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How to spend 2 days in Boston + Get Our Exact Itinerary

Boston is wicked awesome! I could have spent an entire week exploring that amazing city. But I’ll tell you we crammed in as much of Boston as we could into 2 days!

Day 1: Harbor Adventure and Culinary Delights


  • Boston Harbor Cruises: Whale Watch (10:00 AM – 1:45 PM)
    • Location: Boston Harbor Cruises, 1 Long Wharf, Boston, MA 02110, Phone: (617) 227-4321

Kick off your Boston adventure with a thrilling whale-watching tour. As you sail through the picturesque Boston Harbor, keep your eyes peeled for majestic whales breaching the surface. It’s an unforgettable experience that connects you with the ocean’s wonders.


  • Bostonia Public House (2:00 PM)
    • Location: Bostonia Public House, 131 State Street, Boston, MA 02110, Phone: (617) 948-9800

Savor a delectable lunch at Bostonia Public House, where you can relish both classic and contemporary American cuisine. The historic ambiance and hearty food make it a perfect mid-day stop.


  • Sam Adams Brewery Tour (3:30 PM – 4:30 PM)
    • Location: Samuel Adams Boston Brewery – The Boston Beer Company, 30 Germania Street, Boston, MA 02130, Phone: (617) 368-5256

Discover the art of beer brewing on the Sam Adams Brewery Tour. It’s an opportunity to delve into the history and craftsmanship behind one of America’s favorite beers. Enjoy tastings and a glimpse into the brewing process.


  • Beehive in the South End (8:00 PM)
    • Location: Beehive, 541 Tremont Street, Boston, MA 02116, Phone: (617) 423-0069

Wrap up your first day with dinner at Beehive, a lively and artistic eatery in the South End. You’ll relish a mix of flavors, live jazz music, and a vibrant atmosphere.

Day 2: Sports, Adventure, and Culinary Delights


  • Fenway Park Tour (10:00 AM – 11:30 AM)
    • Location: Boston Red Sox, Four Yawkey Way, Boston, MA 02215, Phone: (617) 226-6000

Unearth the rich history of Fenway Park, home to the Boston Red Sox. The guided tour takes you behind the scenes, sharing stories of legendary games and players. It’s a must for sports enthusiasts.


  • Greenway Zipline Experience (12:00 PM – 12:30 PM)
    • Location: Rose Fitzgerald Kennedy Greenway Conservancy, 185 Kneeland Street 2nd Floor, Boston, MA 02110, Phone: (617) 292-0020

Embark on an exhilarating zipline adventure at the Greenway. Soar above the cityscape and savor breathtaking views of Boston. It’s a heart-pounding experience that adds a dash of adrenaline to your trip.


  • Antico Forno (1:00 PM – 2:30 PM)
    • Location: Antico Forno, 93 Salem Street, Boston, MA 02113, Phone: (617) 774-8529

Indulge in a delicious Italian meal at Antico Forno. The restaurant’s warm and welcoming atmosphere, along with its delectable pizzas and pasta, make for a satisfying lunch.


  • Empire (8:30 PM – 10:30 PM)
    • Location: Empire, 55 Northern Avenue (1 Marina Park), Boston, MA 02110, Phone: (617) 295-0001

Conclude your Boston getaway with a memorable dinner at Empire. This chic Asian-inspired restaurant offers a diverse menu of dishes that cater to a variety of tastes.


photos by Jennifer Oetting Photography

Have you been to Boston? What’s your favorite thing to do? What do we need to do on our next visit? Let us know in the comments below!

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