If you only have one day and want to truly experience everything Boston has to offer (or as much as you can in one day), here is a suggested itinerary.
8:00 AM: Breakfast
Start your day at Tatte (1003 Beacon Street, Brookline, MA: Green Line, C Line, St. Mary’s Street Stop), which is just over the city line in Brookline, MA. This European-style bakery has incredible pastries, lattes, and hot brunch options. In the summer months you can sit outside on the sidewalk to enjoy your breakfast, but thanks to a recent renovation there’s ample seating inside as well.
9:00 AM: Tour of Fenway Park
Once you’ve finished your breakfast, walk over to Fenway Park for their 9 AM guided tour of the park. The website recommends arriving 15 minutes early for this one-hour behind the scenes look at America’s oldest ballpark.
10:30 AM: Museum of Fine Arts
Next, walk through the Fens to the Museum of Fine Arts (“MFA”), where you can wander around for a couple of hours viewing either the historical artifacts of Ancient Egypt and Greece, or the more recent artwork from Europe, Asia, and the Americas. If there is a special exhibit, be sure to check it out, they are always worthwhile.
12:30 PM: Lunch Downtown
Take the Green Line, E Line, from the Northeastern T Stop to the Copley T Stop and head to Atlantic Fish on Boylston Street for lunch. Again, if it’s a nice day outside, ask for a table on the sidewalk and watch the busy Bostonians hustle by. If you’re not a fan of seafood, then your destination is Stephanie’s on Newbury, which again has highly-recommended outdoor seating and one of the best brunches in Boston.
2:00 PM: Boston Garden/Freedom Trail
Spend the afternoon after lunch walking the Freedom Trail. I know in another post I recommended starting the trail at the end, at the USS Constitution, and ending at the Boston Garden, but today you’ll start in the Boston Garden, which is only a 15-minute walk away from lunch. Spend time leisurely wandering Boston exploring the first half of the Freedom Trail, from the Boston Common to the North End, where you’ll end for dinner. If you read a guidebook or Google historical sites you can follow a self-guided tour, or you can join an official 90-minute Walk into History tour led by actors in historical costumes. If you choose the 90 minute tour you will also have time for relaxing by the harbor front or finishing the Trail with the Bunker Hill Monument and USS Constitution before dinner.
5:00 PM: Dinner North End
Enjoy a long Italian dinner in the North End, the Italian section of Boston. Pick any restaurant you’d like, you can’t go wrong with anything in the area, especially on the main drag Hanover Street, Salem Street, or any side streets off of these roads. My favorites include Ristorante Fiore, La Famiglia Giorgio’s, and Nico.
8:00 PM: Boston Symphony Orchestra or Boston Pops Show
From the North End you can either hop back on the T, the Green Line, E Line, at the Haymarket Station and take the train all the way to the Symphony stop, or just grab an Uber to Boston Symphony Hall. Depending on who is playing that night you can either watch a performance by the Boston Symphony Orchestra or the Boston Pops. Many world-famous musicians come to play with the BSO such as Yo Yo Ma, and if you are in town during the holiday season, you don’t want to miss the Boston Pops’ Holiday performance!
10:00 PM: Drinks at Top of the Hub
End your night with a couple of cocktails at the Prudential Center’s Top of the Hub restaurant while enjoying the spectacular views of the city. If your day in Boston is a Saturday, you can enjoy the live jazz music while enjoying your drink and the view.
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