least for the Caribbean.
Partly because it’s so popular with cruise ships, Nassau has a fairly well developed town center lined with shops, restaurants, and bars. This isn’t true of many Caribbean islands and it can be a fun place to hang out if you enjoy the Senor Frogs-type vibe. Since hotels are not so cheap, this can still be an affordable place for a long weekend trip because flights are affordable and shorter than most of the others on this list.
- Cheap 3-star hotel average: $224
- Cheapest RT airfare from NYC: $341
- 7-nights + Flight Index: $2,851
- Popular with: Americans, Canadians, Brits
23 – St. Croix, US Virgin Islands
Larger than nearby St. Thomas, the island of St. Croix is also harder to reach, with very few direct flights from far away. There are also fewer cruise ships stopping in St. Croix, so it really does have a bit more of a remote and isolated feeling, for better or for worse.
Hotels are quite expensive in general, though flight deals are sometimes available. The US Virgin Islands were hit pretty hard in the 2017 hurricanes and it took a few years before most of the better places opened back up again. Quite a few of them never reopened, but many that did are now refurbished, so there’s that.
- Cheap 3-star hotel average: $234
- Cheapest RT airfare from NYC: $451
- 7-nights + Flight Index: $2,952
- Popular with: Americans, Danish
24 – Turks & Caicos
A bit north of the real Caribbean, Turks & Caicos has a drier climate than most other islands, giving it a longer in-season range. In other words, November, June, and July can be pretty wet in most of the Caribbean islands in the actual Caribbean, but Turks and Caicos stays dryer and can be a good choice during the shoulder seasons.
There are some extremely posh resorts here, including some all-inclusives, but there are some modestly priced hotels as well, making it a mid-range option overall. The cheap flights often available make it good for late-season or shorter stays.
- Cheap 3-star hotel average: $312
- Cheapest RT airfare from NYC: $325
- 7-nights + Flight Index: $3,269
- Popular with: Americans, Canadians, Brits
25 – Bermuda
Though it’s technically a long way from the Caribbean, Bermuda gets included here because it’s a good alternative, especially from April through June when it’s warm enough.
This is a very British island still, and quite expensive as well, with not a single cheap hotel available online. Flights from the US can be cheap though, so it’s still a decent budget option for a short visit. Check the weather forecast before you book because Bermuda has almost opposite seasons of the rest of the islands on this list, and that can be a really good thing in summer.
- Cheap 3-star hotel average: $306
- Cheapest RT airfare from NYC: $368
- 7-nights + Flight Index: $3,556
- Popular with: Americans, Canadians, Brits
26 – Tortola, British Virgin Islands
Tourism in the British Virgin Islands is mostly restricted to 2 islands, Tortola and Virgin Gorda. They are beautiful and very low key, partly because there are no long-haul flights coming in so everyone has to change planes at least once. Hotels here start quite high and go up from there, so it’s only a good choice for well-heeled folks escaping the crowds elsewhere.
Tortola completed its cruise port in 2015 and visitors by day-trippers had obviously increased exponentially. But then it was hit pretty hard in the 2017 hurricanes. Most of the bigger resorts are back and better than ever. Don’t expect much from Road Town, which is where the cruise ships dock.
- Cheap 3-star hotel average: $323
- Cheapest RT airfare from NYC: $480
- 7-nights + Flight Index: $3,675
- Popular with: Americans, Brits
27 – St. Kitts and Nevis
The twin islands of St. Kitts and Nevis are among the smaller and more modest tourist markets, and this can make them ideal for those not interested in crowds and shopping centers. In fact, even the more populous St. Kitts feels mostly empty with wide-open land, with Nevis even more empty.
There are almost no cheap hotels on either island though. Scuba diving is very good here, with some notable shipwrecks and underwater caves. Flights are a bit pricey too, so this is a good choice for scuba visits for upmarket guests. For the record, St. Kitts is probably my favorite Caribbean island because it’s covered so much in grass instead of thick bush like most of the others.
- Cheap 3-star hotel average: $299
- Cheapest RT airfare from NYC: $624
- 7-nights + Flight Index: $3,806
- Popular with: Americans, Brits
28 – Grand Bahama, Bahamas
Freeport is the second-largest city in the Bahamas and its location on the island of Grand Bahama is also the second-busiest tourist destination in the island chain. While popular as a cruise destination, hotels here are mostly in the mid-range for the Caribbean, and it’s a common short getaway for those coming from nearby Florida.
The main problem with Grand Bahama is that somehow the flights here are incredibly expensive, especially considering the modest distance from the United States. It’s definitely worth checking the airfares before doing much hotel research because there are probably better choices somewhere else.
- Cheap 3-star hotel average: $300
- Cheapest RT airfare from NYC: $689
- 7-nights + Flight Index: $4,047
- Popular with: Americans and cruise-ship passengers
29 – Grand Cayman, Cayman
If you’ve heard of the Cayman Islands then you might be a banker because this territory of the UK has nearly as many banks as it has people. It’s also a fairly luxurious resort island that is geographically off on its own a bit, with prices starting in the mid-range and going way up from there. Cheap flights are often available so package deals might be good value.
Just like in Negril, Jamaica, the highlight here is Seven Mile Beach, which is where most of the island’s hotels and resorts are located. It has been voted as the best beach in the Caribbean a few times, and that is one reason why it has so many upscale resorts and higher prices.
- Cheap 3-star hotel average: $459
- Cheapest RT airfare from NYC: $325
- 7-nights + Flight Index: $4,377
- Popular with: Americans, Brits
30 – Anguilla
Only a few miles off St. Martin, Anguilla is a small and beautiful island that is near the upper end of the price scale for all of the Caribbean.
Flights are expensive, though you can get here by ferry from St. Martin, but hotels are all very expensive as well. A few of the resorts here are among the priciest in all of the Caribbean.
- Cheap 3-star hotel average: $506
- Cheapest RT airfare from NYC: $508
- 7-nights + Flight Index: $4,698
- Popular with: Rich Americans and Brits
31 – St. Thomas, US Virgin Islands
Known largely as a stop for cruise ships and a Caribbean shopping mecca for inexpensive jewelry, St. Thomas also has great scuba diving and all the usual water sports available. Hotels here are quite expensive compared to others higher on this list, but sometimes it’s possible to get a cheap flight.
St. Thomas was pretty badly hit during the 2017 hurricanes and they wiped out pretty much all of the cheaper beach hotels. Being so far down this list you might expect St. Thomas to be a really wonderful and luxurious island, but honestly it’s not all that nice and the reason it’s so far down the page is that the cheap hotels were wiped out and only the expensive ones remain. I wouldn’t really recommend it.
- Cheap 3-star hotel average: $456
- Cheapest RT airfare from NYC: $499
- 7-nights + Flight Index: $4,892
- Popular with: Americans, Canadians
32 – Saint Barthélemy
Saint Barthélemy (AKA St. Barts) is an outlier because it’s not only the most expensive Caribbean island, it also has only a handful of small hotels, and most guests rent villas and condos instead.
St. Barts has lived at the bottom of this “cheapest Caribbean islands” list since we began publishing it over 10 years ago. It used to be that there were only a handful of hotels (since rich guests stayed in condos and private rentals), but this year there is exactly one hotel available and it charges US$1,333 per night in January, including taxes, so that is also the ‘average’ for the 2023 list as well.
- Cheap 3-star hotel average: $1,333
- Cheapest RT airfare from NYC: $957
- 7-nights + Flight Index: $13,298
- Popular with: Celebrities, the idle rich, the working rich, French-speakers
Notes on the Caribbean Destination Index
- Many destinations have some cheaper hotels with mostly-negative reviews, and these were not included in the Index. Just as elsewhere, Caribbean hotels that seem suspiciously cheap are often poorly maintained or located, and not good value.
- Airfares from New York were used because they are often cheaper than from even south Florida, and they are a good gauge of prices from connecting airports. Flights from dominated airports such as Atlanta and Charlotte are usually higher even though they are much closer.
- All the prices researched are for high-season rates, from early January through March, but not “peak-season” rates in late December.
All-inclusive hotels in the Caribbean are even better value
The prices listed above are mostly for hotels that are not all-inclusive, but the cheapest all-inclusive resorts are often only a bit more expensive than the others so they can be excellent value. All-inclusive deals including airfare are often the best deals anywhere, but still the order of islands and destinations will be similar for those as well.
Cheapest flights only
If you are looking for a rental or will be staying in a cheap lodge in a city then you might only be interested in cheap airfare alone. We’ve compiled two lists for you, one with cheapest Caribbean island airfares from North America, and another with the cheapest Caribbean destinations from Europe.
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I’ve been researching a Caribbean-region trip for a while but I appreciate your continued replies. If I wanted a relaxed spot (resort or not) with great swimming/snorkeling that isn’t too crowded and a mid-range price, which islands would you suggest? I’ve looked into St. Lucia, Grenada and Vieques but prefer to stay away from hurricane regions.
Ben,
I think the only place that you can be fairly confident that you are out of a “hurricane region” in the Caribbean is in Aruba, Bonaire, and Curacao. They have not had even a close call in many decades and apparently there are reasons that it’s likely to continue, although eventually they will probably be hit as well. Another thing to consider is that September and October are really the main times for almost all of the damaging hurricanes, so even though the official season lasts from June through the end of November, the chances of being caught in a hurricane that you’d have to flee from outside of those two months are extremely low on any given island.
I haven’t been to the ABC islands, although I have heard good things about them and especially the diving and snorkeling and such. Aruba can be a good value as well, with modest crowds (at least compared to the Dominican Republic and Jamaica etc. I’d look into Aruba first. And St. Lucia is (in my opinion) the most beautiful Caribbean island. The towns and hotels there tend to be small, so it never feels very crowded. Grenada has very few resorts and hotels, which might be a plus for you, but it all feels a bit disorganized to me. I haven’t made it Vieques yet. I hope this helps a bit and I’m happy to answer more questions if you have them. -Roger
Just a heads up. Santo Domingo is 3 hours from Samana not 1 hour. It is beautiful We stayed in Las Galeras nearby and it was rural and unspoiled. Would 100% go back.
Thanks for the information. I think I confused this with a new highway elsewhere in the country. -Roger
I’m happy that I stumbled across your list! I’m looking for suggestions on a destination in the Caribbean for travel in early August with my 16 y/o daughter where we will feel the safest. Thank you.
Elle,
I’m glad you found this list as well. Generally speaking, all of the Caribbean islands are quite safe, but some do have more of a history of incidents with tourists than others. Specifically, Jamaica and Mexico have had a few issues that have made the news in recent years. If you are looking for an affordable all-inclusive resort I think the Dominican Republic is generally very safe. Especially in Punta Cana, the resort complexes are huge and they have large security staffs. Most people don’t even leave the resort until they are heading home, so if that is what you are interested in you’ll have many great choices there.
I’d probably avoid the US Virgin Islands as well. St. Thomas is a bit rough around the edges. The smaller islands seem to be very safe. Personally, I love St. Kitts and also Antigua and Barbados. Those feel among the safer islands. But again, it depends a bit on how much time you might spend outside of your hotel. On some of those islands there isn’t much to do and there aren’t even real cities. I hope this helps. Let me know if you have any other questions. -Roger
Looking for the best place to go over the week of Thanksgiving 2019. There will be 14 of us flying. We would like someplace sunny with nice weather. Cheap to mid-range on price. We will be coming from Oregon and would love some ideas. There will be 3 families with the youngest being 12. We are traveling to Punta Canta in May. Any help would be much appreciated. Anything besides Hawaii and Mexico.
THank you
Lisa,
The article above is specifically about the Caribbean, so I’m unsure whether that is where you are looking or if you are open to other suggestions. As you may know, November is near the end of the wet season in most of the Caribbean and also in Central America, so finding a place that won’t get at least a few showers here and there is difficult. You might have a look at our article about the best cheap destinations in November with great weather. There are a few Caribbean options there as well as other nearby places to consider.
Coming from Oregon and excluding Mexico, my best recommendation is the Guanacaste area of Costa Rica. The wet season usually ends there by the middle of November so you might get a quick rain storm or two, but at least it’s unlikely that it’ll rain for hours at a time late in the month. You can fly into the Liberia Airport nearby and it’ll probably only be one plane change starting at PDX. There are many large chain hotels in that area, but also smaller local hotels as well as airbnbs and other house rentals. For 14 people you might even find one very large rental house big enough for everyone. Costa Rica is very safe and well organized (at least compared to most of its neighbors) so it’s a great option for families. Let me know if you have any other questions. -Roger
Eastern Caribbean islands tends to be more expensive especially renting vehicles. St. Lucia is not cheap either. I have lived there for two years and rising cost will keep many tourists in distress. I recently visited Thailand and it was much much cheaper than the Caribbean islands w/ better food and accommodations.