The 50 best things to do in Boston
Your ultimate guide to the best things to do in Boston, from the city’s top restaurants to museums and sightseeing
Boston may not be the biggest city, but to locals it’s the Hub of the Universe. Numerous Boston attractions and activities can lay claim as the best things to do in Boston; options run the gamut from top-notch eats at Boston’s best restaurants and cool treats at the best ice cream shops to engaging cultural offerings at world-class Boston museums. So whether you’re a newcomer or a lifelong local looking for the best things to do around the area, be sure check off these essential activities.
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Best things to do in Boston
Wander around the Boston Common and Public Garden
What is it? America’s first botanical garden (Public Garden, 1837) and oldest public park (Boston Common, 1634).
Why go? The dual jewels of the Emerald Necklace perfectly reflect the vision of venerated landscape architect Frederick Law Olmsted. Depending on the season, you can ice-skate on Frog Pond, play softball or tennis, or simply lounge with a book on the 50-acre Boston Common. But its smaller adjunct across Charles Street, the Public Garden, is the real star; it’s the perfect park in miniature, with pathways designed for promenading, formal flower beds and a petite lagoon fringed with weeping willows.
Don’t miss: The seasonally operated, waterfowl-shaped Swan Boats (introduced in 1877) are adored by children.
Root for the home team at Fenway Park
What is it? Seeing a game at Fenway Park has been a rite of passage among most locals since it opened in 1912.
Why go? As the oldest ballpark in the majors, it’s one the smallest, with a capacity of around 38,000, meaning tickets can be hard to come by for big games. Fortunately, public tours are offered year-round, wowing even non-baseball types by detailing the park's colorful history and intricate details.
Don’t miss: If you get the chance, take a seat atop the stadium’s most distinctive feature, the 37-foot-high left-field wall known as the Green Monster. Before or after the game, check out all the great restaurants, bars, and other things to do in the Fenway neighborhood.
Explore the Isabella Stewart Gardner Museum
What is it? Modeled on a Venetian palace, the former home of the American art collector Isabella Stewart Gardner is a sightseeing gem.
Why go? As per Gardner’s explicit instructions, the museum stands “for the education and enrichment of the public forever.” The ISG’s most famous treasures remain unlabeled, turning the whole thing into a glorious guessing game (printed guides in each room are on hand to help, as is the museum's website). The museum also boasts a flower-filled courtyard that blooms all year long.
Don’t miss: Enjoy free admission on your birthday; anyone with the first name Isabella gets in for free as well.
Learn something new at the Boston Public Library
What is it? The BPL (1852) contains approximately 19 million volumes and electronic resources, making it the second-largest public library in the US behind only the Library of Congress.
Why go? At nearly 1 million square feet, the BPL impresses like few libraries can. The original structure, designed by Charles McKim and completed in 1895, is now the research library, while an extension (opened in 1972) functions as the general library. Talks, performances, and tours delight culture vultures, and recent renovations have introduced interactive elements to the complex.
Don’t miss: At the center of the library is a cloistered courtyard, one of the city’s most beautiful, tranquil places to read a book.
See world class art at the Museum of Fine Arts
What is it? Founded in 1870, the Museum of Fine Arts—whose globe-spanning collection encompasses more than 500,000 objects—continues to grow and innovate.
Why go? Of particular note is the collection of American art, including Paul Revere’s Liberty Bowl and paintings by John Singleton Copley; the Egyptian collection, much of which was acquired through excavations in conjunction with Harvard University; the Japanese collection (the first in America, and one of the finest in the country); and the Impressionist and Post-Impressionist sections, including one of the largest collections of Monet's work outside Paris.
Don’t miss: The museum offers one of the city’s best freebies on Wednesdays after 4pm, when admission is by voluntary contribution.
Smell the flowers at the Arnold Arboretum
What is it? The 281-acre Arboretum, one of the world’s leading centers for plant study, was planned and designed in collaboration with Frederick Law Olmsted in 1872.
Why go? As a National Historic Landmark, the Arboretum is one of the best preserved of Olmsted’s landscapes. With thousands of trees, shrubs, and woody vines, it's also recognized as one of the most comprehensive and best documented of its kind in the world. Take a stroll on a nice day to see see bursts of green, blooming flowers, and plenty of birds.
Don’t miss: Free guided tours are available on designated days throughout the year.
Take a stroll along the Greenway
What is it? This verdant, mile-long ribbon of grassy parks and outdoor resting places invites the weary traveler (or office warrior) to stop and take a break.
Why go? The linear park covers an expansive 15 acres that connect the Chinatown Gate with the iconic Zakim Bridge. During the day, people stroll, bike and lounge along its length, which is dotted with fountains and serviced by food trucks, making the area the perfect warm-weather hangout.
Don’t miss: Keep an eye out for the periodic festivals, events, and parades taking place on or near the park.
Slurp the freshest local bivalves at a popular oyster bar
What is it? Boston is famous for its fresh seafood; enjoy the fruits of the sea with a visit to one of the city’s top oyster bars.
Why go? Ever since the Union Oyster House opened in 1826, raw oysters have been integral to Boston’s culinary scene. Today, the briny bivalves appear on a wide array of restaurant menus. You'll find locally-sourced varieties including Wellfleet, Cotuit, and Glidden Point as well as popular imports like Kumamotos. Oyster happy hours are a great way to sample these goodies at a lower price.
Don’t miss: Cozy spots like B&G Oysters and North Square Oyster offer oyster-friendly wine pairings, while Row 34 can match the perfect beer.
Explore culinary creations at Boston's best food halls
What is it? The food hall trend is exploding here in Boston, with a wealth of food halls popping up around the city. Most notable is the Time Out Market, which will house some of the city's best chefs and dishes under one roof.
Why Go? Food halls are a great dining choice when you’re with a group of friends with different tastes—there’s something for everyone. Boston food halls offer all types of food—spanning numerous genres and cuisine types—all in one spot. They make for a great anytime meeting spot; just show up and see what kind of mood you’re in.
Don't Miss: Time Out Market will feature some of the best dishes in the city, so you can sample different restaurants in one spot. Eataly is a haven for Italian food enthusiasts. The Boston Public Market has fresh produce in addition to prepared foods.
Find local goods and goodies at SoWa Open Market
What is it? The South End’s SoWa Open Market runs every Sunday from May through October.
Why go?The area becomes a street festival that draws visitors from all over the city and beyond. Around 200 makers and vendors sample and sell their wares, and there's a farmers' market, food truck bazaar, and beer barn. Both kid- and pet-friendly, the market is a favorite area pastime among young families.
Don’t miss: There’s more inside the market building—the SoWa Vintage Market offers stall after stall of quirky vintage clothes and housewares.
Get a feel for Ivy League life with a tour of Harvard
What is it? There’s a lot more on the grounds of Harvard University than elite pupils and posing tourists.
Why go? The iconic red brick walls contain some truly stunning stories, and a visit will connect you to a Who’s Who of American history—alumni include John Hancock, JFK and Barack Obama, while Matt Damon, Bill Gates and Mark Zuckerberg are among the famous dropouts. The campus also features striking architecture designed by such luminaries as Bulfinch, Le Corbusier (his only American building), and Sert.
Don’t miss: Steps from campus, Harvard Square contains some of the best eating and shopping in the city.
Visit the penguins at the New England Aquarium
What is it? New England’s largest aquarium, and one of Boston’s most popular attractions.
Why go? More than 80 African, rockhopper and little blue penguins live in the New England Aquarium’s first-floor display, which surrounds the Giant Ocean Tank, a gigantic coral reef exhibit that's home to myriad marine creatures—including sharks and loggerhead sea turtles. The building is designed in such a way that the penguins can be seen from multiple vantage points.
Don’t miss: Be sure to say hi to the harbor seals at their enclosure out front (free and open to the public), even if you’re not visiting the aquarium.
Splurge on Newbury Street
What is it? Boston’s premier retail strip wins kudos for its sheer volume and variety of shops.
Why go? Between Arlington Street and Massachusetts Avenue, there are eight blocks of bow-fronted brick townhouses stuffed with everything from ultra-luxe designers like Chanel and Burberry to chic boutiques (Intermix, Rag & Bone) and international chains. With a never-ending assortment of galleries, salons, cafés, bars and eateries to explore, you can easily spend an entire day browsing, relaxing and indulging here.
Don’t miss: If you’re more interested in unique, indie finds, head to the neighboring South End.
Watch out for whales and enjoy some fresh air
What is it? The waters surrounding Boston offer some of the best whale watching opportunities in the US.
Why go? Whale watching isn’t just for school field trips. Hop on one of the boats departing Boston Harbor daily and rediscover how awesome it actually is to be within spitting distance of the largest mammals on earth. Bring a sweater and park yourself at the hull of the boat for the day and keep your eyes on the water.
Don’t miss: Don’t make the rookie mistake of shunning sun protection, or you’ll join those who resemble lobsters after picking up a wicked sunburn.
Discover a lost world at the Mapparium
What is it? Located inside the Mary Baker Eddy Library, The Mapparium is essentially a three-story model of the globe built to scale.
Why go? Calling all geography nerds: The Mapparium, the world’s largest walk-in globe, is among the city’s quirkiest landmarks. The perfect sphere runs 30 feet in diameter and can be crossed by means of a glass bridge that bisects its interior. Inside, sound bounces off the globe room’s non-porous glass walls, amplifying it ten-fold—which means that whispered sweet nothings from your partner across the room register directly in your ear.
Don’t miss: The 608 stained-glass panels recreate the world as it was in the mid-1930s, when the project was completed. (Keen eyes will note the outdated borders.)
Drink a proper pint at an authentic Irish pub
What is it? Boston’s collection of cozy, welcoming Irish pubs might just be the most impressive in the country.
Why go? In a city chock full of proud Irish expats and Irish-Americans, it’s little wonder Boston boasts an excess of authentic Irish pubs. To get the full experience, head in on a lively trivia night, or during an authentic Irish live music performance. Longtime favorites such as Doyle’s Cafe, The Burren, and The Druid all but guarantee a lively night of big laughs and fun times.
Don’t miss: For a centrally-located option with nightly live Irish music, look no further than the Black Rose.
Join an Italian festival in the North End
What is it? In the summer months, the North End goes full-throttle as the local Italian community throws a number of lively feasts and festivals in honor of Italian saints.
Why go? The streets fill with participants and bystanders alike, all watching the confetti fly, the banners sway and the processions make their way through the narrow cobblestone streets. The biggest celebrations, such as the Fisherman’s Feast of the Madonna and Saint Anthony’s Feast (both in August), bring out capacity crowds. Expect great food, live entertainment, enthusiastic vendors, and statues covered in dollar bills.
Don’t miss: Given the crowds, traffic, and lack of parking, it’s wise to take the T to Haymarket. Brush up on the best spots for Italian, pizza, and more with the North End neighborhood guide.
Catch a game or a show at the TD Garden
What is it? Besides serving as the home for the NBA’s Celtics and NHL’s Bruins, the city’s premier arena hosts big-name concerts and events.
Why go? While it’s not the original Boston Garden (a no-frills venue that hosted some of the most important cultural events in Boston history), the spirit of Boston sports runs deep throughout the venue. An assortment of fans—from intense locals whose season tickets go back decades to new-school supporters sporting the latest in merch and gear—scream and shout while supporting the local teams.
Don’t miss: Fuel up before a big game with a killer Italian meal in the neighboring North End.
Get swept up in the sonorous sounds of the symphony
What is it? Symphony Hall opened its doors in 1900 as the home of the Boston Symphony Orchestra and the Boston Pops Orchestra.
Why go? Expanded and updated over the years, the venue continues to draw music aficionados from around the globe. Still, it’s the all-important acoustics of the original interior design that have made it one the country’s top auditoriums. Special, collaborative performances with contemporary artists help to bring in new generations of patrons.
Don’t miss: In July and August, the BSO is based at its summer home, Tanglewood, in the Berkshires of Western Massachusetts.
Get an inside view of SoWa’s studios
What is it? As the city’s premier artistic hub, the 450 Harrison building is a veritable hive of artistic activity in the back of the South End.
Why go? Many artists open their doors a few times a month for open studios events where they greet locals and visitors. First Fridays (5-9pm) is the flagship event; held each month, more than 200 artists, galleries, shops and showrooms welcome everyone from art aficionados to afterwork activity-seekers for an evening of art, wine, cheese and mingling.
Don’t miss: Once you’ve had your fill of art, follow the other culture vultures by enjoying the best of the South End.
Ask not what your country can do for you at the JFK Library
What is it? Located behind UMass Boston’s Dorchester campus, the JFK Presidential Library and Museum occupies I.M. Pei’s dramatic concrete-and-glass monolith.
Why go? The well-presented multimedia journey through the former president’s life continues to fascinate, as do temporary exhibits and special events that incorporate politics, culture, and current events. On the ground floor, the stunning atrium commands panoramic views of the sea and the city. Downstairs, the museum contains an extensive display of memorabilia, as well as a series of temporary shows.
Don’t miss: Check the Library’s homepage in advance to learn about special events and award ceremonies.
Discover the deCordova Museum & Sculpture Park
What is it? Head west to suburban Lincoln to visit the former estate of Massachusetts merchant Julian de Cordova.
Why go? Even during the peak of winter or dog days of summer, the deCordova Museum & Sculpture Park lures art lovers to its a 35-acre spread in leafy Lincoln. Open year-round, the region’s premier outdoor sculpture park is the perfect place to get some fresh air while checking out world-class art. The ever-changing indoor exhibits provide shelter from the sometimes-fickle elements.
Don’t miss: Check the museum’s calendar to learn about special outdoor events and the like.
Storm the fort at Castle Island
What is it? South Boston lays claim to one of the city’s most appealing shoreline parks: the 22-acre Castle Island.
Why go? Among the oldest fortified military sites in North America, the centerpiece of Castle Island is Fort Independence, a pentagonal granite structure that was finished in the 1850s. Prior to its construction, seven other forts had been built and destroyed in the area, occupied by American and British troops in turn. Today, the island’s green space provides an exceptionally picturesque spot for an all-day picnic.
Don’t miss: Leave room for lobster rolls and fried clams at Sullivan’s, a Castle Island institution open from the end of February until the Sunday after Thanksgiving.
Browse the Institute of Contemporary Art
What is it? The dramatic, glass-walled ICA is unquestionably the cultural cornerstone of the buzzing Seaport District.
Why go? The 65,000-square-foot building houses galleries, a theater, and a café. The museum staff prides itself on providing a platform for challenging, sometimes controversial works. After you’ve contemplated the art, retreat to the scenic outdoor deck, site of myriad performances and events. Note: Admission is free on Thursdays from 5pm-9pm.
Don’t miss: Across the water in East Boston, the ICA Watershed is a seasonal satellite gallery, open spring through summer.
Go ice skating on the Frog Pond
What is it? Few holiday traditions are as entrenched as an icy spin around Boston Common’s Frog Pond.
Why go? Bundle up, grab your skates (or rent some), and take a spin in the middle of America's oldest public park—preferably on a clear, starlit night. Rink snobs need not worry: the Frog Pond is Zamboni-slick and has its own ice-making system. On special event nights, holidays, and busy weekends, the rink can get crowded, providing colorful people-watching opportunities for those staying on the sidelines.
Don’t miss: Those who prefer to stay on non-slippery ground can snuggle up beside the snack bar with a hot chocolate and free Wi-Fi. Skating enthusiasts can check out other popular skating rinks around Boston.
Cheer on the best teams at the best sports bars
What is it? The next best thing to being at the game, these sports bars are the best spots to cheer on the Red Sox, Celtics, Patriots, and Bruins.
Why Go? Of all the fantastic things to do in Boston, catching a game has got to be somewhere near the top of the list, whether it's hearing the roar of Red Sox fans at Fenway, braving the cold to cheer on the Patriots in Foxborough, or celebrating a Celtics or Bruins win at the Garden. You can't always make it there in person (or travel for away games), but good beer, lively company, and lots of screens make these bars a great alternative.
Don't miss: For fans of memorabilia, McGreevy's is a shrine to the Red Sox (and the Dropkick Murphy's), while the walls of The Fours are plastered with photos, jerseys, balls, and more from all teams.
Take a foodie crawl through Chinatown
What is it? As one of the Boston’s most densely-packed and exotic neighborhoods, Chinatown thrills adventurous gourmands.
Why go? Many of the city’s best Chinese restaurants can be found in Chinatown. Rather than sticking to one spot and doing a big meal, pace yourself by walking around the neighborhood, snacking along the way. Gourmet Dumpling House is a smart place to start; enjoy some house-made dumplings with spicy dipping sauce to fire up your palate. Next, stamp your culinary passport by trying a few Taiwanese specialities at Taiwan Cafe. Finish off with a bang at Peach Farm, where you can select seafood straight from the tanks.
Don’t miss: Exotic hand-pulled noodles at Gene’s Chinese Flatbread Cafe.
Study fine art at the Harvard Art Museums
What is it? Harvard’s history and status help to explain how it has one of the country’s best university art collections.
Why go? Following a lengthy expansion project, Harvard’s three art institutions—the Fogg Museum, the Busch-Reisinger Museum, and the Arthur M. Sackler Museum—were united under one Renzo Piano–designed glass roof. Visitors are able to peruse highlights from the university’s collection of roughly 250,000 pieces, from Neolithic sculpture to 21st-century conceptual installations.
Don’t miss: Harvard’s Museum of Natural History, home to one of the university’s most famous treasures, the acclaimed Ware Collection of Blaschka Glass Models of Plants.
Conquer the Minuteman Bikeway
What is it? Stretching from Cambridge to Bedford, this 11-mile path is a great way to check out some of the area’s most scenic communities.
Why go? Built on a former railway, the Minuteman Bikeway is open to biking, rollerblading, jogging, walking and more—anything sans motor, basically. There’s also plenty to see along the way, including Alewife Brook Reservation, Spy Pond and Arlington’s Great Meadows.
Don’t miss: Arlington Center and Lexington Center—both a short detour from the bike path—provide ample options for a snack or bathroom break.
Go candlepin bowling at Sacco’s Bowl Haven
What is it? A unique, casual Somerville hangout where you can enjoy gourmet pizza and craft brews while trying your hand at candlepin bowling.
Why go? Candlepin bowling is a uniquely New England quirk—the pins are tall and much thinner than those of standard ten-pin, and balls are closer to softball-sized. For those seeking this social, group-friendly activity, the lovingly maintained Sacco’s Bowl Haven (which dates back to 1939) at the Somerville location of Flatbread Company is a local favorite. An eclectic mix waits for lanes to open up while nibbling on organic pizzas with eccentric toppings.
Don’t miss: Reservations are accepted for groups of eight or more; call ahead or expect to wait.
Dance the night away at a hot club
What is it? Boston’s best clubs might not compare to the nightlife in Miami or Vegas, but there are plenty of popular options for late-night fun.
Why go? With hot spots such as Royale, Venu, and Icon, the Theatre District hosts’s biggest concentration of nightclubs. A far cry from the Top 40 club-banging hotspots on the other side of the river, Central Square offers an eclectic assortment of places to shake it like there's no tomorrow. Popular options include house DJ nights at the Middlesex Lounge, the eclectic throwback and hip-hop parties at Phoenix Landing.
Don’t miss: If toe-tapping along to live jazz is more your speed, check out Wally’s, a South End institution.
See Shakespeare for free on the Common
What is it? Boston’s favorite way to see Shakespeare is in the park, sitting on a blanket while (discreetly) enjoying treats from home.
Why go? Claim a grassy spot on the Boston Common and check out the Commonwealth Shakespeare Company's productions of the Bard’s best works, with performances taking place during some of July and August. All performances are free, making for a perfect summertime date or relaxing literary outing.
Don’t miss: Boston is one of America's best cities for theater, with Shakespeare productions taking place regularly. Consult our Theater Guide to learn more.
Catch a concert at the Middle East
What is it? One of New England’s best locations for live music features a kaleidoscope of genres and styles.
Why go? Most nights of the week, the Middle East will host a show on each of its stages—upstairs, downstairs, and the corner. Weekends are especially busy, with frequent matinee concerts. Each Saturday night, the complex’s fourth branch—the bar and restaurant ZuZu—hosts "Soulelujah," a funky throwdown fueled by classic soul tracks.
Don’t miss: Keep the party going by enjoying the best of Central Square or more of the best live music in Boston.
Experience high-end mixology at a top cocktail bar
What is it? Given the area’s focus on academics and the sciences, it’s no surprise that Boston has a bevy of talented mixologists.
Why go? Why merely go out for a meal when you can embark on an immersive sensory trip? Trailblazing bars include Drink and The Hawthorne, both of which offer an endless variety of creative drink options. For a truly mind-blowing experience, head to ArtScience: Culture Lab & Café, where the staff employs scientific techniques—look out for a fractional distiller behind the bar—when whipping up tasty concoctions.
Don’t miss: For a next-level experience, try cocktails featuring house-made spirits at the Bully Boy Tasting Room and GrandTen Distilling.
Look for the stars during public stargazing programs
What is it? A pair of astronomy programs—both free to the public—offer primo star-watching opportunities.
Why go? Every Wednesday night (weather permitting), Boston University’s Coit Observatory offers free (tickets required) public viewings of the stars. The program starts at 7:30pm in fall/winter, 8:30pm in spring/summer. Visitors can use telescopes and binoculars to see the great beyond. At the Museum of Science, the Astronomy After Hours program is offered for free on Friday nights from April through October. Both are weather permitting—call first.
Don’t miss: IMAX movies in the five-story Mugar Omni Theater and multimedia shows at the Charles Hayden Planetarium, when visiting the Museum of Science.
Try one or all of the city’s freshest lobster rolls
What is it? Perhaps the ultimate seafood treat, lobster rolls are found on menus across town.
Why go? The best lobster dishes in Boston feature the beloved crustacean in a variety of ways, but a fresh lobster roll is a go-to option any time of year in Boston. Sourced from cold waters along the New England coast, chunks of sweet lobster meat are removed from the shell, allowing diners to enjoy all of the flavor with none of the messy work. Classic versions, like the famed roll at Neptune Oyster, are served hot or cold on a humble toasted bun, while more modern versions—see Eventide Fenway's brown butter lobster roll on a Chinese-style bun—are a bit more upscale.
Don’t miss: For a low-key, no-frills lobster roll experience, head to Belle Isle Seafood in quiet Winthrop.
Browse a farmers market for local produce
What is it? Over the past decade, the Boston area has become flush with farmers markets, each a colorful display of locally grown fruits and vegetables.
Why go? Environmentally and nutritionally sound, market shopping is a favorite pasttime of local foodies. And while the best market experiences can be had during the warmer months, there are a few markets—e.g. Boston Public Market, Haymarket—that remain open year-round, meaning you can score tempting small-batch dairy and homemade baked goods whenever you like.
Don’t miss: For a centrally-located option, look no further than Boston’s biggest and busiest, the Copley Square Farmers Market (open mid-May through mid-November).
Hit the beach
What is it? There are a number of awesome beaches not far from the city.
Why go? Some of the best can be found north of the city in Essex County. Crane Beach, which can be reached by a shuttle bus that departs from the Ipswich commuter rail station throughout the summer, boasts some of the best wildlife-attracting salt marshes around. Another pair of relaxing destinations—Singing Beach and Good Harbor Beach—are also accessible by the commuter rail.
Don’t miss: If you’re not content with merely relaxing by the waves, hop on the train to Plum Island, where you can also explore the seaside town of Newburyport.
Sample the best of local breweries
What is it? For a city that’s often hamstrung by booze-related blue laws, Boston sure has a fine collection of breweries.
Why go? Historically, the city’s most famous brewer was Samuel Adams, the Revolutionary and “maltster” for whom the city's most famous beer is named. Tours of the Samuel Adams Brewery in Jamaica Plain are as inexpensive ($2 suggested donation) as they are entertaining. But recent years have seen a craft brewery boom across the city. Taste small-batch farmhouse-style ales at Fort Point’s Trillium Brewing Company, or experimental suds at Somerville’s Aeronaut Brewing Company, founded by a science-focused trio with MIT connections.
Don’t miss: Any of the lively, beer-fueled holiday festivals at the Harpoon Brewery.
Stop for a scoop at Boston’s best ice cream shops
What is it? According to some studies, New Englanders eat more ice cream than just about anyone, which explains Boston’s impressive array of ice cream shops.
Why go? J.P. Licks is a local institution, with branches scattered all over the city serving creamy, crowd-pleasing flavors. A bit tougher to get to is Inman Square’s Christina’s, a favorite for painstakingly-crafted, seasonal flavors such as fresh rose, burnt sugar and ginger molasses. Toscanini's is another Cambridge spot with offbeat ingredients; the staff constantly labors to come up with new and interesting varieties like salty caramel or green tea.
Don’t miss: Make an evening of it by checking out Picco in the South End, where you can enjoy gourmet pizza followed by homemade ice cream.
Get a different perspective of the city from a cruise on the water
What is it? Ask locals for a special occasion recommendation and they’ll likely tell you to get out on the water by taking one of the city’s best cruises.
Why go? Nautical types will argue how the best way to truly see the city in all of its glory is through an entertaining, informative cruise. A longtime local favorite, Odyssey Cruises offers a variety of cruises; most feature food, drink, live music, and dancing.
Don’t miss: If time on the water has you fiending for fish, seek out one of Boston’s best seafood restaurants.
See Boston from above at a rooftop bar
What is it? An assortment of rooftop bars provide killer views of the city.
Why go? Boston never looks better than it does when you’re drinking a designer cocktail at a buzzing rooftop bar. Popular options include hip hotel spots such as Rooftop@Revere and Lookout Rooftop and Bar. For a low-key alfresco option, head to Harvard Square, where the rooftop lounge at Daedalus is a favorite of local academics.
Don’t miss: Besides killer water views, the rooftop lounge at Legal Harborside offers the chance to hear live tunes from the neighboring Rockland Trust Bank Pavilion.
Catch a late-night flick at Coolidge After Midnite
What is it? In Brookline’s Coolidge Corner, this beloved non-profit movie house hosts the city’s most popular late-night film series.
Why go? With this weekly late-night film series—screenings are held on most Fridays and Saturdays—the Coolidge Corner Theatre has established itself as the area’s premier destination for campy, weird, avant-garde and niche cinema. The schedule incorporates everything from ’90s cheesefests to horror staples such as Psycho and The Texas Chainsaw Massacre.
Don’t miss: Be sure to fuel up before (or during) the show—late-night food and drink options near the cinema are few and far between. To catch more flicks, check out Boston's best movie theaters.
Retrace historic steps with a top walking tour
What is it? Guided tours of the Freedom Trail and other neighborhoods are a great way to take in local history and culture.
Why go? The Freedom Trail isn’t the only historical walk in town. While the self-guided, 2.5-mile tour provides a useful sightseeing starting point for newcomers, there are numerous specialized walking tours that will help you dig deeper. Expert local guides will lead you around the city on themed tours covering everything from movies to wine and pizza.
Don’t miss: Improve your photo skills with a PhotoWalks Beacon Hill tour.
Make the rounds at Boston’s best donut shops
What is it? Get your fill of fried goodness at some Boston’s top donut shops, spanning the latest cult bakeries and under-the-radar mom-and-pops.
Why go? The antithesis of mass production (sorry, Dunkin), Boston’s best donuts are lovingly made by hand, satisfying even the most discerning sweet tooth. Stick with the classics if you must—cake donuts and honey glazed are local favorites—but we recommend tearing into exotic options such as sea salt bourbon caramel or blackberry lavender, found at popular new-wave spots such as Union Square Donuts and Blackbird Doughnuts.
Don't miss: For an old-school, no-frills, late-night option, head to Allston’s Twin Donuts.
Enjoy a breeze with your meal at a waterfront restaurant
What is it? Some of the best restaurants in Boston feature prime waterfront dining.
Why go? When warm sun and cool breezes are the norm, there's no better place to dine than on the waterfront. From fresh seafood to a simple hot dog, everything tastes better when there's a vew. Waterfront restaurant locations stretch from the Harbor to the beach. Indulge in lobster rolls, elevated Mexican cuisine, or a tasty roast beef sandwich, all with a view of the water.
Don't miss: Legal Harborside, the flagship location of the Legal Seafoods empire, has waterfront dining, rooftop dining with a view of the Harbor, and is within earshot of concerts at the Rockland Trust Bank Pavilion.
Stroll down Memorial Drive on a Sunday
What is it? From the last Sunday of April until the second Sunday of November, the city of Cambridge shuts down Memorial Drive to automobile traffic along the Charles River.
Why go? Celebrate your right to thumb your nose at frustrated motorists as you blithely cruise down the double yellow on in-line skates or sprint down the middle of the street pushing a baby carriage. The vehicle-free days provide locals with the epitome of a relaxing Sunday stroll. Expect to share the pavement with lots of bikers, rollerbladers, and fitness enthusiasts.
Don’t miss: After working up an appetite, reward yourself by walking over to one of Harvard Square’s best restaurants.
Get wild at the Franklin Park Zoo
What is it? The city’s zoo won’t make any national best-of lists, but its compact size and kid-friendly approach make it a local favorite.
Why go? As fascinating as lions and tigers are on the TV screen, they’re far more impressive in the flesh. The zoo—whose mission is to inspire people to protect and sustain endangered species—has them all, as well as zebras, gorillas, giraffes and a host of other exotic animals that wouldn’t normally be seen in the wilds of New England.
Don’t miss: Little visitors are well-served at the children’s zoo, which features everything from a prairie dog neighborhood to a grass maze.
Chase down a food truck
What is it? In Boston, there’s a whole world of food truck cuisine just waiting to be devoured.
Why go? The self-explanatory Roxy’s Gourmet Grilled Cheese has received national attention for its sinful sandwiches. There are plenty of healthy options such as Saté Grill, which offers health-minded Asian cuisine (including an impressive list of curries, some vegan). Bon Me is perhaps the city’s most prolific option, with multiple trucks (and storefronts) selling its fresh take on Asian fare (rice bowls, noodle salads, bánh mì).
Don’t miss: Check the city’s official food truck site for additional options.
Laugh it up at the best Boston comedy clubs
What is it? There are many opportunities to laugh your socks off at one of the city’s veteran comedy clubs, or at one of the regular comedy nights in a club or bar.
Why Go? Some of America’s most popular contemporary comedians (e.g. Conan O’Brien, Jay Leno) honed their craft in Greater Boston. In the Theater District, big name comedians hold court at a variety of venues. Spending your evening yucking it up is a great way to unwind and boost your mood.
Don't miss: The Improv Asylum in the North End has a loyal following, especially the more risque weekend midnight shows.
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