12 Secrets for seeing Boston the un-touristy way

There are hundreds of fantastic reasons to be a tourist in Boston, from famous colonial landmarks like the Freedom Trail to legendary Fenway Park to some of the world’s most respected arts and cultural institutions, all of them popular and deserving of their must-see status. And then, there are the hidden gems. They’re fewer in number but well worth a jaunt off the beaten path in their own fascinating, quirky ways. Check out a dozen of our favorites:

Take in the spectacle of Spectacle Island

What was once a dumping ground for dirt from the city’s ‘Big Dig’ highway project is now a 105-acre island with one of the Harbor Islands’ only sand beaches and five miles of hiking trails. If you’re in town on a sunny day, hop the Boston Harbor Islands Ferry for the quick four-mile ride to Spectacle Island, where you’ll find a public park with a marina, visitor center, cafe, lifeguarded swimming beach, and – if you put in the legwork – spectacular views from the highest point in Boston Harbor.

Don’t overlook the Gardner. 

Despite its prime location in the Fenway neighborhood, the Isabella Stewart Gardner Museum is often missed by unwitting tourists heading straight for Museum of Fine Arts Boston. It’s the Paris version of visiting the Louvre and missing the Musée d’Orsay. The Gardner houses some of the most important European, Asian, and American art including painting, sculpture, tapestries, decorative arts and thousands of archival objects from ancient Rome, Renaissance Italy, Medieval Europe, the Islamic world, Asia, and 19th-century France. Famous paintings on view include works by Titian, Rembrandt, Botticelli, Sargent, Manet, Whistler, and Degas. A stunning example of Italianate palazzo architecture, the Gardner itself is a work of art with a gorgeous courtyard worth exploring in its own right. Art history trivia: The Gardner is the site of the largest art heist in history.

Stroll the South End.

The largest urban Victorian neighborhood in the country is now one of Boston’s loveliest, liveliest, and most culturally diverse neighborhoods. The historically rich area is lined with restored Victorian row houses and quaint English-style squares that share the streets with trendy restaurants, family-friendly eateries, gay bars, quiet pubs, and cool boutiques. The South End is also home to SoWa Art & Design District warehouse galleries, studios, and home decor shops. If you’re there on a Sunday between May and October, be sure to hit the SoWa Open Market for fresh unique food, crafts, and live music. 

See the skyline from a schooner.

The tourist traffic along the Boston waterfront can get pretty packed, and taking in the city skyline from the shore can put a class-A kink in your neck. The best way to take it all in is from the water, and the best time to do it is at sunset. Several companies offer sunset sails on historic 125-foot-tall schooners. Unwind with a drink (or pitch in and help the crew with the sails) while you clock highlights like the Boston Harbor Islands, the U.S.S. Constitution, and Fort Independence as the sun sets on the city.

Stand in the middle of the world at the Mapparium.

One of the most bizarre and intriguing places in Boston is the Mapparium at the Mary Baker Eddy Library. It’s a 3-D, three-story inverted globe built of 608 brightly hued stained-glass panels in 1935. Take the 30-foot glass walkway running through the center of the globe and then look up to find yourself in the middle of the world – or at least the world as it looked in the 1930s. Have fun spotting historic differences in the map and playing with the Mapparium’s extraordinary acoustics: Stand directly under the North Star and hear your own voice in surround sound, then move on to the far end of the walkway and whisper to a friend on the opposite side – they’ll hear you perfectly. LED lights and music have since been added to the structure, making its mesmerizing effects even stronger. 

Browse used books at Brattle Book Shop.

Independent bookstores are scarce these days, but Brattle Book Shop is one of the largest and oldest in the U.S., in operation for almost 200 years. Its three-story building in the heart of downtown Boston offers a colossal selection of books, maps, prints, postcards, and ephemera on all subjects, as well as general and out-of-print titles, first editions, collectibles, and a rare book room. Brattle’s also has an outdoor lot where prices start at $1 – just imagine the literary bargains you could unearth! You may have spotted proprietor Ken Gloss on Antiques Roadshow; he’s a past President of the Antiquarian Booksellers Association of America’s New England Chapter and gives fascinating talks throughout the Boston area; check the store’s website for his schedule.

Paddle the Charles

For some of the best views of the Boston skyline (and bonus views of Cambridge on the opposite side) ditch the harbor tours and get out on the Charles River under your own steam. There are many places along the river to rent single or double kayaks and SUPs; one of the easiest to access is Community Boating, located just a quick walk along the Charles River Esplanade from the Charles/MGH T stop. Spend a couple of careless hours paddling around between the Mass Ave. and Longfellow Bridges, watching runners along the river trail, enjoying views of in-city parks, and taking in sights such as Boston’s iconic Hatch Shell.

Eat real in Chinatown.

Boston’s Chinatown is the third largest in the U.S., the only remaining Chinatown in New England, and the cultural heart of the Chinese community here. You could spend hours exploring narrow streets full of gift shops, food markets and happening late-night clubs, but one of the best reasons to visit is the dozens of dumpling houses and dim sum palaces serving authentic Chinese cuisine. Local favorites include Bubor Cha Cha, China Pearl, and Winsor Dim Sum Cafe. You’ll know you’re there when you reach Chinatown Gate and Chinatown Park, which features a river-inspired fountain, native Asian plantings, and a public square popular with local chess players.

Search for Bodega.

Newbury Guest House’s Back Bay neighborhood conceals a secret retail venue – if you can find it. Past the cluttered racks of chips, cup noodles and soda at a certain Clearway Street convenience store, you’ll find an obsolete Snapple vending machine. Or is it a secret door? If it is, you might find Bodega behind it. The store opened in 2006 and offers shoes, clothing, jackets, beanies, jewelry, and watches from some of the most coveted streetwear brands around. What to know: The staff is cool and polite; taking pictures inside Bodega is neither.

Commune with the departed.

Boston is home to 16 historic cemeteries, the oldest of which is located at King’s Chapel and dates from 1630. One of its most famous denizens is Boston shopkeeper Joseph Tapping (1655-1678), whose gravestone serves as a memento mori for visitors with artwork featuring a winged skull and draining hourglass. You’ll find Boston’s two other oldest burying grounds at Copp’s Hill (1659) and Granary (1660), and they’re worth visiting for the artwork and text on the gravestones alone. If you visit in autumn, don’t miss the arboretum at Forest Hills, one of the most beautiful garden cemeteries in the nation. Bring a picnic, even. It’s peaceful, and the company isn’t noisy.

Visit the Ether Dome – it’s painless.

In 1846, Boston dentist William Thomas Green Morton successfully conducted the first public surgery using ether as an anesthetic in what’s become known as the Ether Dome at Massachusetts General Hospital. Thousands of operations were performed in this elegant, light-filled amphitheater between hospital’s inauguration in 1821 until 1868; today it’s a historical landmark that still serves as a teaching theater. Aside from the building itself – an architectural gem – you can view an Egyptian mummy, an odd collection of artifacts, early surgical tools, and an oil painting of that first operation that doesn’t spare the bloody details.

Brave the Old Bear Dens.

When the Franklin Park Zoo opened in 1912, millions of people flocked to see its wild bears. Frederick Law Olmsted, the park’s original landscape designer, intended it to be a zoological garden and a naturalistic area for native animals. The zoo closed in 1954, but the massive open-air enclosures where the giant bears lived are still intact today, reachable by a woodland path off Playstead Road in an obscure corner of the park. Why go? The abandoned bear pools and rusted iron stonework are still impressive and offer a rather eerie glimpse back to Olmstead’s original vision and what zoos were in the early 20th century; and the main cage features a remarkably large and detailed engraving of two bears holding the 1912 City of Boston seal aloft. The cages are rusted, spooky, creaky, and for some reason, still accessible to visitors. The Old Bear Dens have become a Halloween season favorite of photographers and filmmakers.

Like all great cities, Boston is full of surprising under-the-radar destinations, and the more you dive in, the more you discover. If you book a stay with us at Newbury Guest House, you’ve already chosen the best way to experience town like an insider, so why not explore it like one? These 12 attractions are easily reached from Newbury Guest House, and our staff is happy to provide directions, and suggest even more on-the-DL destinations.