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Expect no less than over-the-top extravagance at Laucala, a resort island in Fiji with its own rental submarine. Bring friends: The island has 25 villas spread out over 4.6 square miles, with a rain forest, beaches, cliffs, a lagoon, and one of the island’s highest hilltops literally in their backyards.

While Cape Point is not, in fact, the southernmost tip of Africa—as is often claimed—it is generally accepted that the Indian and Atlantic oceans meet somewhere between here and the real tip, Cape Agulhas. Still, Cape Point is about as dramatic as you can get, with the land falling steeply away on three sides, the wind whipping around the cliffs, and the ocean churning below. The road to the point, at the end of a drive from Cape Town, goes through 20 miles of nature reserve full of baboons and antelopes. For those who don’t want to walk up to the lighthouse, there is a funicular, but to reach the point itself, you’re going to have to hike.

Serenity is easy to come by on the private-island resort of Petit St. Vincent, a 115-acre property from the 1960s. It recently underwent a multimillion-dollar renovation but retains its original charms—there are no cars or in-room televisions (and don’t even think about WiFi) in the 22 cottages and suites, and anything you might need arrives at your doorstep with the simple raise of a yellow flag. A Balinese-inspired spa soothes the body, while two open-air yoga pavilions quiet the mind. If you’re looking for more action, you can explore the island’s pristine reef formations with expert divers through Jean-Michel Cousteau’s only Caribbean scuba center, or rent one of four yachts to catch local mahi mahi—then have the chefs prepare it for you beachside back at the resort.

You may not know it, but as you peruse the stalls of vendors at Mercado San Juan, you just might be rubbing shoulders or vying for the plumpest, prettiest chayote with one of Mexico City‘s top chefs. San Juan is the market for serious home cooks and pro chefs alike. Here, you can find everything from just-off-the-boat fish and seafood to wild game. There have even been rumors over the years (urban legend or fact?) that if you know who to ask, you can procure true exotics here, including tiger and bear meats. If you’re not in the market for any goods to go, you can let your nose lead the way to a stall where prepared hot foods are sold. And don’t miss trying chapulines, toasted grasshoppers, which are a Mexican snack specialty.

With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.

This elegant bar at the Andaz Maui overlooks tiers of pools, waterfalls, and tropical foliage, all cascading down to the Wailea coast. Hotel guests and visitors alike come here to lounge under umbrellas by day and around a fire pit by night, sipping on cocktails like the Upcountry Buck (white rum, ginger, and pineapple) and the Lahaina Town Fizz (blanco tequila, strawberry, and elderflower). For something unique, try the Silversword, a cocktail designed by legendary Hawaiian mixologist Julie Reiner that features mezcal, sweet vermouth, pineapple, and chocolate bitters. Pair it with snacks like chilled shrimp summer rolls and Thai lettuce wraps, then finish with a ginger ice cream sandwich made in-house.

Sister restaurant to local favorite Serpico’s in Upcountry, this sweet, welcoming spot serves New Jersey–style pizza in an old plantation-style house in West Maui. Tourists dine here, sure, but Prison Street isn’t overrun with overpriced rum cocktails or macadamia-crusted everything. Instead, the pizzeria keeps things simple with subtle nautical decor—a nod to Lahaina’s past as a whaling port—and thin-crust pies in variations like barbecue chicken, Philly cheesesteak, and the Windmills, a curiously named mix of Italian ingredients like pesto, mozzarella, and roasted red peppers. Also available are subs, salads, and calzones, all of which can be delivered if you need a break from dining out one night.

I generally have a thing against beaches next to the road. Usually, they’re unfortunate victims to automotive pollution: obnoxious noises, exhaust fumes, and sneaky greases seeping into everything. Darkwood Beach is different. Sure, it’s right on the road on the southwest coast of Antigua, but somehow it escapes the usual woes of roadside sands. Maybe it’s because the road is fairly quiet. Or maybe it’s the persistent onshore trade winds. Or maybe it’s because people care enough to keep the beach clean. Regardless, what you, the traveler, get is a great beach with good swimming and snorkeling, plus a beach bar serving rum and traditional West Indian eats — complete with white plastic chairs in the sand.

Eat Street Social’s new bar-within-a-bar, the Torpedo Room, serves artisanal tiki cocktails with tasteful kitsch and Midwest flair. Flavors like sweet corn cream (instead of coconut cream) and apple cider (instead of pineapple and orange juice) are termed “Minnesota exotic” for their twist on the classic Painkiller. There are 45 rums to be turned into cocktails and topped with an umbrella or finished with fire, as well as an alcoholic sno cone menu for some added fun.

Swoops of smooth, scarlet earth overlook Dominica’s northeast coast near Calibishie. At Point Baptiste, a mile-long coral reef protects the seashore, creating a calm lagoon. Farther down the coast, however, the Atlantic erodes and slaps waves high onto the dramatic headland. If you visit Point Baptiste Beach, know that a caretaker sometimes requests a donation from foreigners. Still, it’s a small price to pay for exploring this spectacular landscape of black sand, red rock, and splendid mountain views, which are especially beautiful at dusk.

This property is currently closed for hurricane-related repairs.

Peter Island is “an oasis of tranquility,” known as much for its five flawless beaches as its word-class spas and luxurious ocean view villas. The island is the largest of the private islands and the fifth largest of the 60 islands in the BVI. Visitors can hop a ferry to reach the island from Tortola or opt for booking a helicopter, water taxi, or private yacht.

Off the coast of Port Antonio is a small, uninhabited plot called “Pellew Island,” otherwise known as “Monkey Island"--there used to be a colony of imported monkeys here. To get here, you could first head to San San Beach, a beautiful and private stretch open daily (10 a.m.4 p.m daily, US$5). Rent a kayak and snorkel gear and make your way over to the small plot, within clear view ahead. The island is completely covered in vegetation, there’s a small white sand beach, and the waters are shallow. Rest your kayak on shore and snorkel around the island for as long as you please. Visibility is incredible and this is one of the best snorkeling spots in the area. Just watch your step if you’re barefoot, as there can be sea urchins on the seabed.

Give your senses a jolt at Sky Costanera Observatory, on the 61st and 62nd floors of the Costanera Center. A 50-second elevator ride takes you almost 1,000 feet into the sky for a thrilling 360-degree view of the city, population over five million, with the snowcapped Andes as a backdrop. Guides are on hand to point out cityscape highlights. Not for scaredy-cats. Note: In case of rain, return first thing the following day, the best time to visit for the clearest view.

Hotel Atarazana is a simple, airy, and clean hotel a stone’s throw from Plaza España at the north-east of Santo Domingo’s Zona Colonial. There is a cute walled courtyard where you take breakfast, and an open rooftop (with some shade) for sunbathing, reading, and rum; drinking water is included; and the staff are friendly and some speak English. All the Zona Colonial’s sights are within easy walking distance; the pedestrianized El Conde is a ten minute saunter south. (Note: The hotel is so close to the bars / clubs off Plaza España that it can get noisy at night.)

Just next door to crowded Doctor’s Cave Beach in Montego Bay is a quiet and spacious stretch known as Cornwall Beach. You won’t see more than a couple of people at a time here during the week. Late afternoons and weekends attract a few locals who come to relax and enjoy the restaurant and bar. A small entry fee—under US$5—covers the on-site facilities, including lounge chairs and snorkel gear. Cornwall Beach occasionally hosts a sunset beach party on Sunday afternoons with a “bottomless” Appleton mug option (that is, all-you-can-drink rum).