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My sister freaked out when she heard that Kenny Chesney would be playing a special concert at the Atlantis Resort on Memorial Day weekend last year. She begged me to go, and with neither of us having been to the Bahamas, it was an absolutely fabulous experience. We shopped and laid out by the pool during the days, while experiencing all the nightlife and restaurants that the resort has to offer. We had a great weekend, and Kenny was the topping on the cake!

Tucked among the pristine rain forests of Kauai’s remote North Shore, Princeville Resort’s lush 9,000 acres feel like they’re straight out of South Pacific. In fact, the classic musical used neighboring Mount Makana as a stand-in for Bali Hai. The peak’s verdant slopes are visible from many of the property’s 251 rooms, which are clad in ocean- and floral-inspired hues and outfitted with custom wood furnishings and marble baths, but the real draws lie elsewhere on the property: in the private snorkeling beach and massive infinity pool overlooking the cerulean waters of Hanalei Bay, an 11,000-square-foot spa that specializes in traditional Hawaiian clay treatments, and a world-class golf course designed by Robert Trent Jones, Jr.

Opened in 1950, the Jamaica Inn is one of the oldest and most gracefully aged of the classic Jamaica luxury resorts. It sits on its own private beach, which is rare in Jamaica, and each of the 52 suites and cottages has a Caribbean view. It is a timeless place, which may be why there are no TVs, radios, or clocks in the rooms, with a quiet serenity about it that may have been the appeal to such guests as Marilyn Monroe, Ian Fleming, and Katharine Hepburn. The grounds are immaculately kept, and the dining is as romantic as starlight and live music can make it. But the standout feature is that each suite has an oversize covered veranda that guests could literally live on. On it, they’ll find a full-size sofa, wingchair, breakfast table, coffee table, and, should one want to write home about it, writing desk.

A two-minute ferry ride from St. Vincent’s Villa Beach brings you to Young Island—the first of the Grenadines. Here, the Young Island Resort welcomes guests and visitors alike to its beachside restaurant for casual breakfasts, local curry buffet lunches, prix-fixe dinners, and barbecue parties. Seated in an open-air hut surrounded by tropical flowers, you can dine on local specialties like freshly caught fish and lobster while enjoying the ocean breeze. Whatever you order, pair it with the restaurant’s signature bread, which comes in banana, coconut, cinnamon, white, wheat, and raisin varieties and gets sliced tableside right before your eyes. Just know that reservations are required to eat here, no matter the time of day.

On the non-descript, busy corner of Bucareli and Morelos streets in Mexico City is a café with a famous history: Fidel Castro and Che Guevarra met here at Café La Habana several times, chain smoking and drinking strong coffee, to plan the Cuban Revolution. Nowadays, you can still get excellent coffee—and pretty good food—while you plan something a little less dramatic (but more enjoyable), like your vacation itinerary. Old journalists and businessmen congregate here for hours on end while salt-of-the-earth, slightly surly waitresses take your order and bring you your food and drink. Come for breakfast and order their chilaquiles, motuleños, or molletes, and wash it down with an espresso or café americano.

Just a few blocks from the bustle of Old Town and Duval Street, this Caribbean-style resort is a serene retreat with a swath of white-sand beach, a pool concierge, and a private pier for fishing or gazing out over clear turquoise waters. All of the contemporary rooms and suites are generously sized and have private balconies with views of the pool, courtyard, or ocean, but the real draw remains right outside your door. Guests can snorkel off the shore, face off on the giant chess board, or simply sway between two palms in one of the beachside hammocks. They also have privileges at sister resort Casa Marina, just up the beach, including at the oceanfront Spa al Mare. Have kids in tow? The hotel offers a full roster of activities, plus babysitting services for parents who want to hit the town.

Near the southwestern edge of Snow Canyon State Park is this wellness-oriented resort, a sprawling 55-acre property filled with fragrant mesquite trees, black lava gardens, and 106 rooms and villas. Stays here can be as low-key as a swim under the desert sun in one of two outdoor pools or an exfoliating red clay treatment at the renowned Sagestone Spa & Salon, but most visitors come for the full range of adventure offerings, from hiking and kayaking to sunset rappelling and horseback riding deep in red rock country. While the “consciously-planned entrée portions” at the hotel’s Canyon Breeze restaurant are all 500 calories or less—with most well under—dishes like grilled grass-fed strip loin steak with cheesy potato au gratin will leave you feeling anything but deprived. As of 2017, the resort is easier than ever to get to, thanks to new daily flights by United Express from Los Angeles to St. George.

Nestled within the paddies of a fully operational rice farm, the Four Seasons delivers an immersive experience that’s steeped in tradition. When not exploring Chiang Mai’s ancient temples, guests can learn how to make regional curries at the resort’s cooking school, help farmers plant rice sprouts, or bike through leafy grounds overlooking Doi Suthep mountain and the Mae Rim valley. The 99 elegantly appointed guest rooms, each with teak flooring and Siamese artwork, offer a plush landing spot come evening—that is, if a lemongrass-infused massage at the spa doesn’t do the trick. The resort also has something no other hotel does: two resident water buffaloes.

Just 30 minutes from the bustling tourist towns of Gatlinburg and Pigeon Forge sits this secluded bed-and-breakfast surrounded by 200 forested acres. Accommodations at Christopher Place are intended for couples rather than families: Nine individually decorated rooms, four with in-room hot tubs for two and several with fireplaces, have only one bed, and children younger than 12 aren’t allowed.

You can savor in-room breakfasts and dinners in a few of the rooms; everyone else can enjoy meals at the Mountain View Restaurant, which serves an affordable, seasonal four-course menu with a backdrop that’s just as satisfying. Hearty breakfasts will gird you for a full day of exploring Great Smoky Mountains National Park, or just hiking the trails outside the resort’s front door. Return for a dip in the pool, then a cocktail or glass of wine in front of a roaring fire at Marston’s Library Pub, named after the property’s owner.

It’s easy to see why Eagle Beach is touted as one of the world’s best shorelines. Studded with iconic fofoti trees and backed by sparkling waters, the powderlike sand hosts sunworshippers and, a few months out of the year, the highest concentration of nesting turtles on the island. The eco-pioneering Bucuti & Tara Beach Resort is especially mindful of its unique setting, supporting local wildlife initiatives and ensuring it has the lowest electricity usage (per occupied room) of any hotel in Aruba. A focus on health pervades the property, which has its own certified wellness specialist; yoga, Pilates, and meditation classes; a restaurant that sources organic produce; and air dehumidifiers and purifiers in each of its 104 rooms. Yet guests can still expect traditional island-style pampering: romantic offerings include beachside dining in a private, candlelit cabana under the rustle of swaying palm fronds. The resort is adults-only.

Upon your arrival at this 556-room resort, you might be disappointed to find a small pool instead of sandy palapas overlooking the sea. But the Renaissance makes up for its location on a busy thoroughfare in the capital city of Oranjestad with its own private island, a 40-acre oasis dotted with pink flamingos and iguanas. After an eight-minute water-taxi ride, you can choose between two distinct beaches—one adults-only, the other designated for families—plus an array of vacation-friendly amenities. A beachside bar and grill serves up burgers and wood-fired pizzas; an open-air spa offers Swedish and cold stone massages, as well as reflexology; and an extensive water-sports program includes activities like snorkeling, scuba diving, and ocean kayaking. If that’s not enough to tire you out for the evening, a steak house and casino await back at the main resort.

Set on St. Lucia’s westerly Anse Cochon beach, Ti Kaye is a secluded, adults-only oasis that feels worlds away from the rest of the island. Each of the 33 cliffside, gingerbread-style houses feature outdoor showers and verandas with double-wide hammocks, and some even include plunge pools. Since there are no TVs, the focus remains squarely on the picturesque beach, home to a PADI diving center, crashing waves, and breathtaking sunsets. The same is true in the resort’s two open-air restaurants (don’t miss the banana pancakes at the beachfront grill) and treetop spa. Rum connoisseurs can schedule a tasting in Ti Kaye’s wine cave, but if you crave a rowdier scene after all the relaxation, know that it’s a 20-minute drive to the nearest fishing village—you’ll want to make the trek on Friday nights though, when Anse La Raye hosts its weekly street parties.

Situated on the eastern coast of Motu Tevairoa, with magnificent views of Mount Otemanu in the distance, this private beach resort features 80 rooms and villas, ranging from garden villas with thatched roofs and their own private gardens with plunge pools to gorgeous overwater bungalows with private decks and direct access to the lagoon below. The property’s out-of-the-way location attracts a lot of people who want to escape the more active, touristy parts of mainland Bora Bora, with lots of relaxation options right on the property, including a garden spa specializing in Polynesian treatments and massages. For those who do want to get out and about, the resort offers a large range of activities both inside and out of the lagoon, from helicopter tours to helmet dives (in which travelers don weighted helmets pumped full of oxygen and descend into the waters below) to encounters with sharks and rays.

Lanai, a sleepy, 140-square-mile former pineapple plantation, is suddenly in the spotlight. Following the island’s purchase by tech billionaire Larry Ellison in 2012, the bay-facing Four Seasons Resort Lanai underwent a multimillion-dollar overhaul that reduced the number of guest rooms from 286 to 213. The rooms shook off their dated look with mahogany floors and walls clad in slate and teak. Guests can dine at outposts of Nobu and Los Angeles–based Malibu Farm, take private flight lessons and horseback-riding excursions, or book one of the resort’s wellness-focused retreats.

Milan invented the art of bel cafè, the pedicured bar for a delicious morning coffee or afternoon aperitivo. Passerini has a delicious selection of pastries for mornings and afternoons, and is the ideal hideaway for an aperitivo in the city center.