We can't deny it any longer – summer is drawing to a close in New York City, as we start to pull out our leather jackets and suede boots again. But don't pack away your bikini and flip flops just yet. Now is the perfect time to start planning a mid-winter vacation to somewhere where the weather is warm and the beachside margaritas are cool. But where to go that won’t cost three month’s worth of rent and a 24-hour plane ride? Go with a classic, dear friends. Yes, we're talking about the Caribbean. And before you jump to any conclusions, it’s not cheesy family getaways and older folks. Here's why.

Dominican Republic

Think lush jungle, rocky cliffs and dazzling coastlines and you can understand what makes this Caribbean gem so desirable. Then there's two golden words. All. Inclusive. There is nothing, and we mean nothing, that makes you feel like royalty quite like having a cocktail served to your cabana but then receiving no bill. And it's not as ludicrously expensive as it sounds. A resort (with food, drinks and the works included) will cost you no more than a couple hundred dollars per night, which means a surpringly cost-effective week for a slice of absolute paradise.  

Where to Stay: The wellness retreat, Zoëtry Agua Punta Cana, is as glitzy outside as it is inside, surrounded by white sand beaches and azure waters. The four pools (swim-up bar included), gold decor, spa and fitness center won't disappoint either.

Puerto Rico

While Puerto Rico is technically in the United States (which means you can expect plenty of familiar brands like CVS pharmacies), it also has a distinctly unique culture of its own. And one which has buckets of Spanish colonial charm. Be sure to visit the centuries-old fortresses dotted round the island nation, as well as Old San Juan in the capital. There you will find cobblestone streets, lively eateries and La Factoria, a craft cocktail bar that's said to be one of the world's top 50, according to Drinks International magazine.

Where to Stay: There are some unbelievable historic apartments for rent on Airbnb. This one, in particular, has the most exquisite interiors.


If all Jamaica conjures up in your mind is Bob Marley, stop. Stop it right now. Jamaica is an incredibly beautiful and culturally-rich place, plus it's no longer the 70s. Jamaica is decorated with beaches, waterfalls, mountains and other splendors that have to be explored in person to fully appreciate. The city of Kingston has a vibrant nightlife, and being the cultural epicenter of the nation, is filled with art, music, food and history that you have to  explore. Check out the Bob Marley Museum for starters (irresistible, admittedly) and Devon House (the mansion of Jamaica's first black millionaire). Then head northeast to the Blue Mountains, a spectacular coffee-growing region.

Where to Stay: The city has a ton of Airbnbs available, including whole apartments for next to nothing, or sprawling villas for you and literally all of your friends. For a more intimate stay in the capital, check out this cute cottage, complete with landscaped gardens and a pool.


Get it while it’s hot. Havana will only be the peculiarly-preserved time capsule that it is today for so much longer. That is, before the relaxed travel restrictions lead to an overwhelming influx of tourists. Getting to Cuba will likely require you to take the long-route, that is, via Canada or Mexico, but it is well worth the detour. The lights, the colors, the salsa, the rum... Havana is indescribable. But be prepared to unplug. The internet isn’t really a thing here yet. Well, in most places. Not that you'll need it – the retro stores, sugar-white beaches, salsa music and cabaret shows will be sure to keep you happily amused.

Where to Stay: The vibrant district of Old Havana has some fantastic Airbnbs. This historic beauty is loaded with character and is right by Plaza Vieja, Havana's most architecturally dazzling square.