FOOD
Levain Bakery
180 Newbury St. Boston, MA
Neighborhood: Back Bay
Audience: families, locals
You may have noticed the lines waiting to get into this new bakery on Newbury Street. Trust us, the cookies are worth the wait.
OUTDOORS
Rum, Riots, Writers & Revolution Tour
Park Street MBTA station, Boston, MA
Neighborhood: Beacon Hill
Audience: couples, locals, tourists
You’ll hear fun and astonishing stories on this one mile or so romp through downtown, peppered with secret lore, including the location of JFK’s love nest, the crimes of Charles Ponzi, and the escapades of Mayor James Michael Curley, who served the first five months of his term from a jail cell.
SHOPPING
The bodega that hides a sneaker store
6 Clearway Street Boston, MA
Neighborhood: Back Bay
Audience: locals, tourists
Ho-hum, it’s just another convenience store, with dusty candy bars, random foodstuffs of uncertain vintage, and household items. Or is it? This “store” has a secret portal (we won’t reveal it here) that leads to the real store, a super-sleek sneaker and streetwear boutique.
FOOD
A speakeasy tucked beneath a pastry shop
263 Hanover Street Boston, MA
Neighborhood: North End
Audience: locals, couples
Modern Pastry is a North End landmark. Then there’s Modern Underground, its semi-secret basement lair. Enter the pastry shop, hustle past all the patrons waiting in line, and take the stairway to the right. You’ll descend to a 40-seat lounge with multiple TVs (tuned to local sports, naturally), a speakeasy vibe, and killer martinis.
OUTDOORS
The bear dens at Franklin Park
1 Franklin Park Rd., Boston, MA
Neighborhood: Roxbury
Audience: families, locals, tourists
Designed by Frederick Law Olmsted in the 1890s, 527-acre Franklin Park is the city’s geographical center and its largest open space. The park is home to playing fields, a golf course, and the Franklin Park Zoo. Surprise: there are also vestiges of zoo inhabitants long-gone, like a bear house that was one of the zoo’s first exhibits. All that stands now are ghostly dens and cages. The site is located within Long Crouch Woods, a 26-acre woodland that sits above Seaver Street in Roxbury.
FOOD
Fab city views and a cheap ferry
1 8th St, Charlestown, MA
Neighborhood: Charlestown
Audience: families, couples, locals, tourists
For the best views of Boston bar none, head to Charlestown’s Pier 6 restaurant, jutting over the harbor at the end of 8th Street in the Charlestown Navy Yard. Floor-to-ceiling glass doors and windows offer expansive vistas of the city skyline. But the best seats in the house are on the roof deck and the outdoor patio.
OUTDOORS
The sweetest-smelling spot in the city
70 Park Dr., Boston, MA
Neighborhood: Back Bay Fens
Audience: families, couples, locals, tourists
Public rose gardens were all the rage in the early 1900s. Boston has a blooming beauty of its own in the Back Bay Fens, the James P. Kelleher Rose Garden. Part of the Emerald Necklace, the garden consists of 200 different varieties of roses with almost 1,500 roses in total.
OUTDOORS
Underground Donut Tour
90 Oliver St, Boston
Neighborhood: Financial District, North End
Audience: families, tourists
You’ll join a small group of up to 20 fellow pastry lovers (private tours are also available) on a two-hour jaunt to four of Boston’s top donut makers. Tastings are generous, between five and seven different flavors on each tour.
OUTDOORS
Beacon Hill Crime Tour
Park Street MBTA station, Boston, MA
Neighborhood: Beacon Hill
Audience: locals, couples, tourists
Beacon Hill may be posh and beautiful, but it doesn’t have such a pretty history. This was killing grounds for the Boston Strangler; two of his victims were found here. You’ll hear more stories of sordid crime and punishment on this two-hour walk through one of Boston’s most exclusive neighborhoods.
OUTDOORS
Boston Ghosts Tour
139 Tremont St., Boston, MA
Neighborhood: Downtown
Audience: tourists, couples, locals
This fun-loving tour dredges up stories of misery and death in Beantown, and the city’s lingering not always happy spirits. You’ll visit six to 12 haunted locations, covering about a mile and lasting about one hour.
OUTDOORS
North End Pizza Tour
191 Hanover St, Boston, MA
Neighborhood: North End
Audience: tourists, couples, locals
Thin crust, thick crust, triangles and squares, any way you slice it, this tour is two-and-a-half hours of deliciousness. You’ll head to Little Italy and the North End, home to Boston’s most celebrated, award-winning pizza. The tour includes stops at three different pizzerias, each offering a unique style and ambiance.
OUTDOORS
Fenway Park Tour
4 Jersey St, Boston, MA
Neighborhood: Fenway
Audience: families, tourists, locals
Do you know the story behind the lone red seat at Fenway Park? We didn’t until we took this fun-for-all, behind-the-scenes tour of “America’s Most Beloved Ballpark.” Even if you’re not a lover of history or trivia (or a baseball fan), you’ll enjoy this one-hour guided visit that includes a look inside the press box, a stop atop the legendary Green Monster, and lots of stories and facts about Red Sox greats.
FOOD
Gate Comme Des Filles
1 Bow Mkt Wy, Somerville, MA
Neighborhood: Union Square
Audience: families, locals
Pastry chef Alexandra Whisnant is whipping up decadent desserts and beauteous bonbons at a tiny shop at Bow Market. We fell hard for the cocoa waffle cone filled with the best chocolate mousse ever. Grab two tiny spoons and a seat at the outdoor bistro table and prepare for a dizzying jolt of pure chocolate joy.
FOOD
Serenade Chocolatier
5 Harvard Square, Brookline, MA
Neighborhood: Brookline
Audience: families, locals
These locally-sourced chocolates are vegan-friendly, gluten-free (except for the pretzels), and insanely delish.
FOOD
Flour Bakery
1596 Washington St., Boston, MA
Neighborhood: South End
Audience: families, locals
James Beard Award-winning baker/cookbook author Joanne Chang and husband Christopher Myers now own and operate nine outposts of Flour Bakery in Boston and Cambridge, proof that dessert-eating is alive and well in the ‘hood.
FOOD
Mike’s Pastry
300 Hanover St., Boston, MA
Neighborhood: North End
Audience: families, locals
The long lines! The white-and-blue pastry box, tied with string! Bostonians have been loving Mike’s since 1946. Among the dozen-plus flavors of cannoli available ($5 each), chocoholics swear that nothing beats the chocolate-coated cannoli with its signature chocolate-coated shell.
FOOD
FoMu
617 Centre St., Boston, MA
Neighborhood: Jamaica Plain
Audience: families, locals
Vegans know FoMu—this plant-based ice cream is made from scratch in Watertown, using coconut milk and organic natural sweeteners, churned to a creamy, gelato-like consistency. Yum. What you may not know: They also bake their own plant-based chocolate-chip brownies, magic bars, and cookies.
FOOD
Bostonia Public House
131 State St, Boston MA
Neighborhood: Financial District
Audience: locals, tourists, couples
Set within the old (c.1902) Board of Trade building in the Financial District, this upscale bar does a dandy brunch. It can get noisy, so don’t plan on a cozy tete’ a tete. Most likely, you’ll be sharing food, not confidences, anyway; portions are generous.
FOOD
Contessa
3 Newbury St Rooftop, Boston, MA
Neighborhood: Back Bay
Audience: locals, couples
Opened last June on the 17th floor rooftop of the Newbury Hotel (aka the old Ritz), Contessa arrived with plenty of fanfare, and a pedigree: The restaurant is operated by Major Food Group, co-founded by chef Mario Carbone of Michelin-starred Carbone in New York City. Elegant and impeccable are apt descriptors.
FOOD
Darryl’s Corner Bar & Kitchen
604 Columbus Ave, Boston, MA
Neighborhood: South End, Roxbury
Audience: locals, couples
What makes brunch go down as easy as a sweet tea mojito? We’d say a side of live music. That’s what you’ll find at DCBK’s Sunday Jazz and Soul Food Brunch. The all-you-can eat brunch buffet on Sundays (adults, $25.95 per person) features Southern staples like fried chicken and catfish, cheddar grits, BBQ spare ribs, dirty rice and collard greens.
FOOD
Lincoln Tavern & Restaurant
425 W Broadway, South Boston, MA
Neighborhood: South Boston
Audience: locals, couples, families
With its long bar, brick walls, and industrial vibe, this South Boston hotspot has a grown-up vibe, but families fill the booths on weekends. Brunch is so popular here that they offer it seven days a week.
FOOD
North Street Grille
229 North St, Boston, MA
Neighborhood: North End
Audience: locals, couples
Shoehorn your party into this little place near the Paul Revere House and dig into what the owner Robin Sidell and her team shamelessly call the best brunch in Boston. There’s not a lot of elbow room here, but all is forgiven when you dig into plates of gooey deliciousness.
FOOD
James Hook & Co.
440 Atlantic Ave, Boston, MA
Neighborhood: Financial District
Audience: locals, tourists, families
This waterfront landmark has been around since 1925 and is still family owned by four siblings of the third generation of the Hook family. It’s one of our go-to places in the city for seafood (if we can find a seat.)
FOOD
Boston Chowda Co.
1 Faneuil Hall Market Pl., Boston, MA
Neighborhood: Faneuil Hall
Audience: tourists, families
Family-owned Boston Chowda has been serving their version of clam chowder for more than 25 years. Enjoy the creamy broth with a generous helping of fresh clams. Lobster rolls served cold with a touch of mayo is another go-to.
FOOD
Union Oyster House
41 Union St, Boston, MA
Neighborhood: Faneuil Hall
Audience: tourists, families
Boston’s oldest restaurant and a National Historic Landmark. The rambling restaurant, housed in a building dating back to pre-Revolutionary times, is filled with antiques and memorabilia. We sampled raw Wellfleet and Patriot oysters, along with cups of their award-winning chowder.
ENTERTAINMENT
The Mapparium in the Mary Baker Eddy Library
210 Massachusetts Ave, Boston, MA
Neighborhood: Back Bay
Audience: tourists, families, couples
The Mapparium in the Mary Baker Eddy Library is itself a sight to behold. The stained glass dome splotched with brightly colored continents sits like a gem in the city’s jewelry box.
OUTDOORS
Fenway Park
4 Jersey St, Boston, MA
Neighborhood: Fenway
Audience: tourists, families, couples
This spot is a Globe staffer’s favorite.
OUTDOORS
The dog park in the Boston Common
115 Boylston St, Boston, MA
Neighborhood: Downtown
Audience: locals, families, tourists
This spot is a Globe staffer’s favorite.
ENTERTAINMENT
The Cantab Lounge
738 Massachusetts Ave, Cambridge, MA
Neighborhood: Central Square
Audience: locals, couples
This spot is a Globe staffer’s favorite.
SHOPPING
Central Square Farmers Market
76 Bishop Allen Dr, Cambridge, MA
Neighborhood: Central Square
Audience: locals, families, couples
This spot is a Globe staffer’s favorite.
OUTDOORS
The Rose Kennedy Greenway
Atlantic Ave, Boston, MA
Neighborhood: Downtown
Audience: locals, families, couples
This spot is a Globe staffer’s favorite.
OUTDOORS
Mount Auburn Cemetery
580 Mt Auburn St, Cambridge
Neighborhood: Cambridge
Audience: locals, families, couples
This spot is a Globe staffer’s favorite.
OUTDOORS
The wind chimes on Beacon Hill
94 W Cedar St, Boston
Neighborhood: Beacon Hill
Audience: locals
This spot is a Globe staffer’s favorite.
OUTDOORS
The park at Post Office Square
Franklin St, Boston, MA
Neighborhood: Financial District
Audience: locals, families, tourists
This spot is a Globe staffer’s favorite.
OUTDOORS
The Longfellow Bridge
Boston, MA 02114
Neighborhood: Kendall Square, Downtown
Audience: locals, couples
This spot is a Globe staffer’s favorite.
ENTERTAINMENT
The Museum of Fine Arts
465 Huntington Ave, Boston, MA
Neighborhood: Fenway
Audience: families, locals, tourists
The Museum of Fine Arts, Boston’s airy, Norman Foster-designed central atrium is largely occupied by the New American Café, its semiformal, table-service eatery. One floor down, one of the very best urban spaces in town has a more down-market entry point. Through the self-serve cafeteria on the lower level, you’ll find the museum’s internal courtyard, a space crawling with ivy and draped with leafy boughs that dapple the handful of cafe tables here with sun and shade.
OUTDOORS
The Institute of Contemporary Art Boston's stadium seats
25 Harbor Shore Dr, Boston, MA
Neighborhood: Seaport
Audience: families, locals, tourists
The ICA building performs a remarkable public service: Its ascending swath of stadium seats — all in shade, under the canopy of the building’s overhang — face Boston Harbor and East Boston beyond, making for a cool respite with a view, complete with a sea breeze. It’s an ideal spot to unpack takeout from any of the many options all around the museum; or to read a book; or to just gather strength for the evening, which is when the Seaport comes to most boisterous life.
ENTERTAINMENT
Harvard Art Museums
32 Quincy St, Cambridge, MA
Neighborhood: Mid-Cambridge
Audience: families, locals, tourists
Collections here enjoy room to breathe, and galleries are elegant and intuitive in terms of wayfinding. The entire building is organized around a soaring central courtyard with a smattering of cafe tables, where students and locals alike study, work, or gab happily in a cool wash of daylight flooding in from above. It’s a natural gathering space and makes clear that for all the riches found on the walls, the most important element of any museum is the people who come to see it.
FOOD
Revolution Hotel
40 Berkeley St, Boston, MA
Neighborhood: South End
Audience: tourists
If you opt to stay in Boston proper, rooms at the Revolution Hotel in the South End, located in a former YWCA, can be had for under $200 a night. Be warned, some of these rooms have bathrooms down the hall. You’ll pay slightly more for a room with a bathroom inside your room. Otherwise, it’s a well-designed, hip hotel.
FOOD
The Godfrey
505 Washington St, Boston, MA
Neighborhood: Downtown Crossing
Audience: tourists
The Godfrey, a very natty boutique hotel in Downtown Crossing, can be reserved for under $200 a night in the off-season.
FOOD
The Sonder 907
907 Main St, Cambridge, MA
Neighborhood: Central Square
Audience: tourists
For a cross between a hotel and an Airbnb, try the Sonder 907 in Cambridge. It’s located in Central Square, a quick skip into the city, and near enough to Cambridge clubs and restaurants to keep you well-fed and thoroughly entertained.
FOOD
Hotel Commonwealth
500 Commonwealth Ave, Boston, MA
Neighborhood: Fenway
Audience: tourists
Hotel Commonwealth anchors the Fenway neighborhood and a $50 million makeover in 2017 imbued the rooms with a touch of 1960s/early 1970s glam. It’s a solid property for the money.
FOOD
Haymarket
Blackstone St, Boston, MA
Neighborhood: Downtown
Audience: locals, couples, families
Haymarket is the centuries-old fruit-and-veggie bazaar where a bounty of bok choy costs next to nothing. If you're a sucker for bargains, this spot is for you.
FOOD
The Langham Boston
250 Franklin St, Boston, MA
Neighborhood: Financial District
Audience: tourists
If you’re not worried about the price tag (lucky), book a room at the Langham Boston. The recently renovated hotel in the Financial District is an absolute gem. The kind of luxury hotel that has charm to spare.
SHOPPING
I AM Books
124 Salem St, Boston, MA
Neighborhood: North End
Audience: locals, couples, families, tourists
I AM Books is a small, independent bookshop well stocked with volumes of Italian literature, history, and art.
FOOD
The Newbury Boston
1 Newbury St, Boston, MA
Neighborhood: Back Bay
Audience: tourists
A new entry in luxury lodging is the Newbury in the Back Bay, located at one of the best addresses in the city with a beautiful roof-top restaurant.
FOOD
Anthony’s Cafe
252 Commercial St, Boston, MA
Neighborhood: North End
Audience: locals, couples, families, tourists
Try breakfast at Anthony's Cafe on the waterfront. The vibe is friendly and the coffee is hot.
FOOD
The Whitney Hotel
170 Charles St, Boston, MA
Neighborhood: Beacon Hill
Audience: tourists
The Whitney Hotel, a former nurses’ dormitory, is a favorite boutique hotel. If you’re already splurging on the Whitney, splurge and get a room with a river view.
FOOD
Paramount Cafe
667 E Broadway, Boston, MA
Neighborhood: South Boston
Audience: families, couples, locals, tourists
You can't go wrong with breakfast at the Paramount. Try the malted Belgian waffle with a side of maple ham.
OUTDOORS
Old South Meeting House
310 Washington St, Boston, MA
Neighborhood: Downtown
Audience: tourists, families
This is where Sam Adams held a meeting in December of 1773 which became an organizing point for the Boston Tea Party.
OUTDOORS
Boston Common
115 Boylston St, Boston, MA
Neighborhood: Downtown
Audience: families, couples, locals, tourists
Boston Common is often teeming with young moms pushing strollers, clumsy dogs chasing balls, and people dozing here and there on the lawn, occasionally serenaded by calliope music from a carousel near the Frog Pond that goes round and round between April and October.
FOOD
Blackbird Doughnuts
20 Kilmarnock St, Boston, MA
Neighborhood: Fenway
Audience: families, couples, locals, tourists
Swing by Blackbird Doughnuts (multiple locations throughout the city). The salted toffee donut comes highly recommended.
SHOPPING
Alan Bilzerian
34 Newbury St, Boston, MA 02116
Neighborhood: Back Bay
Audience: locals, tourists
Alan Bilzerian, the eponymous boutique full of inventive — and, yes, expensive — clothes for men and women, has dressed the likes of Madonna, Carly Simon, and David Bowie.
SHOPPING
CBD American Shaman
227 Newbury St A, Boston, MA
Neighborhood: Back Bay
Audience: locals, tourists
A colorful sign in a window may entice you: Free CBD. The store, called CBD American Shaman, is a Kansas City-based chain whose mission is “bringing wellness to the world.”
FOOD
Anna's Handcut Donuts
2056 Centre St, Boston, MA
Neighborhood: West Roxbury
Audience: families, couples, locals, tourists
If you’re willing to go the extra mile and hop in an Uber or venture on public transit, Anna’s Handcut Donuts in West Roxbury is a solid stand-by.
ENTERTAINMENT
Boston Public Library
700 Boylston St, Boston, MA
Neighborhood: Back Bay
Audience: locals, tourists, families, couples
Have you looked at this place? Talk about public art. What a marvel. The lobby alone, with its Georgia marble floor and vaulted ceiling clad by Italian immigrant craftsmen in mosaic tile is spectacular.
OUTDOORS
Boston Harborwalk
Seaport District, Boston, MA
Neighborhood: Seaport
Audience: tourists, couples, locals
The Boston Harborwalk is a great place to get your bearings in the Seaport District and downtown Boston. The architecture in this neighborhood looks like an office park in Houston, and the shops and restaurants scream “Lifestyle center!,” but the water views are what matter, and there are many places to sit and be mesmerized by the harbor. Oh, and leave the stilettos at home. There are cobblestones and wooden walkways along this route.
ENTERTAINMENT
ICA Watershed
256 Marginal St, Boston, MA
Neighborhood: Jeffries Point
Audience: tourists, families
One of the best (seasonal) boat rides in town is the quick ICA shuttle to its East Boston Watershed (beginning May 26 this year). This summer, the Watershed, a once-abandoned industrial space, features the large scale show Revival Materials and Monumental Forms. On a beautiful day you can buzz across the harbor with the wind whipping in your hair from the Seaport to the East Boston and see some very cool art on the other side.
FOOD
Rincon Limeño
409 Chelsea St, Boston, MA
Neighborhood: East Boston
Audience: tourists, locals
The essential lunch (or dinner) location in Day Square is Rincon Lomeño. Order tapas, and save some room for ice cream at the nearby Frío Rico.
FOOD
Santarpio's Pizza
111 Chelsea St, Boston, MA
Neighborhood: Jeffries Point
Audience: tourists, locals
If you prefer an East Boston institution, Santarpio’s Pizza is always reliable. Hint: The lamb skewers are better than the pizza, but don’t tell anyone. If you go, check above the end of the bar furthest from the door for a photo of JFK campaigning outside the restaurant (the family lived in Eastie before their more famous house in Brookline).
OUTDOORS
Madonna Queen of the Universe National Shrine
150 Orient Ave, Boston, MA
Neighborhood: Orient Heights
Audience: tourists, families
The 40-foot Madonna Queen of the Universe Shrine along the Greenway is probably the best spot in Boston to watch planes take of and land.
FOOD
Anchovies
433 Columbus Ave, Boston, MA
Neighborhood: South End
Audience: tourists, couples, locals
It’s a neighborhood dive bar. It’s a super-affordable Italian restaurant. It’s a reminder of a time when the South End was quirkier, gayer, artier.
FOOD
Belle Isle Seafood
1 Main St., Winthrop, MA
Neighborhood: Winthrop
Audience: tourists, locals, families, couples
In Winthrop, this casual, cash-only restaurant/fish market is one of the best places to eat seafood in proximity to the city.
FOOD
Shojo
9a Tyler St., Boston, MA
Neighborhood: Chinatown
Audience: tourists, locals, couples
The Moy family has been making Chinatown delicious for more than 60 years. Its China Pearl, on Tyler Street, is a dim sum institution. On the ground floor of the building is Shojo, another family-owned business. Decorated with graffiti-inspired art and blasting hip-hop, the restaurant serves current spins on traditional fare.
FOOD
The Banks Fish House
406 Stuart St., Boston, MA
Neighborhood: Back Bay
Audience: tourists, locals, couples, families
This is the kind of place you might celebrate a family occasion, take an out-of-town business client, or head for an upscale brunch. It is also a real-deal celebration of regional seafood.
FOOD
Dear Annie
1741 Massachusetts Ave., Cambridge, MA
Neighborhood: Porter Square
Audience: tourists, locals, couples
For anyone wondering where hospitality is headed, well, Dear Annie is too — so it’s here to try to learn by doing, maybe shaping one path toward an equitable industry that’s good for humans and the earth.
FOOD
Boston Public Market
100 Hanover St, Boston, MA
Neighborhood: Downtown
Audience: tourists, locals, families
If you’re not from these parts, the Boston Public Market is a great way to get a taste of the region with 30 local vendors.
FOOD
High Street Place
100 High St, Boston, MA
Neighborhood: Downtown
Audience: tourists, locals
At High Street Place you can find burgers, brews, sushi, and champagne. The beauty of High Street Place is you can take every meal of the day at the food hall if you’re too lazy to look around for restaurants. No judgement here. Currently High Street Place is not open on Sunday, so this is a Saturday destination.
FOOD
Tambo 22
22 Adams St., Chelsea, MA
Neighborhood: Chelsea
Audience: tourists, locals, couples
For 20 years, visionary chef Jose Duarte shared his love of Peruvian cuisine at Taranta, an Italian-Andean hybrid in the North End. Chelsea restaurant Tambo 22 is a natural next step. Opened just as the pandemic began, it deserves recognition, showcasing a more purely Peruvian cuisine and all manner of regional ingredients
OUTDOORS
Dillaway-Thomas House
183 Roxbury St, Boston, MA
Neighborhood: Roxbury
Audience: tourists, families
The state’s Department of Conservation and Recreation recently completed $3.6 million in renovations at the Dillaway-Thomas House, which is the oldest surviving house is Roxbury. The house served as the headquarters of Revolutionary War General John Thomas during the 1775 Siege of Boston. The history of the house begins with the Revolutionary War. Exhibits show the evolution of Roxbury from Malcolm X to Presidential Medal of the Arts recipient Elma Lewis.
OUTDOORS
Arnold Arboretum of Harvard University
125 Arborway, Boston, MA
Neighborhood: Jamaica Plain
Audience: tourists, families
It’s a botanical research institution and free public park which straddles Jamaica Plain and Roslindale. Established in 1872, it is the oldest public arboretum in North America.
OUTDOORS
Forest Hill Cemetery
95 Forest Hills Ave, Boston, MA
Neighborhood: Jamaica Plain
Audience: locals, families
The preferred nature preserve/cemetery in nearby Jamaica Plain is the 250-acre Forest Hill Cemetery. Unlike the Common and the Public Garden, you won’t find an accordionist playing “Lady of Spain” on a crowded pedestrian bridge, but you will find a very gothic quiet space.
OUTDOORS
Cambria Hotel Boston
6 W Broadway, Boston, MA
Neighborhood: D Street/West Broadway
Audience: couples, tourists
The roof deck bar and restaurant at the Cambria Hotel in South Boston offers a prime look at the South Boston dating scene, plus great views of Back Bay.
OUTDOORS
Blue Owl Rooftop Bar
907 Main St, Cambridge, MA
Neighborhood: Central Square
Audience: couples, tourists
If you want to step over the boarder to Cambridge, the Blue Owl has the only rooftop terrace and bar in town.
ENTERTAINMENT
Wally’s Cafe Jazz Club
427 Massachusetts Ave, Boston, MA
Neighborhood: South End
Audience: tourists, locals, couples
Swing by Wally’s Cafe Jazz Club (opening May 14) to hear Berklee College of Music students, and longtime musicians from the local scene. Get here early. It quickly fills up.
ENTERTAINMENT
Paradise Rock Club
967 Commonwealth Ave, Boston, MA
Neighborhood: Allston
Audience: tourists
The Paradise Rock Club draws in bands that strut on the border of mainstream and indie. Unlike the cavernous House Of Blues, which hosts the big names, the Paradise has acts such as Cat Power, Bleachers, and Callum Scott.
ENTERTAINMENT
The Grand Boston
58 Seaport Blvd #300, Boston, MA
Neighborhood: Seaport
Audience: tourists, locals, couples
The Grand in the Seaport District is the kind of club where Pauly D would DJ (and he has), along with big names such as Norway’s Kream. It’s all techno, EDM, champagne, and a 70-foot LED wall.
ENTERTAINMENT
Club Café
209 Columbus Ave, Boston, MA
Neighborhood: South End
Audience: couples, tourists, locals
Boston’s long-standing gay fav is Club Café, but if you’ve done your gay bar research you already know that.
ENTERTAINMENT
Blend
1310 Dorchester Ave, Boston, MA
Neighborhood: Dorchester
Audience: couples, tourists, locals
The crowd is a little more diverse at Blend in Dorchester (hence the name) and the dance floor is easier to navigate than Club Cafe.
ENTERTAINMENT
Cathedral Station
1222 Washington St, Boston, MA
Neighborhood: South End
Audience: couples, tourists, locals
Cathedral Station in the South End is a gay sports bar, but they have a fantastic patio area and... parking!
ENTERTAINMENT
Croke Park
268 W Broadway, Boston, MA
Neighborhood: D Street/West Broadway
Audience: tourists, locals
If you want an authentic Irish dive bar and a glimpse of what South Boston was like before the tsunami of gentrification swept in, go to Croke Park (also called Whitey’s, natch). From the outside the place is scary as heck, inside it’s a mix of hammered old-school locals, sassy bartenders, and beer-soaked everything.
SHOPPING
Harvard Book Store
1256 Massachusetts Ave, Cambridge, MA
Neighborhood: Harvard Square
Audience: tourists, locals, families
Harvard Book Store is a 90-year-old shop that stocks general interest titles and frequently hosts readings with well-known authors. Head to the basement to check out the troves of used books, plus the ephemera hanging from the walls.
SHOPPING
Grolier Poetry Book Shop
6 Plympton St, Cambridge, MA
Neighborhood: Harvard Square
Audience: tourists, locals, families
This rhymester’s paradise has sold volumes of verse for close to a century. Pick up a collection of poetry, check out a chapbook, or attend one of their readings.
SHOPPING
Porter Square Books
25 White St, Cambridge, MA
Neighborhood: Porter Square
Audience: tourists, locals, families
A quick jump on the Red Line brings you to the flagship location of Porter Square Books, where you can buy new releases, charming tchotchkes, or a surprise “book bundle” curated by a staff member.
SHOPPING
All She Wrote Books
451 Artisan Way, Somerville, MA
Neighborhood: Assembly Square
Audience: tourists, locals, families
Located in Somerville’s Assembly Row, All She Wrote Books is a one-stop-shop for titles by female, non-binary, and queer authors.
SHOPPING
More Than Words
242 E Berkeley St, Boston, MA
Neighborhood: South End
Audience: tourists, locals, families
This South End nonprofit is based on a unique model: it employs young people who have been court-involved, homeless, or living in the foster-care system, teaching them how to run a business. The spacious shop sells vinyl albums, jewelry, and books of all genres — as an added bonus, there’s plenty of seating to curl up with a good book (or a stack of them).
SHOPPING
Frugal Bookstore
47 Warren St, Boston, MA
Neighborhood: Roxbury
Audience: tourists, locals, families
Located in Roxbury, this Black-owned bookstore focuses on selling the works of writers of color. Browse antiracist literature of all stripes, from the well-known — “How to Be an Antiracist” by Ibram X. Kendi — to the just-released, like “Love and Justice: A Journey of Empowerment, Activism, and Embracing Black Beauty” by Laetitia Ky.
SHOPPING
Papercuts Bookshop
60 South St, Boston, MA
Neighborhood: Jamaica Plain
Audience: tourists, locals, families
This woman-owned Jamaica Plain spot, instantly recognizable by its pink-and-green exterior, might be the cutest bookshop in all of Boston — it’s stuffed to the brim with books, vintage-looking posters, and trinkets aplenty.
SHOPPING
Brookline Booksmith
279 Harvard St, Brookline, MA
Neighborhood: North Brookline
Audience: tourists, locals, families
Brookline Booksmith, a hop, skip, and a jump away from the Coolidge Corner stop on the Green Line, could double as a boutique. In 2020, the shop took over a 4,000-square-foot neighboring storefront, offering “Giftsmith” even more space to display kitchenware, art supplies, and accessories, like funny socks. Oh, yeah, the books are great, too.
SHOPPING
Trident Booksellers and Cafe
338 Newbury St, Boston, MA
Neighborhood: Back Bay
Audience: tourists, locals, families
This Newbury Street shop is open nightly until 10 p.m., making it the perfect spot for late-night browsing. Take your time checking out the two-floor book selection, grabbing a bite from the extensive cafe menu, and taking a peek at some of the zines and novelty items (”Burn the Patriarchy” candle, anyone?) Trident is also home to themed trivia nights, open mics, and writing groups (for those who want to see their name on a book’s spine someday).
SHOPPING
Brattle Book Shop
9 West St, Boston, MA
Neighborhood: Downtown
Audience: tourists, locals, families
Brattle Book Shop bills itself as one of the nation’s oldest antiquarian bookstores. Tucked into a downtown side street, the store often boasts racks of bargain books on display in an outside lot. Inside, treasures await: sprawling shelves, a rare book room, and staff who will decorate your home office with leather-bound beauties (no, really).
ENTERTAINMENT
The Brattle
40 Brattle St, Cambridge, MA
Neighborhood: Harvard Square
Audience: tourists, locals, families, couples
The Brattle, which opened in 1890, spent most of its first six decades as a playhouse. The switch to movies came in 1953. The Brattle became one of America’s first arthouses, with programming that emphasized foreign films and revivals. The Brattle has just one screen.
ENTERTAINMENT
Coolidge Corner Theatre
290 Harvard St, Brookline, MA
Neighborhood: North Brookline
Audience: tourists, locals, families, couples
The Coolidge wasn’t converted to a theater until 1933, and what a theater. Even today, with parts of the original space sliced off to make room for the other screens, the main auditorium remains an Art Deco monument to moviegoing splendor. The gleaming metal bas-reliefs above the proscenium arch are pure ‘30s swank. To sit in one of the main theater’s 700 seats is to be transported to big screen heaven.
ENTERTAINMENT
Somerville Theatre
55 David Sq, Somerville, MA
Neighborhood: Davis Square
Audience: tourists, locals, families, couples
The Somerville Theatre remains a commercial operation, along with its sister theater, the Capitol, in Arlington. The Somerville has three screens. The main auditorium seats 900, a size that’s made it a popular concert venue. Last fall, it added to its concert schedule, opening a 500-person performance space, the Crystal Ballroom.
ENTERTAINMENT
Symphony Hall
301 Massachusetts Ave, Boston, MA
Neighborhood: Back Bay
Audience: tourists, locals, families, couples
Even more iconic, for some, than Fenway Park, Symphony Hall is the home of the Boston Symphony Orchestra and the Boston Pops. It is world-renowned for its superlative acoustics, and it is the symbolic heart of the city’s musical life.
FOOD
Delux Cafe
100 Chandler St., Boston, MA
Neighborhood: South End
Audience: couples
Delux is a restaurant in the South End that’s pretty small with a comfort food menu. The food is tasty, but the best part is the restaurant’s walls, which are covered with albums and tributes to Elvis.
OUTDOORS
Arnold Arboretum
125 Arborway, Boston, MA
Neighborhood: Jamaica Plain
Audience: couples
The Arboretum – a 281-acre park and botanical research spot run by Harvard – is not a thing downtown destination, so perhaps a lot of visitors skip it. But it’s worth finding, and in May there are lilac tours.
ENTERTAINMENT
Charles/MGH station on the Red Line
Cambridge St and Charles St, Boston, MA
Neighborhood: Beacon Hill
Audience: couples
Yes, this is public transportation – some would say a means of travel, as opposed to a destination. But the view over the Charles River is sweet, and for pop culture fans, it’s all about
ENTERTAINMENT
Koch Institute Public Galleries
500 Main St., Cambridge, MA
Neighborhood: Kendall Square
Audience: couples
It’s a collection of biomedical images – art inspired by research. You can go inside during the day (check in before you go; rules change, these days), but at night, the large round cell art is beautiful and sometimes devastating, especially when you read the labels that explain them.
FOOD
Taza Chocolate Factory
561 Windsor St., Somerville, MA
Neighborhood: Ward Two
Audience: couples
The Taza Chocolate Factory includes samples, and the building is in a part of Somerville you might otherwise not see.
FOOD
George Howell Coffee
505 Washington St., Boston, MA
Neighborhood: Downtown
Audience: locals
This spot is a Globe staffer’s favorite.
FOOD
Thinking Cup
165 Tremont St, Boston, MA
Neighborhood: Downtown
Audience: locals
This spot is a Globe staffer’s favorite.
FOOD
The Chinatown Gate
John F Fitzgerald Surface Rd &, Beach St, Boston, MA
Neighborhood: Chinatown
Audience: locals, tourists
This spot is a Globe staffer’s favorite.
FOOD
Winsor Dim Sum Café
10 Tyler St, Boston, MA
Neighborhood: Chinatown
Audience: locals, tourists
This spot is a Globe staffer’s favorite.
OUTDOORS
Arnold Arboretum
125 Arborway, Boston, MA
Neighborhood: Jamaica Plain
Audience: locals, tourists, couples, families
This spot is a Globe staffer’s favorite.
FOOD
Jaho Coffee Roaster & Wine Bar
665 Washington St, Boston, MA
Neighborhood: Downtown
Audience: locals
This spot is a Globe staffer’s favorite.
OUTDOORS
The Boston Harbor Islands
Boston Harbor, MA
Neighborhood: Boston Harbor
Audience: locals, tourists, families, couples
This spot is a Globe staffer’s favorite.
FOOD
The Barking Crab
88 Sleeper St, Boston, MA
Neighborhood: Seaport
Audience: locals, tourists
Since 1994 the Barking Crab has been a classic Seaport restaurant for seafood lovers. Go for the lobster rolls, and ask for Jared at the bar.
FOOD
Boston Harbor Hotel
70 Rowes Wharf, Boston, MA
Neighborhood: Waterfront
Audience: tourists
There's nothing like having a view of the Boston Harbor, and the Boston Harbor Hotel offers just that. If you’re thirsty by the time you get to the hotel (it’s booze o’clock somewhere!), it boasts one of the top hotel bars in the world (according to Forbes), the Rowes Wharf Bar.
ENTERTAINMENT
Boston Children's Museum
308 Congress St, Boston, MA
Neighborhood: Fort Point
Audience: families
Indulge your precious ankle biters and tiny humans in strollers with a stop at the Boston Children’s Museum along the Harbor Walk. They've got a multitute of exhibits and events that are sure to excite your little ones.
OUTDOORS
East Boston Greenway
East Boston, MA
Neighborhood: Jeffries Point
Audience: tourists, families
Visit the East Boston Greenway for some of the city’s best views. It includes Piers Park, Bremen Street Park, Memorial Park, and Constitution Beach. The 40-foot Madonna Queen of the Universe Shrine along the Greenway is probably the best spot in Boston to watch planes take off and land.
SHOPPING
SoWa Open Market
500 Harrison Ave, Boston, MA
Neighborhood: SoWa
Audience: tourists, locals
For half the year, the SoWa Open Market opens every Sunday from 11 a.m. to 4 p.m. More than 100 local artisans sell soap, jewelry, T-shirts, art, honey, and other goodies. There are also DJs and a farmers’ market.
SHOPPING
SoWa Vintage Market
450 Harrison Ave, Boston, MA
Neighborhood: SoWa
Audience: tourists, locals
Unlike the Open Market, the SoWa Vintage Market is open year-round, with vintage tretures ranging from art to fashion to jewelry.
OUTDOORS
Paddle Boston
1071 Soldiers Field Rd, Boston, MA
Neighborhood: Lower Allston
Audience: families, tourists, couples
Paddle Boston has locations throughout Boston and nearby towns and suburbs that allow you to explore the Charles. The nine-mile stretch of river has no current and gives you a water view of local colleges, the Esplanade, and the Boston skyline.
ENTERTAINMENT
John F. Kennedy Presidential Library and Museum
Columbia Point, Boston, MA
Neighborhood: Dorchester
Audience: tourists, families
The John F. Kennedy Presidential Library and Museum on Columbia Point in Dorchester gives an in-depth look at the tragically-short presidency of JFK. The current exhibition in the museum (through Jan. 8, 2023) is “First Children: Caroline and John Jr. in the Kennedy White House.” It features gifts sent to the Kennedy children by both heads of state and the public at large and memos that reveal their mother’s efforts to balance media access and privacy. There are also permanent exhibits looking at the US Space Program and Jacqueline Kennedy’s life.
OUTDOORS
South Boston beaches
South Boston, MA
Neighborhood: South Boston
Audience: tourists, families
On warm days, the South Boston beaches are packed with beach-goers. Be sure to walk down to Castle Island and circle Fort Independence. On breezy days you’ll see Pleasure Bay full of windsurfers. It's always a good idea to make a stop at Sullivan’s Castle Island for some fried clams.
OUTDOORS
Commonwealth Avenue Mall
484 Commonwealth Ave, Boston, MA
Neighborhood: Back Bay
Audience: tourists, families
The Commonwealth Avenue Mall includes 32 acres inspired by French boulevards lined with some of the most beautiful homes in the area. Plus, enjoy beautiful sculptures all around the Mall, including the Boston Women's Memorial.