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An intimate gem whose only shortcoming (in some eyes) is that it does not sit on Pink Sands Beach, the Rock House Hotel & Restaurant was a labor of love for the late Wallace Tutt, an interior designer to the stars who was best known for designing Gianni Versace’s Miami mansion. Ten individually decorated rooms in the 1940s private home turned boutique hotel echo that property’s grandeur with king size beds and seaside motifs, as well as sumptuous linens and stone lion heads mounted on the walls in the restaurant. But the real story here is the service: There is always a picnic basket on-hand in every room, a library of games and books is available for perusal on rainy days, and the concierge is happy to arrange in-room pampering treatments if the walk to the neighboring spa feels like too much trouble.

A stroll of St. Kitt’s capital, whether started at Port Zante Marina or the centrally located Independence Square, is an entertaining way to learn more about the island’s past. While the French named Basseterre (it means “low land”), the British are responsible for the town’s most recognizable landmark—the green, cast-iron Berkeley Memorial Clock in the center of the Circus, where several streets intersect. Make sure to visit the area, as well as Independence Square, St. George’s Anglican Church, and the Old Treasury Building, which now serves as the National Museum of St. Kitts. Along your walk, you’ll also find duty-free shops and local boutiques, plus a lively produce market by the waterfront if you come on the weekend.

The most popular trek in the St. John national park, this trail begins on Centerline Road and descends 937 feet through a shady forest. Along the way, hikers will encounter the remains of four sugar estates, as well as ancient petroglyphs, or rock carvings. The trail ends at the ruins of the Reef Bay Plantation near Genti Bay.

Travelers can now take in the beauty of Oman’s otherworldly desert landscapes from the comfort of Anantara Al Jabal Al Akhdar Resort in the central Al Hajar Mountains. Set on the rim of a massive canyon surrounded by craggy mountains, villages, and date plantations, the 115-room resort is a retreat with stone walls inspired by the region’s ancient citadels.

Sometimes Caribbean travel is about more than just a cold drink and a beach. It takes driving as far as possible (only about 40 minutes) from the tourists on the east side of the island in Nassau to find this moving piece of art, appropriately titled, “Sacred Space.” Located only a few hundred yards from the ruins of old slave quarters, and just above where the slave ships used to dock, these faceless carvings silently stare back across the ocean toward Africa. Trees that typically erode the coastline were cut down to create these powerful pillars that are still rooted in the ground.

Seafood and regional delicacies rule the menu at this charming 19th-century former plantation home—go for the fish tacos, ceviche, or keshi yena, a local entrée consisting of a large sphere of cheese stuffed with seasoned meat. The papaya stew, with delicately spiced cabbage and invigorating ginger, is another local favorite. Savor your meal at one of the rustic picnic tables outside, or head to the dining room for a slightly upscale atmosphere. Landhuis Misjé is a great pick for both a romantic dinner and an outing with a tribe of hungry family members.

Adjacent to Romney Manor and the Caribelle Batik factory, Wingfield Estate is a former sugar plantation dating back to the mid-1600s. Here, you’ll find ruins of the rare St. Kitts sugar mills, which were powered by water instead of wind. Also on-site are the remains of a stone chimney, a distillery, and an aqueduct system that brought water from the Wingfield River down the slopes of Mount Liamuiga.

One of Guadeloupe’s top rhum distilleries is set on beautiful former sugar cane plantation grounds in Basse-Terre. There’s a trolley tour through the grounds that also provides information about Guadeloupe’s rhum and history. Take a walk through the Domaine de Séverin grounds afterwards and see the sugar cane processing if you are there during the February to June harvest season. A half-hour of free tastings of the multiple flavored rhums is, of course, a high point. Shop in the store for your favorites before you leave.

Located 100 miles south of Santiago, the Colchagua Valley has in the past decade become one of Chile‘s wine hotbeds for the production of robust red wines. Stretching from the Andean foothills in the east through the coastal mountains to west, always following the Tinguirrica River, the valley is renowned for its “big” reds like Cabernet Sauvignon, Syrah, and Chile‘s flagship wine, Carmenere. The majority of the vineyards lie in the center of the valley around the small country town of Santa Cruz with its charming colonial plaza and several hotels. New vineyard plantations are also extending into the hillsides in prestigious sub appellations like Apalta nearby and to the west towards the sea. Besides red wine, Colchagua is also steeped heavily in Chile’s country traditions and cowboy culture as an agricultural valley, making it an ideal weekend getaway. For wine enthusiasts, every March during harvest the valley puts on its annual harvest festival during a whole weekend with tastings from valley wineries, regional food, music, dance, and local color.

The only existing French plantation house on St. Kitts, the Fairview Great House was built circa 1701 and originally housed French military officers. Today, guests can tour the beautifully restored property, taking in the period furnishings, kitchen, apiary, chapel, and bathhouse before exploring the two-and-a-half acres of botanical gardens, filled with tropical flowers, fruit trees, and monkeys. Visitors can also purchase day passes to the property’s swimming pool and sunny deck, or sign up for cooking classes and tastings of St. Kitts’ own Brinley Shipwreck Gold Rum.

Said to be the oldest structure on the island, Wallblake House is also the only surviving 18th-century plantation home that has been restored and that can be toured. Located in the Valley, capital of Anguilla, the 1787 property was once part of a 97-acre sugar and cotton plantation. Bestowed to the Catholic Church in 1976, it was abandoned until it was finally refurbished in 2004. The main home, which suffered a fire at the hands of the invading French forces, and the outbuildings are intact in design. Though the house is currently used as a rectory, tours can be arranged by emailing in advance.

A Hawaiian fantasyland on Oahu’s more remote leeward coast, about 40 minutes from Waikiki, Aulani is so seductive—for all ages—that many guests are loath to leave the property at all. And who can blame them? The beach is an idyllic cove (albeit a man-made one) stocked with kayaks, boogie boards, and everything else little beach bums could want. Then there are the three pools, including one for adults only and one filled with tropical fish for snorkelers-in-training, two impressive waterslides, and the biggest crowd-pleaser of them all, a 900-foot-long lazy river where guests, big and small, splash around on inner tubes as they meander around a faux-rock grotto. Goofy, Minnie, Mickey, and the rest—all in their vacation outfits—make occasional cameos at the breakfast buffet or by (sometimes, in) the pool. But while Aulani is most assuredly every kid’s dream, it is not every parent’s nightmare. The resort decor is more traditionally Hawaiian than obnoxiously Magic Kingdom; the lobby is built to recall an old canoe house, on a grand scale, and is covered in murals, painted by local artists, depicting island life. Hawaiian storytellers gather around a fire pit at night, and rooms have warm woods, with a single subtle reference to the Mouse King—a wooden carving of Mickey with a surfboard and ukulele that doubles as a desk lamp. Perhaps best of all, the Aulani has an outstanding, supervised kids’ club that’s free to guests ages 3 to 12. Babysitters are available for kids as young as six weeks old.

The most enviable address in Waikiki, the beachfront Halekulani is all about restrained elegance and pitch-perfect service. The hotel dates back a century, though it was entirely rebuilt in the 1980s—and the room decor—fifty shades of white and plantation shutters framing the turquoise sea—complements the scene outside. The beach itself is small and usually mobbed, but the pool is a dream—a giant oval big enough for laps, and quiet enough (few kids here) for a long doze under your chaise’s umbrella. The grassy courtyards and seaside restaurants are just as improbably serene; some might say stuffy, but for others, the reliably hushed atmosphere is a welcome tonic to the hubbub of Waikiki, just outside the Halekulani’s marbled entrance.

Up in the rolling hills of Colombia’s Caldas, Quindío, and Risaralda regions, some coffee plantations offer guest accommodations for visitors looking to lap up traditional coffee culture (pardon the pun). Many of the farms give tours that involve arabica picking, drying, and roasting…and that always wrap with a fabulous cup of joe. You’ll also see beloved cultural symbols: the Jeeps that serve as the region’s pack mules. (Local Jeep festivals, called Yipaos, celebrate the vehicles with contests—those that most artfully pack and haul the biggest loads win prizes.) Not far from the town of Armenia, the Parque del Café, a veritable coffee-themed amusement park, is a great option for those traveling with children.

Once the center of commerce in Charleston, the City Market is now the heart of tourism. Although its location near the cruise terminal can make it feel like a kitschy open-air market in the Caribbean, the tackiness is part of its charm. Yes, you’ll find Christmas ornaments painted with Rainbow Row and enough cutely packaged pralines to give you a stomachache, but you’ll also see Gullah artisans weaving the finest examples of sweetgrass baskets available. Peak season brings 140 different merchants, and weekends include live music and food vendors. The market’s a requisite stop for any visitor and a one-stop gift shop for loved ones back home.