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Rick’s is probably the most touristy spot in all of Jamaica, but there’s a reason it’s listed in 1,000 Places to See Before You Die, so don’t miss experiencing it at least once. Get there around 4 p.m. to avoid the crush of tour bus traffic that happens closer to sunset, then order a couple of cocktails—Rick’s serves up a myriad of options—and stake your claim on a prime viewing spot for the sunset and cliff-diving. Local divers swing from trees and drop into the surf or plummet from the surrounding cliffs, some of which rise more than 30 feet above the sea. Even the occasional tourist will brave the jump into the water below. A reggae band adds to the animated vibe. Lest you feel like just another tourist sheep at the sunset very-happy hour, console yourself in knowing that locals enjoy it almost as much as visitors do.

Swimming and snorkeling around Xtabi (pronounced “X-tah-bee”) Resort’s underwater caves are a unique experience and a well-kept secret from first-timers. While it’s a great place to stay, overshadowed by places like Rockhouse Hotel, you don’t have to be a guest to enjoy this “meeting place of the Gods” as the name describes. You’ll want to have lunch at the casual, outdoor restaurant first--choices are excellent and include club sandwiches to jerk chicken (even if a tad pricier than from the street grills). After lunch and a rest, change into your swimwear and make your way carefully down the steps until you reach a sandy cove entrance into the sea, beside caves and jutting rocks. Splash in and come out on the front side of the cliffs, where there are ladders to exit or enter as well, if you’re feeling a bit timid. A laid back environment, gorgeous waters--just a tad more jade-colored on this end, for some reason--and underground caves ideal for photo ops make Xtabi a great spot to spend the afternoon. When you tire, climb back up to sip on a Dirty Banana and sunbathe on one of the platforms beside splashing waves.

Why we love it: A design-savvy boutique hotel with direct beach access

The Highlights:
- Bright design that’s full of personality
- A focus on exploring the hotel’s natural surroundings
- Direct access to pristine Seven Mile Beach

The Review:
A welcome departure from the classic Negril resort scene, this stylish boutique hotel—opened in 2018—melds local flavor, a vintage Havana feel, and a contemporary sensibility in a way that speaks to the curious, independent traveler. Set along 220 pristine feet of Seven Mile Beach, the hotel features a clean-lined, mid-century modern-inspired aesthetic throughout, accented by bright textiles, artwork, and a curated soundtrack that celebrates the history of Jamaican music.

Room options range from studios set on the second floor of the accommodation wing, to options with patios or balconies looking out at either the garden or the ocean. All have air conditioning, USB outlets, Bluetooth radio, free Wi-Fi, and mini-bars. Skylark is big on encouraging guests to explore the area, whether that means taking advantage of the direct beach access (the hotel provides loungers, paddleboards, snorkeling gear, and beach games, plus food and beverage service), going for a boat ride, hiking to a waterfall, or zip-lining through the jungle.

Despite the industrialized patty chain stores across Jamaica, the love for handmade patties continues in some parts of the island. Miss Sonia’s entrée-size, crusty patties are served at a small roadside restaurant across from the beach in Negril. She offers traditional fillings like beef or callaloo, as well as others like lobster and conch that she introduced at the suggestion of her numerous return visitors to Jamaica. When you get your order, be sure to shake on some of the secret spicy sauce—Miss Sonia won’t tell you what’s in it—and then dig in.

Set directly above rocky low cliffs of Negril and lit at night by torches and candles, Rockhouse Restaurant provides the setting for an elegant and romantic evening. (The setting’s pretty great during the day, too—breakfast, lunch, and dinner are served in this open-sided palapa and patio.) The New Jamaican cuisine means a refined and more health-conscious preparation of classic island recipes, with as many ingredients as possible from the hotel’s small organic garden across the road. Among the notable dinner offerings are the blackened mahimahi with mango chutney, snapper steamed in a banana leaf, and coconut shrimp.

Located an hour’s drive from Negril on the southwestern coast, Bluefields Bay is a popular beach. It’s crescent-shaped and rocky on the left hand side, but sandy on the right, and the water is an iridescent turquoise. You’ll find more local families than tourists here, as it’s a convenient pit stop on the road between the west and the south to cool off on a hot afternoon. The beach has a handful of food vendors but not much else, and that’s also what makes it special.

Remember the oldie “Under the Boardwalk” by The Drifters? The owner of Drifters Bar, Luddy Samms, tells stories of his career with The Drifters, as well as tales of singing with Eric Clapton and Stevie Winwood and Bruce Willis. Samms opened this hot-spot bar and performance venue on Seven Mile Beach in 2011, and expats, locals, and tourists flock here for cold Red Stripe, good food, and lots of live music in a variety of genres. Because this is an authentic Jamaican beach bar, though, reggae is king.

See Jamaica’s natural beauty, from waterfalls to bioluminescent lagoons, enjoy spa treatments, and savor local cuisine with this five-day itinerary.