Where to Travel in the Caribbean in Your 20s, 30s, 40s, 50s, and Beyond

See recent posts by Krystin Arneson

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.

Your 20s: San Juan and Vieques

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. 

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.

Where to Stay on Vieques: Undeniably romantic, the 10-room Blue Horizon Boutique Resort comes with phenomenal ocean views from the stone infinity pool and open-air lobby; airy, Mediterranean-style architecture; and wild horses roaming the grounds. The on-site beach is a bit rocky, but some of the best beaches in the Caribbean are a short drive away. Just make sure you’re splitting the room rates with a friend.

Your 30s: Dominican Republic

Known for its reasonable prices, the Dominican Republic has something for everyone in their 30s: romantic hotels for couples’ getaways and honeymoons, party resorts for those looking to cut loose, all-inclusive resorts for groups who don’t want to worry money while on vacation, and more. Because it’s such a tourist hot spot, expect to find properties that cater to pretty much any budget and personality. There’s also plenty to do on and off the resorts here, including soaking up the sun and sand on one of the many white-sand beaches. As far as where to stay, many people opt for Punta Cana, but those looking for a more off-the-beaten-path experience can head to Barahona. Here, you’ll find rainforests, quiet beaches, and not nearly as many tourists.

Where to Stay: Despite its kid-friendly mantra, The Reserve at Paradisus Punta Cana is a relaxing, appealing pick for both couples and families. The beach area is a good hike away, but the tangerine bikes are useful for getting around, and it’s not too far to walk to the large pool complex, fitness center, yoga studio, and Asian-themed spa.

Your 40s: Anguilla

Travelers in their 40s generally have the advantage of being more financially secure than they were in their 20s and 30s, and are often looking for a comfortable place to return to after a day of being out and about. Anguilla, a small British territory in the Caribbean, offers pristine, white-sand beaches like many other destinations, but it’s quieter, smaller (spanning fewer than 40 square miles), and less overrun with tourists. Golf is also huge draw for the low-key island. With both an upscale and happy-go-lucky vibe, Anguilla is the ultimate place to unplug and unwind.

Where to Stay: Foodies should stay at the CuisinArt Resort and Spa, one of the best-known resorts in Anguilla. It features numerous amenities, from an extensive spa to the only golf course on the island, but the real standout here (not surprisingly given its CuisinArt ownership) is the food; several on-site restaurants offer gourmet meals with a focus on fresh ingredients from the resort’s hydroponic farm, and guests can nosh on Japanese, Italian, or Mediterranean fare. When you’re not fueling up, relax on the beach or enjoy one of the other on-site activities, including tennis, croquet, water sports, and more.

Your 50s: Turks and Caicos Islands

Turks and Caicos, a 37-mile chain of islands, is packed with dreamy blue waters, golden beaches, and excellent snorkeling. But here’s the kicker — technically, these islands are in the North Atlantic Ocean, about 500 miles south of Florida. Rent a car to see as much of the place as possible. Each of the beach areas offers a different vibe — some specialize in snorkeling and caves, while others are more about lighthouses and whales. Others, like Grace Bay listed below, focus on golf and pristine beach time. Thankfully, nightclubs are scarce, so you won’t find a huge party crowd here. In other words, it’s a relaxing place to count down the days until retirement.

Where to Stay: Point Grace, a luxury boutique beachfront hotel on arguably the island’s best beach, is heavy on style and refinement. Property highlights include a tranquil pool, personal beachfront service, a small but spectacular spa, and one of the Providenciales’ most romantic dinner spots. And its remote location on the point of the beautiful, 12-mile Grace Bay beach means you’ll be met with a peaceful and quiet vibe. 

Your 60s: St. John

St. John is definitely the place to go if you’re looking for some peace and quiet. Whether you’d like to snorkel at Trunk Bay, relax at Hawksnest and Cinnamon Bay beaches, or check out the Annaberg Sugar Plantation ruins, there’s something for everyone here. Plus, a vast portion of the island is covered by a preserved national park, which provides gorgeous walking and hiking trails. A friendly, slow-paced local culture tops it all off.

Where to Stay: Built from a historic sugar plantation, the profoundly serene Caneel Bay Resort sits on 170 acres of a protected national park dotted with seven remote beaches. Even with a quaint pool and rustic rooms that lack TVs and phones, Caneel’s attentive service and unparalleled setting make it one of the Caribbean’s best resorts. It’s not easy to get to — and it’s inarguably expensive — but those who are looking for somewhere special to celebrate a milestone wedding anniversary should consider this property. But it also caters to families seeking a little quiet.

Your 70s, 80s, & Beyond: Aruba

Aruba is far enough away to feel like an adventure, but familiar enough not cause any undue anxiety. The terrain is flat, water is potable, and English is widely spoken. Plus, lots of tour excursions cater specifically to folks in their 70s and 80s. There are also stunning white-sand beaches and two golf courses on offer. While an all-inclusive might be tempting, book half board or less, so you can try the island’s offerings. While you’re out, check out the butterfly farm in the capital or do some shopping for the kids and grandkids. 

Where to Stay: Check in to the adult-only Bucuti & Tara Beach Resort, which takes up a prime stretch of sand at the southern end of Eagle Beach. This eco-friendly hotel has 14 acres of beach, and the main activity here involves lingering on the sand under shaded palapas. There’s also a chic infinity pool. Every evening before and after dinner, the Sand Bar becomes a hub for guests to relax, with happy hour drink specials and live steel drum music. In addition, weekly movie nights allow guests to watch a new release or an old classic right on the beach.

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