See full version: Where to Travel in the Caribbean in Your 20s, 30s, 40s, 50s, and Beyond
So many islands, so little time. If you're contemplating a trip to the Caribbean, the choice of where to go can sometimes be overwhelming. But no matter where you are in life, there's a destination for you. In fact, taking into consideration factors like activity offerings, price point, and overall vibe, we've put together a list of the best Caribbean destinations to visit in your 20s, 90s, and every decade in between. Start checking off your bucket list.
For 20-somethings who might or might not have a passport (and for whom this might be a first trip abroad), San Juan, Puerto Rico, is a great Caribbean stop. Those traveling with a group of pals will appreciate the nightlife (think salsa, Latin, and rock clubs), while everyone — couples, solo travelers, and friend groups — will enjoy the beaches as well as the Spanish colonial architecture, museums, art galleries, and other cultural and historic offerings in Old San Juan. Folks can also choose to spend a couple of days on Vieques, a Caribbean island off Puerto Rico’s eastern coast. It’s perfect if you want the cultural and nightlife attractions of the city plus a few days of beach time that’s just a bit more cut off from the tourist crowd. [links]
Where to Stay in San Juan: Located in the heart of Old San Juan, Da House Hotel and its boutique vibes come at a rate that’s agreeable to 20-somethings. It’s perfect for guests looking to disconnect during their holiday, as Wi-Fi can only be found in the common areas. It’s also close to everything (beaches are 15 minutes by taxi) and features a spacious rooftop terrace. Best of all, the hotel is located directly above the Nuyorican Cafe, which is known for its live music and salsa nights. more
Whether you're in the mood to relax or to mingle, the adults-only CHIC by Royalton Resorts checks both boxes. Its 323 rooms are sleek and modern, you'll have your pick from seven restaurants, and there's not one but two swim-up pool bars get the party started early. You might feel like you're in South Beach by the pool, which comes with a private area reserved for guests who’ve booked a cabana for the day (or week) and a separate glass-walled mermaid pool where you can stay dry while taking in underwater views. more
Are you a social butterfly who thrives in a sea of fresh faces? One of the best all-inclusive resorts in the Bahamas, this sprawling but attractive resort near Nassau is massive—we’re talking 694 rooms and suites all with private balconies or patios that look towards the ocean—but it still manages to deliver a quality experience. Treat yourself to one of the recently renovated rooms on The Level, which now come with pillow menus and VIP perks like nightly turndown service, then get ready to mix and mingle. There's a busy main pool with a swim up bar, plus two less crowded satellite pools, and you've also got access to a serene stretch of powdery white beach for soaking in that glorious Bahamian sun. more
When it’s time to recharge, treat yo’ self to an indulgent week of R&R at BodyHoliday. This wellness-focused all-inclusive facing St. Lucia’s crescent-shaped Cariblue Beach has endless diversions to keep your mind and body moving, from tai chi to sailing and spinning, not to mention three pools (including a hilltop infinity number), direct access to the sand, and zero supplemental fees for booking a dedicated singles room. Meals are organic and locally sourced, though our favorite perk might be the daily, and included (yes, you read that right), spa treatments. Follow up a pampering ayurvedic massage in one of the wellness center’s 33 treatment rooms with an afternoon nap in one of the hammocks strung between palm trees. here
Those who come to cash in on Cancun’s high-octane energy will find everything they’re looking for at ME Cancun. This upscale all-inclusive, right in the heart of the Hotel Zone, is sleek and modern, with original art sculptures and roomy suites with their own terraces and daybeds. Of the three pools, two are adults-only—though the beach is open to all, and features fast and free WiFi—a godsend for meeting up with friends during weekend beach parties. The restaurants and bars are also lively and excellent, and a vibrant nightlife scene means there's never a need to head off-property to get your fix.
Sunset at the Palms is for those who prefer a little rest and relaxation to the typical techno-pumping, nightclubby singles’ life in the Caribbean. With just 85 rooms on the grounds, all treehouse style, you’ll feel like you’re secluded in paradise until you’re ready to go out and seek adventure. Negril is not only close to some of the most beautiful hikes and sites in Jamaica, it’s also ground zero for Jamaican nightlife. [links]
When you’re unattached to a partner, travel can be a great way to meet new people. And there are few regions better suited for single travelers than the Caribbean. With no shortage of activities ranging from world-class nightlife to jaw-dropping hiking, snorkeling, and more, the Caribbean is the perfect place to live your best single life.
If you feel compelled to leave the resort, Punta Cana is home to some of the best nightclubs in the DR, so you’ll have plenty of places to dance the night away and maybe even meet someone special. [links]
We recommend you stay at La Concha Resort in Condado, just outside of Old San Juan, which caters to a young crowd but still gives you a luxury experience. Feel free to hang out at the resort on lazy days, then mosey on down to Old San Juan or catch a ferry to one of the outer islands.
Head into town to hit up any number of indoor/outdoor bars that take advantage of the dreamy weather. Just make sure you don’t skip The Jungle , a legendary nightclub with two floors, seven bars, and four DJs, located on the north side of the city. Thursday night is ladies night, which means cheap drinks and plenty of new people to meet. [links]
Find a pristine beach and beautiful pool, and then when you’re ready to get your heart pumping and meet people, take the free shuttle to the main resort, where you have access to both a casino and a nightclub. here
Receiving over a million tourists every year makes Barbados one of the top destinations in the Caribbean. It is best for a solo trip if you are looking for a famous destination that’s also insanely gorgeous, excellent nightlife, and tons of travelers to meet and connect.
One of the most incredible destinations for solo travel in the Caribbean is Jamaica, known for its gorgeous waterfalls, fantastic hiking trails, and beaches offering splendid views.
If you are hesitant for some reason to try Caribbean destinations for traveling alone, how about going with any of these?