3.5 days in Boston: Lobster rolls, lots of history + local tips


The last time I was in Boston, I was 18 and visiting colleges. I wanted to go for years throughout my 20s, but budget and being with a hardcore Yankees fan pushed it lower on the list. When inexpensive flights opened for Memorial Day weekend, I finally convinced Steve that we needed to spend it in Boston.

I knew that we wanted to stay in a pretty central location, so I looked in Beacon Hill and Back Bay. We ended up with a good deal through hotels.com for the John Jefferies House, a B&B on the edge of Beacon Hill.

I’m going back to sharing our trip by days because I used Visit a City (another planning site/app I recently shared with Becky) and it’s broken down by days. 



First, I have to give credit to our B&B. It was in a great location and the room was really big (with a kitchenette!) and clean. For $188/night on weekend nights in Beacon Hill, I couldn’t complain. (Keep reading for a better hotel suggestion, though!)

We started the morning walking along Charles Street, which is packed with restaurants and bars. I was craving an acai bowl, so we stopped at Pressed and we ate at Boston Common. We walked through the park — it was in the high 60s — and ended up at the State House. Its dome is gilded, just like Denver’s capital building.

From there, we stopped a few places along the Freedom Trail: Granary Burial Grounds (to see the graves of Revere, Adams, and Hancock), the Old State Museum (just for the building), Faneuil Market, Quincy Market, the Paul Revere House, Copp’s Hill, and Old North Church. We’d planned to have lunch at Quincy Market, but we stopped at a pop-up shop with local artisans, 1630, and were told to avoid the market and try Neptune’s Oyster or Boston Public Market. Steve and I are huge market fans, so we ended up at the latter. (We did walked through Quincy Market and it was PACKED. No thanks.)


Steve had 4 Boston food goals: Lobster rolls, oysters, fried clams, and clam chowder. After checking out all of the stalls (don’t miss the lavender grey tea macarons from Finesse Pastries), we both settled on Red’s Best. Of course, Steve had the lobster roll and I had the salmon kale salad. Spoiler alert: This was Steve’s favorite lobster roll of the weekend — and he had three.

To polish off lunch, we stopped for drinks at The Bell in Hand Tavern, the country’s oldest bar. We passed King’s Chapel on the way back to Beacon Hill, where I went searching for Acorn Street, the most famous street in Boston. (Search #Boston on Instagram and it’s likely in the top 9.) I started laughing when we turned the corner because there were SO MANY people and so many guys taking pics of their girlfriends/wives. (I did swoop in for a pic, but didn’t make Steve take one of me/us.)

After about 5 hours of walking, I wanted to hit a few shops on Charles Street. We stopped at Flat of the Hill, December Thieves, Rugg Road Paper Company, and Black Ink. For dinner, we went to Back Bay with attempts to eat at Saltie Girl, but the wait was 1.5 hours. A quick Google search and Uber had us in South Boston at B&G Oyster, sitting on the patio under the lights.

We split a delicious half dozen of oysters (all from Maine) and I opted for the scallops, which were delicious. Steve went for lobster roll #2, a BLT version. While we waited, we ended up talking with the couple next to us, who gave us great recommendations: Alden + Harlow (Harvard Square, Cambridge), Little Donkey (Central Square, Cambridge), Toro (South End), Bin 26 Enoteca (Beacon Hill), and Select Oyster (Back Bay). (We were planning to have dinner at 75 Chestnut in Beacon Hill on Sunday, but they guided us away from it. Love locals.) After about 6 hours of walking, we retired Day 1.



We loved starting our day with breakfast in the park, so we stopped at Tatte on Charles (ham croissant for him, pear muffin and muesli for me) and ate in the Public Gardens. I planned for Day 2 to be in the South End and South Boston, but we knew that it was going to rain on Monday, so we moved South Boston (with breweries) to then. (Reminder: Always check openings when planning travel on holiday weekends!)

We walked through Copley Square, by Boston Public Library (sadly, closed), strolled through the faux streets of Italy at Eataly, and made our way to the Skywalk of the Prudential Center. Touristy? Yep. Amazing views? Yes.

Next we were off to the South End to Tremont Street’s shops, including Heartbreak Hill Running, niche, a b.willow-esque shop full of amazing plants, Gifted, where I bought some really cute jewelry, and Sault, a fairly preppy men’s store where Steve got awesome nautical socks. (I wanted to go to Olives & Grace, but they were closed.)

I’d planned to have lunch at the SoWa Market food truck gathering (per the local couple’s recommendation), but none of the trucks were fitting our lunch wants. We ended up at The Gallows, where I had the strawberry pancakes and Steve went for the soft-shell crab lettuce wrap. (“Best lettuce I’ve ever had,” and he was serious.) They have amazing cocktails, so I definitely recommend it for the evening.


We went back to SoWa Market to the farmers’ market, which was packed with vendors. After picking up a few things, we hopped the T to Cambridge. Harvard Yard was closed for reunions, but we were able to walk around the rest of campus and Harvard Square. To my PURE AMAZEMENT, I spotted a Pressed Juicery (different from Pressed) and made a beeline for the Instagram-approved freeze. (It’s basically fro-yo but made from the juices.) I may have crumbled in a pile of tears when he told me the machine wasn’t working. I consoled myself candy from Cabot’s while we walked to MIT.

Another 5-6 hours of walking down and we were ready for dinner. We went back to Cambridge, to The Hourly and enjoyed more oysters and the most delicious spring. We wandered the (completely packed) streets and grabbed drinks at Russell Tavern.



Our third day in Boston called for rain most of the day, so we’d planned breweries. We went to Southie and had lunch at Row 34, where Steve had — you guessed it — a lobster roll. I had ridiculously good salmon with English peas, which are probably one of my favorite foods ever. I mean, look at this dish.


We walked over to Harpoon and waited in a line … in the rain … for about 45 minutes. Yep. BUT the brewery was really cool. We grabbed a seat at the communal wooden tables. Steve loved the beer (his favorite was the UFO huckleberry, a seasonal draft) and I loved the soft pretzels, so all around success. (We were also told to go to Trillium Brewery, but it was closed when we walked by.)

We had to catch a late flight, so we went back to Beacon Hill and decided to grab one last drink at a hole in the wall on Charles Street, Sevens, and were alerted that our flight was cancelled. WOMP. We quickly hopped on Hotels.com and booked a night at Chandler Inn in South End. It’s a boutique hotel with very small rooms, but I loved the location and it was modern, clean and affordable.


A quick ask on social pointed us to Barcelona for dinner, which featured lots of (shocker) Spanish tapas. I ordered the flight of Tempranillo wines and they arrived in glasses half the size of my head. Every tapas dish we ordered was delicious and the service was excellent; I highly recommend Barcelona. (It was my favorite meal of the trip.)


DAY 3.5

We only had a few hours before we had to be at the airport, so I grabbed breakfast for us at Flour and stumbled on an awesome mural in Frieda Park. We walked around the South End a little more before heading to the airport. I think my Yankees fan was pretty happy with our weekend on enemy turf.


Want to read more about my 2017 travels? Check out my posts on Charleston and Phoenix, Sedona, the Grand Canyon, and Vegas. Posts on St. Michaels, Asheville, and Tulum to come!


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