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Like nearly every Latin American city, Santiago has at its heart a civic square open to the public and brimming with life (and these squares are often named Plaza de Armas). Santiago’s Plaza de Armas is distinguished by two fine buildings, the Central Post Office and the Metropolitan Cathedral. Both buildings were constructed in the 18th century, although the cathedral was much altered in later years. The square is full of lively activity—an excellent spot for people-watching and getting to know this city’s energy.

Manifiesto Café is known for its wide-ranging menu of coffees and careful brewing methods. Order a cup with beans grown in Mexico, Colombia, Costa Rica, El Salvador, or a handful of varieties from Europe. No matter which coffee you choose, it will be freshly-roasted. Manifiesto doesn’t serve coffee that was roasted more than 48 hours earlier. But that’s not the owners’ only rules for the coffee they serve. They also prefer beans harvested at plantations that are about 4200 feet above sea level. If you’re looking for a quick cup of coffee, go elsewhere. Manifiesto takes its coffee very seriously and uses a variety extraction methods. The payoff? Quite easily the best cup of coffee you’ve had in a good long time.

Cañón de la Zorra (Fox Canyon) and its 40-foot waterfall are just north of Santiago, a sleepy yet charming colonial-style town 35 miles north of San José del Cabo, across the Tropic of Cancer. The hike to the waterfall takes you through oases with endemic plants and gives you glimpses into a Baja outback that existed before the region became a popular tourism destination. There’s a great area for swimming as you admire the waterfall and multicolored granite cliffs. Tip: On your trip back to Los Cabos, stop by the Agua Caliente, Santa Rita, and El Chorro hot springs about five miles south of Santiago.

Situated in a candy-colored colonial-style building, the Diplomat Boutique Hotel feels like a cool friend’s house. With just four guest rooms, the property has an intimate vibe and personal service, beginning with welcome drinks and botanas (Mexican snacks) served on arrival by the inviting Canadian owners. Each of the crisp, contemporary accommodations is embellished with hints of history, from the wrought-iron beds to knick-knacks like antique typewriters, yet talavera-tiled bathrooms feature modern touches like walk-in rainfall showers and organic toiletries infused with local honey. It’s easy to lose track of time while swinging in a hammock, cooling off in the pool, or sampling different varieties of tequila and mezcal from the free poolside bar. Just pace yourself. You don’t want to miss the complimentary morning spread, loaded with fresh fruit from the market, homemade breads, and delicious dishes like breakfast tacos, French toast with caramel sauce and passionfruit jam, or quinoa-crusted quiche.

Tucked in a condo complex just north of the bridge, Coco Loco’s is a cozy little pool and beach bar. On hot days, take advantage of the swim-up bar stools or hang out on the picnic tables closer to the beach. What Coco Loco’s lacks in size, it definitely makes up for in personality. Owners Sue and Steve have done a wonderful job with fostering a community spirit, especially with many of the expats on the island. Look for a number of weekly activities like trivia and cribbage that keep the bar hoppin’ pretty much every day. Open daily noon to 10 p.m.

Head south of town to the tiny beach bar at Mata Rocks Resort. Squirrel’s Nest is a peaceful spot to enjoy a few cocktails while taking in views of Belize’s well-renowned Barrier Reef. For years, I called Mata Rocks my hotel of choice when I visited Belize as a tourist. I spent the bulk of my days lounging by the pool and chatting with the bartenders at Squirrel’s Nest. Longtime bartenders Sherilyn and Criselda are two of the nicest people on the island and serve up some pretty awesome drinks. Try Mata Rock’s specialties like the Mata Colada or Pink Squirrel. Open daily, closing hours vary but usually around 8-8:30pm.

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.

Many Central American countries have coasts dotted with mangroves, a brackish ecosystem that is a sheltering habitat to numerous flora and fauna. Visitors can kayak through many of the mangrove systems, getting an eye-level view of the mangroves’ spreading root systems and being on the look-out for everything from crabs to crocodiles. Barra de Jiquilisco and Barra de Santiago are two of the navigable mangroves, and visitors who want to explore them can hire an outfitter or guide for a day trip.

No visit to Ambergris Caye is complete without an afternoon at the Palapa Bar. Situated at the end of a dock surrounded by turquoise waters and cool breezes, Palapa Bar attracts a mix of locals, travelers, and some of the coolest bartenders on the island. On a warm day, eschew the barstools and opt instead to float in inner tubes beside the dock; you can even have cold buckets of Belize’s Belikin beers lowered down to you. In addition to beer and standard cocktails, fun creations like Scotty’s Palapa Punch (three different types of rum, triple sec, mango, pineapple, and a squeeze of lime) offer some island-inspired refreshment. Up in the palapa, recommended items from the menu include sausage dip, pulled pork sandwiches, and the immense half-pound burger. Palapa Bar is 1.5 miles north of town and easily reached by golf cart, taxi, bicycle, or water taxi, which drops you right off at the dock.

If there were ever a hotel with history, it’s the Singular Patagonia. Opened as a hotel in November 2011, the original building once served as a post-Victorian cold-storage factory built by the British in 1915 for the purpose of processing sheep’s wool and meat to be shipped back to England. Overlooking the waters of Last Hope Sound, the long, red-brick building is located just outside the town of Puerto Natales. After operating for almost 70 years as a factory, it was declared a national historic landmark before being transformed into a luxury hotel.

History is by no means forgotten. The hallways are still stocked with brightly colored machinery—from steam condensers to boilers and forges—all stamped with the name of the British city in which they were built: Derby, Birmingham, London, or Glasgow. Designed by Chilean interior designer Enrique Concha and local architect Pedro Kovacic, the 57 bedrooms stretch along a new wing that was added to the original buildings, and these rooms are furnished with Victorian-inspired furniture.

From the first time I set foot on the island of Ambergris Caye, Caramba became my favorite restaurant in San Pedro. And that’s not changed, even ten years later. Rene Reyes, Sr. and his wife Patty have done a remarkable job with the restaurant. Every season brings something new and exciting – whether it be décor changes, menu enhancements or even new cocktail creations. The Reyes’ sons Jonathan and Renesito are now involved in day-to-day operations, keeping Caramba one of the long-standing family-owned and operated businesses on the island. Personal recommendations include Conch Fritters (seasonal), Sopa de Lima, Fish Tacos, Pibil Pork Sub and the Coconut Shrimp. Any of the seafood dishes are spectacular – go for the Maya or Tour Guide cooking options. Be sure to try one of bartender Charlie’s cocktails, like the Strawberry Beerita, King Margarita, or a special mojito. Not a drinker? Caramba has some of the best fruit smoothies on the island. Closed Wednesdays. Check Foursquare for current specials.

South of San Pedro is the award-winning luxury resort of Victoria House. The plantation style property is unlike any other on Ambergris Caye, offering some of the best views of the Caribbean Sea. Despite being one of the larger properties with 42 rooms spread out over 10 acres, Victoria House is one of the most intimate resorts. A majority of the staff at Victoria House have been there for years and it shows. Their love for Victoria House and its guests is genuine and evident throughout every part of the resort. Look for several dining options on property, including the more casual Admiral Nelson Bar, perfect for daytime dining, and the more high-end Palmilla, an ideal spot for a romantic dinner. Meal plans are available for guests looking for a more all-inclusive experience. Victoria House offers a range of room styles, from staterooms and plantation rooms to private suites and villas. Rates start at $195 for staterooms all the way up to $1,775 for a five-bedroom villa.

This understated beach bar is one of Ambergris Caye’s best-kept secrets that is quickly getting out. Owned by “Wayo from Cayo”, Wayo’s has become my regular hang out spot over the past two years. Wayo and his wife Dee can be found at the bar every day, often sharing a drink with many of the regulars. They’ve developed longstanding relationships with countless locals and a number of tourists, many of whom come back every few months to see Wayo and the crew. The main bartenders, Ruby and Archie, will not only serve up some great drinks, they are a wealth of information on what to do and see in San Pedro. You’d be hard put to find a more chill spot to relax right on the beach. Be sure to try a local specialty — the Michelada. Made with beer and a mix of spices, this is Belize’s version of the Bloody Mary and the best cure for a hangover! Open daily, 10am to midnight.

Housed in what was once a church rectory, this eatery is named for the iconic enclosed amusement park right next door. The theme of the shabby-chic decor is functional recycling but with creative, amusing twists: School desks, century-old park benches, an assortment of mismatched chairs, a gigantic chandelier made from beer bottles, and a staircase fashioned of crutches are just some of the ways familiar objects have been given a second life here. Meet your cholesterol quota for the month with the amazing shared appetizer pan de campo, a large round loaf of bread hollowed out and filled with melted cheese.

For more than two decades, Chef Volker Romeike’s standout restaurant has charmed patrons at the Sheraton Grand Los Cabos Hacienda del Mar with its Pacific Rim concept, ocean views, and dramatic design. Pitahayas—both space and the menu—got an updated look in 2015. A newer focus on blending Mexican and Asian flavors has allowed Romeike to show off his culinary creativity. Duck lumpia (like a spring roll) is served with a papaya salsa; a taro tostada comes topped with carnitas (braised pork); and tuna poke comes with watermelon and chili powder. For special occasions, consider the Cava de Santiago wine cellar, which houses some 400 vintages. The restaurant’s bar also offers Social Fridays, when limitless drinks can be had for a not unreasonable tariff.