Everyone will say, you must take the off-the-beaten path. But then they will also say, there are must-sees that you just cannot miss. So really, it would depend on what you’re really looking for. Our travel focus is usually around history, architecture, and food. With the help of friends who frequent Boston, locals I’ve connected with, subscriptions to travel magazines, and guidebooks, here’s a suggested itinerary that worked for us first time visitors. Much like any major city, 48 hours is not enough to explore Boston. But for 48 hours, I do think it’s possible to get some sense of the city - its geography, its food, and even its people.
Grab a Finagle a Bagel breakfast. The only bagel I could get around where I live is from Panera Bread so this local staple is a nice thing to have. You can make your breakfast as light or as heavy as you want by ordering just toasted bagel and cream cheese or a full on breakfast sandwich.
Orient yourself (and get your history fix) with a 90 minute Freedom Trail Walking Tour through the Freedom Trail Foundation. You may want to arrive a bit early to walk around Boston Common. You follow the historic sites of Boston, with stops at 11 of the 16 trail sites, connected via a red brick line all over the city. But what makes it special is that your guide is dressed in 18th century garb and it becomes an animated and colorful tour. Ours was Nate Fisher as Le Chevalier de Saint-Sauveur and he was funny and informative - he has a Sam Adams joke that I’d like to share, but that’s his money maker. Word of advice, if you can, book a private tour. I contacted the operators prior to see what would work best with my husband who walks with a cane and they suggested a private tour for $125 (there were 11 of us). A non-private tour can have a group as big as 40 people.
You can grab a quick bite around Fanuiel Hall Marketplace since the tour ends in Fanuiel Hall. There are live performers, street art, and other entertainment in the marketplace. Regina’s Pizzeria has been around a long time, and there’s one around here. I grabbed a slice and I understood why.
#Boston Looking at the tallest building in Boston, the I. M Pei/Cobb-designed Hancock Place, from the second tallest building in Boston, the Prudential Tower. That is cool in my book. #architecturegeek Skywalk Observatory, Prudential Tower, Boston, Massachusetts USA 2015 #travelingb #GetThereGetLost
Head across the river to Cambridge for self-guided (or guided if available) University Tours. You can make your visit here short and sweet and just visit one university, or visit like a prospective student. Both Harvard and MIT have apps for self-guided tours (iOS apps linked). So really, you can visit as many (or as few) buildings as you wish. When at MIT, try to get to the esplanade to get a view of the Boston skyline. Architecture / Art watch: The only Le Corbusier building in North America is the Carpenter Center for Visual Arts in Harvard. Frank Gehry’s stamp here is MIT’s Stata Center. Alexander Calder also left his mark at MIT with “La Grande Voile” at the McDermott Court.
Oh hey, there’s a J. P. Licks in Harvard Square. Other than the super creamy but not too sweet treat, I found the grass decor on the wall pretty cool.
I’m a big fan of city views, and you can get Boston’s from Prudential Tower via the Skywalk Observatory. Or you can grab dinner or a drink from the Top of the Hub. This may be your only option if the observatory is rented out. Whenever I do these observation deck type things, I always check sunset times. There something magical about witnessing a city light up from above.
Walk around Back Bay through Newbury Street or Boylston Street. Plenty of dinner options here. L’Espalier was one on my list that I didn’t get to try. You can do this before or after Prudential Tower, since the deck closes late. If you do cap off with the Prudential Tower, around the area is Copley Square where you can visit sites like the Trinity Church and the Boston Public Library.
Make life super sweet and eat dessert for breakfast at Flour. Actually, you can start your day with sticky buns if you so choose but they do have sandwiches, even hard boiled eggs. And then you can make life sweeter.
Pick between exploring the Boston Tea Party Ships and Museum or the Institute of Contemporary Art. They are walking distance from each other so if you’re energetic, you may be able to do both. But if I were you, I would rather spend more time on one - experience the past or marvel at the modern with these options, really. From either of these, you can complete the Harborwalk to check out the Waterfront.
Make a tough choice between Neptune Oyster and The Daily Catch in the North End, but follow it up with cannoli’s from Mike’s Pastry. At The Daily Catch, the thick noodles of their black pasta (made black by squid ink) is simply scrumptious. But the star is the lobster fra diavolo. The serving that they say for 1 is really big enough for 2. And that one for 2 is good for 4 if you’re ordering other dishes.
The North End is lively, so you can explore this after lunch or do a Beacon Hill walking tour (self-guided or not). If you’re just walking around, and depending on what time you finish lunch, it’s possible to do both. If you are doing the guided Beacon Hill, it starts at 5:30 PM. Depending on your time at the North End, this may work out well. There are steep streets for the Beacon Hill tour so be ready for that. The lover of literature in me thoroughly enjoyed this because I learned this was the neighborhood of celebrated writers Louisa May Alcott, Robert Frost and Sylvia Plath. Of course, something oldie but goodie here is the Cheers bar, which seem to have made the trip for my dad.
You may have time to refresh yourself with a power nap or a wardrobe change at your hotel. Then you may be able to catch a game at Fenwey Park if it’s baseball season, or grab a nice dinner. We tried Oishii based on numerous recommendations from friends who knew I’m quite the sushi lover, and my husband the sashimi lover. In my opinion, the service is sub-par. One would think at a place where the chef comes out and greets everyone gratefully, the receptionists could be bothered to smile. But, you come here for the food. And my goodness it’s on-point with the buttery toro, earthy truffles and added dimension of the caviar. Oh my mouth waters at the thought of what I devoured.
Even with a short stay, it could be enjoyable. Boston has a lot to offer so don’t waste your time going to chains (food and shopping). Switch up the neighborhoods suggested here based on your interests. Depending on the activities you decide to do, the Go Select Boston pass may work for you to build your own attraction pass at a discount.