When friends and relatives (or even strangers) come to Boston and ask for recommendations about what they should do, where do you send them? Do you take the easy way out and point them to the Freedom Trail, the Museum of Fine Arts, Newbury Street, and the North End?
I’m not knocking those options. I’d never refuse anything that came in the ubiquitous white and blue Mike’s Pastry box from the North End, and I love the MFA. But I also crave the brambles at Sugar Baking Co. in West Roxbury and the doughnut muffins (and used vinyl) from Monumental Market in Jamaica Plain. Duck Boat tours are fun, but I prefer the freedom of renting a kayak and hitting the Charles River freestyle. Do you like a bar where nobody knows your name? The intimate Tasting Room at Bully Boy Distillers in Newmarket Square is the best speakeasy in Boston that doesn’t claim to be a speakeasy. You won’t find a better Negroni in town.
You, your friends, and even your pesky aunt Linda, who gives you lousy birthday gifts, deserve better than tired and lazy autopilot Boston recommendations. Trust me, they already know about the Swan Boats and the “Make Way for Ducklings” sculpture. So I’ve come up with a few suggestions for you. First, there’s a disclaimer: This list is by no means complete or perfect, but it doesn’t include Faneuil Hall or Acorn Street, so it’s already better than most. Geographically, this guide stays in Boston as much as possible. Also, check the ever-changing COVID-19 guidelines before you head out.
WHERE TO STAY: Boston has experienced a hotel boom over the past five years. Many of these new properties are high-end, with a smattering of budget-friendly options. No matter which you pick, hotels in the city are not cheap. If you need inexpensive lodging, look at towns just outside the city or in less touristed neighborhoods. There’s even a five-star hotel at a casino nearby, which is cheaper than five-star offerings in the city. 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. Boston has a trio of micro hotels — Yotel Boston Seaport, Citizen M Boston North Station Hotel, and the Moxy Boston Downtown. The rooms are small; the price tags usually are not.
I’m consistently astounded that rooms at the Godfrey Hotel Boston, a very natty boutique hotel in Downtown Crossing, can be reserved for under $200 a night in the off-season (and often year-round on the app HotelTonight). If you’d prefer a cross between a hotel and an Airbnb, try the Sonder 907 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. The Boston Park Plaza and Stay Pineapple in the South End tend to be less expensive than other hotels in the Back Bay and South End.
My favorite midrange hotel (midrange by Boston price standards) is the Hotel Commonwealth. It 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.
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. Another new entry in luxury lodging is The Newbury Boston in the Back Bay, located at one of the best addresses in the city with a beautiful rooftop restaurant. The Whitney Hotel Boston, a former nurses’ dormitory, is another of my favorite boutique hotels. If you’re already splurging on the Whitney, splurge and get a room with a river view.
BREAKFAST, DAY ONE: With your lodging out of the way, it’s time to plan your weekend. We’re going to start where every weekend should start: A malted Belgian waffle, with a side of maple ham, at The Paramount (located in South Boston and Beacon Hill). If you’re looking for something just as sweet but more portable, swing by Blackbird Doughnuts (multiple locations throughout the city). The salted toffee doughnut comes highly recommended … by me. If you’re willing to go the extra mile and hop in an Uber or venture on public transit, Anna’s Hand Cut Donuts in West Roxbury is a solid standby, as is the iconic Twin Donuts in Allston.
MORNING ACTIVITIES: The Boston Harborwalk is a great place to get your bearings in the Seaport District and downtown Boston. The world is divided into two camps: People who have never heard of the Seaport District, and people who don’t like the Seaport District. 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. I often start the Harborwalk behind the Institute of Contemporary Art, following the curve of the water for about 30 to 45 minutes down the meandering walkway past the Barking Crab (get all lobster rolls here and ask for Jared at the bar), up to the five-star Boston Harbor Hotel. 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. If you opt for the Harborwalk, leave the stilettos at home. There are plenty of cobblestones here, in addition to wooden walkways.
If you’ve brought along your precious ankle biters and tiny humans in strollers, indulge them with a stop at the Boston Children’s Museum, which is along the Harbor Walk.
If you’re not in a walking mood, one of the best (seasonal) boat rides in town is the quick ICA shuttle to its East Boston Watershed (beginning May 26 this year). If you opt for the ICA and the water shuttle, please remember to purchase tickets in advance. This summer, the Watershed, a once-abandoned industrial space on the water, 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. And, lo-and-behold! It’s almost time for lunch.
LUNCH (EAST BOSTON): If you’ve gone the Seaport-to-East Boston boat route, my recommendation is to stay in East Boston and venture to Day Square, which has a fine selection of Peruvian restaurants. The essential lunch (or dinner) location is Rincon Lomeño. Order tapas, and save some room for ice cream at the nearby Frío Rico. There’s only one flavor you need to order here: the lúcuma ice cream. Just try it, and thank me later.
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 moving to their more famous house in Brookline). East Boston is mainly thought of as “that part of the city where the airport is located,” but the East Boston Greenway has 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. Calm down Madonna fans, this is a shrine to the Virgin Mary, not your pop priestess.
LUNCH (DOWNTOWN) If you hoofed it up the Harborwalk to the Rose Kennedy Greenway, you should first reward any children in tow with a ride on the Greenway Carousel. It’s also a suitable activity for adults. Your reward for morning walking is food halls and markets. 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. Also in the neighborhood is a new food hall! You can find burgers, brews, sushi, and champagne at High Street Place. The beauty of High Street Place is that you can take every meal of the day at the food hall if you’re too lazy to look around for restaurants. No judgment here. Currently, High Street Place is not open on Sunday, so this is a Saturday destination.
AFTERNOON ACTIVITIES: Those with a taste for luxury chain stores and high fashion should go to Newbury Street. But I’m not sending you there. If you want to go shopping, browse the expansive Brattle Book Shop. Nor am I putting you on an amphibious Boston Duck Tour or an Old Town Trolley. They are both great ways to get a feel for the city if you’ve never been here or have a limited window of time, but I know you’re savvier than that. Boston’s history is more than the Freedom Trail and the Old North Church, that’s why your next stop is the Roxbury Heritage State Park and the Colonial-era Dillaway-Thomas House. The state’s Department of Conservation and Recreation completed $3.6 million in renovations at the Dillaway-Thomas House in 2019, which is the oldest surviving house in Roxbury. The house served as the headquarters of Revolutionary War General John Thomas during the 1775 Siege of Boston. The home includes exhibits that show the evolution of Roxbury — from Malcolm X to Presidential Medal of the Arts recipient Elma Lewis.
Instead of Boston Common and the Public Garden (you already know to go there), we’re headed to the Arnold Arboretum of Harvard University. It’s a botanical research institution and free public park that straddles Jamaica Plain and Roslindale. Established in 1872, it is the oldest public arboretum in North America. You can’t go wrong in a garden designed by Charles Sprague Sargent and Frederick Law Olmsted. Too academic? The preferred nature preserve/cemetery in nearby Jamaica Plain is the 275-acre Forest Hills 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.
EVENING: Enough with the nature — I hope you were wearing sunscreen — we’re headed back into the city center to enjoy Boston’s new hotel rooftop bar scene. It began in earnest less than a decade ago with the opening of an epic rooftop bar and restaurant at The Envoy Hotel in the Seaport District and has since spread to other hotels, such as the nearby Yotel and Omni Boston Hotel at the Seaport. The roof deck bar and restaurant at the Cambria Hotel in South Boston offers a prime look at the South Boston mating, sorry, dating scene, plus great views of the Back Bay. The Rooftop at the Revere Hotel adjacent to the Theater District claims to be Boston’s largest. If you want to step over the border to Cambridge, the Blue Owl has the only rooftop terrace and bar in Cambridge. Nosh on appetizers at these spots, or sip whatever makes you happy. It’s time to finally return to your room, relax, nap, change, and get ready for your night out.
DINNER: Nope, I’m not even going to attempt this one. There are far more qualified people to give you dinner suggestions. The Globe’s food writer Devra First offers a handy set of options in this same guide (or follow this handy link). I defer to her.
SATURDAY NIGHT: If you’ve made it this far, then you’re headed out. I’m not taking no for an answer. Don’t worry, it won’t be a late night. This is a 2 a.m. kind of city. I’m going to break your Saturday night activities down by category. Apologies in advance if your category is missing. There’s much more nightlife in Cambridge and Somerville, but we’re sticking to Boston.
- Culture — See what’s playing at the SpeakEasy Stage Company or the Huntington Theatre Company. If you prefer touring companies of Broadway shows, look for offerings from Broadway in Boston. The 2022/2023 season includes “Tina,” “Hairspray,” “Six,” and “Jagged Little Pill.” I wish I could recommend a cool indie movie theater in Boston, but they’re all outside the city limits (the Coolidge Corner Theatre in Brookline, the Brattle Theatre in Cambridge, and the Somerville Theatre). It isn’t easy to pick one, but the Coolidge Corner Theatre is a beautiful spot. The Celebrity Series of Boston presents classical music, vocalists, world music, and dance. It also sponsors free events throughout the city. After two years of virtual performances, it’s going live again later this year.
- Chill — Swing by Wally’s Cafe Jazz Club (currently scheduled to reopen May 14) to hear Berklee College of Music students and longtime musicians from the local scene. If this is your destination, get here early. It quickly fills up. Do you want even more chill? Hang out at the bar at The Newbury (called Street Bar), and people watch.
- Active — There are Kings Dining and Entertainment venues around Boston, these are places to eat, drink, and bowl. But don’t be fooled. Authentic New England bowling is not ten-pin (known here as “the one with the big balls”), it’s candlepin. If you’ve never experienced it, candlepin involves rolling frustratingly small bowling balls at skinny pins that never seem to fall. I think candlepin, invented in Worcester, flourished in Boston because each frame consists of three balls rather than two, giving participants more opportunities to swear at the pins. On Saturday nights, Boston Bowl in Dorchester is open late and offers ten-pin and candlepin. Southie Bowl Candlepin is all candlepin with a midcentury vibe. Both are great Saturday night options for families.
- Loud — 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. 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, table service, and a 70-foot LED wall.
- Gay — Boston’s long-standing gay fav is Club Cafe, but if you’ve done your gay bar research, you already know that. The Saturday crowd is a little more diverse at Blend in Dorchester (hence the name), and the dance floor is easier to navigate than Club Cafe. From Blend you can walk precisely three minutes and arrive at another gay restaurant and watering hole, dbar. Cathedral Station in the South End is a gay sports bar, but they have a fantastic outdoor patio area if you’re not keen on sitting at the bar and watching the game.
- Dive — You don’t need me to recommend an Irish pub because this is Boston; go on a pub crawl or just follow a pack of feral Bros. But, 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 there’s a mix of hammered old-school locals, sassy bartenders, and graffiti-covered walls. It’s cash only, and there’s no website. I once asked the bartender for a Dark ‘n’ Stormy and the response was “Piss off! We don’t make that [expletive].” You can’t get more Boston than that. In the South End, the Delux is more quirky than dive-y but worth a visit. If you need more dive options, head to Allston and hang with the hipsters at the Model Cafe. Spoiler alert: There are no actual models here, but plenty of DJs.
BRUNCH, DAY TWO: Some of Boston’s best dining options are in Chinatown, so your brunch is dim sum and buns. My favorite, China Pearl Restaurant, is currently closed for renovations, but there are plenty of other dim sum options in the neighborhood. The recently relocated Hei La Moon was situated in cavernous digs for years. The restaurant recently moved to a smaller, hipper location, but the dumplings and buns are no less appealing. The choices here can be overwhelming, so I’ll just point you to my favorites: Try the pork shiu mai steamed dumplings and the egg custard buns. After that, let your imagination run wild. If you try the soybean Jell-O, tell me how it is. If you want the full experience, you can hit Empire Garden, at least to see the novelty of an old theater that was transformed into a bonkers banquet hall. Winsor Dim Sum Café gets high marks for its menu.
AFTERNOON ACTIVITIES: A post-brunch Sunday tradition in these parts is the SoWa Open Market and the SoWa Vintage Market in the South End. SoWa refers to “South of Washington” Street, an area filled with art and design studios. Every Sunday from 11 a.m. until it starts raining or getting windy (otherwise known as 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. The market runs from May to October. As of this writing the market’s website has not gone live, so find the action at 450 Harrison Ave. (via Thayer Street) and 365 Albany St. In case you didn’t get enough dim sum, there are plenty of food trucks. Along with the new goods, you can also find vintage treasures, plus open artist studios.
While you’re in this hood, I strongly suggest you stroll into the residential areas and get a feel for the old brownstones and brick sidewalks. The most charming street of them all is Union Park. Thirty years ago, this area was Boston’s gayborhood. It still is, to some degree, but now you’ll see an equal ratio of baby strollers and Dockers to same-sex hand-holding.
Jock types, I have not forgotten you. A great way to see Boston is from the Charles River. Urban kayaking in Boston is easy and relatively inexpensive. Paddle Boston has locations throughout Boston and nearby towns and suburbs, but the best place to rent a kayak (90 minutes for $30, $54 for a full day) is at the Allston/Brighton location. The nine-mile stretch of river has no current and gives you a water view of local colleges, the Esplanade, and the Boston skyline. You can also rent a paddle board but c’mon, really? You want to be that person?
You already know that Boston has a lot of top-notch museums, so I don’t need to regurgitate another list here. So let’s try a museum with very local roots. 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.
Because Boston is a walking city, it’s time to end your visit with a walk along the beach. A quick subway trip from the JFK Library on the MBTA’s Red Line to the Broadway stop will bring you to South Boston, which has a long stretch of sandy beaches. On warm days, the beaches are packed with what looks like a sorority/fraternity party. These are actually adults, and they now fill the neighborhood. Keep walking down to Castle Island (it’s not really an island) and circle Fort Independence. On breezy days you’ll see Pleasure Bay full of windsurfers. At the end of your walk, it’s essential to stop at the iconic Sullivan’s Castle Island. My favorite is the fried clams with a side of onion rings.
If you’re looking to stay focused on the Back Bay neighborhood, take your walk along the Commonwealth Avenue Mall. It’s 32 acres inspired by French boulevards lined with some of the most beautiful homes in the area. Winston Churchill once declared it “the grandest boulevard in North America.” I take umbrage with Churchill on that, but it’s a leafy, scenic break from nearby Newbury Street.
By now you are likely as worn out as a cat that’s been chasing her tail for a day, so we’ll call it a weekend. But this guide is just the beginning of what you’ll find in Boston. There are also surrounding cities and towns to be explored. You’ll be back, I’m sure of it, the only difference is next time, plan your own dang itinerary.