The 10 Cheapest Caribbean Destinations to Visit in Winter 2020, Ranked

Laid-back and unpretentious, St. Kitts is an ideal destination for travelers looking for an authentic Caribbean experience as well as beautiful landscapes. St. Kitts’s wealth of public beaches means you don’t have to splurge on a seaside property to access the island’s finest stretches of sand. Head to the island’s southern tip in search of its best white-sand beaches -- Cockleshell, Banana Bay, and Major’s Bay. Cockleshell’s calm water, easygoing beach bars, and superb views of nearby Nevis have made it a popular stop for cruise ships, so plan to visit early or later in the afternoon. The adjacent crescent of sand, Banana Bay Beach, has a couple casual spots and sees less crowds. Less than a mile to the west, Major’s Bay sees even fewer crowds, despite offering comparable views of Nevis’ rising conical peak. Furthermore, an abandoned barge resting in the shallows of Major’s Bay creates a unique setting and excellent snorkeling.

Beyond the beach, St. Kitts’s Mount Liamuiga warrants a day trip, especially for adventurous types. Ascending the 3,792-foot dormant volcano rewards hikers with views of the crater and surrounding sea. On the way, hikers traverse steep terrain and thick rainforest, which is home to numerous bird species and mischievous monkeys. It’s advisable to book a guide (typically $75 to $100 per person) to navigate the minimally-marked trails. Brimstone Hill Fortress National Park is a less arduous day trip. The UNESCO World Heritage site sits on St. Kitts’s western coast. Built by enslaved Africans during British colonization, the well-preserved fortress survived numerous French navy attacks from its perch over the Caribbean. The $10 entry fee grants access to the on-site museum and grounds, which includes the Fort George Citadel, barracks facilities, and surrounding ramparts.

Though modest in size, St. Kitts’s mountainous interior means it’s hard to cross the island by road, making for lengthier trips along the coast. Public buses run from Basseterre along the coastal roads north and to the southern ferry terminal near Major’s Bay, but most travelers opt for taxis. Be sure to negotiate the fare beforehand and determine if the price is in U.S. dollars or East Caribbean dollars, as the conversion rate is $1 USD to $2.70 ECD.

While St. Kitts was spared from Hurricane Dorian, it was hit in 2017 by Irma and Maria, totaling $53.2 million in damages between St. Kitts and neighboring Nevis. However, the island’s infrastructure has largely been restored.

Direct flights from New York and Charlotte can be had for around $550 and $750, respectively. Departing from other major U.S. cities typically requires a connection through Miami, which operates daily flights to St. Kitts’s Basseterre airport.

Located within walking distance of Frigate Bay Beach, Royal St. Kitts Hotel is a solid choice for budget-conscious travelers who don’t want to compromise on beach access. Other property perks include two outdoor pools with loungers and on-site restaurants.

The larger and more populated of the two islands comprising Trinidad and Tobago, Trinidad has plenty in store for travelers, from lively cities to coral reefs to remote rainforests teeming with biodiversity. Winter is an opportune time to visit Trinidad for several reasons. First off, hurricane season has passed and the island enjoys ample sunshine and limited rainfall. Also, the world-renowned Carnival celebration is set for the week of February 19 through 26 in Port of Spain, Trinidad and Tobago’s capital. The festivities include street parades of masqueraders and traditional characters, a steel-pan band competition, and late-night dancing to soca music. While many of the performers invest significant funds in their costumes, participating is free, though sporting something more festive and flamboyant is encouraged.

Outside the main cities of Port of Spain and San Fernando, visitors will find laid-back fishing villages, a scenic coastline, and densely forested hill country. Trinidad’s northern coast packs some of its most remarkable natural wonders. Maracas Beach’s swaying palms and tranquil bay make for a convenient day trip from Port of Spain. Continuing east promises more solitude, starting at Las Cuevas Beach, which has nearby caves to explore on top of its idyllic setting. Further east, the sleepy village of Grande Riviere sees leatherback, hawksbill, and green turtles arrive each March to lay their eggs on the beach. To view the nesting turtles while supporting conservation and the local economy, book a nighttime excursion for just 100 Trinidad and Tobago dollars (roughly $15 USD) with the Grande Riviere Nature Tour Guide Association. Further inland, Asa Wright Nature Centre and Brasso Seco are excellent bases for hiking, spotting colorful bird species, cocoa cultivation tours, or just learning about the slow pace of life in rural Trinidad.

Winter flights to Trinidad are some of the most affordable from the United States. The five-hour direct flight from New York will only set you back $363. Flights from Chicago and Washington, D.C. will require a layover in Miami, but can be had for under $400 each.

Located just a few minutes from palm-fringed Las Cuevas Beach, the aptly named Las Cuevas Beach Lodge

Lying just north of Venezuela, the Dutch territory of Curacao blends a variety of cultural influences. The island’s capital, Willemstad, features Dutch colonial architecture reminiscent of Amsterdam, except with bright hues of yellow, turquoise, and orange in place of the brick facades. Strolling the city’s most historic sections -- Punda and Pietermaai -- will take visitors to numerous museums, shops, and cafes. The circular Ronde Markt (New Market) is a great spot for cheap eats like ayaka meat tamales or keshi yena (balls of gouda stuffed with meat and other ingredients). Meanwhile, the Museum Kura Hulanda’s $10 entrance fee is well worth it for the in-depth exhibits on the history of slavery in the New World, which include art and a sculpture garden.

For its size, Curacao possesses a diverse topography. To the north, Christoffel National Park includes hiking trails that lead to the summit of Mount Christoffel through the arid landscape of cacti and scrubby trees. Further up the coast, Shete Boka National Park’s series of craggy limestone inlets and caves have been picturesquely weathered away by pounding waves. With over 30 beaches -- many of which are public -- Curacao’s coastline offers a spot for everyone. For a livelier environment of beach bars and shops, Mambo Beach’s sandy shores will do the trick. Alternatively, Grote Knip’s expansive sand, crystalline water, and offshore reef are perfect for sunbathing and snorkeling. Excursions to nearby shipwrecks and other reefs with dive operators like Ocean Encounters can be had for well under $100.

Direct flights from Newark cost less than $600, but adding a short stopover can get you prices as low as $325. Other cities, like D.C., will require a connection in Miami and come in at around $500 round-trip.

Located in the artsy Pietermaai neighborhood, this hip, vibrant boutique hotel offers a laid-back island vibe and two small pools. As the name suggests, the Scuba Lodge

The most mountainous island in the Lesser Antilles, Dominica is a nature lover’s paradise. The island’s tourism industry is still developing, with annual overnight visitors barely exceeding the population of 74,000 in years past. Winter is well outside the hurricane season, so expect daily temperatures in the 80s plus plenty of sunshine. Much of the island’s landscape, flora, and fauna lie within protected areas, such as Morne Trois Pitons National Park. This UNESCO World Heritage site is home to plenty of waterfalls and Boiling Lake, a 200-foot-wide geothermal lake in Dominica’s mountainous interior. Along the way, hikers will pass a diverse array of landscapes, including gushing Titou Gorge and the Valley of Desolation. Though access is free to the public, hiring a local guide for the full-day hike will add insight and help you navigate the trail safely. For a more leisurely outing, the dramatic cascade and refreshing pool at Trafalgar Falls are well worth the $5 entry fee. Another option is Emerald Pool, a swimming hole set deep in the rainforest. Public transportation is limited across the island, so those traveling in pairs or groups can cover more ground by renting a car. QB Vehicle has affordable options, with compact SUVs available for one-day rentals ($49) or two- to six-day rentals ($38 per day).

Dominica was hit hard by Hurricane Maria in 2017, with roughly 95 percent of buildings and many fruit trees receiving damage. Most of the island’s attractions are its natural assets, which remain largely pristine beyond fallen trees across some of the mountain trails. The return of cruise ships in 2018 was another promising sign for recovery. That being said, the people of Dominica have work ahead to rebuild homes and communities. Tourism dollars can certainly contribute to these efforts, especially when shopping and dining at locally run establishments.

Reaching Dominica requires connecting in main Caribbean hubs like Barbados or San Juan, Puerto Rico. Prices from New York average around $800 round-trip, while traveling from Chicago costs around $1,000. To truly see the savings, you’ll need to visit Dominica for at least a week-long vacation.

A secluded boutique resort, Secret Bay

An overseas department of France, Martinique’s unique blend of French and Creole culture is further enhanced by extraordinary beaches and tropical landscapes. On the island’s southwestern tip, publicly accessible Plage des Salines is a postcard-perfect arc of sand ringed by palms. With only a few casual eateries and beach bars on-site, it retains an unspoiled atmosphere while providing enough amenities to spend the whole day relaxing on the soft, sandy shore and swimming in the clear, tranquil sea.

On the wilder northern coast, a 16-kilometer hiking trail connects the fishing village of Grand'Rivière to the black-sand beaches at Le Prêcheur along the foothills of looming Mount Pelée. The trail crosses varied terrain and dense forest -- be on the lookout for hermit crabs, tarantulas, and lizards scurrying and hiding underfoot. Accessing volcanic Mount Pelée is free and there are multiple options for reaching its summit and crater (the Grande Savane trail from Le Prêcheur provides the most gradual ascent).

Mount Pelée’s last eruption was in 1902, which virtually destroyed Martinique’s capital at the time, St. Pierre, along with nearly all of its 30,000 inhabitants. This prompted the capital’s relocation to Fort-de-France. Since the eruption, St. Pierre has reemerged as a quaint seaside town, with unique sites left by the eruption, including the ruins of an 18th-century theater and shipwrecks in the harbor for scuba diving. For a more cosmopolitan atmosphere, Martinique’s bustling capital, Fort-de-France, is home to historic gems like Fort Saint Louis, a fortress dating back to the 17th century that still functions as a French naval base. A one-hour English-language tour takes in the museum and portions of the grounds for eight euros per person. The nearby Jardin de Balata features thousands of tropical plant varieties. If you’d rather forgo the 13 euro entry fee, venture out of town to Cascade Absalon, a stunning waterfall with a refreshing swimming hole enshrouded by the jungle.

Direct flights from the U.S. are limited aside from Miami, though just over the border, Montreal has non-stop service for around $550. Traveling from New York with a layover in Miami costs approximately $750 round-trip.

Residence Oceane

Often overlooked for neighboring Barbados, Grenada (or the “Spice Island”) possesses a stunning coastline, natural beauty, and a charming capital that merit more attention. Winter temperatures typically hover around the 80s, and reliable sunshine is the norm. The island’s most famous beach, Grand Anse, enjoys a sheltered position on Grenada’s southwestern coastline. Grand Anse’s two miles of powdery golden sand are open to the public. For a more secluded environment, check out La Sagesse Beach, located in a sheltered cove on the southeastern shore. Technically an island, Hog Island can be reached by foot across the shallows of Woburn Bay or via chartered boat. The island’s only establishment, Roger’s Barefoot Beach Bar, is a no-frills rum bar serving up refreshing drinks and barbecue food on the weekends.

Grenada’s capital, St. George’s, is one of the Caribbean’s most picturesque cities. Its harbor and narrow streets are lined with pastel-hued homes, displaying the island’s British past. For just five East Caribbean dollars (less than $2), the French-built Fort George delivers excellent harbor views, as well as insight into the island’s colonial history and coup in the 1980s. Be sure to stop by Market Square to peruse local crafts, fruit, and, of course, spices. For a deeper dive into Grenada’s history of spice production, check out the Belmont Estate’s 400-acre grounds. The 300-year-old plantation offers tours of its gardens, museum, and facilities for just 10 ECD. The aroma of turmeric and nutmeg will likely tempt you to grab a meal at the on-site restaurant.

Flights to St. George’s from New York can be had for as little as $375 round-trip. Charlotte has direct flights for around $700, while trips from other cities like Washington, D.C. require a stopover and cost around $500 round-trip.

On the beautiful Grand Anse beach, the Radisson

Known for its reggae music, idyllic beaches, and vibrant culture, Jamaica has something for every type of traveler in terms of budget and experiences. Jamaica’s northern coast is evocative of what most Caribbean-bound travelers expect: white-sand beaches, all-inclusive resorts, and pulsing nightlife. Jamaica’s second city, Montego Bay, has long delivered these expectations to a steady stream of visitors. Sandy beaches stretch for miles east of the harbor, with only a brief interruption by Sangster International Airport. Gloucester Avenue, known as the Hip Strip, is the touristic hub with a wide selection of bars, restaurants, and beachfront hotels, plus beautiful beaches. Staying at a budget property located on the inland side of the strip, such as the El Greco Resort, can help cut costs without skimping on easy beach access.

Further east on Jamaica’s northern coast, Ocho Rios is equally abuzz. However, compared to Montego Bay, it’s easier to step outside the tourist hubbub in Ocho Rios to nearby fishing villages and jungle excursions. Although popular, Dunn’s River Falls and its adjoining beach stand out on this section of gorgeous coastline. The $25 entrance fee is a bit steep, though. A higher section of the falls outside the enclosure is free to visit, but it requires some hiking and determination to find the unmarked way.

Jamaica’s capital, Kingston, often gets a bad reputation from travelers. Although visitors should exercise basic caution, especially at night, much of the city is safe for exploring. For a dose of Jamaican art, head to the National Gallery, which waives its admission fee on the last Sunday of each month. Meanwhile, the murals along the warehouses lining Fleet Street are free to visit at any time.

Flights to Montego Bay are truly a bargain, thanks to Spirit Airlines, which offers nonstop service from Baltimore/Washington International Airport and Fort Lauderdale for just over $200. Meanwhile, direct flights from New York and Chicago cost around $400 and $500, respectively.

With a prime location on Seven Mile Beach, a pool and whirlpool, and clean, comfortable rooms, the Negril Tree House Resort

Situated beside Curacao, Aruba sees far more visitors than its fellow Dutch territory. Aruba’s coastline and interior offer plenty of publicly accessible beaches as well as hikes to pack a week-long itinerary. The island’s most famous strip of sand, Eagle Beach, is spacious enough not to feel overcrowded. Interspersed palms and thatched umbrellas provide shade if desired, while the calm water is excellent for swimming. On Aruba’s southern tip, Baby Beach provides a more laid-back setting, with just a few beachside eateries. For just a few euros, snorkeling equipment can be rented from Jads Dive Center to explore the nearby reef. Beyond the beach, Aruba’s natural assets include the Arashi dunes and conical Hooiberg peak.

The island’s capital, Oranjestad, has free single- and double-decker trolleys that allow for leisurely sightseeing during the midday heat. To avoid the cruise ship crowds, aim for the earliest or latest departure times of 10 a.m. and 5 p.m. Stops along the trolley line include Fort Zoutman, the Parliament Building, and National Archaeological Museum. Despite receiving heavy cruise ship traffic, many restaurants in Oranjestad’s harbor cater to locals. Right on Havenstraat, Lolita’s street-side stand serves up local specialties like curry and chicken roti for just $5 to $6. Several public beaches are also within walking distance of downtown Oranjestad, including Renaissance Beach and Surfside Beach.

Nonstop flight service from New York and Boston make it easy to escape the harsh northeastern winter. Fares from New York cost under $400, while Boston is a bit steeper at $580 round-trip.

Located in a less touristy section of Aruba’s southwestern coast, Club Arias B&B

Puerto Rico is an unincorporated territory of the United States, meaning that passports aren’t necessary to access this culturally and ecologically rich island. Most international passengers arrive in San Juan, Puerto Rico’s energetic capital of one-and-a-half million people. Although there are some glimpses of American influence -- namely fast-food chains and a subway system -- the city exudes Spanish colonial charm. Strolling Old San Juan’s cobblestone streets between brightly colored homes and quaint plazas won’t cost a thing. On the first Tuesday of every month, the neighborhood puts on a Noche de Galerias (Gallery Night) event that grants free entry to about 20 galleries, which showcase some of the island’s best modern works. Meanwhile, the imposing 16th-century El Morro fortress sits just north of Old San Juan and can be toured for $7 (children 15 and under are free). Today, magazines and soldiers’ quarters have been repurposed as a museum within the UNESCO World Heritage site, while the exterior ramparts provide some of the best views of the harbor. Visible from El Morro’s western walls, Casa Bacardi sits across the harbor and is a must-see for rum enthusiasts. The historical tour is the cheapest option at $15 and comes with a rum-based cocktail.

Most of Puerto Rico’s stunning landscapes can be enjoyed for free, granted you’re willing to stretch your legs a little. The island’s southwestern tip is home to two its finest beaches: Playa Sucia and Playa Combate. The former is scenically encircled by craggy bluffs and maintains a more laid-back vibe due to its remoteness. Meanwhile, Playa Combate claims the title as the longest beach in Puerto Rico, with soft sand, shallow water, and beach bars drawing a younger crowd. Aside from the beach, Puerto Rico’s largest swath of wilderness, El Yunque National Forest, permits free entry. There are hiking opportunities for all skill levels. At just 0.7 miles long, the Big Tree Trail’s paved surface is a relaxing walk that leads to the stunning Cascada La Mina waterfall. For more solitude, take the El Yunque Trail, which ascends 1,300 feet through the jungle to an observation deck. The effort is rewarded with panoramic views of the surrounding forest and sea.

Traveling to San Juan is affordable. Discount airlines like Spirit and Frontier tempt travelers with fares from Baltimore-Washington (BWI) and New York for $207 and $128, respectively. Direct flights from Chicago won’t set you back much either, at $366 round-trip.

Set on a beautiful stretch of beach, the Courtyard by Marriott Isla Verde Beach Resort

Occupying the eastern end of Hispaniola, the Dominican Republic boasts a vibrant capital, hundreds of miles of beaches, and jungle-clad mountains. Amenity-packed all-inclusive resorts abutting impressive beaches draw many families and honeymooners to Punta Cana on the easternmost point of the island. Although relaxing and comfortable, there’s far more to the Dominican Republic. The busy capital, Santo Domingo, is centered around the Zona Colonial, a historic quarter containing cobblestone streets and well-preserved Spanish colonial architecture. The compact district lends itself to self-guided wanderings, but be sure to stop at the ruins of the Monasterio de San Francisco and Catedral Primada de América -- the first cathedral built in the Americas. Come nightfall, the Zona Colonial becomes a popular spot for locals and tourists to drink at dive bars and dance at clubs. For starters, check out the cluster of bars and restaurants on Plaza España. The nightclubs on Avenida Venezuela draw Santo Domingo’s trendiest crowds, though cover charges are usually a modest $5 to $10. If you’re visiting in January, be mindful of the Dominican Republic baseball league’s schedule, as playoffs run until the end of the month and are a dominant part of the local culture.

Aside from Punta Cana, other top beach destinations include Samaná Peninsula. The winter months coincide with the migration of thousands of humpback whales. While half-day tours can cost as much as $60 per person, sightings are essentially guaranteed during the migration season from January through March. On the norther tip of the peninsula, the fishing village of Las Galeras is gifted with some of the most immaculate beaches. Playa Galeras is ideal for snorkeling and relaxing on the powdery soft sand. Nestled in a bay to the west of Las Galeras, Playa Rincon’s swaying palms provide shade and seclusion along its half-moon beach.

Direct flights to Punta Cana depart from many U.S. cities, including New York and Chicago for $350 and $430 each. Spirit Airlines has deals on nonstop flights for as little as $200 round-trip as well. Additionally, Santo Domingo can be visited for a bargain rate of $187 round-trip from Newark.

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