The 3 Best Cities for Solo Travelers

Strike out on your own in Boston, Portland or Chicago with our tips for making the most of your solo travel adventure.

Young woman in downtown Chicago with the U.S. flag flying in the background

by NEA Member Benefits

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Sharing a trip and new adventures with friends, a partner or family can be very meaningful, but there’s also a compelling case for traveling alone. Solo travel can work for anyone, whether you’re single, in a relationship, outgoing or shy, and it lets you learn more about yourself as you visit a new destination. You have the freedom to enjoy yourself entirely on your own schedule and see the attractions that interest you most—no need to compromise. You get to do everything you want and nothing you don’t. Sounds pretty fantastic, doesn’t it? Here are some tips for traveling alone, as well as 3 cities that are perfect for your first solo trip.

Tip #1: Before your trip, research how much it costs to get from the airport to your hotel or to the city center. Solo travelers are more likely to be taken advantage of, so ask the taxi driver for an estimated fare before you leave. If it’s considerably different from what you investigated, take a different cab.

Tip #2: Be confident and walk purposefully. Everyone gets lost sometimes, but do your best to study a map of the city beforehand and be aware of your surroundings. If you appear to know where you’re going, people will assume that you do and you won’t be a target. If you’re using your smartphone for directions, pop in your earphones. You’ll look like you’re just grooving to some tunes as you stroll down the street.

Tip #3: Carry identification at all times and make a few copies—leave that information with someone you trust back home and keep another copy in your bag that’s back at the hotel.

Tip #4: If you want to check out a more formal restaurant but feel squeamish about eating alone, see if they’re open for lunch. It’s the same chef and quality of food but the prices are often lower and the crowd is less romantic. Plus, you’ll get lots of business people—some also dining solo—not focused on you. Alternatively, eat at the bar or a communal table. Aside from making you stick out less, you’ll be mixing with locals or meeting other travelers.

Tip #5: Let family and friends know where you are going. Provide loved ones with a copy of your itinerary, including where you’re staying and where you’ll go at night.

Tip #6: If you’re interested in traveling solo but are nervous, start with a day trip to a city near you. See the sights, use public transportation and get a feel for traveling on your own. Do you want to do more of it? Read on.

3 cities that welcome solo travelers

Here are three places that welcome solo travelers with open arms. (Restaurants are rated as budget ($, less than $15 per person), moderate ($$, $16 to $35 per person) and expensive ($$$, $36+ per person).

Going solo in Boston: Boston is a great city for a solo traveler: It’s easy to navigate and people are friendly. Plus, there are some great activities and attractions, like taking a tour of Fenway Park ($15 to $35 per person); visiting art museums such as the Museum of Fine Arts ($25), the Isabella Stewart Gardner Museum ($15) and the Institute of Contemporary Art ($15); and strolling through Boston Common and the Boston Public Garden (free). If you go for a weekend, hit up the flea market at the South End and get brunch at the Beehive ($$) for a meal accompanied by live soul music. For history buffs, explore the John F Kennedy Presidential Library & Museum ($14) or the Freedom Trail (free). Ending your day with an Italian dinner in the North End is a must, or head to the Waterfront for seafood.

Taking on Portland, Oregon: Portland’s combination of quirky shops, hip cafes and miles of parks and nearby hiking trails make it ideal for exploring on your own. Highlights include mining Powell’s City of Books, the world’s largest used and new bookstore, for literary treasures; eating your way through the Portland Saturday Market (free); comparing Voodoo Doughnut ($) and Blue Star Donuts ($); and visiting Pittock Mansion ($12), a historic French-style château with views of the city skyline. There are plenty of solo-friendly places to eat, such as a counter seat at Le Pigeon ($$) or the bar at Tasty n Alder ($$). And of course, the coffee shops are top-notch and the perfect place to cozy up when it starts to rain.

Chicago as a single: The city by the lake makes a perfect spot for solo travelers thanks to easy transportation and loads of stellar attractions that are great to do alone. An architecture boat tour is a great way to get oriented and learn about the city before setting out on foot to check out Millennium Park (free) and the famous “bean” sculpture; Navy Pier (free) and the Chicago Riverwalk (free). Get lost in the Art Institute of Chicago ($21 for general admission) or Field Museum of Natural History ($38) with its T.rex—the world’s largest. Of course, no trip to Chicago is complete without checking out the shops and restaurants along the Magnificent Mile (free) and the 360 Chicago Observation Deck ($18, formerly the John Hancock Observatory).

Chicago has some of the country’s best restaurants and since you’re alone you can often get a reservation—at least at the bar—at hot spots such as Avec ($$$) and Frontera Grill ($$).

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