Downtown Crossing

When you check in, you can choose rooms looking out on the cityscape or on the historic and verdant Boston Common. Go with the latter. If you go in the fall, you’ll wake up to sweeping views of the changing leaves in America’s oldest public park. It’s pretty unbeatable. The hotel is attached to an Equinox gym, and guests are welcome to use the facilities as well as the spa (where therapists are particularly good at sports massages). Aside from the sumptuously comfortable interiors and amenities, the real draw here is the hotel’s walkability factor. You’re only a few steps away from the boutiques of Newbury Street and the charming cobblestoned roads of Beacon Hill, home to many of the city's best restaurants. If you’re traveling with littles in tow, the toy-laden red wagon in the lobby means you don’t have to bring half the playroom on your trip, and Boston Common makes a great playground.

We go weak for a good independent bookstore, and Brattle meets all of our criteria. Three floors heaped haphazardly with new and used books, more than a few antiquarian and first editions, and an adjacent alley down the side of the store stacked with the overfill. Brattle has been fueling Boston’s literary curiosities since 1825, and the current proprietor, Kenneth Gloss, is a past president of the Antiquarian Booksellers' Association and sits on the Boston Public Library’s board. Not only is he a man who loves a good book, but Gloss knows his stuff. So much of the pleasure of finding yourself in an independent bookstore is spending an hour or two getting lost among the titles and maybe sitting down with a bundle of books on your lap reading some, discarding others. Brattle regularly hosts readings and literary events, enthusiastically attended by this university city’s more erudite crowd.

Located in the same building that was once Locke-Ober (one of Boston’s oldest restaurants dating to the 1870s), Yvonne's is a supper club and whiskey bar with the most glamorous, over-the-top opulent decor in the city. The walls are done in dark Dominican mahogany and jewel-toned wallpaper, the bar—a long marble slab—is tricked out in crystal, brass, and gold accessories, decadent chandeliers hanging from the ceilings. The menu has a Mediterranean bent with giant bean hummus, chicken & quinoa meatballs, and crispy tuna. Reservations are necessary, but the pro move is to come for a nightcap on a weeknight, when the crowds are thin, leaving more room to sip a whiskey at the bar or in the library room.

A long, narrow, galley enclosed by brick walls sounds a little…bare-bones. But the smooth walnut counters and softly muted lighting give O Ya, a former firehouse, a seductive, intimate vibe. Come with a friend or lover and ask for a seat at the counter. Chef and owner Tim Cushman is one of those multihyphenate creative types: a music graduate turned chef who spent years in Europe and Asia before opening a Japanese-style restaurant in Boston. The menu is not strictly traditional—the sushi, sashimi, and sides are certainly rooted in the Japanese tradition but are finished with Cushman’s gone-rogue flair. The menu is divided into nigiri, sashimi, truffles and eggs, and other unexpected pairings to give an idea of the breadth. For a taste of (almost) everything, order the seventeen-course omakase menu. For a more considered meal, choose a few plates off the à la carte menu and be sure to include the legs and eggs (teeny, meaty lobster legs dotted with white sturgeon caviar) and the completely unexpected (in a Japanese restaurant anyway) tea-brined pork ribs caramelized with hot sesame oil and sweet honey.

Right on the water in scenic Rowes Wharf, this hotel manages to give a subtle nod to Boston’s colonial past by way of décor—heavy, dark wood, a billowing American flag in the lobby, and windows overlooking the harbor in practically every room. Guest rooms are traditional and comfortable, with blue accents underscoring the hotel’s proximity to the sea. Even the rooms that don’t overlook the harbor have a great view (of the city skyline), and the deep tubs are a welcome relief after long days of historical sightseeing. Summer is the season to visit, as the location is right by the Rose Kennedy Greenway, a lush green space with flower gardens and water fixtures perfect for an early beat-the-summer-heat run, and the hotel hosts live music and movie screenings on its deck. Conveniently, guests have the option to avoid the traffic and take a scenic water taxi to the hotel’s marina from Logan airport.

Housed in a prerevolutionary building and open since 1826, Union Oyster House is a little touristy but it makes sense why: It’s iconic Boston, and the clam chowder is out of this world. Go at least once—it’s located on the Freedom Trail so you can stop in along your walk. Bonus: It’s also steps from the famous New England Aquarium (which is right on the water), where littles can check out a multistory tank, a gorgeous penguin sanctuary, and get up close and personal with seals.

This cheery little spot is right next door to city hall, meaning that it’s within striking distance of countless offices come lunchtime. Founder Kyle actually started the business when his wife, Lydia, was diagnosed with breast cancer and their doctor recommended trying out a “plant-packed” diet for her recovery. There’s a lot going on here—a juice bar with multiple-day meal plans, made-to-order smoothies and lunches, and a cooler stocked with premade meals. Everything is fresh, organic, vegan, and non-GMO; fan favorites include the chia seed pudding and quinoa sliders.

Ogawa coffee is a big deal in Japan, and this outpost is the company's first stab at bringing its traditions to the United States. The shop has a distinctly Japanese feel—bright, minimalist décor that's really peaceful and dotted with sleek white benches and tables. Haruna Murayama, a legend from the World Latte Art Championships (who knew?) is in charge, and the latte art here is seriously next-level—ask for flowers or her awesome bears.