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There aren’t too many opportunities in the Caribbean to ride on horseback to a cave. In Los Haitises National Park, located three hours west of the resorts of Punta Cana, Fun Fun (pronounced “Foon Foon”) Cave is officially known as the largest cave in the Caribbean. Though the cave itself is in the National Park, access to the land goes across a private ranch and requires a guided tour. While the nearly three-hour drive from the resorts of Punta Cana is a lengthy, bumpy, journey into the interior, the scenes from the window provide an authentic glimpse into rural Dominican life. Sugar cane sways, schoolchildren wave, and mangoes drip from the trees. Upon reaching the ranch where you begin the tour you are shimmied into a jumpsuit and saddled onto your horse. A 45-minute ride through the shaded forest brings you to the edge of the National Park. From here it’s another 30 minute walk through sun-swallowing trees until you reach the entrance of Fun Fun Cave. Sliding into a harness and climbing gear, entering the cave requires a 50 ft. repel into a tiny hole which can barely fit your shoulders. Once at the bottom, it’s a one hour slog through the depths of the darkness before reaching the other exit. Inside the cave, stalactites and stalagmites pepper the areas which fall in the beam of your flashlight, and at some areas you are forced to swim through the soothing, subterranean waters. Here, a lone rope helps guide visitors through the hidden recesses of the cave.

Dornier’s modern cellar and production facility is quite different from the traditional 18th- and 19th-century buildings you’ll see in the winelands. For example, a pool above the cellar regulates the temperature of the wines in an eco-friendly way. Its reflective surface also helps keep the entire subterranean building cool. The cellar’s overall design pays homage to the Dornier family’s history in the aviation industry. Contact the winery in advance to arrange a tour of the facility, then enjoy a tasting of award-winning wines like the Dornier Donatus White (a blend of chenin blanc and rich sémillon), the Dornier Merlot (with hints of plum, mint, and roasted nuts), and the Cocoa Hill Sauvignon Blanc (featuring notes of mulberry, roasted oak, vanilla, and spice).

This leather workshop is hidden away in a former Franciscan monastery next to Santa Croce. The Scuola del Cuoio was originally founded to provide skills and work for some of the city’s orphans after World War II; masters and apprentices still produce wallets, purses, journals, and jackets. Take a quick tour of the beautiful cloisters, frescoed corridors, and workspace, or sign up for a full workshop and try your hand at making something of your own. Everything is crafted on-site using traditional methods. Be sure to get your purchases personalized with a gold-stamped monogram.

The mercury during summer afternoons can hit 34C (or around 95F). How to stay cool during the hottest time of the day (4-6pm)? Besides seeking shade or air-conditioning, Santiaguinos seek solace in a traditional drink called “mote con huesillos.” Huesillos, sun-dried peaches, are cooked with water and a touch of sugar. The liquid and fruit are chilled and served with a scoop of toothy golden barley. Mote con huesillo is sold by vendors throughout downtown. More than a drink, it’s a satisfying, healthy snack.

The church of the mission of San Jose del Cabo is simple, both inside and out, but one of its charms is a special area where locals tie ribbons with petitions for divine intervention or expressions of thanks written on them. If you’d like to join in on the tradition and express your thanks, choose a white ribbon and write about what you’re grateful for on it. Then, tie it to the rack near St. Charbel Mahklouf, the somewhat obscure Lebanese saint who is believed to work miracles.

A local favorite, Bar La Ranita (Little Frog) is attached to the Hotel Rana Cansada (Tired Frog) and has been around since 1984. The ambiance is laid back, but the prices are affordable and the margaritas pack a powerful punch.

One of the oldest restaurants in Park City, the “Double E,” as locals call it, opened in 1972. When I first lived in town in the mid-1980s, they’d have $1.95 breakfast specials of eggs and bacon. Can’t beat that. They serve breakfast, lunch, and dinner, but the stick-to-the-ribs breakfasts are what they’re really famous for. Try the signature Miner’s Dawn, seasoned potatoes with melted cheddar cheese, topped with basted eggs and served in a skillet with wheat toast.

Italy’s beloved region of Tuscany brings to mind bucolic vineyards, rolling hills, and roads lined with towering cypress trees. But there’s plenty else to delight and even surprise travelers. Consider the quaint town of Punta Ala: located along the southern Tuscan coast, it’s under the radar of most travelers, yet the go-to summer escape of generations of Romans and Florentines.

Punta Ala strikes a balance between relaxation and understated elegance that encourages lingering, and the same goes for its premier place to stay: Baglioni Hotel Cala del Porto. Set against the backdrop of the Mediterranean Sea and with two adjacent beach clubs (La Vela and Alleluja), the hotel’s 38 airy rooms offer views of the gardens and marina. In the heart of Maremma, Hotel Cala del Porto is perfectly located for day boating trips out to the island of Elba, wine tasting at notable Tuscan wineries, and some of the best golfing in Italy. The regional park Bandite di Scarlino beckons with hiking trails ideal for early morning risers.

One of Playa’s newest hotels, Cacao is being touted as a “kicked-back, relaxed ‘hippie chic’ boutique, 60-room hotel. Conveniently situated on Playa del Carmen’s 5th Ave. in the heart of the destination’s fashionable restaurant, club and boutique scene it is also walking distance to the beach. Spacious, modern rooms and suites provide comfortable amenities, including bathroom toiletries by Italian fashion designer Missoni and distinctive touches by architect Rodrigo de la Peña. Dramatic architectural elements such as huge canvas accents in geometric shapes and a central court with a hyacinth lily pond combine with clean interior design and contemporary, bold color accents. The roof-top bar boasts innovative “coctelería” (mixology) experiences, along with spectacular views of the Caribbean and Cozumel Island as a scenic backdrop. Onsite Nibs Restaurant dishes up gourmet food in a serene setting, while a rooftop pool provides a refreshing escape

This Cuzco corner presents a notable juxtaposition between ancient Incan and Spanish colonial architecture. Since the Incas worshipped their sun god, Inti, above all others, this temple in their imperial capital was the most important of the entire realm. It was here that they brought the idols of all peoples they assimilated, to offer them representation as they demanded allegiance in Cuzco. When the Spanish arrived, they tore down much of the temple and built a monastery on top of it. However, the walls that do remain provide stunning examples of pre-Hispanic engineering, particularly the rounded outer wall that can be seen from Avenida del Sol.

At this luxury collection of six historic homes—some from the 16th century—guests can book a bedroom or an entire house, all within blocks of Santo Domingo’s most important attractions. You won’t find out which room or home you’ll be staying in until your arrival, but you’re sure to be pleased. Located in the heart of the Zona Colonial, the casas are exquisite. Two were part of former convents, one was a monastery, and another was once the private home of a famous Dominican fashion designer. Each one features unique decor and its own courtyard, and five of the six have private swimming pools. Upon check-in, you’ll receive a loaner iPhone to communicate with your house butler and the round-the-clock concierge team, who can help arrange excursions like culinary tours in the Old City and visits to one of the Caribbean’s largest organic cocoa producers.

Behind one of the most popular surf spots in Rincon is a breathtaking view of the northwest coast of PR. Domes Beach during fall/winter will be packed with surfers, but if you want to enjoy the location without being slapped by boards or crowds, then take the short dirt walk behind the “dome” (old nuclear center) and hike along the raised seawall for a gorgeous and unobstructed view of the rugged, lush, tropical cliffside and the waters below. You can take this trail all the way to Pools Beach (in Puntas, the upper part of Rincon) and watch more surfers pick off waves in another great surf spot. This photo was shot with my iPhone 4S, and edited as HDR.

The historic and modern center of the city, the Piazza del Duomo (the square surrounding the cathedral’s base) remains a popular meeting place, hangout and hub of Milanese life. Local vendors setup shop (selling fresh coconut in the summer, toys and tourist wares), kids run and play (free from traffic) and shoppers trickle in from the walking street surrounding the huge plaza. The statue of Victor Emmanuel II, the first king of Italy, is the best place to meet, sit, recharge and watch the city go by.

A Starwood Luxury Collection hotel in the heart of historic Cuzco, Palacio del Inka occupies a former palace, built by the Incans as part of the Coricancha (the centerpiece of their empire). Since ancient times, it’s had many lives—it was seized by the Spaniards in the 16th century, served as a museum in the 1800s, and finally became a hotel in the 1970s. Today, the property features artwork and artifacts from both the Incan and colonial eras, which guests can tour each day at 5 p.m.

Situated around a large central courtyard, the 203 rooms are decorated in a colonial motif, with carved-wood furnishings, jewel tones, and gold accents. Also on-site is a small but very nice spa with a hydrotherapy pool, dry sauna, Turkish bath, whirlpool tub, and showers with lighting effects, as well as a small gym with cardio machines and weights. While Palacio del Inka is just a few minutes to Plaza de Armas and its many eateries, guests would be remiss to not dine at least once at the hotel’s Inti Raymi Restaurant, which serves Andean and international dishes made with locally sourced ingredients. Before dinner, grab a drink at the Rumi Bar, which offers excellent cocktails and a free pisco tasting each night at 6 p.m.

At Boschendal, guests can slow down and savor “Le Pique Nique,” a pre-packed picnic basket that you can order in advance of your visit to the vineyard. When you arrive, collect your wicker basket filled with sweet and savory treats, pick up a bottle of wine to pair with your snacks, and find a spot under the pine trees to sit for the afternoon, relaxing and enjoying the sunshine.

Boschendal is right on the edge of Stellenbosch, about an hour’s drive from Cape Town through the beautiful hills and valleys of the winelands. The owners transformed several farm laborers’ cottages into luxury accommodations, should you wish to spend the night after a day of vineyard tours, winetastings, and dining at the estate’s several restaurants.