Cupid's Pulse Article: Take a Walk on the Wild Side of the CaribbeanCupid's Pulse Article: Take a Walk on the Wild Side of the Caribbean

By Max Milano

It’s that time of year again when the winter blues start to kick in and people begin to daydream of a tropical holiday vacation.  Many of us push aside the idea of a Caribbean getaway because we feel that it’s either too expensive or not a place for folks who are single. Well, if you think the Caribbean is for couples only or people with money, it’s time to think again.

Following are some undiscovered destinations where singles and groups of friends can take a walk on the wild side full of rum, salsa, reggae and the real Pirates of the Caribbean. The best news is that these locations are all a fraction of the price.

Old San Juan, Puerto Rico

Puerto Ricans take partying seriously, and Old San Juan is stunningly beautiful.  Surrounded by a fortified wall, it is one of the best preserved Spanish Colonial towns in the Caribbean. Narrow cobblestoned streets open into airy plazas where colonial mansions have been transformed into Nuevo Latino restaurants and trendy lounges. Stay at Da House ($80 to $150 per night).  It’s a boutique hotel in the middle of all the action.  Make sure that you sign up for the daytime salsa lessons at the Nuyorican Cafe downstairs, because once the sun sets, Old San Juan is the place to meet and mingle with beautiful people.

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Cartagena, Colombia

Cartagena is the best kept secret of the Caribbean. This brightly colored Spanish colonial city knows how to party, while offering the best in regional Colombian food. Try the Aguardiente, Colombia’s firewater moonshine, mixed in with fresh tropical fruits. The best clubs don’t get going until 4 am and don’t close until the sun comes out. Recover with a hearty fish soup and a cold beer under a palm tree. The Hotel Casa la Fe ($150-$200 per night) is a beautifully refurbished colonial mansion with shady interior courtyards and a refreshing pool.

Isla Mujeres, Mexico

If Cancun is Spring Break central, Isla Mujeres is the thinking person’s tropical party island. Reachable by water Taxi from Cancun, Isla Mujeres is a tiny island that is all about beach shack restaurants, turquoise water, powdery sand and wild nightlife. Go for an early swim, have some lobster or the catch of the day for lunch, and then a snorkel in the afternoon before the evening festivities. The lively beach bars on Isla Mujeres run the gamut, from reggae beach bum joints to trendy Mexican cantinas. Casa Sirena (from $100 per night) is a remodeled colonial home with ocean views. It’s the perfect place to enjoy it all.

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Havana, Cuba

With the gradual easing of travel restrictions, Havana is back on the American travel map (Canadians never stopped visiting).  Start your stay with a walk from the historical Hotel Inglaterra (from $65 per night) to one of Ernest Hemingway’s favorite Havana bars, La Floridita, for a cool daiquiri. Havana’s restored colonial core is home to numerous bars and restaurants, including the world famous “La Bodeguita del Medio,” perfect for that afternoon Mojito.  Cuban music is best live, so reserve your spot at the Tropicana Cabaret for that Mambo Kings experience. Americans should check the state department website to learn how to book trips to Cuba.

Kingston, Jamaica

Kingston Jamaica is not your typical Jamaican beach resort, but that is what makes it interesting. Visit Port Royal for the refurbished ruins of the original fort and docks of the real Pirates of the Caribbean. Hit Kingston’s many bars, restaurants, jerk shacks and dance halls for Red Stripes, jerk chicken and wild times. Save some energy for a visit to the Bob Marley Museum or rent a car to drive up the Blue Mountains for the views and the coffee. James Bond fans may want to drive north to Ocho Rios to visit Ian Flemming’s Goldeneye estate and stop by James Bond beach. The Courtleigh Hotel and Suites in Kingston (from $200 per night) is the perfect base, with all the amenities you would expect from a business hotel.

Airfare Booking

Are you sold on these affordable tropical destinations, but not on the cost of airfare? The secret of scoring the lowest airfares during the holiday is to book early (no last minute deals here). While flying out on Dec 22-23 and returning on January 2nd or 3rd will probably be expensive (these dates sell out first), you may consider flying out on Dec 24 or 25th and back on Jan 1st to save some money. The best recommendation is to leave the week before December 20th. Fares usually remain low until Dec 18th – 20th and then go back down after January 7th.

The Caribbean is affordable and anyone can have a good time. It’s not just for romance. The place is swimming with activities and parties for anyone who wants to soak up some sun and have an overall good time.

Max Milano is an international travel expert with, the only online travel booking site focused entirely on international travel — airfare, hotels and activities. He’s also the author of The Mechanicals Recoleta, which is available on Amazon.