4 day Boston itinerary

I have had a blast playing travel guide for several folks traveling to Boston this summer! And in the spirits of hoping to have more folks come to visit us in our final year of school, here’s what I would propose as a 4-5 day travel itinerary in Boston and our North Shore!

Begin by looking at Google maps and orienting yourself to the Charles River and the Gardens/Commons. You can’t get lost if you know where these 2 landmarks are.

I recommend staying in the Back Bay.

Afternoon post-airport. You could start as late as 3 or 4pm.
Freedom Trail (beginning at Boston Commons/Gardens ending in North End (aka Little Italy))

Dinner in Little Italy at Giacomo’s. You’ll want the butternut squash ravioli. You need cash.

Dessert just a block closer to downtown on Hanover Street at Mike’s Pastries.

Walk back to the Boston Gardens via Charles St. (where the signs are pictoral)
Full day: Exploration of Back Bay and Cambridge
Begin again near the Boston Gardens

Walk Newbury Street, enjoying the fancy shops

Track back on Boylston, hit the 3 story Apple store, the Boston Public Library, Copley Square, and Filene’s basement

Take the Copley Plaza subway (to the left of the library, up the hill 1/2 a block if you’re looking at the library) to Fenway
Fenway Park

EITHER Take the red line to Cambridge/Harvard. Enjoy the campus, Harvard Square, and maybe grab dinner there. Walk along the Charles. Take the subway back to Back Bay or your hotel.

OR Take public transportation to the Sam Adams Brewery for a tour.

North Shore/Cape Ann

1st stop- me at Gordon-Conwell!

You’ll want my pass to go onto Crane’s Beach (a couple dollars) and maybe the Crane Estate (free) if you’re interested in that.

Pick apples at Russell Orchards on the way to/from or at least stop for fresh cider donuts.

Have brunch at Sugar Magnolias in Gloucester. You’ll want the carrot cake pancakes. Breakfast only until 1pm.

Maybe pop through Rockport. It’s a bit touristy, but quintessential New England. The Proposal with Sandra Bullock was filmed here.

Drive up the coast to Halibut State Park
Catch a sunset dinner at the Lobster Pool

Either spend the night at an Inn in Rockport, or go ahead and drive up to Newburyport


Spend the morning walking around, looking at boats, trying to find the jean store, Katwalk, and popping through Azure

Have lunch either at Michael’s Harborside (a bit expensive, but good local seafood) or The Black Cow (yummy local pub). Both have amazing porches on the water

Spend the afternoon driving up 1A to Portsmouth

Walk around and enjoy an evening in Portsmouth. Not sure where to eat here for dinner, but I’m sure you’ll find somewhere amazing either there or on the way.

Spend the night in Portsmouth.
Grab breakfast at The Friendly Toast on your way out.
Stop at the Kittery Outlets if you haven’t had enough shopping.

Back to Boston! That’ll do you, I think!


One thought on “4 day Boston itinerary

  1. If ministry doesn't work out for you, you have a bright future with being a travel guide! Our trip to Boston was a blast b/c of the Hackman travel team. I would add the Fine Arts Museum and the JFK Museum to the Boston list. Say "hi" to the gang at Giacomo's!


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