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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.

Located at the Westin Puntacana Resort & Club, this open-air restaurant specializes in grilled meats and seafood but also offers several delicious pastas. The executive chef hails from Peru, which explains why the menu includes a traditional ceviche with sweet potato garnish, along with a few other Peruvian dishes. Look forward to everything from grilled rib-eye and salmon to penne with chicken and prosciutto, and be sure to save room for desserts like lemon pie and flan.

The best of several great Atlantic beaches around Punta Rucia, Playa La Ensenada is made up of a fishing village and 4.5-mile stretch of sand with calm, crystal-clear water. Here, you can snorkel around submerged reefs in waist-deep water, or take a 12-minute boat ride through mangroves to a dreamy sandbar (named Cayo Arena but also called Cayo Paraiso, or Paradise Island) to see even more colorful fish. The size and shape of the sandbar change depending on the currents and season, so you’re always in for a bit of a surprise.

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.)

Susana Balbo, Argentina’s first female winemaker, owns the Agrelo winery Dominio del Plata. The restaurant, Osadia de Crear, which translates to “dare to create,” offers a fusion of Argentinian and Mediterranean seasonal cuisine using local ingredients like Mendocenean tomatoes, domestic goat meat, and herbs from the garden. The caprese salad, the roll of suckling goat, and the cheese and sweets dessert are highlights on the menu. The restaurant also has a deli, offering meat and cheese platters, fresh salads, and gourmet sandwiches made with homemade bread. Picnic baskets are available for guests who want to dine alfresco among the vines. Don’t leave without trying the Susana Balbo Signature Cabernet Sauvignon, which is the winemaker’s personal favorite. Cochabamba 7801, Agrelo, Lujan de Cuyo, Mendoza; [email protected]; +54 261 498 9200

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.

El Burrito is a casual little Mexican cantina that serves excellent fajitas, tacos, and burritos, and legendary coconut margaritas that might make it difficult for you to find your way back to your hotel. But hey, you’re on vacation, and deserve to let loose every now and then. El Burrito sits at the heart of the Puntacana Village complex, a short ride from the beach, Playa Blanca, the Westin, the ecological reserve, and more.

Fifteen minutes south of the Puntacana Resort & Club, Eden Roc at Cap Cana is the most exclusive of the six hotels in the gated Cap Cana Reserve. At this Relais & Châteaux property, guests have their choice of beachfront suites with kitchens; stand-alone suites with private pools, gardens, and verandas; and oceanfront villas that come with butler service. Whichever you pick, you’ll also have access to an oceanfront infinity pool, a 30,000-square-foot spa and wellness center, and a private, Blue Flag–certified beach. There’s even a kids’ club in a lagoon-side treehouse for when adults need some alone time.

When hunger strikes, head to La Palapa for seafood and Caribbean fare, or Blue Grill Bar + Restaurant for Nikkei and robatayaki cuisine. Should you want to venture off-property, know that Cap Cana is home to an 18-hole Jack Nicklaus signature golf course. Bespoke helicopter outings, visits to the Punta Espada equestrian ranch, and days at Scape Park (a natural theme park with attractions like zip-lining and cave expeditions) can also be arranged.

In the past few years, Las Terrenas has become a popular bohemian style destination alternative for those you are not into all inclusive resorts in Punta Cana. The European expat community has infused an international flavor into the local hotel, b&b, and dining scene. Las Terrenas is a bit over 2 hours by car from the capital Santo Domingo on the new highway. Caribe Tours bus terminal in Santo Domingo has frequent buses to town of Sanchez, and from there one takes a local mini bus to Las Terrenas. This way it can take up to 4 hours. Pueblo de los Pescadores (Fishermen’s Village) is a small area of charming restaurants and bars close to the beach. Years ago, this cluster of new establishments used to be a fishing village. There are still many fishermen who use the area as a base for daily fishing. At night the area is a great spot to try some of the local Dominican cuisine, and fusion restaurants. For a nice breakfast, stop by French-owned bakery El Pan de Antes (Plaza Kanesh on Calle Carmen ) in the center of town for delicious croissants, quiche, bread, and strong tasty Dominican coffee. A small, cozy, romantic bungalow style hotel to stay at is Casa Robinson, located at Calle E Prud’Homme 2, a few steps away from the ocean. The atmosphere of the hotel is wonderful along with great staff and service. At the end of the day, walk along the beach around sunset time and watch gorgeous colors come alive.

The Municipal House, built in 1912, is a civic hall and concert theater in Prague. This Art Nouveau gem, decorated with allegorical sculptures, gold trim, and stained glass on the exterior, and topped with a glass dome, is a national heritage site. The Royal Court Palace was situated in this location from 1383 to 1485, Czechoslovakia’s independence was proclaimed here in 1918, and the first meetings between the communist government and Vaclav Havel were held here in 1989. The lobby features a sweeping, red-carpeted marble staircase, and the concert hall is decorated in carved stone, gold, shimmering lights, and frescoes. The romantic Francouzska Restaurant opened at the same time as the building did, and is known for its soaring ceilings, glass and gold chandeliers, and early 20th-century atmosphere.

A UNESCO World Heritage site, this hotel was the home of Hispaniola’s first governor, Nicolás de Ovando, and one of the first colonial structures built at the top of cobbled Calle Las Damas (the first paved street in the Americas). Built in 1502 and connected in 1974 during a reconstruction ordered by then President Joaquín Balaguer, the three stone buildings retain their original coffered ceilings, massive arches, tile floors, and brick and stone walls. In addition to 92 rooms and suites, including a dozen Imperial Club rooms overlooking the Ozama River and Don Diego Harbor (Room 4015 has a particularly stunning view and gorgeous bathroom), you’ll find a lovely reading nook, gourmet restaurant, lobby mojito bar, and tranquil garden, which features herbs and fruit trees used by the hotel kitchen.

Like the island nation’s other famous export—rum—cigar crafting is an art form. The best puros are made from aged tobacco and hand-rolled. And this intimate company, owned by a German expat, prides itself of small, quality productions. The shop at the factory is the best bet for freshness. A tour offers a sample. By request, tours take visitors through the 40 steps of cigar making. They include tobacco selection, as well as rolling and pressing. The shop at the factory is the best bet for superfresh cigars.

Unlike most people who arrive at the property fresh off a plane and short cab ride, I showed up after spending an hour searching for waterfalls on horseback in the Samana wilderness. Basically, I was tired, smelly, dirty… And by no definition sublime. The moment I walked into the shady, chic reception area, everything changed. I was immediately relieved of my bulky, mud-splattered belongings by practiced staff and my newly emptied hands were then wrapped around a fresh coconut. At first, you might think the stylish surroundings would clash with such local, earthen niceties, but you’d be wrong. Sublime makes an art out of weaving local and luxury together in almost every aspect of their experience. In the three-story main building, 50 one- and two-bedroom Suites (16 for guests, the rest privately owned) form an arc around the property’s centerpiece: a sheltered and soothing pool area that’s a mix of interconnecting canals, larger pools for swimming, beds wrapped in billowing fabrics, grassy expanses and simple walking paths. This place is truly Sublime!

Antonio de Montesinos held it down in the New World and defended the rights of the indegenous people. He was truly ahead of his time. This statue located in Santo Domingo’s colonial section is dear to my heart. I used to go play and ride my bike there all the time. The stone and bronze statue was a gift from Mexico and was made by artist Antonio Castellanos in 1982, a year before my birth. Below is Montecino’s famous quote, which as you could imagine enraged the Spanish King and all of the aristocracy at the time. #Legendary. “Tell me by what right of justice do you hold these Indians in such a cruel and horrible servitude? On what authority have you waged such detestable wars against these people who dealt quietly and peacefully on their own lands? Wars in which you have destroyed such an infinite number of them by homicides and slaughters never heard of before. Why do you keep them so oppressed and exhausted, without giving them enough to eat or curing them of the sicknesses they incur from the excessive labor you give them, and they die, or rather you kill them, in order to extract and acquire gold every day.”

This is a great place to spend a free day in Puerto Rico. There are many interpretative trails in this park, and all are free and open to the public. Some lead to caves, others lead to beautiful views.

There are also many covered areas for picnics. The trails are mostly leveled off and easy hikes, although some can be a bit more challenging. Be sure to bring lots of water, as it can be humid. Also, bug spray will be your friend! If you plan to take a trail that leads to a cave, be sure to have a flashlight with you as well.