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On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

The salmon-colored stucco buildings comprising the Elliott House Inn have a long history that runs parallel with the city’s. Built in the aftermath of a citywide fire, the property’s main structure was then shaken in an 1886 earthquake (the characteristic Charleston earthquake bolts are visible on the building’s facade) and battered by 1989’s Hurricane Hugo. The bed-and-breakfast reopened in 2011 after two years of renovation and redecoration, reinventing itself yet again. The main building is a classic Charleston single house, built with its narrow end on the street and a long piazza running along its length.

The rooms, with their botanical prints, hardwood floors, and Oriental rugs, are traditional in a way that’s elegant and charming rather than fussy. Rooms are available both in the main house and the single-story building across. The quiet courtyard provides an oasis from the city streets with its wisteria-dotted pergola and light-draped palmetto trees.

This landmark inn has been around since 1936, when it was known as the Hotel Martin—and the adobe homes that comprise the property date back even earlier. Originally built in the 1800s, the structures are clustered around a central plaza that, today, serves as the hotel lobby. The largest residence is now the restaurant Doc Martin’s, named after its onetime owner, Dr. Thomas Paul Martin, the county physician as well as an avid supporter of the arts. In fact, the Taos Society of Artists was founded in his dining room in 1912, and he later bought the neighboring houses to rent out to writers and artists. When the only hotel in town burned to the ground, Doc bought the Tartleton House (the last on the square and now home to the Adobe Bar) and he and his wife Helen opened for business. The property has been maintained and upgraded over the years (most recently in 2006), but the look (Spanish colonial antiques and brightly patterned bedspreads) hasn’t changed much since then—and that’s part of the charm.

With more than 125 years of history under its belt, the Brown Palace Hotel is one of Denver’s quirkiest landmarks. It was the country’s first fireproof lodging—built with terracotta floors, cast-iron railings, and onyx paneling but no wood—and though it has welcomed every president since Teddy Roosevelt, save Calvin Coolidge, it also hosts grand champion steer from the National Western Stock Show and Rodeo as they take a victory lap through the lobby each year.


Given its Italian Renaissance–style architecture and frontier legacy, English afternoon tea has become an unexpected institution in the hotel’s soaring nine-story atrium, with imported Devonshire cream, an exclusive blend of Assam-Ceylon tea, and live piano music. And instead of bottled Evian, contemporary-skewing guest rooms are stocked with natural artisan water from a well more than 700 feet underground.

Regular tours are offered to those who wish to uncover hidden details of the past—don’t miss the 26 stone-carved animal medallions that are perched outside seventh-floor windows.

Tastemakers and A-listers abound at this East Village mainstay, which celebrated its 10-year anniversary in 2017. Travelers feel like insiders the moment they slip through the door, thanks to over-the-top service, celeb sightings, and a lobby design that recalls salon parties of bygone eras. The cool factor only continues upon check-in, when guests receive metal room keys linked to lavish, oversized red tassels. Each of the 135 rooms offers visitors a mix of lived-in comfort and luxurious detail, with everything from mohair-upholstered chairs, Turkish Oushak rugs, and hardwood floors to iPod stereos, hi-def televisions, and marble bathrooms with deep-soaking tubs. When hunger hits, guests can head downstairs for authentic Italian plates at Gemma and a nightcap at the Lobby Bar, a lower Manhattan staple known for its timeless ambiance and clever riffs on cocktail classics.

Sometimes only a sandwich — thick and hearty, piled with meat and cheese and toppings — will do. The Other Coast Cafe won’t blow your mind with some revolutionary take on the sandwich, but what they do, they do well: hot and cold sandwiches, pickles and potato salad, and friendly service. Their house specialty is the Rajun Cajun (cajun turkey, pepper jack cheese, tomato, onion, spicy salsa mayo), and their reuben is also popular, but don’t overlook the daily specials, like the grilled chicken pesto served on a baguette. If you have very specific sandwich needs, you can also custom-build your dreamwich; seitan is on the menu for non-meat-eaters. Oh, and grab a stack of napkins, because these saucy sandwiches can get messy quick.

Built as a people mover for the 1962 Seattle World’s Fair, the Seattle Monorail is a surprisingly popular attraction, especially given that it’s not very practical. It goes from downtown to the Seattle Center and back, and that’s it. The ride is short—just a couple of minutes—but if you’re staying downtown, it’s an easy way to get to places like the Space Needle, the EMP and Sci-Fi museums, the Pacific Science Center, Chihuly Garden and Glass, and Key Arena. Its midcentury-futuristic design is charming, and the view of downtown from above is unique. The monorail is wheelchair accessible (by elevator at Westlake and by ramp at Seattle Center), and reduced fares are available for children, seniors, and U.S. military members.

The Flying Biscuit, owned by waitress and chef Delia Champion and Indigo Girls member Emily Saliers, opened in 1993 and since then has expanded its original Candler Park location and franchised all around town. At least 5,000 of their famous biscuits are made every day at each location. As you can tell, those biscuits are the main attraction. They’re sweeter than the standard biscuit and are served with cranberry apple butter. Also recommended: an omelet with a side of their “creamy dreamy” grits or the Eggstra-Ordinary Breakfast, pictured here.

I have dreams about the family style BBQ from the Salt Lick, it’s that good. Located beneath the oak trees in a sprawling space in Driftwood, Texas, it is the perfect place to gather with friends and family and celebrate all things Texan. On the weekends, there’ll be live music to entertain you or dance to during the wait for your table and you’ll want to bring your own alcoholic drinks if you agree that a Shiner Bock beer is a must to wash down all that meat. All you can eat ‘Family Style’ is $19.95 per person and make sure that you bring cash, they don’t accept credit cards. Thankfully for me, they’re now shipping their goods worldwide!

Dinosaurs, pyramids, cave paintings, sharks—if you don’t like the Field Museum then you must never have been a kid. Home to an extensive assortment of magical displays highlighting all facets of natural history from around the world, the Field Museum is a great way to spend a day getting your culture fix. If you start to lose steam, just pop into the café for a meal to reenergize before continuing to explore the multitude of exhibits that await you. And while the museum is a showcase for natural history, it’s been at this spot since 1893, which makes it a part of history as well.

The Caves, just west of Negril, is aptly named. While the 12 cottages and one villa sit atop honeycombed cliffs, the Blackwell Rum Bar, a private dining venue, and the massage table of the hotel’s Aveda Concept Spa are actually in underground grottos open to the sea. The setup is very Treasure Island, and the flicker of candlelight and the echo of waves off cave walls make it uniquely romantic. Each of the thatch-roofed cottages is as colorful as a paint box, and each gives a sense of being alone at the end of the land. This is one of music mogul Chris Blackwell’s Island Outpost properties, so the vibe at the Jacuzzi, sauna, or salt-water swimming pool is hip but relaxed. Although famed Seven Mile Beach begins almost where the cliffs end, the hotel itself has no beach, which is why a tradition at the Caves is to begin the day by jumping from the cliffs into the usually calm Caribbean below—or at least thinking about it.

The Art is a worthy base for those looking to explore the galleries of the Denver Art Museum, the Clyfford Still Museum, and the Kirkland Museum of Fine and Decorative Arts, which are all within a few minutes’ walking distance. In fact, the glass-walled property feels a bit like an exhibition space in its own right: Upon arrival, guests are greeted by Leo Villareal’s dazzling 22,000 LED–bulb installation above the entrance, while hundreds of other works by the likes of Frank Gehry appear throughout the public spaces—see them on a guided tour of the hotel’s art collection, offered on Saturdays. Minimal guest rooms have light wood furnishings, luxury linens, and neutral walls—the better to serve as a blank canvas for more original artwork—as well as windows overlooking the mountains or city lights. If you’ve worked up an appetite with all that cultural appreciation, order the signature burger with spicy mayo at FIRE restaurant, or sip a Matisse martini with Colorado-made vodka on the fire pit–warmed terrace.

It’s no surprise that the opening of this beloved gastropub back in 2007 coincided with Orlando’s rise as a culinary hot spot. While its owners James and Julie Petrakis have not stopped opening other ventures around the city (including at Disney Springs), this local favorite—known for its Cask & Larder beers and sophisticated Southern fare—has hardly waned in popularity. Start with the charcuterie platter (a spread of rillettes, dried sausage, and salami), then choose from favorites like shrimp and grits and the enormous Pub Burger, which comes topped with caramelized onions and buttermilk blue cheese. Whether you come for happy hour, dinner, or something in between, expect a lively atmosphere that’s perfectly suited to groups.

Just 10 minutes from downtown Orlando, in village-like Winter Park, the Alfond Inn has a unique legacy: The boutique lodging was created to provide income for scholarship funds at neighboring Rollins College, one of Florida’s oldest liberal arts schools. If helping students isn’t reason enough to book a stay, the hotel offers lots more incentive. A skylit domed atrium in the Spanish colonial–inspired main building draws your eye to a rotating collection of artwork curated by Cornell Fine Arts Museum, and pet-friendly guest rooms are simple and cheerful. While the hotel is not a full-fledged resort, it offers guests plenty of opportunities to linger. Fire pits and rocking chairs are dotted around the property, and shaded areas for loungers enhance the rooftop pool’s already undeniable appeal. Hamilton’s Kitchen restaurant serves modern Southern cuisine paired with wines selected by an award-winning sommelier. And shops, wine bars, and independent boutiques like Rifle Paper Co. line the town’s Park Avenue, a few blocks away. You can also take a pontoon boat tour for views of many of the Mediterranean-style mansions along the waterfront. Perhaps best of all, Disney and Universal theme parks are only a half-hour drive away.

While the Liberty Hotel may have deep roots in Boston lore, it’s not for the reasons you think. For more than 100 years the hotel existed as the Charles Street Jail, an in-city penitentiary that housed (in)famous inmates like James Michael Curley, Malcolm X, and Sacco and Vanzetti. Its inspired transformation came in 2007, but the owners maintained some of the jail’s vestiges, from the exercise yard to several jail cells, while turning the building into a 298-room luxury hotel. Richly appointed rooms offer sweeping views of the city skyline and the Charles River.

The hotel houses five distinct restaurant and bar venues, all of which attract large swaths of locals, especially on the weekends. Located at the foot of Beacon Hill, the hotel is steps away from the boutique and antique stores along Charles Street and also sits next to the picturesque Charles River Esplanade.