A Long Weekend in Boston: Ballparks, Bites & Big Wins

Boston surprised us in the best way—rich in history, full of charm, and packed with unforgettable food, views, and energy. Evan and I are on a mission to visit every MLB stadium, and Fenway Park was high on our list. But our weekend in Boston turned into so much more than just baseball. Here's a look into our trip, packed with food, local spots, and must-dos if you’re planning your own Boston getaway.

Saturday: North End Views & Fenway Vibes

We landed in Boston and hopped on the train straight from the airport to East Boston, where we grabbed coffee and enjoyed views of the city skyline and the Bunker Hill Monument while waiting for our friend to pick us up. From there, we headed into the city and parked in Back Bay near the Prudential Center—an ideal location to walk to Fenway Park, where our day really began.

We had tickets for a Fenway Park guided tour (check out the full breakdown here), which was an awesome way to kick off our MLB stop. After the tour, we picked up sandwiches from Tatte—the Turkey BLAT was one of the best sandwiches I’ve had in a long time. Fresh sourdough. Game changer.

We stayed up in Revere Beach to save on lodging costs—easy train access and quieter at night. After a quick change, we made our way back into the city, bar-hopped from Game On to Cheeky Monkey (skip the espresso martini), then headed into Fenway for an epic night game.

The Sox won in a walk-off against the Braves, making it a night to remember. Post-game, we hit Bill’s Bar & Lounge, which was the spot. Live music, great energy, and the perfect cap to a perfect Boston night.

Sunday: Back Bay, Gardens, and Pastries

Sunday was low-key, by design. We started the day in Back Bay, exploring the charming architecture and grabbing brunch from Tatte (again—this time the chicken salad sandwich and strawberry turnover). We ate in the Boston Public Garden, walked around, and popped into a few local shops.

Later we ventured toward TD Garden, hit the Pro Shop, saw the Samuel Adams statue, and walked through the Holocaust Memorial before dinner. We had reservations at Union Oyster House, which dates back to 1826 and is Boston’s oldest restaurant. Iconic. Historic. Worth it.

After dinner, we wandered through Little Italy, caught views of the waterfront and the Paul Revere House, and finished with pastries from Bova’s Bakery—lobster tails, whoopie pies, cannolis. All 10/10.

Monday: Stadiums & Harvard

We kicked off Monday with (you guessed it) Tatte—this time the lamb hash, which was easily the best meal of the trip. We headed to Foxborough to explore Gillette Stadium, the Patriots Hall of Fame, and even climbed America’s tallest lighthouse. The whole area around the stadium was surprisingly cool and family-friendly.

In the afternoon, we went up to Cambridge and grabbed ramen at Hokkaido Ramen Santouka, then strolled through Harvard’s campus before our final dinner in Little Italy at Ristorante Villa Francesca. The steamed calamari in tomato sauce was incredible, and I went all-in on a pasta alfredo served in a cheese wheel with grilled chicken—because protein, obviously. We closed it all out with divine espresso martinis and a final Bova’s run to grab pastries for the flight home.

Tuesday: See You Again, Boston

Packed up, made our way to the train, and headed for the airport. Boston left its mark.

Must-See Highlights

• Fenway Park (tour & game)

• Boston Public Garden

• Little Italy & North End

• Gillette Stadium & Hall of Fame

• Union Oyster House

• Freedom Trail stops along your route

• Bova’s Bakery for a late-night sweet fix

Things to Know Before You Go

• Boston is expensive. Expect to spend—food, drinks, and attractions add up.

• Parking is a pain. It’s limited and pricey. We recommend public transportation or parking outside the city.

• Walk the city. Boston is best seen on foot. Wear good shoes and skip the car.

• Reserve early. For food, tours, and big-name spots—book ahead.

• Weather can flip. Layers are a smart move, especially by the water.