How to Vacation in the Caribbean for $1,500 or Less—Including Flights

When Is The Best Time to Visit the Caribbean on a Budget?

Seasonality is a huge factor in Caribbean costs. Winter in the Caribbean has nearly perfect weather, with little rain fall, gentle breezes, and warm temps. It’s also the time when prices surge, especially on resort-heavy destinations like Jamaica, the Bahamas, and the Dominican Republic. That’s not to say you can’t score a good deal in the winter, especially if you book ahead and avoid the most popular times: Christmas and New Years, Martin Luther King, Jr. Day weekend, President’s Day weekend, around Valentine’s Day, Easter, and during the early spring break weeks of March.

Speaking of spring, the Caribbean gets more affordable around this time—with the exception of Easter week. March and April are still pricey, and hotel rates spike. By May, there are bargains abound. Temps do start to rise and humidity gets real, but a Caribbean vacation in the spring means money saved. By late June, the Caribbean is officially in low season. Temperatures in the northern Caribbean are hot, hot, hot, humidity is high, and bursts of rain are likely. Hurricane season officially kicks off, but it doesn’t get into full gear until the fall. This is when Caribbean deals are at their best. But don’t be afraid that booking a resort in hurricane season means you’ll be battling major storms instead of lounging by the pool. Hurricanes are statistically rare, and the sun does shine during hurricane season. By early December, you’re likely to find the same perfect weather as during January and February.

Pro tip: Hotel rates for the first two weeks of December are still on par with what’s offered in low season. Budget Caribbean vacationers should plan a trip for the first two weeks of December. It offers the perfect combination of low rates and sunny skies. Truly, the best time to visit the Caribbean on a budget.

Which Is The Best Caribbean Island to Visit on a Budget?

The Caribbean is home to three main island groups: the Lesser Antilles, the Greater Antilles, and the Lucayan Archipelago, which includes the Bahamas and Turks and Caicos. These islands are technically in the Atlantic, but we’re counting them here. There are 13 sovereign island nations and 12 dependent island territories, plus another 10 Latin American countries have Caribbean coastlines, and the islands along the coasts of Central and South America usually get included in this group as well. All that to say, the Caribbean islands are wildly different—even in terms of price. St. Barts and Anguilla are two of the more expensive islands in the region year round, with luxury hotels hitting the four-figure mark per night during high season. Much better deals can be found (especially at all-inclusive resorts) in Jamaica, Riviera Maya, Cozumel, the Dominican Republic, Puerto Rico, and Cuba.

How Can I Find Cheap Flights to the Caribbean?

To start, set up flight alerts across airfare sites and apps like Airfarewatchdog. TripAdvisor and Kayak offer global explore features that allow you to hone in on flight prices to Caribbean destinations on a given set of dates—making it easy to see which island is to cheapest to fly to from your nearest airport. Jet Blue, Spirit, and Southwest carriers often run flash sales, so get on their mailing lists and social media feeds. We crunched some numbers and found a non-stop flight from Newark to San Juan in February for $107 roundtrip. For the same time period, Chicago to Aruba is just $355 and Chicago to Punta Cana is only $300.

What is the Cheapest Way to Get Around the Caribbean?

Getting around the Caribbean isn’t entirely cheap or easy. The most straightforward thing to do is book a shuttle or take a taxi from the arrival airport to your resort. If you want the type of Caribbean vacation where you lay by the beach all day, then it’s important to spend a little more money to book a beachfront (or walking distance) hotel. If exploring is more important to you, consider renting a car or staying in a hotel with a walkable location. Local busses are also a consideration on most islands. Note that they’re very cheap, but the bus routes may be confusing, lengthy, or irregular. Some islands, like the Dominican Republic, have moto taxis that cost around $4 for a ride. But, safety and lack of helmets are a concern. If you’re hoping to Uber, we have some bad news: the rideshare service isn’t available everywhere throughout the Caribbean, and it’s limited. For instance, San Juan has some Uber access—but not usually from the airport. As of publishing, Jamaica, Barbados, and Aruba don’t have Uber service. Truly, the cheapest (but not always the easiest, hello hot weather) way to get around your Caribbean island is by foot.

How Much Do Food and Drinks Cost in the Caribbean?

Getting food and beverages imported to Caribbean destinations is expensive. That’s why you’ll see high prices at restaurants in touristy locations and hotels. Of course, going all-inclusive is an excellent way to get a lot of value out of your meals. You won’t have to nickel-and-dime appetizers and desserts, or count cocktail prices by the pool. If you do choose to pay a la carte for meals, look for local favorites. That means jerk chicken in Jamaica. Empanadas in Colombia. Fish fry in Barbados. Most islands make local beers (pick a Presidente over a Corona in the Dominican Republic) and rums which will save you loads in alcohol prices, and support the local economy. Win win.

Is it Cheaper to Book an All-Inclusive Resort or a Regular Hotel in the Caribbean?

If you want your Caribbean vacation to cost only airfare, the hotel room, and tips—then going all-inclusive is a major money saver. At the very least, all-inclusive resorts give you a whole lot of vacation value for your buck. With one payment, you’ll get unlimited food, drinks, fun activities like nightly shows, dance lessons, and water sports. Be warned, there is some fine print to go over and not every all-inclusive truly covers every spending category. Extras like Wi-Fi, top-shelf alcohol, and excursions can add up. Check out our guide to the cold, hard truths about all-inclusives and this breakdown of all-inclusive resorts versus regular hotels, before you book a Caribbean hotel.

What Are the 3 Best Budget-Friendly Itineraries in the Caribbean?

To really make your Caribbean on a budget planning easier, we broke down three popular island destinations that you can visit for $1500 or less. Yes, that includes the flights!

Cozumel, Mexico Itinerary for Under $1500

Cozumel is a small, touristy island with sandy beaches, excellent snorkeling, and Maya ruins—just off the coast of Mexico’s Yucatan Peninsula. It’s a favorite stop among cruise ships, so there are lots of things to do for the day—like beach club passes with an open bar, a drive to the east side of the island (also known as the Wild Side) for sea turtles and the Celarain Lighthouse, and standup paddleboarding. And since you’re saving so much on room rates, you can splurge with a night out at Coconuts and also take a catamaran snorkel cruise while staying within your budget of $1500.

Cozumel has a tiny international airport, and according to Kayak.com, the cheapest way to get there is to fly from Newark in February—with flights starting in the $300 range. Can’t find an affordable flight from your preferred airport? Check flight deals into Cancun, and then take the ferry from nearby Playa del Carmen over to Cozumel. The ferry crossing takes under an hour and costs about $10. Once you arrive on the island, we suggest booking an affordable all-inclusive resort that’s on the beach.

Our Affordable Cozumel All-Inclusive Resort Pick 

The Melia Cozumel Golf – All Inclusive starts at around $150 a night (in April) and it’s on an idyllic stretch of beach in the North Hotel Zone. Spacious rooms have marble bathrooms and furnished balconies. For fun, there’s an adults-only pool with a swim-up bar, kids’ club, and several dining options and nightly shows. Golfers can walk across the street to Cozumel Country Club, the only golf course on the island.

San Juan, Puerto Rico Itinerary for Under $1500

San Juan is an easy sell. The capital city of Puerto Rico is under a four-hour flight from New York City, but it may as well be located on another planet. Expect white-sand beaches, swaying palm trees, surfable and swimmable waves—plus a glamorous nightlife scene and an historic Old Town complete with cobblestone streets and military forts. There truly is something for every kind of traveler, and every budget in San Juan.

According to Kayak, San Juan airfare has some truly amazing deals. Flights range between the $55 (!) to around $250 mark—leaving you with extra room in the budget for a hotel upgrade—especially if you book on Spirit or Frontier Airlines’ budget-saving routes. With all the money you saved on airfare and walking to the beach and cafe dinners, you can still afford a bioluminescent tour of Mosquito Bay (a must if you visit during a full moon) and a half-day trip to El Yunque rainforest. Budgeting never looked so easy.

Our Affordable San Juan Hotel Pick

Olive Boutique Hotel is an affordable, but memorable, budget-friendly boutique option. We found average rates around $200 a night, which includes free breakfast, free daily cookies, and thoughtful upgrades like premium bathroom toiletries and a rooftop bar with a plunge pool. The hotel is an especially good value for it’s swanky neighborhood of Condado, a posh enclave lined with impressive Art Deco architecture, high-end shops, and scores of cafes and eateries. The safe neighborhood has its own stretch of public beach, the western end of which begins less than a five-minute walk from the hotel. Locals also enjoy swimming in the gentler waters at the tip of Avenida Ashford, a 10-minute walk west of the hotel.

Montego Bay, Jamaica Itinerary for Under $1500

Jamaica is at the top of most travelers’ Caribbean island wishlists for very good reasons: epic beaches, an unbeatable reggae scene, jerk chicken shacks, and sunsets that will blow up your Instagram feed. Since you’re saving money on airfare, hotel, and meals—you can still book a few Montego Bay excursions. We’d recommend scenic ocean horseback riding in the Caribbean, visiting a rum distillery, or taking an adventurous waterfall climb at Dunns River Falls. Music lovers can pay homage to reggae’s king at the Bob Marley Museum.

The cheapest month to fly to Montego Bay, according to Kayak, is September—with flights from $250 from Ft. Lauderdale. You might find cheaper flights into Kingston, but we don’t recommend flying into Kingston, as it’s over a three-hour drive to Montego Bay.

Our Affordable Montego Bay Hotel Pick 

Just like in Cozumel, an all-inclusive vacation in Montego Bay will likely bring you the best value (unless you want to price out every pina colada and rum and coke). The Hotel Riu Reggae starts around $225 a night in September, and the all-inclusive wow factor with its bang-for-your-buck deals is very real. This resort is just for adults, and each of the contemporary room comes with a liquor dispenser and furnished balcony. Three infinity pools, a beach with loungers, non-motorized water sports, five restaurants, and access to the neighboring sister hotel’s nightclub means you won’t have to leave the property at all. But of course, you’ll want to check out Montego Bay and all of Jamaica’s beauty.

What to Wear in the Caribbean:

• The Best Bang-For-Your-Buck All-Inclusive Resorts in the Caribbean
• The 20 Best All-Inclusive Resorts in the Caribbean 
• 20 Amazing Resorts in the Caribbean for Families