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Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

A black, awe-inspiring lava landscape is the welcome mat to our trek into Oregon’s iconic volcano reserve. The Three Sisters: Faith/North, Hope/Middle, and Charity/South are ringed by a trail network that includes a stretch on the infamous Pacific Crest Trail (PCT). The wilderness circumnavigation of these dramatic, dormant peaks challenges hikers to keep their eyes on the trail at every bend. The big diversion on our journey is the climb to the saddle between Middle and South sisters. The area holds a short necklace of glacial lakes and challenging access through snow and ice. Great accommodations when you need to chill that cocktail at 7,500 feet. Trails up to the saddle are well defined but not maintained or officially marked, making getting lost or disoriented par for the course. The weather in August quickly goes from blazing in the lava beds to long sleeves at altitude. One night I had every bit of clothing on inside my sleeping bag to stay warm. Lower elevations produce brilliant meadows of lupine and paintbrush this time of year. Water sources are limited, but two “springs” provide gourmet liquid bubbling out of volcanic rock. This is a moderately strenuous 48-mile walk without the difficult detour to the saddle. The east-side Green Lakes trail has a restricted burn area and is less populated, while the west side PCT portion tends to be busy. Don’t let the 5,000-foot elevation gain/loss scare you off. Every step is like walking through geologic time.

This silk mill turned cultural center on Lake Zurich’s left bank hosts over a hundred concerts, parties and festivals a year and is home to 60 art studios. It’s also a popular bar, especially come summer, when locals flock to the communal outdoor tables steps from the water’s edge (a favorite place to sit is in one of the handful of old-school ski lifts for prime views of the Alps). The setting is colorful and edgy—graffiti everywhere, plants shooting out from clawfoot bathtubs—a rarity so far from Kreis 4 and 5. Photo © Christian Beutler/Zürich Tourismus.

The province of Quebec is notorious for its quaint, picturesque villages. The compact forests and the thousands of lakes in the Laurentides region certainly make for the picture-perfect Canadian postcard, including the beautiful lakeside chapel in Saint-Alphonse or the wholesome locals of Old-Town Saint-Sauveur. On the other hand, the rolling hills of the Eastern Townships are as bucolic as it gets: villages like Hudson, with its gourmet market, microbrewery and century-old houses have a slight England feel, as does nearby Sutton. However, the ultimate wintery escape from Montreal surely is Quebec City, with the snow-capped Château Frontenac, 400+ year old historic center and festive winter Carnival every February.

Move over cupcakes: Popsicles are the next big dessert craze in Orlando. After my stroll around Lake Eola, I stopped at the popsicle shop Hyppo. You won’t find the popsicles of your childhood here. Hyppo’s version is inspired by Mexican paletas (ice pops) and comes in two varieties: milk-based and ice-based. When you walk in, you’re greeted by a colorful cooler of pops with seasonal flavors that might include pistachio-coconut, the Elvis (peanut butter, banana, and honey), cantaloupe-black pepper, strawberry-basil, key lime, and even some bourbon-based options.

The vibe in Waikiki is the most frenetic of all the spots in the islands, but there is an escape. The scene at the current iteration of the classic Hawaiian hangout, Duke’s, is a step back even by Oahu standards. Best approached via the beach to enhance the original feel and avoid the mall-like carnival from the street entrance, this is the kind of bar that welcomes sand on your flips. Slip in for happy hour and be prepared to jockey for a spot. Even with the crowd, the music, the food, the drinks are all designed draw you back to a simpler time when Duke was still riding the longboard. I’m partial to the beers and french fries, but will never refuse a fish taco. With a long relationship with the Kona Brewing brand, I opt for the Longboard larger or Fire Rock Pale ale. The umbrella drinks don’t disappoint, but neither do the gin and tonics. The local musical talent that ply the stage at Duke’s are traditional Hawaiian in style and like to keep the island theme front and center. There is a family vibe to the musical community, much like the rest of Hawaiian culture, and it’s not unusual to get a sibling or cousin to come up on stage and do some traditional Hawaiian dance or help out on a song or two. There was an 8 year old girl that got asked to come up on one of our visits and she blew the crowd away! The strip a Waikiki can be a bit daunting in terms of relaxation, but Duke’s remains my refuge from the madness. Aloha.

Nuzzled up against the Arizona border about 100 miles west of Four Corners are some 30 square miles of the most iconic scenery in the American West. Monument Valley is one of those places that you’ll recognize as soon as you see it, even if you’ve never been there before, as dozens of movies, TV shows, and even video games have used the area as a setting. It’s made up of mesas both small and large reaching up from the valley floor, some rising as high as 1,000 feet into the sky. Part of the Navajo Reservation, the area charges a $20-per-vehicle entrance fee to drive the dirt-road loop. Once in, however, you can also enjoy a number of hikes, or hire a guide for a horseback tour.

Continental’s downstairs bar—with a marble countertop and chilies, garlic, and aged ham hanging overhead—transports diners to Spain or Portugal. Despite the old-world ambience, however, the menu and staff are young and playful. Pop in for a meatball sub and vermouth at lunch, or enjoy king-crab-stuffed zucchini flowers before moving on to slow-roasted lamb in the upstairs bistro. In either case, complement your meal with something canned—the deli’s specialty— whether it’s the seafood plate of the day or a “Cosmopoli-tin” cocktail. A whole wall of canned and jarred concoctions are also available to take home. In 2018, a second, and larger, outpost of Continental Deli was opened in the CBD.

Gothic and grand, this 18th-century former nobleman’s home stands proudly on the banks of the Grand Canal in the San Marco district. Venetian-born owner and interior designer (among her many talents) Francesca Possati has restored this historic home to its regal glory. She has worked with local artists to breathe new life into original woodwork, ornate trompe l’oeil ceilings, and silk wall hangings, resulting in a once-again polished and posh palazzo. The distinctly Venetian rooms—many with canal views—are styled with rich fabrics, bold wall coverings, and pristine period antiques and illuminated by Murano glass chandeliers. Of course, they’ve been updated with the latest modern perks (like Italian marble and whirlpool tubs in the bathroom).

Stroll the art-filled hallways, splurge for a tasting menu at the elegant restaurant, and watch the gondolas float by from the red-awninged terrace. La dolce vita, indeed.

Business travelers might help keep it quiet enough during the week, but when the weekend rolls around, the W Scottsdale earns its rep as a party hotel. By day, a young, trendy, and sometimes noisy crowd hangs at Wet, the rooftop pool, keeping well oiled with sunscreen and bar drinks. By night, the scene remains trendy, and noisy, at the lobby’s Living Room Lounge, or at Shade Lounge upstairs by the pool, often to a background of live music or a DJ, until the revelers are off to bed, or off to some of the many bars and clubs within walking distance. Rooms have all the tech gadgets, and the use of color and frosted glass makes them feel light and playful without going overboard.

Zurriola beach is slightly off the radar, or at least as much off the radar as one of a city’s three beaches can be. The only tourists that typically venture over are of the surfing persuasion, and sitting to watch the sunset on the wall that borders the beach. Surf lessons are available from the stores that line the promenade. It’s the locals’ spot for hanging out, and the one beach that you should spend your days on if you are slumming in San Sebastián.

A pioneer of the East Nashville restaurant scene, Margot McCormack created this stylish spot in a repurposed service station in the heart of East Nashville’s Five Points long before the area was considered a destination for fine dining. The Nashville native, who moved away for the Culinary Institute of America and a stint at restaurants in New York City, serves from her collection of mismatched china in a cozy space with copper pots hanging from exposed brick walls. After more than a decade, the restaurant remains a favorite for dinner and Sunday brunch. The menu changes daily, but entrées might include pan-roasted scallops with parsnip purée, baby carrots, and preserved lemon, or house-made fettuccine with butternut squash, walnuts, and goat cheese.

Saddle-shaped Cradle Mountain is the state’s most popular peak and the starting point for the 64-kilometer (40-mile), six-day Overland Track. For day-trippers, there are quicker walks, including the Dove Lake Loop, which traverses temperate rain forest on the slopes of the park’s namesake peak, as well as rafting and rappelling adventures run by outfitters such as Cradle Mountain Canyons Tours. Other highlights include Waldheim Chalet, a replica of the home of Gustav Weindorfer, the park’s founding father.

This lake filled with giant, translucent chunks of iceberg is one of Iceland’s most distinctive and photogenic sights. Featured in high-profile movies, including two of the James Bond series and Batman Begins (as well as many local TV commercials), the sight is reached via a scenic drive along the country’s main ring road (Route 1). The icebergs originate at the Breiðamerkurjökull glacier, which looms in the distance behind the lagoon, and look especially otherworldly when they reach the nearby black-sand beach. The area is also a paradise for bird lovers, with arctic terns and skuas nesting in the area (they may dive-bomb you if you get too close to their nests), and it’s possible to spot the occasional seal. A nearby visitor center offers simple fast food and drinks as well as souvenirs.

Building on Montreux’s growing popularity as a tourist destination in the early 1900s, two Swiss hospitality pioneers joined an existing hotel with a newly constructed palace section, creating what was then one of the most cutting-edge hotels around—with such “modern” touches as electricity, heating, and private bathrooms. Officially opened in 1906, Le Montreux Palace went on to host everything from glamorous masquerade balls to the signing of international peace treaties, and everyone from New York tycoons to Indian maharajas.

The history lives on in today’s incarnation, which has been under the Fairmont umbrella since 2007. Following several years—and stages—of renovations, the Palace is as majestic as ever, with the 236 rooms and suites all featuring classic décor and balconies showcasing the lake or Alps. The hotel’s location at the edge of Lake Geneva is echoed in the seafood dishes at on-site restaurant MP’s Bar & Grill, where fresh catches (and fine cuts of meat) pair well with top Swiss wines. Additionally, both La Palmeraie and the seasonal La Terrasse du Petit Palais offer flavorful menus backed by spectacular views. Nightlife is big here, particularly at the Montreux Jazz Café and Funky Claude’s Bar, both of which serve casual cuisine, potent cocktails, and a good time. As a partner to the famous Montreux Jazz Festival, Claude’s also hosts live music six days a week, including jam sessions with festival members. Recuperate at the lakeside spa, which has indoor and outdoor pools, a gym, saunas, and a lengthy menu of face and body therapies.