Boston: 5-Day City Experience Itinerary

  1. Day 1: Freedom Trail
    Start at Boston Common, 10:00 AM
    1.8 miles, 2 hours

    Walk the famous Freedom Trail and visit historic sites from the American Revolution. Highlights include Boston Common, Massachusetts State House, Paul Revere House, and Bunker Hill Monument.

  2. Day 2: Seaport District
    Start at Institute of Contemporary Art, 10:00 AM
    2.3 miles, 3 hours

    Explore Boston's trendy Seaport District, also known as the Innovation District. Visit the Institute of Contemporary Art, walk along the HarborWalk, and enjoy a seafood lunch at Row 34.

  3. Day 3: Fenway/Kenmore
    Start at Fenway Park, 11:00 AM
    2.5 miles, 3 hours

    Experience Boston's sports culture with a behind-the-scenes tour of Fenway Park, the oldest Major League ballpark in America. Afterwards, head to the nearby Kenmore Square for a beer at the iconic Cheers bar.

  4. Day 4: Back Bay
    Start at Boston Public Library, 11:00 AM
    1.8 miles, 2 hours

    Stroll through picturesque Back Bay and admire its Victorian brownstones and high-end shopping district. Visit the Boston Public Library and Trinity Church before indulging in a sweet treat at Flour Bakery.

  5. Day 5: North End
    Start at Paul Revere House, 10:00 AM
    1.6 miles, 2 hours

    Experience Boston's Italian heritage with a visit to the historic North End neighborhood. Highlights include Paul Revere House, Old North Church, and the best cannolis in town from Mike's Pastry.

Time and Cost Estimates

  • Boston Common (2 hours, free)
  • Massachusetts State House (30 minutes, free)
  • Paul Revere House (30 minutes, $5)
  • Bunker Hill Monument (1 hour, free)
  • Institute of Contemporary Art (1.5 hours, $15)
  • HarborWalk (1 hour, free)
  • Row 34 (1 hour, $30)
  • Fenway Park (1 hour, $25)
  • Cheers bar (1 hour, $20)
  • Boston Public Library (1 hour, free)
  • Trinity Church (30 minutes, free)
  • Flour Bakery (30 minutes, $10)
  • Paul Revere House (30 minutes, $5)
  • Old North Church (30 minutes, $8)
  • Mike's Pastry (30 minutes, $10)
  • Total Estimated Costs: $138

Useful Tips

If you have more time, consider taking a day trip to Salem or Cambridge to visit Harvard University. If you have less time, skip the Fenway/Kenmore and Back Bay neighborhoods and spend more time on the Freedom Trail and in the North End.

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