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One of Seattle‘s most postcard-friendly areas, Pioneer Square is a beautiful, historical neighborhood with plenty to do. The galleries come alive for First Thursday art walks, not to mention the delicious lunch spots, quirky boutiques, and vibrant nightlife. Every Tuesday, a different food truck parks at the First & King Loading Dock (505 1st Ave S.), so there’s always something new to try. By night, the bars, pubs, and clubs fill up with tourists and locals looking for fun. The Seattle Underground Tour and Smith Tower attractions can be found here, as well as the Seattle Metropolitan Police Museum and its collection of vintage police cars. But there’s plenty to see if you just amble around and explore, too.

For quality quick eats on the Westside, Flake on Rose Ave. is a cheap and cheerful delight. Breakfast is their bread and butter with pieces of toast literally hanging on the walls. Okay, they are actually art; the toast slices are framed and burnt with images of celebrities like Bill Murray and Pee-wee Herman, and on the opposite wall hangs vintage cereal box fronts. They serve cereal, granola, oatmeal, and yogurt bowls with over 20 ingredients, including fruits, nuts, and sweets to concoct your own mix. Their hot savory dishes include favorites like ‘The Super Cro-Jo!’ (scrambled eggs, gouda, bacon, lettuce, tomato and secret sauce on a croissant) and ‘The Veggie Rad!’ (egg white, avocado, veggie sausage, American cheese and secret sauce on an English muffin), both of which are the only menu items with an exclamation mark to their name. Flake’s retro charm, old-timey playlist, indoor/outdoor seating (or simply to-go), and friendly staff make for an overall enjoyable and tasty experience.

This Little Burgundy mainstay is the headquarters of chefs David McMillan and Frédéric Morin, the acclaimed and enterprising minds behind an evolving blackboard menu that has been known to feature smoked meat croquettes, house-cured ham with truffles, lobster spaghetti and horse meat steaks. The duo is known to do absolutely everything in-house, even brew their own beer and distil their own absinthe. Stroll down Rue Notre-Dame, past their other restaurant, Liverpool House, to the nearby Lachine Canal after an evening at this inviting space with vintage wooden chairs, leather banquettes and a permanent air of celebration.

Located along the Mississippi riverfront, the Mill City Museum rises eight stories from the limestone ruins of what was once the world’s largest flour mill. Today, this National Historic Landmark houses antique milling equipment, vintage advertising, and exhibitions on the wheat farms, and visitors can ride the grain elevator, watch a movie about Minneapolis’s humble beginnings, learn how the Mississippi River powered all the local mills, and sample freshly made treats in the Baking Lab. There’s also an observation deck with panoramic views over the city, and the Ruin Courtyard, which hosts events and live music throughout the year. When hunger strikes, head to the on-site restaurant, Bushel & Peck, for lunch fare like burgers, sandwiches, and salads.

Opened in 1891, the city’s oldest hotel is a throwback to a bygone era. Individually decorated guest rooms combine old-fashioned details, like claw-foot tubs and antique wood headboards, with modern amenities like USB ports and Bose sound systems; other nods to the past include vintage brass keys with tassels and a second-floor writing desk with functional typewriter (rest assured the front desk will stamp and mail your letter faster than the Pony Express). Inspired by a bar on the Queen Mary, the Art Deco Cruise Room was Denver’s first drinking establishment to open after Prohibition; today it’s known for its collaborations with local distilleries and classic cocktails. Follow them up with the confit chicken pops at the Urban Farmer restaurant, or call it a night and wake early for a honey exfoliating scrub or chocolate-ginger wrap at the on-site spa.

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.

Right in the center of town, Capri Tiberio Palace mixes la dolce vita glamour with a globe-trotting sensibility that’s equal parts quirky and elegant. Wanderlust-inducing knickknacks such as globes, vintage trunks, and an eclectic collection of art stud the public spaces, and bookshelves are stocked with coffee-table tomes from the publisher Taschen. A white baby grand provides the soundtrack for aperitivo hour at the Jacky Bar, where wicker poufs, striped blue-and-white banquettes, and Panama hats repurposed as wall decor signal vacation vibes; things are slightly more reserved at the terrace restaurant, a formal space whose brightly colored dishes (think seared scallops with almond sauce and beef tartare with chestnut cream as well as kosher fare) are rivaled only by the panoramic views of the island’s craggy peaks coast and azure sea. And the indoor-outdoor swimming pool, though small, is a savior in the summer heat.

This designer budget hotel, set in a former brothel, is the brainchild of Andre Saraiva, a graffiti artist and nightlife entrepreneur who worked with Parisian artists and designers to pull off an edgy balance of style and substance. Rooms, which are on the small side, are painted in unconventional palettes and decorated with graffiti, and curated flea market and auction finds, vary in their level of provocation, though each could double as a contemporary art gallery installation or soft-porn concept store. While traditional services are nonexistent, the hotel is perfectly located for exploring SoPi, the more upper-crust residential part of the 9^th arrondissement just south of the transvestite cabarets and tourist zones of Montmartre, where classical mansions and 19th-century buildings are being colonized by young Parisians and expats opening bars, restaurants, vintage shops, and fashion boutiques. The restaurant that occupies most of the lobby and garden is a perennial favorite among Parisians of all ages for dinner and Sunday brunch.

Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.

Around since the 18th century, the Avila Beach Hotel is Curaçao’s longest operating hotel. The property’s signature Pen restaurant got its name from the English and Dutch governors who once used the hotel as a country residence, while its classic Schooner Bar has been a beach fixture since the 1950s. A variety of room types all have bright, modern décor and private balconies or patios. Some even have kitchenettes or fully outfitted apartments, which are perfect for families. For a distinctly Caribbean experience, book one of the Ocean Front Blues rooms, housed in an all-wood building on the pier with unbeatable water views.

The resort features two beaches (one of which is exclusive to guests staying in suites), an infinity pool, and a fitness center with a sauna, steam room, and outdoor Jacuzzi. About a 20-minute walk from Willemstad’s UNESCO World Heritage buildings, it also offers a shuttle to town—a very welcome amenity on hot days. Check the resort schedule for weekly happy hours, live music, classical concerts, and arts events, and be sure to look for the vintage Rolls Royce inside the gift shop.

Mexico City’s fabulous Sundays-only flea market—in a down-at-the-heels neighborhood near the Centro Histórico that looks worse than it is—is a must-do for anyone who loves the nostalgic or the campy. No fewer than six block-long aisles host dozens of stalls featuring all manner of trash and treasure, including antique furniture and light fixtures; frilly housewares that get you back in touch with your inner grandmother; books and vinyl LPs (record players, too); artworks that might be worth a fortune; toys; dolls and action figures; and fantastic vintage beer and soft-drink trays that make great, practical CDMX souvenirs.

I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and unwind in the shade.... I’ve been to this area multiple times and still I manage to find a street I’ve never wandered down. Some are more popular than others, in particular Calle San Sebastian, which hosts eateries, bars, and shops, and Calle San Francisco. At the corner of this street is my particular favorite, Franky’s antiques. It’s in a four-story building, loaded with vintage goodies. There’s so much to see, one trip is not enough. If you want to shop, consider wandering all morning and into the early afternoon. You’ll be delighted by all the unique shops. Then, take a break at my favorite restaurant, Triana, for Spanish-style tapas and their famous sangria. It’s a must-stop place any time I’m in the old city. You don’t need a car to get around. Just park at one of the garages and explore by foot. There’s lots to see and do in Old San Juan.

Nestled among the boutiques and restaurants that line the city’s main shopping street, the historic Hotel Goldener Hirsch has all the hallmarks of a Tyrolean hunting lodge right in the heart of medieval Old Town, from vaulted ceilings and mounted antlers to staff dressed in lederhosen and dirndls. Vintage guest-room keys are embellished with stag silhouettes, and even the tableware and linens in the two restaurants (one a former blacksmith, the other a goldsmith) feature the signature leaping-deer motif. Both serve hearty local fare—stop in for schnitzels, beef goulash, and bratwurst with sauerkraut, then call it a night in one of 70 cozy guest rooms, which balance cheerful country textiles and antique furnishings with modern amenities like flat-screen TVs, minibars, and free Wi-Fi.

Hyperlocalism has fueled Portland’s Old Port District revitalization, with buzzy restaurants and shops with a deep sense of place opening in recent years. The stylish Press Hotel is no exception. A publishing motif runs throughout the 110-room property, which occupies a corner building that once housed the Portland Press Herald. Custom-made wallpaper printed with old headlines adorns the corridors, and desks inspired by those found in 1920s newsrooms are in each room. Works by local artists—including a dramatic installation of vintage typewriters from the late 19th and early 20th centuries by Portland artist Erin Hutton—and woven-wall tapestries by Portland home-goods designer Angela Adams also abound. (There are even a few notable—and welcome—nods to the global luxury market, including Frette linens from Italy atop the plush beds.) The focus at the 65-seat hotel restaurant, Union, is proudly farm- and sea-to-table, with dishes like house-smoked local mussels served with celery cream.

An old shoemaker’s workshop hidden above a tiny café has been transformed into what Copenhageners call the world’s smallest hotel—a 12-square-meter room outfitted in vintage-inspired decor and the highest quality gadgets. It feels like a hideaway from reality, on the border of two of Copenhagen’s coolest, undiscovered-by-tourists neighborhoods. With a Royal Eden bed, hidden flat-screen TV, iPhone with stereo dock, and free Wi-Fi, Central Hotel & Café has thought of every requisite modern convenience. The 1950s-style decor even feels straight out of a movie—not surprising, actually, since one of the owners previously worked as a set designer.

Downstairs, the café feels like your own, even if just for a day, with its sounds and smells wafting up through the windows and vents. Open the flower-framed window to get a better smell, and arrange to have your coffee delivered to your door, or simply head downstairs to order in the café.