Boston Usa 5 Day Itinerary

Boston, MA 5-Day Itinerary

(Markdown format)

Day 1: Arrival & Downtown Boston

  • Arrive at Logan International Airport (BOS)

  • Check-in at your preferred accommodation:

    • Luxury: The Ritz-Carlton, Boston (1 Avery St)
    • Mid-range: The Boxer Hotel (486 Harrison Ave)
    • Budget: Hostelling International Boston (19 Stuart St)

  • Breakfast at Flour Bakery + Cafe (131 Clarendon St)

  • Visit Freedom Trail (Start at Boston Common, self-guided tour)

  • Explore Faneuil Hall Marketplace and Quincy Market

  • Lunch at Boston’s North End: Try Mike’s Pastry for cannoli or Lucca Ristorante Italiano for authentic Italian dishes.

  • Afternoon visit to USS Constitution Museum and the warship itself, docked in Charlestown Navy Yard.

  • Dinner at Tarantino’s Ristorante (133 Salem St) - famous for its seafood pasta dishes.

  • Evening stroll along North End waterfront or catch a Red Sox game at Fenway Park (if in season).

Day 2: Museums & Fenway-Kenmore

  • Breakfast at My Thai Café (1435 Massachusetts Ave)

  • Visit Museum of Fine Arts (465 Huntington Ave) or Boston Museum of Science (1 Science Park)

  • Lunch at Jamaica Plain, try Amy’s Bakery & Bistro (658 Centre St) or Sarma (348 W Boston Ave) for modern Armenian cuisine.

  • Afternoon at Fenway Park - guided tour if there’s no game on, or catch a Red Sox game if it’s the season.

  • Dinner at The Capital Grille (1 Boylston St) or Bukowski Tavern (82A Charles St), depending on your taste preference.

Day 3: Harvard & MIT

  • Breakfast at Brick & Mortar Kitchen (45 Cochituate Rd, Newton Centre)

  • Head to Harvard University (1350 Massachusetts Ave, Cambridge) and tour the campus, including Harvard Yard, Widener Library, and John Harvard Statue.

  • Lunch at Harvard Square: Try Henry’s Dallas Bar & Grill for American comfort food or Clover Food Lab for healthy options.

  • Afternoon visit to MIT (77 Massachusetts Ave, Cambridge) and the MIT Museum (265 Massachusetts Ave).

  • Dinner at The Porto birra rossa e cucina (413 Mass Ave) or Oleana (134 Hampshire St), both in Cambridge.

Day 4: Beacon Hill & Boston Harbor

  • Breakfast at Cafe du Pays (40 Brattle St) or Mike & Patty’s (169 Charles St) in Beacon Hill.

  • Morning exploration of Beacon Hill, including Louisburg Square, Acorn Street, and Boston Common.

  • Lunch at Mamma Maria (135 Cambridge St), famous for its homemade pasta dishes.

  • Afternoon visit to the Boston Tea Party Ships & Museum or take a ferry to Boston Harbor Islands.

  • Dinner at Island Creek Oyster Bar (500 Commonwealth Ave) or Toraya Sushi & Grill (461A Boston Ave).

Day 5: Departure

  • Breakfast at your accommodation or nearby café.

  • Spend the morning at leisure, exploring any missed attractions or shopping at Newbury Street.

  • Lunch at The Friendly Toast (561 Tremont St) before heading to the airport.

  • Depart from Logan International Airport (BOS) for your next destination.

Things to Know:

  • Tipping: 18-20% is standard in restaurants and bars.
  • Public Transportation: Boston’s MBTA (MBTA.com) provides buses, subways, and commuter rail services.
  • Weather: Be prepared for unpredictable weather; layered clothing is advised.
  • Covid-19 Guidelines: Follow all local regulations and guidelines related to masks, social distancing, and capacity limits.
  • Parking: Street parking can be difficult to find in downtown areas; consider using parking garages or apps like ParkMobile or SpotHero.