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There is a reason why renting a villa in Tuscany is so popular - rustic farmhouses, rolling hills filled with olive and plum trees, golden sunsets, locally-harvested wine, creamy cheeses, and cool evenings spent with friends and family. Renting a villa provides a relaxing base for your sightseeing in the region. Almost all Tuscan towns allow easy day trips to the main sights: - Florence‘s art and Renaissance history (Duomo, Uffizi Gallery, Michelangelo’s David) - Cortona’s steep, narrow streets and medieval walls - Siena’s cultural city center, now a UNESCO World Heritage Site - San Gimignano’s fortified towers set amidst picture-perfect Tuscan hillsides - Montelpulciano’s world-famous wineries and more This offers the best of both worlds - after a dusty day of sightseeing, you can relax at your villa with a jump in the pool and a glass of wine. Watch the sun go down in a purplish haze, unwind with friends, and enjoy the lovely moment. I recommend YourTuscany.com, which is where we found Villa Coloniale (above) in the town of Pergine Valdarno. The infinity pool and covered patio are guaranteed to put you in a relaxed, Italian frame of mind!

Go Bar occupies an old colonial house on a leafy Mendoza street (formerly Winery & Company). Its old, worn wooden floors speckled with sunlight have just the right vintage feel for wine browsing. It’s several rooms are stacked with wrought iron shelves featuring the region’s numerous wine labels. The staff is friendly and knowledgeable and will give you the perfect packaging to carry wines in your suitcase back home. Chile 898 (corner of Montevideo)

Once upon a time, Europe (mostly Switzerland, France, Belgium, and the UK) dominated the chocolate market and through aggressive marketing and downright colonialist extraction methods, became erroneously known for being the world’s experts on cacao, yet cacao came from South and Central America and didn’t grow anywhere near Europe. Recent years have seen the best chocolate rightfully return to the source where it originated—Peru, Ecuador, Colombia, and Venezuela, where a boom of quality chocolate has replaced reimported European milk chocolate sold to those cacao producing countries for generations. But Switzerland is back in the game with this excellent new chocolate shop by local food expert Dieter Meier and his patented cold pressed extraction method that brings out the botanicals and nuances of these sourced cacaos in ways other chocolate manufactures cannot. The results are Cuban, Bolivian, and Guatemalan single bean bars ranging from white to 80% dark that are unlike anything else on the market. The tiny shop overlooking the Limmat River opened in December 2017 and is not cheap, but worth every rappen for its exquisite expression of flavors.

A Carib chief and national hero, Joseph Chatoyer led revolts against British colonists in 1772 and again in 1795. During the latter revolt, his soldiers and their French allies were planning to attack Kingstown from Dorsetshire Hill, but British soldiers marched up from the city and attacked first, killing Chatoyer. Today, he’s memorialized in a monument on that very hill, overlooking the city he fought so hard to regain.

Walking through the narrow streets of Boston‘s North End might have you thinking about a delicious Italian meal. Take the time, however to explore the area on Hanover Street where the surrounding brick buildings suddenly give way to a park where Paul Revere stands guard. Commemorating his ride to warn the colonists of the impending British Invasion, the statue stands in front of a small park leading to the famous Old North Church. The setting is a perfect spot to relive the beginning of the American Revolution, and after exploring, leaves you in a location filled to the brim with restaurants and cafes to recharge before moving on.

Eleanor Tinsley Park in Houston is a great place to spend time outdoors. There’s the Waugh Bridge Bat Colony, hiking and biking trails, and tons of green space to enjoy.

Willemstad’s first colonial settlement started as a hub for Dutch slave traders. Now a World Heritage site, this modern city center has a distinct Euro-Caribbean atmosphere, its preserved colonial buildings housing fashion boutiques, art galleries, and sidewalk cafés. Wander down Punda’s narrow cobblestoned alleys, then snap a signature photo at the Queen Wilhelmina Park’s giant Curaçao and Dushi signs. The neighborhood gets extra lively during the free Punda Vibes event every Thursday from 6 p.m. to 10 p.m., featuring an outdoor market, live music, and local folkloric dancing.

Tucked away on a quiet San Miguel Chapultepec street, but just next door to lively Colonia Condesa, this odd restaurant’s yellow façade leads to a culinary experience that goes way beyond the food served. Under the direction of Norma Listman and Saqib Keval, Masala y Maíz is a space of culinary encounter between Mexico and India; entrees often mix pickled fruits and vegetables in Latin American styles. The makai pakka combines Mexican esquites with a similar dish from Kenya. The partner-chefs connect food and current events as well; they commit to a socially responsible work environment and the restaurant serves as a progressive events forum. Open for breakfast and lunch, plus Saturday-only brunch.

Nestled on beautiful Playa Dorado in Puerto Plata, this elegant hotel features 50 stylish suites, complete with neutral decor, flowering orchids, and private furnished balconies. Some suites can be connected, but for even more space book the penthouse, which includes three bedrooms, a large living room, and a freestanding outdoor tub. In addition to a pristine beach, Casa Colonial boasts a sleek rooftop pool, a restaurant that serves fine French-Caribbean cuisine, and a spa with a treatment gazebo above a tropical pond. When staying here, don’t miss the chance to explore Puerto Plata and its charming main square surrounded by Spanish colonial and Victorian buildings, as well as the more-than-500-year-old remains of Fort San Felipe. Fifteen minutes from the resort, you can also swim in freshwater lagoons in El Choco National Park.

This shop, down a tiny sunny alley off a sidestreet in Colonia Roma (Córdoba 67 interior 7), is like many other Mexico City’s shops that support women’s crafts collective, but it’s slightly different in that it carefully curates its inventory—made using the local traditional crafts of weaving, embroidery, jewelry-making—choosing only those pieces that complement a more modern lifestyle. Yes, that’s a traditional huipil, or pullover tunic, from Guerrero, but while this simple embroidered piece would work for your abuela, it would also look cool at your graphic design gig in LA. The shop has outlets at Hotel Condesa DF and its products are carried by stores in Puebla and Tulum.

Oaxaca is known for its moles. The most famous is mole negro, the black mole—a thick, rich mixture of ground chiles, nuts, chocolate, and other ingredients. But that’s not the only type of mole you’ll find here. Los Pacos specializes in these rich sauces and you can sample seven different kinds to compare and see which you like best. If you find one you really love, they sell mole paste to take home with you, so you can prepare Oaxacan mole yourself. Los Pacos has two locations. The original is on Belisario Dominguez in the Colonia Reforma (north of the city center). This location is more popular among locals, and has an outdoor children’s play area. The other is on Abasolo in the historical center. The centrally located one has a roof terrace, perfect for enjoying warm evenings in Oaxaca.

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.

This 23-room hotel has colonial charm even though the building is relatively new. The word “sotano” means basement in Spanish and the Hotel Casa del Sotano is thus named because the building’s first story is below street level. The lower level has a central patio with water features and lots of plants, so it’s both cheery and tranquil. The colonial furnishings, wrought iron, Mexican tile and artistic touches throughout the property add to its appeal. In the morning you can enjoy a cup of coffee on the terrace while you enjoy the view of the towers of Santo Domingo over the rooftops of Oaxaca city.

A brother-sister expat duo has opened this chic slice of Brooklyn in Colonia Juárez, the neighborhood currently angling to be Mexico City’s hippest. No complaints on that account at Cicatriz, whose open, industrial-styled storefront is a forum for several daily moods. No-compromise coffee and a variety of alternative baked goods form the morning agenda; lunch means a major emphasis on locally sourced greens in great salads and roasted iterations; the meatball and fried-chicken sandwich are both major crowd-pleasers as well. After five, it’s time to get your drink on; the bartenders deliver superior, crafted quaffs, but free from all the fuss you’ll see at other haute mixology spots. The earnest, healthful menu is enhanced by an overall vibe of do-it-yourself chic.

Just across the Ashley River from the Charleston Peninsula, Charles Towne Landing marks the site of the forerunner to Charleston, Charles Towne. Settlers from Barbados founded the town in 1670, though after ten years—and a series of attacks by French, Spanish, Native Americans and pirates—they wisely decided to move to the easier-to-defend Charleston peninsula and start over. A recreation of a 17th-century trip, the Adventure, and replica of a colonial home provide insights into life in the earliest years of colonial America.