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Cheeca Lodge manages to be upscale and relaxed at the same time. This duality is perhaps best embodied in Cheeca’s flagship restaurant Atlantic’s Edge, which offers a refreshed take on island cuisine (like the roasted red snapper with dragon fruit or the hibiscus swordfish) in an elegant but breezy oceanfront setting. The 27-acre luxury resort on Islamorada Key—one of the sport-fishing capitals of the world—was renovated following damage from Hurricane Irma in 2017. The revamped lobby, fully rebuilt fishing pier, 214 redesigned guest rooms, and new Italian restaurant have made Cheeca even better than before. Airy suites feature curated artwork, hand-tufted rugs, and rattan accents, and each suite opens to a private lanai with a partially enclosed open-air jacuzzi. A new point of pride is the refreshed 5,700-square-foot spa, which now has seven treatment rooms, a wet room with Vichy shower, hydrotherapy facilities with a steam room, and a fully equipped fitness center. Still to come in early 2019 is a brand new oceanfront pool (bringing the resort’s total to three, including a saltwater lagoon) and tiki bar, 25 South. If you must leave, book a fishing excursion, sunset cruise, or round of golf at the 9-hole Jack Nicklaus-designed course—and enroll the kids in the eco-focused Camp Cheeca.

Okay, let me start by saying that I am not trying to ignite a war with fans of In-N-Out Burger or Shake Shack. But, if you come to D.C., Five Guys is your place for burgers—we don’t go in/out or shake a shack for our bite! Yes, the burger patties at the Five Guys chain are hand-formed and cooked atop a flat top griddle. Yes, they come sandwiched between the halves of a sesame seed topped bun. Yes, you can get them in two different sizes and topped with your choice of condiments. Yes, there are some awesome fries to go with it but only fries; there are no onion rings here. You should know that Five Guys prides itself on its fries. If you want to know the type of spud that gave birth to that day’s fries, check the chalkboard for the name of the farm and location. Unless you are really, really hungry and really, really love fries, go with the small order. It’s more than what most people can devour in one sitting! For the full Five Guys experience, order your meal at the counter and while you wait, munch on the free roasted, in-shell peanuts, but don’t eat too many! You need to leave room for that awesome burger that will soon make its way to you! There are various locations around D.C. (The first Five Guys restaurant opened in 1986 here in Arlington County, Virginia.) Check the website for the one nearest you and order online to beat the line.

“Have you heard about d’Mongo’s? It is Ryan Gosling’s favorite place to visit when he comes to town!” Although I never saw Ryan Gosling, bartender Red knew immediately that I was new in Detroit and that I’d never been in before. She recommended I try the Detroit Brown, made with Michigan’s own ginger ale: Vernors. As I sipped gently from the cold glass and looked over the top of its rim at the eclectic crowd filling the speakeasy, I couldn’t help but think, “Who cares what celebrity does or doesn’t frequent this place, I’d come back here for the drinks and the crowd any day!” Cafe d’Mongo’s draws a crowd every night it is open—which is usually only on Friday, maybe Saturday—and whether the customers come because of the drinks, the music, the crowd, or because they hope to see Ryan Gosling or Mark Wahlberg, the point is they keep coming. There’s an element of secrecy that has kept even my hotel’s valet from being able to tell me how to get to the revered speakeasy, yet it’s one of the first places I heard about when I asked people on the street where I needed to go get a drink in Detroit. If you find yourself at Cafe d’Mongo’s, tell Red I say hello, and order the Detroit Brown.

The Museum of Glass is in Tacoma, about a half-hour away from Seattle, and it’s well worth the trip for art glass enthusiasts. The permanent collection includes some Chihuly pieces, work by 20th and 21st-century artists, and a charming collection of sculptural pieces interpreting children’s drawings. The temporary exhibits often feature a Northwest theme, and a theater features a rotation of short films about glass art. The real highlight of the museum, though, is the Hot Shop, where resident glassmakers and their assistants blow glass all day long for the entertainment of visitors. Often, their work is being filmed, and a narrator is on hand to explain what you’re seeing. You can walk all around the Hot Shop via overhead walkways, and photography is allowed throughout the museum, so it’s a great opportunity for photographers as well. The museum isn’t huge and takes only a couple of hours to go through, so it’s an ideal destination for a rainy afternoon. But don’t miss the striking outdoor art, like the Chihuly Bridge of Glass, outside the museum (free).

The Cloisters, a museum devoted to medieval art and architecture, is a delightful respite from the hustle and bustle of NYC. This tranquil treasure is definitely worth a half day (or more) trip on your next visit. A branch of the Metropolitan Museum of Art, The Cloisters opened in 1938 and is located in Fort Tryon Park in northern Manhattan. Perched on a towering cliff, the museum offers commanding views over the Hudson River to New Jersey and the George Washington Bridge. The buildings include elements from medieval sites from Europe (primarily France) and renowned artwork includes the Unicorn Tapestries and the Annunciation Triptych, but the heart of the museum is the cloistered garden. This lush space consists of an interior courtyard surrounded by covered walkways. The flowering garden within invites contemplation and appreciation of a different time. The Cloisters includes a broad terrace with expansive views across the Hudson. The view is so prized that in 1901, J.P. Morgan purchased 12 miles of the New Jersey coastline to protect it from excessive quarrying and in 1933 John D. Rockefeller, Jr. donated 700 additional acres of NJ to preserve The Cloisters’ view. Be sure to include time in your visit to explore beautiful Fort Tryon Park.

If you want to check out where the San Diego locals hang out, you have to stop by Bootlegger, located on the border of Gaslamp. The bar itself is unique, with a beautiful stone top and lined with hand-carved wooden panels imported from Mexico. There are comfortable seats no matter where you look. Although the decor is going for that dive bar feel, it’s got a touch of hidden elegance. When you come in, as long as it’s not too crowded, the service is highly personable. The Bootlegger is designed somewhat to look like a 1920s speakeasy, and has some interesting art on the walls. The drinks are poured using top-grade liquors; my favorite so far (pictured) is the ‘Old Fashioned'—Bulleit Bourbon, Angostura bitters, sugar, fresh lemon and orange peel. They have a good number of beers on tap and a great selection from the local micro-breweries. I recommend the happy hour—it’s not too crowded and select drinks and all appetizers are half price. For a neighborhood bar, the food is really good. The Bootlegger bar is a great place to experience the San Diego vibe. Another cool thing is that they don’t allow smoking out on the patio around the bar, so if you want to enjoy a smoke-free night, this is the place to be. Tip: It gets impossibly crowded during any game going on at Petco Park, which is the local baseball stadium. During the late week to weekend it also gets crowded. If you want to come and chill before a night on the town, come by for the happy hour, from 3–8 p.m.

This restaurant feels like you stepped back in time - think Mexico in the 70s. The story goes - it all began in the VW van in Playa del Carmen. Tacombi used to sell tacos out of the van, and now he has a nice, cozy spot in Soho where the van is parked. It’s a garage with lights strung in the air. It just feels cool to be in. The design is great, but the food is even better. Virtually any tacos you order are wonderful. I also recommend the guacamole appetizer - yum! And don’t leave without ordering a drink.

Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.

Sure, Faneuil Hall and Quincy Market make up the most touristy part of Boston, complete with street performers, a light show, and the obligatory Yankee Candle store and Cheers restaurant; we nonetheless defy you to stay away. This part of the Boston waterfront has thrived on commerce since colonial times: Faneuil Hall was crowded with merchant’s shops as early as 1743, and the larger Quincy Market was added in 1824 to provide more space (it also was the site of speeches by Samuel Adams and other early patriot leaders). If you’re looking for a Red Sox hat or a “Boston Strong” T-shirt, you’ll find it here.

Sitting near Mount Hollywood in Griffith Park, the Griffith Observatory has a vantage point that allows visitors great views of the HOLLYWOOD sign during the day, and even more fantastic views of the stars at night. The space has plenty of telescopes for stargazing, but it’s also a great informal setting for learning about the universe, thanks to a large exhibit space and a 290-seat planetarium that puts on rotating shows about topics ranging from the northern lights to water—and possibly alien life—on other planets. There is no entrance fee for the institution and just a small admission price for the planetarium itself.

The JP Morgan Library’s grand, old-world elegance immediately transports you to turn-of-the-century New York. And at that time, there was almost no one more powerful than financier JP Morgan. He launched U.S. Steel and even served as the unofficial central bank of the U.S. for a time. Though some considered him a national hero, his tight control of banks, corporations and railroads led others to label him one of the original “robber barons.” Morgan was an avid collector of art and books with holdings so vast they were housed at multiple locations in New York and England. Eventually, he decided to consolidate his holdings in a huge library next to his mansion in NYC. Designed by renowned architect Charles McKim and completed in 1906, the Italian Renaissance palazzo-style library holds a staggering collection of illuminated books, historical manuscripts, and old master drawings. The library is rightfully considered McKim’s masterpiece—a majestic, soaring space which is both intimate and warm. It features 30-foot ceilings, three tiers of bronze and walnut bookcases, stained glass, a huge marble fireplace and grand tapestries. Also visit Mr. Morgan’s study, with its red silk damask walls and antique wooden ceiling brought over from Florence. The library is off the typical tourist’s radar. Imagine yourself as Morgan in your private quarters, reveling in the power and wealth at your command.

Few cities in the U.S. can claim to be ‘sandwiched’ by a National Park; Tucson might well be the only one. Saguaro National Park is divided into Eastern and Western divisions that flank the city--plenty of wilderness hiking within a half-an-hour’s drive from the middle of town. If you’re here, like most visitors, in the winter, a perfect half-day’s hike is up to Wasson Peak in Saguaro National Park, on the western edge of the city. Seven-miles round-trip with a nearly 2000-ft elevation gain: it’s a moderate climb with 360-degree views from the top. (You do NOT want to hike this in the summer; there is no shade.) At 4687ft/1428m, it’s low compared to some of the 9000+ ft peaks on Tucson’s other horizons, but the panoramas are unbeatable, and the trek up through a saguaro forest is unforgettable. There are several routes, but perhaps the most popular is the Kings Canyon trailhead--directly across the road from the Arizona-Sonora Desert Museum. Hike the peak in the morning (give yourself around four hours so you can enjoy lunch and the view from the summit), and spend the afternoon visiting the animals across the road. (A new aquarium featuring the Sea of Cortez just opened; fall through spring also offer ‘raptor free flight’ demonstrations.) (From the top, the views: trail to the peak, looking south toward the distant Santa Rita mountains, looking over the NW part of the city to the forested peak of Mt. Lemmon in the Santa Catalina Mtns.)

The tram gives Portland visitors stunning views of the city, river, and mountains beyond. Grab the streetcar from downtown out to the waterfront. You’re delivered to the lower terminal for the three-minute ride carrying you 3,300 feet at 20 MPH to the upper terminal at OHSU. Linger for photo ops then head back down to explore. If it’s nice, skip the streetcar and walk back along the river. Daily workout, check. Roundtrip cost: $4. At the lower terminal, the Daily Cafe is an easy find in the atrium of the OHSU Clinical building as you disembark the pill-shaped car, built with precision by the Swiss. Head for the river and stroll along the shore in any weather. Double back along SW Bond Ave and consider lunch at Bambuza Vietnamese Bistro. Check out the pricey high-rise condos on the market in the real estate office windows, then relax in one of the pocket parks to people watch. It snows in Portland. A couple of times a winter, even downtown gets dusted and it’s a huge mess. I’ve dreamed about getting my ski gear on, grabbing my boards and heading for the PDX Tram at the South Waterfront. I’d casually climb aboard with the patients and medical folks heading up to “Pill Hill” and blow their minds.

Sunday brunch at Perry’s is not your usual run-of-the-mill affair. Yes, there is an all-you-can-eat buffet bar filled with typical brunch fare. Yes, there are the usual boozy drinks to go with your brunch meal. Yes, there is music piped over stereo speakers. But this is far, far, far from an ordinary brunch because it has fabulous drag queens to entertain you while you eat! Perry’s Drag Brunch is among D.C’s most loved institutions. There are two seatings each Sunday and they don’t take reservations. The line forms outside around 9am for first seating which is at 10am. Make sure you’re in that line. As soon as the doors open, ask to be seated toward the center of the room—the bad seats are on the periphery. A split second after you get to your table, throw your stuff down and RUN to stand in the buffet line. After you get your food, then flag your waiter down to get your drinks. At about 11am, the show will begin. The drag show features queens that are campy and witty, and the show is raunchy and HILARIOUS! Perry’s Drag Brunch is definitely not for the timid, though! You may get called out, and next thing you know you’re a part of the show. Whatever happens, you can be certain your friends will have captured the moment on their smartphones and before the red blush leaves your face, they will have already posted it up on Facebook! It’s all in good fun! Just remember to bring along a wad of $1 bills for tips. The ladies do work hard for the money!

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.