Traveling by yourself isn’t for the faint of heart. There’s the dreaded “dining alone” phenomenon to face and, of course, in the oft chance you make a wrong turn, there will be no one to blame but yourself. Going at it alone doesn’t have to be dreadful or dangerous, though. With a little forethought and some expert guidance, a solo sojourn can be downright blissful. Because let’s face it, no matter how much we love our significant others, every now and then, we all need a chance to get away on our own.
Steeped in early American history, Boston is a brisk and beautiful city on a peninsula — large enough to keep any traveler busy, but not so large as to feel overwhelming. Take the 2.5-mile walk along Freedom Trail to experience 16 different historic sites,or choose a different neighborhood to explore each day by foot. From eateries in the Italian North End to the storied halls of Harvard in Cambridge, Boston is a perfect place to dive into the history books, indulge in high-end shopping or explore cobblestoned streets that make superb selfie backdrops. Thankfully for solo-travelers, Boston is also connected by one of the nation’s cleanest and safest public transit systems.
Don’t miss: a chance to see the Boston Bruins at TD Garden. If there’s a home game during your visit, buy tickets through the official Bruins website, and don’t forget to wear your black and gold. If hockey isn’t your jam, book a spot with Charles Riverboat Company to see the city by water — or make a reservation at The Top of the Hub to take in the metropolis from 52 floors up.
Stay here: Fairmont Copley Plaza is located in the historic Copley Square, near the Boston Public Library, The Shops at Prudential Center and much of the great shopping along Newbury Street. Thanks to a recent $20 million renovation that spruced up guest rooms and public spaces, this 100-year-old hotel is better than ever.
Eat here: For the best lobster ravioli you’ll ever have in your life, drop everything and head straight to Piattini, a wine café on Newbury Street that’s open daily for lunch and dinner, but with room for only a few dozen diners at a time. Order a glass of Asti Spumante from the extensive wine list while noshing on some of New England’s freshest ingredients prepared with authentic Italian flair.
All too often, travelers only experience Milan en route to another destination. A hub for trains, planes and automobiles, Milan is a modern, cosmopolitan locale in its own right, a place full of adventure, history and art. From the Quadrilatero della Moda, where you’ll find the power fashion labels such as Gucci, Prada, Missoni and Dolce & Gabbana, to the towering spires of the Duomo, the third-largest Gothic cathedral in the world, Milan has plenty to admire and discover by yourself.
Don’t miss: On a clear day, it’s worth it to climb to the top of the Duomo for a spectacular view of the city, and the Alps to the north. If you’re an artist at heart, make reservations at Santa Maria delle Grazie, a church and convent in northern Milan, for a 15-minute window to take in Leonardo da Vinci’s masterpiece “Il Cenacolo (The Last Supper).”
Stay here: For a hotel with luxe accommodations and a top-notch location, stay at the Grand Hotel et de Milan, which recently celebrated its 150th anniversary. Its rooms, though historic, offer modern and refined comfort — think sweeping frescoes, high thread-count sheets and traditional Milanese cuisine at three onsite restaurants. Walk to the Museo Poldi Pezzoli, and ask for a south-facing room for a chance at views of the Duomo.
Eat here: Stop in as many cafés and trattorias as you can during your stay, and always order an aperitivo, like the Milanese. If you can have only one meal in Milan, make it the Rustin negàa (veal osso buco in homemade gremolata) with risotto at El Brellin Ristorante, located in the Vicolo dei Lavandai. This charming and historic alleyway takes its name from the laundry that operated there until the 1950s.
The City of Brotherly Love is having a moment. Last year, a remarkable 19 Philadelphian chefs, restaurants and restaurateurs became James Beard Award semifinalists, including Best New Restaurant nominee Laurel, a semi-new 26-seat French bistro near Passyunk Square that invites guests to BYOB (bring your own booze) to pair with chef Nicholas Elmi’s intricate tasting dishes such as lamb loin served with lamb sausage, braised pork belly, black trumpet mushrooms and a pistachio and olive crumble. Of course, no trip to Philadelphia is complete without a stop to hip-hop group The Root’s favorite cheesesteak joint, Tony Luke’s, or a visit to Independence Hall, the site where America’s forefathers debated, perfected and signed the Declaration of Independence and the U.S. Constitution.
Don’t miss: The Philadelphia Museum of Art, home to the famous staircase that got Rocky in shape, is also a great place to spend an afternoon working out your cultural muscles. “Full Circle: Works on Paper by Richard Pousette-Dart,” a collection of nearly 60 of the famed draftsman’s pieces, shows through November 30. While you’re in town, also make sure to take a stroll through Reading Terminal Market, an enclosed hub perfect for grazing, featuring homemade doughnuts, locally grown produce and a host of fresh seafood and meats.
Stay here: Four Seasons Hotel Philadelphia has unbeatable glittering nighttime views of Logan Square, one of the five public squares William Penn designed for the city’s grid-like design. During the day, if you’re not enjoying a spa service or swimming a few laps in the 45-foot indoor pool, the Forbes Travel Guide Four-Star hotel provides complimentary water bottles and towels for joggers returning from a jaunt around Independence National Historical Park.
Eat here: Though there’s no lack of options in Philadelphia, locals have long clamored over Le Virtù, a restaurant committed to the slow, purposeful tradition of Abruzzese cuisine, serving northwestern Italian specialties such as palott cac’e ove (braised egg and cheese croquettes in tomato sauce) and coniglio in porchetta (rabbit “porchetta” style with braised lentil and chestnut ragu). If you’re looking for something more casual, locals love Los Gallos, arguably South Philly’s best taquería joint.