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A signature experience in Negril is to go on a two-hour glass-bottom boat snorkel trip, toward the cliffside or to the nearby reef around Booby Cay. Truth be told, snorkeling isn’t a must if you’re not up for it—but floating on a small boat amid deep jade and turquoise waters and being able to see marine life 20 feet or more below through the glass is a memorable experience. If you do want to snorkel, the cliffside has stunning limestone formations and underwater caves, while the reef is filled with all sorts of marine life, from stingrays to barracuda. A glass-bottom boat ride shouldn’t cost you more than US$20 per person. Look out for Famous Vincent‘s boat—the best pick—or approach one you see resting along Seven Mile Beach, across any reputable resort. The boats—including Famous Vincent—occasionally ride along the cliffside resorts in the mornings or afternoons, looking for anyone interested in an impromptu adventure.

If you’re looking for a place reminiscent of the smoke-filled cafés of bohemian Paris, look no further than Cafe Cinema. Sitting alongside a popular tourist route in Hackescher Markt, the small, hole-in-the-wall cafe attracts both tourists and locals. In the evenings it’s a great spot for a beer and interesting conversations, and the daytime sees visitors working quietly and enjoying coffee. In summertime, the alleyway nearby has picnic tables, which make a great spot for people watching. The alternative atmosphere can be hard to find in Berlin Mitte, and this is one of the coolest spots in the area.

This is one of the most hectic and lively courtyards in Berlin. Located in Mitte, it is named after the Hackeschen Market, which is across the street. As in many of Berlin’s courtyards, the building complex around it consists of offices, businesses, factories, and apartment buildings. In this specific one sits a well-known movie theater, which makes it even busier. As this was the first courtyard and quite successful, today there are eight other courtyards between Rosenthal and the Sophienstraße. All around the courtyards, you’ll find numerous bars, restaurants, and clubs. The area has become one of the coolest places to go at night.

If you’re a shopper, then Bologna is the city for you. Thanks to the combination of a large student population and a robust corporate climate, the ability to spend some money shopping abounds. One of the top buys can be found at the many food shops around town. Bologna is one of the culinary centers of Italy and you can find everything from the freshest of foods to the coolest of kitchen gadgets around town. This is also northern Italy, so fashion is always close at hand as well. If high-end labels are your thing, then a walk through the main shopping district won’t leave you disappointed.

Find cool pieces by an array of new and noteworthy Australian brands at this small concept store, founded to showcase independent designers in an artistic shopping environment. The Melbourne space stocks a monthly edit of men’s, women’s, and children’s clothing, with original and limited-edition pieces by around 100 local lines. With so many unique options on offer, you’ve got an excellent chance of finding something that perfectly suits your aesthetic, be it a little black dress by Ella Fashion, or attention-grabbing earrings by Plain Janes. If you can’t find what you’re looking for downtown, you can always check out the other Design a Space locations in Fitzroy and Windsor—the selection is different at each store.

When Chef Richard Reddington was tasked with concepting a new, casual restaurant in Yountville to compliment his Michelin-starred Redd, he brought in a wood-burning oven from Italy and Liza Shaw from A16 to work her magic with yeast and flour and fire. Success. Shaw has since moved on, but the eatery maintains its stellar reputation for Italian fare and a relaxed atmosphere. The best seats at Redd Wood are at the bar, where you can see into the open kitchen and the charcuterie cooler, enjoy a respectable Manhattan, and avoid the tourist hordes.

Usually, when you travel, it’s to experience a different side of yourself. The more adventurous side, the slightly less scheduled side, the sleep-in-without-guilt side. And when you stay at the Drake Hotel in Toronto, you can’t help but feel like your cooler side is making a much-needed appearance. The recently renovated property on Queen Street West features the kind of interior design that radiates style whether it’s in the kaleidoscopic lobby, the next door theater, or in two wings of suites. That’s because the hotel commissioned artists to showcase their work on plenty of open surfaces — from a black-and-white squiggle accent wall in guest rooms to personality-driven drawings in the elevator — and the results make for surroundings that are the material equivalent of black sunglasses. Paired with of-the-moment details like pink terrazzo showers and wraparound midcentury sofas, and the Drake Hotel is meant to cultivate a see-and-be-seen vibe.

But that’s not to say that the hotel sacrifices comfort for being camera-ready. The staff is kind and always available through text, the beds are soft and squarely stationed in front of a well-appointed bar and flatscreen television, and designer toiletries are filled to the brim. It’s also possible to eat throughout the day at the hotel’s delicious cafe and patio (get the French toast), and then spend the night at its second-floor bar or ground floor lounge. On weekends, even if you’re not a guest, you can stop by for regularly scheduled events including a DJ who spins old and new tunes. If you do plan on leaving the hotel to see the city, then you’re right in the midst of it, and the surrounding neighborhood can keep you readily entertained.

When you stay at the Drake Hotel, don’t be surprised if you feel relaxed, in-the-know, and decidedly cooler once you check out. These are sides of yourself the hotel may have encouraged, but feel free to hold on to them after you return home.

Inside this 1876 market, you can see the footprint of 18th century Barcelona and read about what life was like before the city’s siege during the War of Spanish Succession. The airy iron and glass market, modeled on Parisian architecture is the largest covered square in Europe and marked the beginning of Modernisme in Catalan architecture. Check out seasonal exhibits or get up close and personal with the ruins on a tour (prior reservation necessary).

When the Evok Collection opened Brach inside a former postal sorting facility in 2018, the hotel was an instant hit. Now, this residential corner of the posh 16th arrondissement is the cool rendezvous spot for in-the-know Parisians. The energetic vibe starts with the design, courtesy of Philippe Starck’s famous melange of styles—an African mask here, a sculptural lamp there. This warmth infuses the 59 guest rooms, done up in a marvelous mix of marble, leather, and wood. The city’s glitterati rub shoulders at the popular (and family-friendly) brunch and covet memberships at the next-level sports club, styled as a 1930s boxing club, complete with a 72-foot pool. Come summer, the rooftop terrace turns into a trendy hangout with 360-degree views of the city from the vegetable garden and henhouse. Take a dip in the terrace’s Norwegian bath, cocktail in hand, and you’ll see why Brach is the darling of the district.

Located in Wood Dale, Yesterday’s Farm Museum is trip to a different era. The barn pictured above is part of the Wood Dale Historical Society, and it was constructed back in the 1850s. This massive structure is referred to as a ‘T’ barn due to the unique design for its time period. It features a hayloft, a feeding area for the horses, and a place for the cows to get their grub on as well (pictured above). But the coolest part is that during October, as Halloween approaches, the folks here provide hayrides for family and friends, and also feature spooky ghost stories at night in the barn. They don’t currently have a website, so please call 630-595-8777 for information and upcoming events.

Copenhagen (and Denmark) are famous for being incredibly environmentally friendly. Windmills play a huge role in making that possible. One of the best places to see the large windmills installed just off Copenhagen’s coast is from the beach at Amager Beach Park. I find that the fact that they are marine windmills makes them even cooler and more fascinating than those installed on land.

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.

Restaurateur Brooks Reitz built his name with this chicken-and-oyster joint that feels old-school despite its carefully crafted ambiance. On a first visit, it’s sinful not to order the perfectly salted, crispy/juicy fried chicken amalgam shellacked with a glaze of Old Bay and cayenne suspended in melted lard. That necessitates a second visit to gorge on the poached char-grilled lobster and sausage, or the Leon’s Fish Fry, a platter of shrimp, oysters and catfish. Leon’s was the first to open way-Upper King, now the restaurant hotbed, and it’s held onto its cool status thanks to its thoughtful buildout in a restored auto body shop, retaining the exposed rafters and a rollup garage door that opens to a patio out front.

For the coolest and most unique clothing in Buffalo, head to this streetwear-focused consignment shop in Allentown. While everything here is vintage, the selection puts a special focus on the 1980s to the present, with pieces from Supreme, Bape, Palace, Off-White, Anti Social Social Club, and more. Sneakerheads will be particularly impressed with the collection of vintage kicks in pristine condition, while sports fanatics will love all the old-school team gear, from Sabres sweatpants to a Bills Super Bowl T-shirt from 1991. Prices are affordable, especially considering the quality of products for sale, and the selection is updated regularly so you’re always guaranteed to find something new.

The drive from Launceston through the Tamar River Valley meanders for 37 miles past orchards, lavender farms, and more than 30 vineyards. For good vibes alongside your cool-climate wines, head to Goaty Hill, which occupies a beautiful perch in Kayena. The chalet-style Jansz cellar door, or tasting room, pours premium sparkling wines, and Holm Oak Vineyards is loved for its pinot noir, chardonnay, and cider. The mascot there is a well-fed pig named Pinot, and kids are encouraged to toss apples to him over the fence. End the day at Narawntapu National Park for a picnic and bubbles overlooking Badger Head and the Bass Strait.