Boston Pops Maestro Keith Lockhart Plans His Perfect Day in Boston

Boston Pops conductor Keith Lockhart plans his perfect day itinerary for 24 hours in Boston

The conductor of the Boston Pops, Keith Lockhart has lived in and loved Boston since 2007. Here, he shares some of his favorite places around the city.

8 am: Breakfast Benedict

Since I live in Brookline, a great place to start is Eastern Standard (528 Commonwealth Ave., Boston, 617.532.9100). They serve a great breakfast and a beautiful eggs benedict. Though, if it were a Sunday, I would go a little further down the street to Island Creek Oyster Bar (500 Commonwealth Ave., Boston, 617.532.5300) because then you can eat oysters for breakfast and what's better than that?

9:30 am: Duck Tour

It's the best way to see the most places in Boston in a short period of time. Besides, the vehicle is really cool and it goes into the water.
Departs daily from Museum of Science and The Shops at Prudential Center, 617.267.3825

10 am: History Hike

Bite off part of the Freedom Trail [and] get some context for Boston, how deep the roots go, how there are places that people still live in that are 300-plus years old. I would include the [USS] Constitution. I remember it fondly from my first trip to Boston, which was when I was eight years old. My dad, who went to school at Northeastern, took us, and I remember standing on the deck of the ship and looking up the mast and thinking, “How cool is this?”
Boston, 617.357.8300, 

11:30 am: Historic 'Hood

I would also spend some time in Beacon Hill for the same reason: The roots go so deep there you can feel the echoes of history as you walk through some of those smaller streets. 

A street in Beacon Hill
The historic neighborhood of Beacon Hill is well worth exploring. (©Jorge Salcedo/Shutterstock)

12:30 pm: Lunch with a View

I would end up on the Boston waterfront for lunch. Being out there, watching the boats, and watching the planes land at Logan, is very cool. I might go to Legal Harborside. There are a couple of great restaurant choices right in that general area, but the cool thing about Legal's is that it has that rooftop bar, which is a view unlike any other. And, you can't leave Boston without having a lobster and a cup of chowder.
270 Northern Ave., Boston, 617.477.2900

The view from the rooftop at Legal Harborside
The view from the rooftop bar at Legal Harborside (©Chip Nestor)

3 pm: Be A Fan at Fenway Park

We are going to assume that there is an afternoon game. So we would head via the Green Line to Kenmore Square and walk to Fenway to see a Sox game. We live in Brookline, and my wife and I moved in two days after our honeymoon in October of 2007. The Sox were in the World Series, so we closed up the house with the boxes still here and walked over to Fenway Park, and I thought, "How cool is this that this is a city that the scale is so approachable."
4 Yawkey Way, Boston, 617.482.4769

7:30 pm: Chic Date for Dinner

We'd do dinner in the Back Bay. Here's where I run into the trouble of not knowing what to recommend because there are so many places that we like to frequent. I might go to Via Matta and order the Bolognese, or to Towne Stove and Spirits. Or to Clio at the Eliot Hotel—the sushi-sashimi bar there, Uni, is amazing. [I would] tell the guest to bring their wallet, and hopefully they'll pay as a result of me taking them to all these cool places! If we were going a little further afield, No. 9 Park is and remains one of my favorite restaurants in Boston. And all these things would be fairly close to Symphony Hall, because we'd of course be going to a Boston Pops concert that night.

9:30 pm: Concert

[If it is May, June or December] we'd hear America's Orchestra (the Pops) play a concert that could be absolutely anything from Broadway to jazz to Grateful Dead to a kid show.
301 Massachusetts Ave., Boston, 617.266.1492

11:30 pm: One Nice Nightcap

We'd retire to the Top of the Hub because it's a clear day and we are assuming the weather is perfect, and there is no place better to see Boston from above.
800 Boylston St., Boston, 617.536.1775