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In the warm months, the Rosemont Park District’s Barry Recreational Center offers a fun, inexpensive way to keep kids cool—by splashing around in a safe play area with lots of fountains. At $5 a head for non-residents, it’s as cheap and easy a thrill as you can imagine (especially if you’re five years old).

The Alley on Bitters is a great place to wander. It occupies the land where a 19th century dairy farm once stood, and there’s still a great deal of character and old school charm. Meander past arts & crafts shops, antique dealers, and boutiques, and maybe even stay for a meal at Meadow Neighborhood Eatery + Bar, which serves seasonal Texas and Southern dishes.

The churros here supposedly get their crispy exterior from being cooked over an ax-cut beech-wood fire. You can sample the results when the 140-year-old shop is open: only two Saturdays in June, every day during the San Fermín festival in July, and Sundays in October. 34/948-227-627. This appeared in the May/June 2012 issue.

The beef is local and grass-fed, the french fries and french toast are good, the people are nice, and it’s got views of a little bay. We ate one meal here, then another, and another. Sometimes when you find a good thing, you stick with it. Especially when you’re traveling with a 5-year-old.

Old Québec can be a little hard on the wallets of budget travelers. It’s not that the restaurants are overpriced, but they definitely cater to the tourists who fill its streets most days, especially in the warmer months, and who are happy to pay a little extra for the location and the opportunity to enjoy a long meal savoring some Québecois dishes. Le Chic Shack is a good option, however, if you are looking for a quick meal that’s a good value. The restaurant’s gourmet burgers include beef, bison, chicken, and veggie ones, all served on brioche rolls. There are also three different choices of poutine—classic cheese, braised beef, and wild mushroom. Try the restaurant’s rendition of a milkshake, or lait frappé, spiked with Baileys, Kahlua, or whiskey if you are in the mood for something stronger.

La Pignasecca is renowned for its abundance of cheese, pastry, and fresh fish stalls. As you shop, don’t miss snacking on the biscuits (tarrale) from Panificio Vincenzo Coppola. Open daily, Via Pignasecca.

One of the oldest buildings on the Royal Mile, Gladstone’s Land stands as a tribute to tenement life in Edinburgh’s Old Town. It was once owned by merchant Thomas Gladstone, who extended and remodeled it to include opulently decorated apartments, attracting wealthy tenants like Lord Crichton and the minister of St Giles’ Cathedral. By the mid-1800s, however, only the city’s poorest residents remained in the Old Town, and the building fell into disrepair. It was rescued from demolition in 1934 by the National Trust for Scotland and today serves as a tourist attraction where visitors can learn about the fascinating—and sometimes scandalous—lives of the people who lived on property. Guests can also view rare, hand-painted Renaissance interiors dating from the 1620s; seek shelter under Edinburgh’s only surviving 17th-century arched store frontage (designed to protect shoppers from the weather); and admire the gilded bird of prey that hangs outside the house.

As the name suggests, this hotel’s personality is one part laid-back Californian, one part British aristocrat. Nowhere is that clearer than at the 10th-floor rooftop pool, where plantings inspired by formal English gardens stand out against a backdrop of palm trees and sunny views of the Hollywood Hills. Downstairs, the London Bar channels both influences, too, with an orangeries-style latticework frieze inspired by English conservatories along with a living wall of exotic plants and a menu that ranges from classic (Moscow Mules, Pimm’s Cups) to creative (the Winston Churchill made with Bulldog gin and Laphroig scotch is a favorite).

Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).

One of the best strolls through Venice begins in the neighborhood of Arsenale and finishes on the Island of Sant’Elena. Walk along the main drag of Via Giuseppe Garibaldi, a street full of shops and colourful local life until it dead ends. Make a right on to Viale Giuseppe Garibaldi where a monument to the streets namesake stands. From here the streets become very quiet. Follow Viale Giuseppe Garibaldi to the end and turn left onto the Fondamenta San Giuseppe. This is a mostly residential area where you see laundry hanging from pastel painted houses and hear small fishing boats tapping against the sides of the canal. Make the first right off the Fondamenta and get lost in the twist of back streets here until you come upon the Via XXIV Maggio. From here, look for signs pointing to the Church of Sant’Elena, a beautiful 12th-century monastery on the island.

Santorini, Greece is an unquestionably beautiful island, but you can take the island experience up a notch, from beautiful to breathtaking, by hiking the ancient footpath from Thira to Oia. Start just before sunrise and meander the ancient dirt and cobblestone path, which is perfectly nestled at the cliffs edge, providing breathtaking views of the caldera. I set out on this path alone for a 4 hour hike, not too sure of what I would find along the way. Way up high, above the sea, away from the island crowds, as if walking through the clouds, I experienced the true beauty of the island- obvious natural beauty that surrounds you in every direction, but an ancient, deeply rooted beauty that can only be found in the silence, in the white washed churches scattered along the path, in the sun-smoothed cobblestone of the path ... in the clouds. Don’t forget layered clothes as once the sun rises the temperature does as well, comfortable walking shoes, bottled water & a camera!

One of the newer boutique inns to emerge in the Catskills, this 11-room property is a gorgeous mix of old-fashioned elegance and urban styling. Guests can expect classic features such as stone fireplaces and sheepskin rugs along with a glorious hodgepodge of vintage sofas, Moroccan tiling, and framed butterflies. Rooms feature white walls and matching linens, with pops of color in the form of grass-green rugs, tufted velvet chairs, bright wallpaper, and serene, forest-inspired art prints. Just be aware that about half the rooms—specifically, those on the third floor of the old house—share common bathrooms. There’s also a cottage with three bedrooms and its own kitchen, where guests can bring their pets provided they let the owners know ahead of time. Don’t miss the Sunday brunch served in the intimate Bar Room—one of the inn’s owners is a chef by profession, and his culinary artistry gets consistently rave reviews.

There’s a touch of Old World glamour to the Cape Royale—the imposing facade, the dramatic lobby, the bellmen in top hats—but just when you start to wonder if the whole experience is going to be resolutely old-school, you’ll find yourself pleasantly surprised by the sleek rooms. They feature contemporary furniture, granite and porcelain bathrooms, and a soothing palette of mostly grays and whites with the occasional punch of lime green or aqua blue. It’s also the site of six restaurants, cafes, and bars, each with its own theme, from Italian cuisine to healthy eating to Thai or Middle Eastern fare.

The city’s best beaches and nightlife—not to mention Green Point’s dazzling Cape Town Stadium, erected for the 2010 World Cup and now the site of many a mega-concert and local soccer match—are minutes away.

Lake Geneva is one of the gems of the Cloud Peak Wilderness. The picturesque lake, nestled in between great rocky mountains and old pine forest, is roughly 3.5-miles from the Coffeen Park trailhead, which makes it a breeze to access for hikers of even moderate experience. The trail to Geneva skirts Edelman Creek and runs past beautiful Duncan Lake, a host of old mine camps, and finally runs through the Big Goose Creek at a crossing that is at once thrilling and quite safe.

Geneva is one of my favorite destinations in the Cloud Peak Wilderness because it serves so many purposes - I love to overnight near the shore when taking off on long backpacking adventures, I get a kick out of running the trail to the lake when I’m feeling spry, and I’ve found few places this picturesque during all my time in the mountains. The view from Geneva Pass (pictured here) is simply unparalleled.

The Adriatic Luxury Hotels group offers a number of lodging options in the city. The landmark Excelsior is a short walk from Old Town and faces the Adriatic. A recent renovation updated the 158 large guest rooms with natural tones and dark-wood furnishings.—David Farley

This appeared in the March/April 2018 issue.