Courtesy Greater Boston Convention and Visitors Bureau

Despite continuously serving for more than 200 years as the political, economic and cultural hub of New England, Boston’s reputation as a staid municipality with rabid sports fans hadn’t changed much over the years. Now home to a bevy of charming neighborhoods and some great restaurants, not to mention a stellar selection of colleges, Boston is one of the most historic places on the East Coast for a long weekend.

  • Perfect for
    Families | Intellectuals
  • When to go
    March-May | June-August | September-November
  • Ideal length of stay
    1-2 Nights

Designing Your Journey

Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.

  • 3 Days: Essential Boston-LP

    3 Days: Essential Boston

    Indagare can help with a customized itinerary in Boston that includes guided historical walks and boat charters. Here is just one example of what our destination experts can create for you.

    • Aerial View - Boston Duck Tours, Boston, New England

      Day 1: Intro to Boston

      Get your bearings with a walk through the Boston Common, a 50-acre park that is the oldest in the country. If you have children in tow, take a duck boat tour of the city. The über-perky guides border on corny, but the 80-minute ride includes a drive-by of the city’s major landmarks (another option is chartering a private boat around the harbor). After lunch, take a guided tour of the Paul Revere House, one of the few remaining early colonial homes in Boston. Enjoy dinner at an elegant restaurant on Newbury street before hitting the Beehive, a bohemian-chic spot for live music.

    • View from Bar - Bleacher Bar, Boston, New England

      Day 2: Museums and Baseball

      Today, you have the option to visit several of Boston’s world-class museums. Favorites include the Museum of Fine Arts, the city’s primary cultural institution which boasts the largest collection of Monets outside of France; and the Institute of Contemporary Art, which contains fascinating exhibitions across all mediums (be sure to go with an Indagare-approved guide who can bring the pieces to life and provide context). In the evening, head to a game at Fenway Park.

    • Day 3: Beyond Boston

      Begin your day with a visit to the Isabella Stewart Gardner Museum, a Venetian-style palace with Italian Renaissance works. After lunch, drive to historic Concord and take a guided walk of Walden Pond, the famous 62-acre reservation that includes a web of hiking trails and a replica of the philosopher’s one-room cabin. In the evening, head to concert at Symphony Hall, or stroll through the South End or Beacon Hill before dinner.

Indagare's Blair West
“There is something irresistible about Boston. Its many identities–from a thriving college town to a sports mecca and world-class artistic hub–conspire to make it one of America’s loveliest cities to visit, at any time of year.”
Ready to go and in need of expert trip planning? Contact us today.

What To Read

Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.

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