Only have one day to see all of Boston’s many sites and unsure where to start? We’ve got you covered. There are so many wonderfully vibrant neighborhoods and so many historic sites to see, it’s hard to know where to begin, or how to narrow it down. But don’t worry; we’ve put together an ideal one-day-in-Boston itinerary so you can stop researching, and start touring.
10am: Get the lay of the land with a Freedom Trail walking tour
We may be biased since it’s kind of our specialty, but we know we’re not alone in thinking that walking tours are a great way to get to know a city and its major sites easily and efficiently. There are many outstanding Boston tours to choose from, and we encourage you to find your favorite, but if you’d like a suggestion, may we humbly share our three-hour VIP Freedom Trail Tour?
Our Freedom Trail walking tour starts right in the center of Boston history at the corner of America’s oldest public park, Boston Common, and across from the golden-domed Massachusetts State House. Visit 13 of the 16 sites on Boston’s famous Freedom Trail, including the Old North Church and the Paul Revere House, and end up in the scrumptious North End (Boston’s Little Italy) just in time for lunch.
1pm: Pasta, chowdah, and cannoli in Boston’s North End
The VIP Freedom Trail Tour’s last stop (the Paul Revere House) leaves you perfectly situated for lunch in Boston’s famous North End (aka Boston’s Little Italy).
Overwhelmed by all the food options? We’ve got you covered here, too, with our list of the best North End restaurants and bakeries. And although not exactly Italian, we’d be remiss not to suggest another famous Boston lunch option, our beloved New England Clam Chowder (pronounced “chowdah” by the locals).
So if you prefer seafood to pasta, the North End is also home to the landmark Neptune Oyster, and they’ve got a killer clam chowdah to tide you over. But be careful! Make sure to save some room for cannoli from Boston’s famous Mike’s Pastry. You don’t want to be the only one on the “T” (more on the “T” later) without a white Mike’s Pastry to-go box filled with sweet treats and tied with that signature blue and white string.
3pm: Take Boston’s historic “T” to our beloved Fenway Park
Historic Fenway Park is one of the most famous and beloved Boston landmarks. If you love baseball, get some tickets and head to the game. Or, for history and sports fans alike, check the website schedule ahead of time, and book tickets for the Fenway Park tour (runs year round). If time allows, do both.
You can combine getting to Fenway Park with another important Beantown rite of passage called riding the “T.” The “T” is what Bostonians affectionately call the local train system. It may be very old – we built the first subway tunnel in the United States, after all! – very loud, and questionable in terms of getting you places on time, but it’s an important part of Boston’s history and a great taste of the local experience.
Once you’ve had your cannoli at Mike’s Pastry, you can start walking it off with a short 10-minute walk to the Government Center “T” stop. Hop on any green line train labeled C, B, or D and take it 6 stops to the stop called Kenmore, and then Fenway Park is just a 7-minute walk away.
Traveler’s tip: DO NOT take the “T” to the stop called “Fenway”. In true Boston form, that is not the right stop for Fenway Park.
7pm: Dine like a celebrity on Back Bay’s famous Newbury Street
If you’ve decided to go to a Red Sox game at Fenway Park, then perhaps you’ll be enjoying a Fenway Frank (hot dog) and beer for dinner – yum! But if you’ve just done the Fenway Park tour and still want to continue maximizing your Boston sightseeing day, then you can walk, Uber, or “T” it to Boston’s high-end Back Bay neighborhood (Copley Square “T” stop), and experience some luxury dining on Boston’s famous Newbury Street.
If the weather is nice, and you’ve got time, you can wander around Back Bay and check out other important Boston landmarks, including the historic Boston Public Library (BPL), Trinity Church (named “one of the ten most important buildings in America” by the American Institute of Architects), and the beautiful Boston Public Garden (first public botanical garden in the U.S.).
There are dining options all over Back Bay – you can browse menus on Newbury Street, or check Google and Yelp! for recommendations.
But, if you’d like a personal, local’s recommendation, we love Casa Romero, authentic Mexican food on a little hidden alleyway off Gloucester Street between Newbury Street and Commonwealth Avenue. In nice weather, ask for a patio seat and unwind with chips, freshly prepared guacamole, and sangria. Don’t miss their signature pork dish, Puerco Adobado con Chipotle y Naranja.
10pm: Still going? Time for Boston nightlife in the South End
We’ve covered so many Boston neighborhoods and attractions today, your feet must be aching. But if you had a post-dinner cappuccino and the caffeine is coursing, then why not end your ideal one-day-in-Boston with an ideal night out in Boston’s awesome South End?
In this area, there are so many wonderful bars and clubs to choose from that it’s difficult to narrow it down. However, for this itinerary we’ve decided to share a popular live music venue and an old school beloved Boston Irish pub.
Achieving almost three thousand reviews on Google, the Beehive in Boston’s South End is a longstanding A-plus place to party. Featuring live jazz and blues, Bohemian art, and two full bars, there’s almost no excuse not to have a good time. And, if you’ve skipped the aforementioned Newbury Street dining experience, the Beehive has a buzzing menu too.
Feeling something a tad more chill? Head just a half mile deeper into the South End and visit the venerable J.J. Foley’s Cafe. Family-owned and operated in the same spot on East Berkeley Street since 1909, J.J. Foley’s offers up frothy pints and a cozy atmosphere for the perfect Irish pub experience to end your ideal day in Boston. Sláinte!
