Winter weather has lots of Americans looking to the Caribbean for some fun in the sun. But when it comes to choosing between a vacation to the Dominican Republic or Jamaica, there's a lot more to think about than tiny umbrellas and pina coladas (though both of those things are very important). At first glance, the two Caribbean countries have a lot in common: idyllic sandy beaches, sunny skies, local music scenes, and some of the best all-inclusive resorts on the planet. But there are also some major political and geographical differences that might make one destination a better spot than the other for you. We went deep into both destinations to bring you the pros and the cons of a vacation in Jamaica and the Dominican Republic.

Already sold on Punta Cana? Here are the best bang-for-your-buck all-inclusives in Punta Cana.

Couples Swept Away Negril/zzdtravel

Of course, flight times to anywhere in the Caribbean are shorter from the South and east coast in the United States. Most flights from the west coast or the Midwest will likely require a layover. All major cruise lines offer sailings with Jamaica and Dominican Republic port calls (though these may be too brief to really get a feel for either place). Both destinations require a valid passport for entry. Visas are not required for U.S. and Canadian citizens in Jamaica, but visitors to the Dominican Republic are charged a $10 arrival tax, rolled into the airline ticket cost.

Jamaica: There are three international airports in Jamaica: Sangster International Airport in Montego Bay, Norman Manley International Airport in the capital city of Kingston, and (for smaller aircrafts) the Ian Fleming International Airport in Ocho Rios. Getting to Negril or Ocho Rios requires a two-hour taxi or shuttle ride from Montego Bay. Visitors can rent a car, but driving on the opposite side of the road may be too confusing for some and GPS systems don’t work well. There’s also very little public transportation on the island, so non-metered taxis are the most popular way to get around. Haggling for the rate is expected and visitors should always follow common sense safety tips.

Dominican Republic: Approximately six million people visit the Dominican Republic every year, and most of them arrive by air at one of the three international airports. Punta Cana International Airport sees the most visits, and it’s a privately owned commercial airport. Roads can be narrow and poorly paved, but the D.R. does have an inexpensive bus service that covers much of the country. Another option is to hire a guagua (pronounced wawa), an informal taxi network with vehicles that range from old vans to nice minibuses. These get packed with tourists and locals hitching a cheap ride. Note that tourists are usually charged much more than locals, so it’s smart to agree on a rate beforehand. Taxis are also available, but this option is super pricey.

Hard Rock Hotel & Casino Punta Cana/zzdtravel

Tourism makes up a giant percentage of both Caribbean nations’ economies, so it’s no surprise that both destinations have seemingly endless hotel options from which to choose. Whether you want a cheap all-inclusive beach hotel or designer boutique digs with privacy and butler service, you can find all levels of luxury and budget in both destinations. That said, we do think that Jamaica has a slight leg up in terms of overall quality — especially for mid-range resorts.

Jamaica: The island is one of the all-inclusive capitals of the world, and one of the first Caribbean islands to introduce the leave-your-wallet-at-home (don’t really do that) concept to attract tourists who were tired of paying a la carte prices and hidden fees. All-inclusive resorts are especially popular around Montego Bay. The adults-only Secrets Wild Orchid Montego Bay offers 10 restaurants, eight bars, and free dance lessons on the beach. Negril is still home to cozy and rustic boutique properties with lower rates. Negril Tree House Resort is right on famous Seven Mile Beach, and provides free breakfast and yoga classes.

Dominican Republic: Punta Cana is the epicenter for tourism in the country, so it’s no surprise that the biggest hotel names are clustered together on the long stretches of white sandy beaches that make the area a favorite for family vacations, party-seekers, and honeymoons. One of the top contenders is the Hard Rock Hotel & Casino Punta Cana, a massive all-inclusive resort with something for everyone: a large casino, 13 pools, 13 restaurants, waterslides, beach access, and an 18-hole Jack Nicklaus golf course. For something more intimate, Tortuga Bay Hotel Puntacana Resort & Club has just 13 rooms designed by Oscar de la Renta. To get away from Punta Cana’s tourist scene, Natura Cabana Boutique Hotel & Spa is a six-hour drive north and offers eco-friendly bungalows, an excellent spa, and a quiet beach.

Office of Nature lobster shack, Negril/zzdtravel

It would be entirely possible to visit either country and subsist completely off of American chain fare: McDonald’s, Jimmy Buffett’s Margaritaville, TGI Friday’s, Applebee’s, and Burger King are just a few of the Western restaurants that cater to homesick (or maybe just picky) Americans. But it would be a giant mistake to miss out on the local food scenes in Dominican Republic and Jamaica.

Jamaica: One of the best parts of eating in Jamaica is how pervasive and affordable the local cuisine is. Casual jerk shops (jerk is shorthand for a spicy marinade rubbed on meats) line the roads and beaches. The menu usually consists of the aforementioned jerk meats, like chicken or fish, smoked over pimento wood and served with rice, beans, and plantains. Scotch bonnet peppers add serious heat, so be forewarned. Other easily accessible gourmet items include Jamaican Blue Mountain coffee, sweet sapodilla fruit, and coconut water. The island’s history as an English colony means that tea is still regularly served in the late afternoons. Red Stripe is one of the most popular Jamaican beers.

Dominican Republic: Dominican dishes combine African, Spanish, and Taíno (indigenous people living in Cuba, Trinidad, Jamaica, Hispaniola, and Puerto Rico) food flavors, using ingredients that are easily accessible in the Caribbean. Dominican staples to try include mangú, made from boiled, green plantains that are mashed and topped with sauteed red onions; fried plantains called tostones; and rice cooked with black or red kidney beans. Passion fruit juice, glass bottles of Refresco Country Club soda, and strong coffee with lots of sugar are favorite beverages. For the truly adventurous, have a slow shot of mamajuana, a homemade liquor made with rum, red wine, tree bark, spices, and herbs — it’s considered an aphrodisiac.

Tensing Pen, Negril/zzdtravel

Apart from the obvious plethora of beach activities — swimming, paddleboarding, parasailing, and catamaran cruises — both Jamaica and the Dominican Republic offer tons for tourists to see and do. Most all-inclusive resorts put on some sort of evening entertainment, which can include traditional dances, comedy, and magic shows. Quality truly varies, and many American guests at budget D.R. resorts complain that these activities tend to be conducted in Spanish. We suggest getting away from the resorts for the best entertainment.

Jamaica: Jamaica does have beautiful sand beaches, but Negril is better known for its adrenaline-pumping cliff jump into the crystal-clear water below at Rick’s Cafe. Other popular activities include horseback riding in the ocean (the horses actually swim for part of the trek), waterfall swimming in Blue Hole, and taking the Bob Marley Nine Mile Tour to learn about reggae. Speaking of which, the island hosts several annual musical festivals and there’s almost always a dance party on the beach or in the nightclubs. In Kingston, Olympic runner Usain Bolt opened a sports bar and restaurant called Tracks and Records.

Dominican Republic: Activities in the Dominican Republic range from adventure (zip-lining through rain forest canopy) to history (walking tour of Santo Domingo). Ocean World Adventure Park is a popular place for sea lion shows. Scape Park at Cap Cana is a must-visit for a cenote swim, cave swim, and indigenous cultural exhibits. Outside of Punta Cana, most of the nightlife caters to locals and can feel intimidating to tourists, but Punta Cana has an epic nightlife scene that includes cave bars. Note that the water isn’t ideal for snorkeling or surfing in the D.R.

You Might Also Like: Jamaica Excursions: 6 Top Things to do in Jamaica

Occidental Punta Cana/zzdtravel

Though both destinations are extremely safe for tourists (especially most parts of Montego Bay and Punta Cana), there are two very specific caveats that might make some visitors uncomfortable.

Jamaica: Marijuana was decriminalized in 2015, and though trafficking and possession of the herb is still illegal, possessing less than two ounces of marijuana is considered a petty offense. Drugs are regularly offered to tourists on the beaches and in the streets, though a polite “no thanks” is usually all it takes to deter a sale. Visitors should be cautious of petty theft in Kingston. Also note that homosexuality among men is illegal and there’s a general hostility toward LGBT individuals. English is the predominant language in Jamaica.

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Dominican Republic: Prostitution is legal and visible in the Dominican Republic. With a quarter of the population living below the poverty line, it’s no surprise that many women turn to sex work. Boca Chica and the north coast’s Sosua are the two big areas for prostitution, and male tourists are targeted. Some of the smaller (and cheaper) hotels cater to this clientele, which can feel unsafe for families and female travelers. Spanish is the predominant language, which can make exploring the island and communicating outside of the tourist areas difficult for non-Spanish speakers.

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The Caves/zzdtravel

With its upscale boutique vibe, and dramatic cliffside setting, The Caves is considered one of Jamaica’s most romantic escapes. The 12 unique, private cottages and suites at this upscale all-inclusive property unfold along lush garden paths and dramatic seaside cliffs carved with steep stairways down to the water and into incredible grottos. There’s a clifftop bar, a grotto bar, and private candlelit cave dining on offer.

Majestic Colonial Punta Cana/zzdtravel

The Majestic Colonial Punta Cana is one of three upscale all-inclusive sister properties on a beautiful stretch of Bavaro Beach. The property closed completely for two months in 2017 to thoroughly renovate the lobby and restaurants. It now operates almost as two resorts: the family-friendly side and the adult-only Colonial Club side. The 658 suites are attractive with marble floors, jetted tubs, and some ocean views.

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