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Chris Colin experiences a Caribbean paradise from both sides of a resort’s walls.

Witnessing ceremonies of love take place around the world can reveal some pretty profound life lessons.

Spectacular hilltop villages are a dime a dozen on the Greek islands, but Astypalea, a distant speck in the Dodecanese, has the quintessential sugar-cube capital cascading over a rocky outcrop to a sheltered harbor. The oldest houses are huddled along the cliffs circling the Venetian Querini Castle. Castro Bar is built right into the 15th-century castle walls (which look even more dramatic when illuminated by moonlight). A series of small terraces on different levels, painted in white, burgundy, and blue, all offer stupendous views across the island and what feels like the whole Aegean. The vibe is mellow, and the drinks are strong. Stay until the sun rises out of the sea, a trippy experience you won’t forget.

An overview of traveling to San Francisco, California.

Overview

Mission Dolores Park, aka “Dolo”, is one of the most popular parks in San Francisco, especially when the sun is out, since this neighborhood is known for being one of the sunniest in the city.

On a sunny weekend, you’ll be hard pressed to find a patch of green to plant yourself on, but that’s what makes Dolores Park so much fun. Yes there is a playground for kids, and basketball and tennis courts, too. But the real sport here is people watching.

You’ll hear music booming between dog barks; people toss footballs, tightrope walk, and fling their Frisbees. Bodies slathered in oil glisten in the sun; ice cream melts down the arms of laughing children; the whiff of cut grass (and other questionable varieties) linger in the air. Vendors will also come around to sell a variety of snacks and drinks, and you’ll also encounter people collecting your cans after they’re empty.

The abundant restaurants and markets in the area (Bi-Rite and Tartine are two popular ones on 18th street, just a block from the downhill portion of the park) make make it easy to pack a picnic and fuel your day out. All you need to do is bring a blanket, plop down on a hill where the views reach to downtown, and chill out San Francisco-style.

Dolores Park is named for Miguel Hidalgo, a priest in Dolores, Mexico who urged his countrymen to overthrow their Spanish rulers in 1810, sparking Mexico’s battle for independence. A statue in his tribute stands in the center of the park.

This museum was once the home and studio of famed Ecuadorian painter Oswaldo Guayasamín, who happened to be a supporter of the Cuban Revolution and painted Fidel Castro on several occasions. Exhibitions in the patio-like first floor feature international artists of diverse backgrounds, while the permanent exhibitions upstairs give you a view of the artist’s work and living quarters.

In response to the popularity of a large chain of coffee shops in Mexico selling “Italian” coffee, this family of coffee producers set up a little shop near Santo Domingo church and called it The Oaxacan Coffee Company. Here they proudly serve organic coffee that is exclusively from the area of San Miguel Talea de Castro, Oaxaca. It’s a small cafe with wooden benches and stools, and they serve the coffee in handmade pottery cups. The owner is friendly, the coffee is strong, and they also serve fresh pastries. You can get some coffee beans to go, as well as Oaxacan chocolate. If you like chocolate-covered coffee beans, stock up here!

On the non-descript, busy corner of Bucareli and Morelos streets in Mexico City is a café with a famous history: Fidel Castro and Che Guevarra met here at Café La Habana several times, chain smoking and drinking strong coffee, to plan the Cuban Revolution. Nowadays, you can still get excellent coffee—and pretty good food—while you plan something a little less dramatic (but more enjoyable), like your vacation itinerary. Old journalists and businessmen congregate here for hours on end while salt-of-the-earth, slightly surly waitresses take your order and bring you your food and drink. Come for breakfast and order their chilaquiles, motuleños, or molletes, and wash it down with an espresso or café americano.

The first luxury lodge to come to Chile’s second biggest island, Tierra Chiloé opened in 2012 and became a member of the Tierra hotel group in 2014. Designed by Chilean architect Patricio Browne, the hotel looks like a boat on stilts and was inspired by the homes of local fishermen, which take the same form and are known as palafitos. The exterior is made from picturesque larch wood shingles—a building technique that’s very typical on Chiloé and is seen on the famous UNESCO World Heritage churches that dot the islands.

Inside, guests find more wood. The hotel’s wood walls and ceilings are made from indigenous species . The decorations are locally inspired with plenty of handicrafts such as wicker baskets, handwoven rugs, and wooden carvings. The focal point is the meadow and Reloncaví Sound below, where the hotel’s boat is harbored. Large windows line the building on both floors and provide excellent views. Guests can relax in a small spa, a winetasting room, or a book-filled upstairs studio upstairs. The living room with fireplace makes a perfect spot for an end-of-day pisco sour.

Embrace the diverse community of Toronto and support LGBTQ+-owned businesses during a memorable three-day trip.