A weekend in Boston

Published March 25, 2023 by: MB

An important caveat is that this itinerary is far from comprehensive and is not for everyone. It's targeted at young adults or family friends who are hoping to see Boston itself - not Cambridge, not Dorchester, just Boston -- and hit some of the highlights. I have a recommended weekend 'playbook' at the end, for how I recommend combining the activities, but the best trips are customized to what you're most excited about!

Where to stay:

• It can be pricey depending on the season, but my top recommendation for experience and location is the Omni Parker House. It's in the historic part of downtown, so offers easy access to top historic sites and some unique facets of Boston culture (it's the home of both the Parker Roll and the Boston Creme Pie!).
  • Fun/crazy fact: Ho Chi Minh was radicalized while working as a dishwasher there. Malcolm X also worked there at the Parker House one point (more info)
• If you opt not to stay at the Parker House downtown, I instead would recommend to stay in Back Bay, which is fairly central and nice/upscale/lots of hotel options. A few to call out:
  • Fairmont Copley - Expensive but super nice; a splurge or special occasion option
  • Marriott Copley Place, Westin Copley - Classic Westin/Marriott properties; both nice + well located!

Things to do:

"Must-dos"

• North End: Boston's Little Italy and a bustling/windy neighborhood. Start from ~the Haymarket T station and walk up Hanover St to see the main stretch!
  • For Dinner: Tragically my favorite restaurant in the North End closed and I'm still hunting for a new go-to recommendation. That said, while Grotto is not 'core North End,' it's a fun little spot and has great Italian food. I often go to Tony & Elaine's because they take reservations online (rare for North End) and have a fun and casual checkered cloth vibe patio if probably not the absolute best Italian food the North End has. So those are good options, but Trip Advisor/Open Table may do better than I can here
  • For Dessert: Mike's Pastry is a must do for famous cannolis. The line gets long, but moves crazy fast; they're cash only. A fun and kid friendly activity if you're willing to wait in two lines: While Mike's is the most famous, many people swear that Modern Pastry across the street is better. Get cannolis from both + do a taste test to decide for yourself!
  • Sightseeing: Paul Revere's childhood home (original to 1680) and the church of the famous 'one if by land / two if by sea' story (Old North Church) are also in the North End for post-dinner sightseeing/wandering
• Revolutionary War History: Obviously lots of it in Boston! Two main tour recommendations depending on your crowd/vibe:
  • Duck Tour: Duck tours are iconic Boston fun. The tours (and the duck boats!) are everywhere in the summer. If you have kids, this is likely the way to go. It's expensive (~$50/pp) but fun/a quick way to get some lightweight history + a lot of jokes thrown in! If you stay in Back Bay, leave from the Prudential Center. From the Omni Parker house/downtown, would probably leave from the Aquarium.
  • Walking Tour: I'm biased, but used to volunteer as a tour guide with Boston by Foot + give the 'Heart of the Freedom Trail' tour. It's ~1 hour walking, much more history-dense + fewer jokes than a Duck Tour, but really informative. While BBF guides don't dress up, Boston by Foot is also almost guaranteed to be less expensive (~$15/pp) and a smaller tour (15 max) than the bigger commercial tour outfits you'll find on Trip Advisor. They also offer a 'Little Feet' tour that's designed for a younger crowd.

Other activity ideas

• Isabella Stewart Gardner Museum: (~1-2 hour activity, in Fenway). Scene of the biggest art heist in history and just SUCH a cool and unconventional museum, organized based on ISG's personal curation and style vs. by eras or geographies. Would be tough for young kids, but cool for middle/high school. Weird but important is to bring headphones. There are no placards - so to hear the story of the heist + understand the vision behind the rooms, you'll need the audio tour.
• Red Sox game: Really fun experience to watch them play at Fenway - a small and historic ballpark where every seat is a good seat. If you get lucky someone will hit a homerun over the 'Green Monster'. Highly recommend if they're at home during the visit.
• Museum of Science: A great, highly interactive museum if you have children. If you go just as an adult, you'll feel somewhat out of place, but probably still have fun.
• Kayak along the Charles River Esplanade: The Esplanade is the name of Boston's river walk along the Charles. It's a great place to stroll around and see the city. You can rent kayaks in the summer and paddle around the edges, which is lots of fun. I usually book kayaking online, but I think it's also possible to rent walk up and rent them in the moment.
• Shopping on Newbury St: Boston's upscale shopping street in Back Bay. Fun to walk up and down, window shop, and lots of options for things like ice cream on the way.
• Places to just see / walk around: These are not really activities so much as sightseeing, but are recommended stops!
  • Boston Public Garden: Lovely garden to walk around or have a lunch picnic. Make sure you see the duckling statue (based on Robert McCloskey's famous 'Make Way for Ducklings'). Easy walking from both Back Bay + Downtown/Omni Parker House. In the winter, if the pond is frozen over, you might see folks skating or playing hockey on the ice. In the summer, you can take a ride on one of the Swan Boats for a casual cruise around the pond.
  • Harvard Square: Cross the River to Cambridge (via Uber or the Red Line T) to walk around Harvard + Harvard square. Harvard Book Store is big and always fun to wander into, and good lunch options around here (e.g. a Tatte, El Jefe's/Felipes both have good tacos)
  • Copley Square: Heart of Back Bay - has some really cool architecture in Trinity Church and the Boston Public Library if not much to actually do. If it's raining, the Boston Public LIbrary offers a high tea service at 11 / 1 / 3 that's pretty fun!

Putting it all together: A sample Boston weekend itinerary

Friday Evening:

• Arrive in Boston!
• Explore the North End. Grab dinner and dessert on Hanover Street in the North End, Boston's Little Italy.

Saturday Day:

• Explore Boston's Revolutionary History, either via a Duck Tour or via a walking tour like Boston by Foot.
• Get lunch at Tatte or Flour - they're Boston-local, ubiquitous, and consistently good!
• As time, energy, and weather allow, add one more activity:
  • Explore the Boston Public Garden and walk along the Charles River Explanade (and rent a kayak if the weather is nice!)
  • With kids, visit the Museum of Science
  • Walk around Harvard Square

Saturday Evening:

• If it's the summer & the Red Sox are playing, go to a Red Sox game!
• If not, grab dinner in a new neighborhood. As a former South End resident, I recommend it because I'm biased. A few favorite spots:
  • Coppa
  • Kava
  • Toro
  • Myers + Chang
  • B&G Oyster

Sunday Day:

• If you didn't seen the Boston Public Garden and Esplanade yet, this is a must-do.
• Otherwise, use this morning to visit the Isabella Stewart Gardener Museum. This is right by Fenway Park, so you can admire the green monster while you're there, if not take in a game.

Appendix

More ideas for where to eat

As a disclaimer, refer once again to the extreme neighborhood bias. These recs are heavily Back Bay/South End focused!

Sit-down restaurants

Brunch

• Beehive (South End): Nice brunch spot. Great outdoor seating when it's warm, sometimes has Jazz inside.
• Friendly Toast (Back Bay): Classic brunch spot! Join the Yelp waitlist online before you go, there's often a long wait
• Mike’s City Diner (South End): Cash only diner
• Stephanie’s (Back Bay): Ok food, great people watching, very convenient to Newbury for shopping

Dinner

One day I will add links & descriptions for these. One day!

• Buttermilk and Bourbon (Back Bay)
• Coppa (South End)
• B&G Oysters (South End)
• Barcelona (South End)
• Grotto (North End)
• Citrus and Salt (Back Bay)
• Haley Henry (Downtown)
• Kava (South End)
• Toro (South End)
• Myers + Chang (South End)
• Gourmet Dumpling House (Chinatown) and Dumpling House (Cambridge)

Grab-and-go / Casual seating

Brunch

• South End Buttery (South End): Great pastries and actually also good sit down brunch. Service is slow, so everything backs up - visit on a weekend morning expecting a wait/slow service.
• Mike and Patty’s (Bay Village): Great spot for breakfast sandwiches to go; try the Crack and order ahead online, they’re quite slow
• Render Coffee (South End/Back Bay): Also great breakfast sandwiches but with a more egg on a bagel tilt, get the version with rosemary and potato
• Tatte (many neighborhoods): Boston classic, great bakery and food, can be sit down or to go. They’re famous for the Shakshouka but everything is good

Lunch

• Flour (many neighborhoods): Another Boston classic, great pastries but the highlights are the sandwiches - I like the lamb and the BLT but everyone has their own faves
• Picco (South End): Great pizza, better ice cream.
• A’noushella (South End): A little pricey for what it is, but great mediterranean bowl things

Late night

• Dumpling Palace (Back Bay): Don’t go if it’s not 2 am. Definitely go if it’s 2 am.

Casual drinks

• Felipe’s (Cambridge): Fun rooftop, great margs
• Citrus and Salt (Back Bay): Also good for margs, I like margs I admit it
• Earl’s at the Pru (Back Bay): Fun after work drinks spot
• Harpoon Brewery (Seaport): Harpoon = Boston classic, really fun for Oktoberfest and St. Patrick’s
• Aeronaut (Somerville): Fun space and has this amazing embedded Venezuelan restaurant pop-up
• City Winery, Trillium at The Greenway (Downtown): Outdoor beer/wine gardens, super fun
• Night Shift Owl’s Nest Esplanade (Back Bay): Would pick the others first, but another solid beer garden option
• Downeast Cider House (East Boston): They don’t have a liquor license so can’t serve full drinks but in non COVID times they will give you 4 ish free samples of flavors of your choosing (they have some fun seasonal ones) and you can buy to go
• Lookout Rooftop & Bar (Seaport): Located on the rooftop of the Envoy hotel. Great view of Boston!

Dessert

• Toscanini’s Ice Cream (Cambridge) - Get the B3.
• Mike’s Pastry (North End): iconic cannolis, bring cash, be prepared to order instantly
• Kane’s Donuts (Downtown): For gluten-free donuts, get the maine blueberry
• Blackbird Donuts (South End, Fenway): For gluten-full donuts
• Union Square Donuts (Cambridge or Time out Market): Also good donuts
• JP Licks (multiple locations): Ice cream. Get one of their cookies & cream variations!

Bonus activities

Other Activity Ideas

These are incremental to all the ideas above; think of them as good fodder for second visits or for Boston residents looking for a new activity

• Check The Boston Calendar for the latest happenings. This website is truly great.
• Get Richardson’s ice cream from Code 10 and sit and eat it in Blackstone Park in the South End
• Go bowling at King’s ($23 pp)
• Visit Station KTV - rentable rooms for karaoke, best with a group of ~6-10
• Candlepin Bowling at Sacco’s/the flatbread company in either Brighton or Cambridge
• Clery’s trivia on Wednesday nights
• Other museums: Museum of Fine Arts (MFA), Institute for Contemporary Art (ICA)
• Black Heritage Trail
• SoWa - market, artist exhibitions, vintage shop, etc.
• Arnold Arboretum
• Walk around the Rose Garden at the Fens (if it's in season)
• Explore the Boston Public Library and see the Harry Potter room
• Day trips (Blue Hills, Middlesex Fells, Walden Pond, North Shore, NH, Vermont, Maine)
• Encore (casino ~20 min from Boston), bring cash or else pay the crazy casino atm fees
• Other sports games - Bruins, Celtics, Patriots

Nice places to run/walk:

• Charles River Esplanade
• Emerald Necklace/Jamaica Pond
• Fresh Pond
• Chestnut Hill Reservoir
• Castle Island/Harborwalk
• Boston Common/Public Garden/Commonwealth Avenue
• A bit further out: Battle Road Trail from Lexington to Concord, Mystic River Path, Newton Hills, Minuteman Commuter Bikeway, Concord Great Meadows