Boston (June 2014)

About this Trip

Eric and I flew direct to and from Boston on American Airlines. We stayed in a really cute and convenient Airbnb in the North End. After arriving, we got reloadable Charlie Cards for the "T" to make traveling around the city easy. Back Bay streets are in alphabetical order: Arlington, Berkeley, Clarendon, Dartmouth. So are South Boston streets: A, B, C, D.

Boston's top attractions are concentrated in several areas. The North End is rich in history and Italian culture, while Back Bay boasts stunning architecture and upscale shopping. Visitors can explore the natural beauty of Boston Common and the Charles River, visit prestigious universities like Harvard and MIT, or enjoy entertainment at the Prudential Center, TD Garden, and Fenway Park.

 

Day 1

For a mid-afternoon pick-me-up, we stopped at Modern Pastry on Hanover Street for cannolis—definitely worth it. After that, we spent some time wandering through Boston Common and the Boston Public Garden, checking out the Make Way for Ducklings statue and watching the Swan Boats glide by. It’s a great spot to just relax and soak in the city.

Before dinner, we grabbed a drink at the Cheers bar in Quincy Market—yes, it’s touristy, but sometimes you just have to lean into it. For dinner, we had a tough choice with so many great options. The Daily Catch is famous but has a long wait, so Wednesday is probably the best bet if you want to try it. Other solid picks are Al Dente, Giacomo’s, and Panza for classic Italian, or Bottega Fiorentina on Newbury Street if you’re looking for something more budget-friendly. If you’re up for something different, Cuchi Cuchi in Cambridge, Coppa, Union, and a few other spots came highly recommended. Plenty of good food no matter what you’re in the mood for.

Day 2

We started the day with breakfast at Faneuil Hall – Quincy Market at 9:00 a.m. It’s a lively spot with plenty of food options.

For the morning, we walked part of the Freedom Trail, a 2.5-mile stretch packed with 16 sites from the Revolutionary War. You can either take a guided tour or do a shorter, self-led version if you don’t want to commit to the whole thing. Some of the most interesting stops are Paul Revere’s House, the Old North Church, Bunker Hill, and the USS Constitution.

By noon, we were ready for lunch and some World Cup action, so we headed to The Banshee at 934 Dorchester Ave. If you're a soccer fan, this is the place to be. In a city as sports-obsessed as Boston, The Banshee stands out as the go-to bar for Premier League matches, and during the World Cup, it’s packed with fans from all over. (This was obviously not MY plan but when you travel with a sports enthusiast you have to make concessions.)

After lunch, we made a stop at the Boston Public Library in Copley Square. The Italian Renaissance-inspired courtyard is stunning, and inside, you’ll find murals by prominent artists that are worth a look.

For dinner, we had plenty of options in the North End: The Daily Catch, Al Dente, Giacomo’s, and Panza. We heard all are solid bets if you’re craving Italian. We chose Al Dente and weren't disappointed.

To wrap up the night, we caught a show at the Improv Asylum. So funny, and so fun!

Day 3

It was an early wake-up call this day, with a quick breakfast on the go before heading straight to Fenway Park for a stadium tour. We made sure to be there by 8:00 a.m. since tours run on a first-come, first-served basis and only operate from 9 a.m. to 1 p.m. on certain days. Tickets ($17 for adults) are sold at the Gate D Ticket Booth on the corner of Yawkey Way and Van Ness Street, but availability can be limited, so getting there early is key. The tour itself was a must for any baseball fan—stepping into Fenway’s history, seeing the Green Monster up close, and walking through the same tunnels as legends was well worth it.

After the tour, we grabbed a drink at Bleacher Bar, which sits right inside the stadium with a view of the field, and then stopped at Cask ‘n Flagon, a classic Fenway-area sports bar.

For the evening, we headed to the South Side for a night out. Dinner was at Sportello, an Italian spot with a modern diner feel, followed by dessert at Flour Bakery (because you can never go wrong with something sweet from there). We wrapped up the night with drinks at L Street Tavern—the bar from Good Will Hunting—a cool little spot that’s got that true neighborhood feel.

Day 4

We started the day with brunch at Eastern Standard, which was a solid choice to fuel up before a day of sightseeing. Afterward, we made our way to Harvard University for a relaxed stroll around campus. We stopped by Memorial Church, explored the Peabody Museum, and took in the exhibits at the Sackler Art Museum. The Harvard Museum of Natural History was another must-see, with its incredible collections. You can find a handy campus map online if you want to plan your visit ahead of time: Harvard Campus Map.

For lunch, we headed to Harvard Square, where the vibe is laid-back and casual—perfect for a little sightseeing. My top recommendation is Mr. Bartley’s Burger Cottage at 1246 Massachusetts Ave. The onion rings here are incredible, and the burgers are top-notch too. Just a heads-up, it’s closed on Sundays.

We left the Square around 3:30 or 4:00 p.m. to head back to the house and grab our things. We were on our way to the airport by 5:30 p.m., ready to catch our 7:00 p.m. flight back to Dallas.