Best of Boston in 3 Days

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Elizabeth Trainham
Curated By

Elizabeth Trainham

  • City Travel

  • Weekend Getaways

  • Boston

  • Sightseeing

Advisor - Best of Boston in 3 Days
Curator’s statement

Boston is a city where rich history, incredible food, and passionate sports culture come together. Spend your days walking the same streets that shaped the nation, then catch the electric atmosphere of a game in one of the city’s iconic venues. With its unique blend of historic charm and modern energy, Boston makes the perfect weekend getaway.

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Day 1: The Freedom Trail

Old City Hall

Grab breakfast at Tatte, then walk through the public gardens to the start of the Freedom Trail. Follow the 2.5-mile Freedom Trail as you see sights of Boston and adjust to the city and where things are located. Grab a snack or lunch at Faneuil Hall. Visit the USS Constitution and end at Bunker Hill. Check out the Boston Harbor and Tea Party Ships, then head to Boston Sail Loft for the best clam chowder in Boston.

Day 2: Newberry Street & Beacon Hill

Boston Public Library

Wake up and hit up the Friendly Toast for brunch. Head to the Boston Public Library and explore the amazing architecture. Shop on Newberry Street, visit the Beacon Hill area, and stop by Beacon Hill Books. Grab lunch at the Cheers bar or Saltie Girl. Spend the afternoon at Harvard—get a coffee at Blank Street and then take a self-guided or guided tour of the campus. Get an Italian dinner in the North End and grab a cannoli from Bova's.

Day 3: Fenway

Fenway Park tour

Head to breakfast at Mike and Patty's for the best breakfast burrito in Boston. Take a tour of Fenway Park and grab some merch! Stop by the Isabella Stewart Gardner museum if you're interested. Explore the Fenway area and grab lunch. Rest or finish shopping and then head back to Fenway Park for a game!

Need to know

The "T" or the subway in Boston is easy to use to get around!

Elizabeth Trainham

Travel Advisor

Elizabeth Trainham

Advisor - Elizabeth Trainham

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For more inspiration and insider recommendations, visit our Boston page.