A Weekend Guide to Boston, Massachusetts

Boston, Massachusetts one of the country’s oldest and most historic cities. It’s the perfect balance of small-town charm and big-city hustle. Enjoy a stroll along cobblestone streets. Visit Harvard, the most profound university in the world. Catch a Red Sox game at Fenway. Eat at some of the best Italian restaurants. Boston has a little something for everyone!

I wanted to share my exact weekend Boston itinerary with you all since I worked hard planning my first trip to Boston. First things first, I would recommend renting a car in Boston to get the most out of your stay!

Day One

• Check into your hotel.
  • We stayed at the Kimpton Marlowe Hotel. It’s located in Cambridge but is only a quick ride to downtown Boston.
• Visit Harvard Square and walk around the campus and town. The architecture and the cute little shops and restaurants are the best part of Harvard Square.
• Have a late lunch at Russell House Tavern. I highly recommend the burger and delicious Mojitos!
• For dinner, Uber to North End which is Boston’s Little Italy.
  • North End in Boston is super fun and lively at night. After dinner, you can people-watch along the streets and post up in a park.
• Visit Mike’s Pastry Shop it’s an iconic pastry shop located in Boston and always has a super long line. We visited right at closing so luckily didn’t have to wait long.

Day Two

• Start the morning off at Caffe Nero for a light breakfast and coffee.
• Walk around Boston Common and Boston Public Garden for the most picturesque Boston sights (and the park where Good Will Hunting was filmed).
• Visit the Back Bay neighborhood to do some shopping.
• Explore the Boston Public Library (a must-see!) it’s architecture alone is reason enough to see this gem!
• Uber to Faneuil Hall Marketplace for lunch. It’s a marketplace that houses many different food vendors and shops.
• Post up at Fanueil Hall for drinks and watch the street performers perform.
• Grab an early dinner at Bambara. We loved the warm atmosphere and great cocktails!

Day Three

• Grab brunch in Beacon Hill and explore one of the cutest neighborhoods in Boston.
• Rent bikes and bike along the waterfront of Cambridge (this was easily my favorite part of the trip).
• Stop at Cambridge Square and grab a coffee at Blue Bottle.
• If it is baseball season make sure to visit Fenway Park. We went for a night game and the matchup of the century — Yankees VS. Red Sox
  • Make sure to get there early to partake in the block party they have prior to every game, such fun energy!

I hope you enjoyed my Weekend Guide to Boston. Comment below any fun things you like to do in Boston so I can note it for my next visit. Thanks for reading for more of my travel guides’ head here!

XO,

Courtney

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