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36 Hours in Boston

Welcome to the first of a new series on this blog, 36 Hours In

This series will be curated for the quick trip. If you get 36-48 hours in a new city with time for one or two meals and possibly sightseeing, as is often the case when I travel for business, this will be a guide for how to spend your limited time.

Having recently returned from a night in Boston, my favorite city in the United States, I’ll start there.

36 Hours in Boston

Hotel: Omni Parker House

The Omni Parker House is the oldest continually operating hotel in the United States. Unfortunately, this means you will get a room the size of a shoe box. BUT, they invented the Boston Creme Pie and the Parker House dinner roll here! Charles Dickens liked to stay here! And, it’s so conveniently located that for your 36 hours in Boston you couldn’t ask for a better location.

Pro-tip: The corner table at the Last Hurrah bar is an excellent spot to enjoy a nice glass of wine and watch the crowds pass by on the street. In the dead of winter, when steam is rising up from the manhole covers as people huddle against the wind and snow, it’s quite magical.

The lobby of the Omni Parker House at Christmas.

Dinner: North End

If you only get one meal in Boston, go to the North End. It’s a delightful Italian neighborhood full of bustling, delicious restaurants and pastry shops and a 10-15 minute walk from the Parker House. The only downside to this neighborhood is how to choose the ONE restaurant you get to eat at. Dessert is easier, don’t worry!

If you luck out on the length of the line, Giacomo’s is a small, cash-only Italian restaurant with great food that's worth the wait. On my last trip, the line was too long and we had time constraints to get back to the airport, so we chose Benevento’s instead. We enjoyed the bolognese and rigatoni with short rib so much we carried our leftovers home to DC on the flight. Other spots I enjoy in the North End include: Limoncello, Lo Conte’s, La Famiglia Giorgio’s (huge, family style portions), and Regina Pizzeria (my favorite pizza).

Dessert: Mike’s Pastry

DO NOT order dessert at dinner in the North End. Instead, after dinner, walk to Hanover St to Mike’s Pastry and get a chocolate chip cannoli. Or whatever kind of cannoli suits your fancy - they have a dozen types. I’ve probably tried them all over the years. The chocolate chip remains my favorite followed closely by the Florentine.

Pro-tip: If you end up in Cambridge, Mike’s now has a Harvard Sq outlet that is way less crowded than the original with the same cannoli.

Disclaimer: There is a raging debate among cannoli lovers about whether Mike’s or Modern Pastry is better. I am 100% Mike’s, but you could always get both and decide for yourself.

I encourage walking around eating your cannoli for the full Boston experience. The Old North Church (one if by land, two if by sea, people!) and the Paul Revere statue are part of the Freedom Trail and worth a quick stop and photo while in the neighborhood.

Second Meal: Clam Chowder and Lobster Roll

If your schedule allows for a second meal, get clam chowder and a lobstah roll. If the weather is nice, go to James Hook & Co., a lobster shack with outdoor seating. Two indoor options in the Fenway are Eventide and Island Creek Oyster Bar. A more casual food hall option is Boston Chowda Co in Faneuil Hall (also along the Freedom Trail).

Local Coffee Shop: Dunkin’ Donuts

In future 36 Hours In posts, I plan to include actual local coffee shops (even though I don’t drink coffee so you probably shouldn’t listen to my recommendations anyway), but Dunkin’ is such a Boston institution you must go. And there’s one approximately every half block so you won’t have trouble finding one.

Being a Tourist: The Freedom Trail and Fenway Park

If your schedule allows and the Red Sox are in town, go to a baseball game. If you were interested in Pizzeria Regina but the line was too long in the North End, they have an outlet by Fenway were you can grab a slice before the game. They also serve Regina at the game, along with delicious hot dogs on split top buns.

If you have any time during the day, walk the Freedom Trail. The start of the Freedom Trail is located in Boston Common, the first public park in America, and a quick 4 minute walk from the Parker House. You can do a guided 1.5 hour tour or walk the trail yourself. There is a red brick line you follow through the city past tons of historical sites, graveyards, etc. The Freedom Trail conveniently takes you to the North End where you can enjoy dinner after your walk.

Guided tour of the Freedom Trail.

Arriving from Logan Airport

There are two options for public transportation from Logan Airport (the blue line T or the silver line bus to South Station). A cab to the Parker House is about $25.

And if, after reading this, you’ve decided that 36 hours in Boston isn’t enough for you, be on the lookout for a more thorough discussion of the city I’ve debated moving back to once a year for the last 15 years on the blog soon.

Ready to Go?

Omni Parker House: 60 School St

Giacomo’s (no website so you know it's good): 355 Hanover St

Benevento’s: 111 Salem St

Limoncello: 190 North St

Lo Conte’s: 114-116 Salem St

Regina Pizzeria: 11 ½ Thacher St (original); 1330 Boylston St (Fenway)

Mike’s Pastry: 300 Hanover St (original); 11 Dunster St (Cambridge)

Modern Pastry: 257 Hanover St

Old North Church: 193 Salem St

James Hook & Co: 440 Atlantic Ave

Eventide Fenway: 1321 Boylston St

Island Creek Oyster Bar: 500 Commonwealth Ave

Boston Chowda Company: Faneuil Hall

Fenway Park: 4 Jersey St

Freedom Trail: Tours start at Boston Common Visitor Center; 193 Tremont St

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