Vacationing Your Way: 6 Distinctive Destinations

If you’re a lover of food, history, golf, adventure, wellness or the beach, these six destinations will fulfill your dreams of the ultimate getaway.

(Choose Chicago)

Eat Your Way Through Chicago

A passion for food runs deep in Chicago. Condé Nast Traveler named it “America’s Best Restaurant City” in 2017, and Bon Appétit named it the “2017 Restaurant City of the Year.” The trend shows no sign of abating. Deep-dish pizza is just one of the dishes invented here; the city has 22 Michelin-starred restaurants; and local talent swept the category for Best Chef, Great Lakes in the 2019 James Beard nominations. So how do you bite into a city with so much flavor? Slowly, one dish at a time, using your taste buds as a way to get know the city’s past.

Chicago was founded in the 1800s as a meat-packing city, connecting Western cattle ranches to East Coast diners—which means a steakhouse is a great place to start. Family-owned Gene and Georgetti’s was founded in 1941. Celebrities from Frank Sinatra to local Vince Vaughn have eaten here, drawn by stellar bone-in rib-eyes and classic dishes like chicken Vesuvio, a Chicago invention. Set in River North, just west of the Magnificent Mile, this former industrial area is now home to a thriving arts district.

Speaking of beef, Italian beef is a classic, with thin slices of meat simmered au jus and served on a roll (think cheesesteak without the cheese). Al’s Italian Beef came up with the concept back in 1938 as a way to make beef last longer during the Great Depression. A visit to their original location in Little Italy gives you the chance to wander about this neighborhood, home to beautiful churches and a thriving college scene at University of Illinois at Chicago.

Of course, you can’t come to Chicago without having deep-dish pizza. The pie was invented at Pizzeria Uno, but some food historians give the inspiration credit not to the restaurant, but to the chef who worked there at the time, Rudy Malnati. His family went on to create their own empire of pizza shops, called Lou Malnati’s, based on Rudy’s recipe. Their South Loop location is a great stop when you’re wandering waterfront Grant Park or visiting the Art Institute of Chicago, one the country’s largest art museums and a top attraction in the Windy City.

(Choose Chicago)

Stay Over:  The Langham Chicago is one of the city’s top hotels, located riverside and two blocks from Millennium Park. Architectural cred comes from its setting in a landmark Mies van der Rohe tower, and your appetite will be sated by creative American cuisine at Travelle, or traditional afternoon tea at the Pavilion, in tribute to the Langham Hotels’ London roots. Bring your swimsuit to hit the fourth-floor infinity pool, and bed down in chic, cozy rooms with floor-to-ceiling windows that drink in the city skyscape.

Stay up: Chicago’s other claim to fame is booze—or the lack of it during the Prohibition era, when bootleg liquor led to the rise of the Chicago mob. Back in the 1920s, the Green Mill was a favorite hangout of gangster Al Capone. Today you can settle in at his favorite booth and listen to live jazz, or catch the acclaimed Uptown Poetry Slam on Sunday nights. Over in River North, tucked in the basement of the former speakeasy Green Door Tavern, The Drifter serves vintage cocktails with pop-up burlesque-style entertainment.

Inside Tip: Hot dogs never taste better than when eaten at Wrigley Field during a Cubs game. The traditional Chicago take is a Vienna beef frank topped with yellow mustard, chopped onions, sweet pickle relish, tomato, sport peppers and a dash of celery salt. Humble but tasty Wrigleyville Dogs will hook you up with a full meal for under $10, and the century-old ballpark is open for tours on non-game days.

(Boone Clemmons, Seersucker Studios/Courtesy of Visit St. Pete Clearwater)

Enjoy The Beach In Clearwater

Clearwater Beach has long been a favorite go-to for Floridians, escaping from snowbird crowds at better-known beaches on the Atlantic coast. But the secret is out nationwide, thanks to the strand being named “America’s Best Beach” two years in a row by TripAdvisor. But there’s a way to enjoy it and avoid the increased traffic; park your car, stay on the beach and do it all from the sand.

Clearwater is made up of two beaches: North and South, with Pier 60 as the middle connecting point. A new pedestrian-friendly Beach Walk extends south from the pier, making it a breeze to get around on foot. Most beachfront hotels offer chaises or cabanas, but if you don’t have that option, stroll along the beach near Pier 60 and plop down at one of the blue sets; an attendant will come along and collect the rental fee. During the day, you can sate your appetite from the concession stand, vending burgers, pizza and frozen lemonade. Stay to enjoy the nightly sunset celebration, featuring street performers and craftspeople. Weekend evenings means Sunset Cinema; bring a blanket and spread out to watch family friendly classics, with popcorn available from the concession stand.

When you want to explore off-beach, walk over to the marina and hop on the Clearwater Ferry; with three routes across Mandalay Channel, it makes it easy to get around. The Clearwater Marine Aquarium is a nonprofit marine research facility, and a definite must-do. It’s home to Dolphin Tale stars Winter and Hope (like Cher, these dolphins are known by first name only), as well as Harold the sea turtle, Rufus the pelican and a pair of roly-poly river otters, among other critters. Admission proceeds go to the facility’s renowned rescue team, which saves and rehabilitates injured marine animals from all over the Gulf.

Prefer to view sea creatures in their natural habitat? Tropics Boat Tours offers double-decker boat tours (dolphin sightings are guaranteed) and lively sunset party cruises with a selection of drinks packages.

(Boone Clemmons, Seersucker Studios/Courtesy of Visit St. Pete Clearwater)

Stay Over: Clearwater’s newest stay is the Wyndham Grand, which opened right next to Pier 60 in 2018. A flagship property for the brand, it offers 343 rooms, two restaurants (including the area’s only Asian-fusion spot) and a 6,000-foot spa. Families will love the king- and-twin-bunk-bedded rooms, some designed after Winter the dolphin, who lives just half a mile away. As a thoughtful amenity, all guests get two beach chairs for enjoying the sand.

Dine Out: Frenchy’s Rockaway Grill is located on the beach, with open-air dining for unbeatable views. Enjoy their signature She Crab soup, grouper sandwiches served six ways and potent cocktails, all with a side of live music. For something more romantic, Caretta on the Gulf, located beachside at Sandpearl Resort, serves up fresh seafood, steaks and sushi in an elegant dining room with floor-to-ceiling windows that let in the light—or better yet, score a table on the patio.

Inside Tip: Clearwater’s air-conditioned Jolley Trolley runs all day on a continuous loop along Clearwater Beach, and into downtown Clearwater as well. Pay per ride, or get an unlimited pass for $5 per day; kids under 5 always ride free. Don’t know when the next one is coming? Download their Trolley Tracker app on your smartphone and never miss a ride.

(Courtesy of

Tee Off In Scottsdale

With an average of 299 days of sunshine per year, Arizona is a natural for outdoor fun. And with about 200 golf courses in the metro Phoenix area alone, it’s one of the country’s top golf destinations. So how do you choose from that many options? Make it manageable by sticking to a smaller area. The tony town of Scottsdale, just next to Phoenix, has 50 courses and a stylish, historic downtown that blends the Old West with the good life.

TPC Scottsdale is the best-known course, thanks to its position as host of the Phoenix Open, one of the key events on the PGA Tour. The Stadium Course, designed with the pros in mind, is an exciting place for amateurs to play the same greens they’ve seen on TV. Over at The Phoenician, what’s old is new. The course underwent a 10-month renovation in 2018, rerouting it along existing fairways and adding new holes. The result is a smaller, tighter course, with 19 holes (instead of the previous 27) that showcase the Sonoran landscape.

If you don’t want to commit to a long day of golf, head over to Mountain Shadows. This fun, 18-hole course was built in 1961 but underwent a full restoration in 2017, earning kudos as one of the best par-3 courses in the United States by Golf Magazine.

When you want a little respite from the sun, head to Top Golf, which offers 100 climate-controlled hitting bays as well as a restaurant and a rooftop terrace. If you’re looking to upgrade your golf clubs, Cool Clubs uses technology to custom fit equipment using the same method as the pros.

Take a break from the fairway and enjoy the unmanicured desertscape. The granite crags at Pinnacle Peak are a magnet for climbers. Or hit  the McDowell Sonoran Conservancy, home to 215 miles of trails. Arizona Outback Adventures will set you up with mountain bikes, plus trail maps and advice on the best routes.

(Courtesy of

Stay Over: Set outside the city in the high desert, The Boulders is a Scottsdale classic. The name comes from the striking boulder-pile rock formation that provides its backdrop, and the two Jay Morrish-designed courses are considered the most scenic holes in Scottsdale. Stay in one of the adobe-style casitas, with wood beam ceilings, native textiles and patios that take in the view. The one- to three-bedroom haciendas are ideal for groups, with separate living room and outdoor gas grill. Ease any post-play soreness at the onsite Golden Door spa.

Dine Out: The menu at FnB is constantly changing, but the focus is always the same: creative cuisine with a hyper-local slant, from locally grown ingredients to a stellar selection of Arizona-produced wines. If you like what you sip, take it a step further with a visit to the myriad wine tasting rooms in Old Town. Carlson Creek’s merlot is a silver medalist from the San Francisco Chronicle, while Su Vino has a tasty un-oaked chardonnay.

Inside Tip: Greens fees can add up, especially here. But there are ways to work around it. Troon North offers a 36 Holes Special, with 20 percent off your second round if you play twice that same day. If you travel in summer, some courses—including TPC, The Phoenician and the Boulders—offer vastly reduced fees, at 50 to 75 percent off peak season rates.

(Courtesy of

Rediscover History In Washington,D.C.

The nation’s capital is a fantastic place to explore with your kids, delving into America’s historical roots while strolling past presidential monuments along the Tidal Basin or taking advantage of the city’s abundant cultural options.

The Smithsonian has 17 museums, all open to the public and free of charge. Start off at the Castle—the original Smithsonian Institution building, built in 1855 and unmistakable with its red sandstone Gothic façade. The Visitor’s Center will give you a schedule of what’s happening where that day so you can plan accordingly.

Most museums are within walking distance along the National Mall, a 2-mile-long park that extends from the Lincoln Memorial to the U.S. Capitol. The popular Air and Space Museum is undergoing a progressive, multiyear renovation, but key exhibits remain on display, including the Spirit of St. Louis, the monoplane flown across the Atlantic Ocean by Charles Lindbergh. The National Museum of American History is an eclectic treasure trove, housing everything from Abraham Lincoln’s top hat to Judy Garland’s ruby slippers from the movie The Wizard of Oz. You could easily spend a day at the National Museum of African American History, where kid-friendly exhibits include a dance-off in the Step Afrika demo and an interactive, touch-screen soundboard (plus Chuck Berry’s Cadillac) in the sprawling Musical Crossroads exhibit. Across town at the National Zoo, the giant pandas are the celebrity attraction, and activities from feedings to talks by animal keepers keeps kids enthralled.

When you’re ready for a treat, hit the cobblestone streets of Georgetown, the city’s prettiest neighborhood, and stop at Georgetown Cupcakes. End with playtime at Yards  Park, a multi-use park on the Capitol Riverfront that is complete with dancing fountains and a wading pool, and also offers open-air concerts.

(Courtesy of

Stay Over: Kimpton Hotel Madera is that magical combination of a child-friendly hotel that offers sophistication for parents as well. Rooms and suites feature family friendly amenities such as bunk beds and complimentary rollaway beds, and the hotel offers perks like loaner goldfish, kid-sized bathrobes and surprise welcome gifts. Everyone will love the treehouse vibe of onsite restaurant Firefly, with a special menu for kids and cool ambiance that makes it a draw for locals as well. The ideal setting just off Dupont Circle puts you within steps of restaurants, shops and a Metro station.

Dine Out: Make an event out of your meal at Pinstripes in Georgetown. The Italian bistro serves up tasty wood-fired pizzas, pastas and entrées like espresso-crusted filet mignon, and you can work off some energy at the onsite bowling lanes or bocce courts. Or head to Ben’s Chili Bowl for burgers, dogs and chili; with four locations around town, this no-frills eatery has been a D.C. institution since 1958. 

Inside Tip: D.C. is a breeze to get around, thanks to the Metro system. But for a fun twist, hop on the Potomac RiverBoat water taxi. The bright yellow boats offer sightseeing cruises along the river, and a ferry route with stops in Georgetown, the Wharf (convenient to the Mall), Old Town Alexandria and National Harbor, an open-air riverfront plaza filled with shops, restaurants and the Capital Wheel, a 180-foot Ferris wheel.

(Courtesy of Visit Jackson Hole)

Get Adventurous In Jackson, Wyoming

If you’re looking for adventure in beautiful, wide-open spaces, head west to Wyoming. Jackson Hole gets its name from its location in a 50-mile-long valley that runs through the Teton Mountains on the western edge of the state. The ski resort uses the name Jackson Hole, but the town itself is called Jackson and dates back to the 1820s. The historic downtown is beautifully intact, with Old West wooden storefronts centered around a scenic square—only these days, the 19th-century buildings are selling everything from the latest high-tech outdoor gear to designer jewelry and fine art. (The surrounding county is considered one of the richest in the U.S.)

In Jackson, you can’t turn around without embracing the epic scenery. On the drive in from the airport, you go past the National Elk Refuge, 27,000-plus acres that are home to grazing elk, bison, pronghorn antelope and mule deer. During the winter months, you can take a sleigh ride out to the wintering elk herd for up-close viewing, or explore by foot or bicycle in the summer.

Yellowstone National Park is 80 miles north, and a perfect day trip. Scenic Safaris will take you for full-day excursions by bus (or snow bus in winter) into the park. Eco Tour Adventures specializes in wildlife viewing, with half- and full-day hiking tours into Grand Teton National Park, where you may encounter moose, bison, mule deer or bears. Or stay closer to home and rent a Side by Side—a street-legal, four-seat UTV—and take to the back roads of the Gros Ventre Mountains.

This is cowboy country, so horseback riding is a natural, and multiple outfitters will saddle you up and take you out into the hills. Jackson Hole Outfitters offers backcountry treks that include an overnight, where you can sleep in a teepee. In winter months, snowmobiles substitute for natural horsepower.

(Courtesy of Visit Jackson Hole)

Stay Over: The Wort Hotel has been welcoming visitors since 1941, when it opened as the town’s first luxury option. The 55 guestrooms feature custom furnishing, Western-themed art and convenient touches like in-room mini fridges. Pop into the Silver Dollar Bar for thick steaks and live music, and to take a gander at the 2,032 silver dollars inlaid in the bar. During ski season, a free shuttle runs to Jackson Hole Mountain Ski Resort.

Dine Out: Snake River Grill is a perennial favorite, thanks to its location on Jackson Square, attention to fine service, and fantastic modern-Western cuisine, embodied in dishes like green chile onion rings and Snake River Farms zabuton-cut steak. Afterward, amble over for drinks at the Million Dollar Cowboy Bar, one of the Old West’s best watering holes, with plentiful animal mounts on the walls, saddles for barstools and a clientele that includes cowhands and CEOs.

Inside Tip: Head out to Granite Hot Springs for a soak. Located 30 miles southeast of Jackson, this no-frills pool is fed by natural springs and managed by the U.S. Forest Service. But the road there is bumpy and cell phone service is limited, so bring a map if you go solo, or sign up with a guided excursion and leave the directions to your guide.

(Kara Thornton)

Find Inner Peace In The Berkshires

The bucolic hills of Western Massachusetts have long been a haven for people seeking a better life, from the religious Shakers who settled here in the 19th century to artists of every tradition. Today the collection of towns known as the Berkshires has become a thriving wellness destination, with world-class spas offering daily or multiday experiences. Add historic sites, great food and abundant natural beauty, and you have a vacation spot that benefits mind, body and soul.

Yoga is synonymous with wellness, and the Berkshires has it in every shape and form. Kripalu Center for Yoga & Health is the longtime leader in the area, offering yoga and wellness programs for more than 30 years. Visitors can sign up for a multiday stay, or buy a day pass that gets you access to the 100-acre campus and daily slate of options from yoga dance to guided hikes to journaling workshops.

Over in Pittsfield, Hancock Shaker Village offers monthly goat yoga, with assistance from the four-legged residents of their onsite working farm. Stay after class to explore this open-air museum, which showcases the way of life of the peace-loving religious community that thrived here in the 1900s in what they called their City of Peace.

For something a little more daring, head to Berkcirque, the Circus School of the Berkshires, and take your practice off the floor with aerial yoga, which combines traditional poses with trapeze, fabric and lyra. Classes are available for all ages, as well as instruction in juggling and unicycling.

One of the biggest trends in wellness is the Japanese art of forest bathing—going out into nature with intention, taking your time and noticing details along the way. The Berkshires are laced with well-marked hiking trails, including 90 miles of pathway along the Appalachian Trail. If you find serenity near water, take a guided kayak trip along the Housatonic, or raise your heart rate doing a rafting trip with Crab Apple Whitewater.

Of course, wellness isn’t all about the body. Take inspiration from artists and writers who have lived and worked in the Berkshires. Edith Wharton, Norman Rockwell and Herman Melville all had homes here, which are open to the public for tours. For contemporary arts, summer is the season. Tanglewood, the summer home of the Boston Symphony Orchestra since 1937, hosts the biggest names in classical and pop at open-air concerts, while Jacob’s Pillow in Becket is the nation’s oldest dance festival, with more than 200 free performances.

(Courtesy of

Stay Over: The iconic destination spa Canyon Ranch began in Tucson in 1979, and the Lenox branch—set in a Gilded Age-era mansion in Lenox—has been the go-to spa on the East Coast for 30 years. Guests can check in for a week, or for just one night. Nightly rates include tasty, healthful meals and snacks; access to their packed slate of classes, from pilates and interval training to drawing; free range at the state-of-the-art gym; as well as a credit toward a massage or facial.

Dine Out: Start your day at the aptly named Haven Café & Bakery, a cozy Lenox restaurant with delicious food using mindful ingredients (cage-free eggs, hormone-free beef) and an onsite bakery that offers tasty reasons to work out later. For dinner, Alta Restaurant & Wine Bar serves Mediterranean-meets-American cuisine, with vegetarian and vegan options and an extensive selection of wines by the glass—because balance is everything.

Inside Tip: The Berkshires are open year-round, but summer is peak time, especially for events at Tanglewood and Jacob’s Pillow. That means accommodations at all price ranges go for a premium and sell out in advance. If you want a quieter time, look to spring and fall shoulder seasons.

Categories: Current Issue, Destinations