Boston in a Weekend: Quick Travel Guide & Highlights

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

• Arrival: Took the train from Logan Airport to East Boston—great views of the skyline and Bunker Hill Monument.

• Lunch Stop: Grabbed coffee from Cafe Iterum and walked the waterfront before being picked up.

• Back Bay: Parked near the Prudential Center and walked to Fenway.

• Fenway Tour: Explored the Green Monster, learned about rooftop gardens, and soaked in baseball history.

• Tatte Bakery: Grabbed a Turkey BLAT on sourdough—10/10 recommend.

• Game Night: Enjoyed the walk-off win over the Braves. Pregame drinks at Cheeky Monkey & Game On!, postgame at Bill’s Bar & Lounge (live music + energy).

Sunday: Back Bay, Gardens, and Pastries

• Back Bay Morning: Admired brownstones and got brunch from Tatte again (chicken salad sandwich + strawberry turnover).

• Boston Public Garden: Perfect picnic spot with great people-watching.

• Afternoon: Visited TD Garden, Samuel Adams statue, and the Holocaust Memorial.

• Dinner: Historic Union Oyster House (since 1826!).

• Evening: Explored Little Italy, visited Paul Revere’s House, and hit up Bova’s Bakery—famous for lobster tails, cannoli, and whoopie pies.

Monday: Stadiums & Harvard

• Tatte Again: This time the lamb hash—best meal of the trip.

• Gillette Stadium: Patriots Hall of Fame and America’s tallest lighthouse—family-friendly and fun.

• Cambridge: Ramen at Hokkaido Ramen Santouka, strolled around Harvard’s campus.

• Dinner: Ristorante Villa Francesca—pasta in a cheese wheel, plus espresso martinis.

• Pastry Pickup: One last stop at Bova’s before heading 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

Don’t Miss (Even Though We Did!)

If you’ve got extra time, here are a few top-rated spots:

• Museum of Fine Arts

• Isabella Stewart Gardner Museum

• Boston Tea Party Ships & Museum

• Boston Common (America’s oldest public park)

• Newbury Street (shopping & cafes)

• Boston Aquarium

• Beacon Hill (gas lamps + cobblestone streets)

• Freedom Trail (we hit parts in passing, but the full route is worth it)

Things to Know Before You Go

• Boston is not cheap. 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.