Fall in Love with Boston in 23 Hours

In the late nineties I cashed in a savings bond gifted to me by my godmother and used the $80 to pay for my first-ever flight. The trip was full of firsts: the first time I saw snow on the ground; the first time I got kicked out of a bar; the first time I saw the lights be turned on in a club to signal the end of the night. It was a thrill ride from the moment my cab drove on the sidewalk to when I stumbled into a comedy show headlined by Wendy Liebman to the simplest of delights of buying tulips at a corner shop.

After two decades, I returned to Boston. And in the span of a day, I rekindled my love for the City on a Hill. If you can spare 23 hours here, she may be able to charm you as well.

Lunch on Lobster

Let’s get down to business. You’re here for a lobster roll and you’re short on time. You can’t spend all day reading reviews and weighing your options, so keep it simple. Go directly to Luke’s Lobster Seaport (53 Northern Ave), it’s a 10-minute drive from the airport. Walk up to the counter and ask for the trio (three half sandwiches of lobster, crab and shrimp). If you’re starving, throw in a small clam chowder for good measure. Now you’re truly ready for the day.

Walk the Park

If the weather is nice, join the rest of the city at Boston Common. There are organized tours led by costumed guides if you’re into that sort of thing. You can also download an app for a self-guided tour or pick up a map at the visitor’s center. If the weather is miserable, head indoors for a couple of well-spent hours at the John F. Kennedy Presidential Library and Museum (Columbia Point).

Hidden Gems

If you’ve been to Boston a few times and want to see something different, head to the Mapparium (200 Massachusetts Ave). Tours are always guided and are timed, so expect that your wait time may be longer than the actual time spent on the tour.

There’s also the Boston Athenæum (10 ½ Beacon St) one of Boston’s most enduring, treasured cultural institutions. Behind its red door are half a million volumes, fascinating art on display and rotating exhibitions.

Night Watch

A good way to kick-off the evening is at Bostonia Public House (131 State St). With a belly full of drink and food, walk to Faneuil Hall for dessert (if it’s still open). Now remember, this city is not big on late night, so it’s best to have a plan. My go to is to catch a comedy show. Either check out whose headlining at the Wilbur Theatre (246 Tremont St) or at Laugh Boston (425 Summer St, inside the Westin).

Morning After

In Boston its early to sleep, early to rise, so you’ll also need a solid breakfast plan. I like breakfast at Tatte Bakery & Cafe and there’s a bunch to choose from throughout the city. After that, squeeze one more sight that will seal the deal on your love for Boston: Go for a stroll down Newbury Street. Pop in and out of cool boutique shops and high-end stores; walk shoulder to shoulder with locals, and remind yourself that these eight blocks were once underwater.


If you’re doing Boston on a budget, consider staying at Yotel (65 Seaport Blvd). The rooms are cruise-ship-cabin small, but the rooftop offers plenty of space to stretch out. The location is pretty great too. For a more traditional stay, you can’t go wrong at the  InterContinental® Boston (510 Atlantic Ave). You’re within easy reach of the Freedom Trail, Faneuil Hall marketplace and the city’s business district. And if you prefer a more non-conforming Gen-X-leaning lodging experience, there’s always The Verb Hotel (1271 Boylston St). You’re steps from Fenway Park and Kenmore Square, and also near the Boston Museum of Fine Arts.

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