I've spent quite some time in Boston over the last year with my husband living there for 3 months. So I complied a list of things to do both in and out of the city, as well as some amazing photo opportunities and of course great eats!
WHERE TO STAY:
If you don't have friends to stay with can I recommend this AMAZING Air BnB I found during my most recent trip to Boston.
This amazing, Victorian Air BnB - is in walking distance of the red line (which is the public transportation system) that can get you basically anywhere you want to go in the city.
DAY 1: HISTORICAL/TOURIST BOSTON
Of course the first day in Boston I wanted to hit up the toursit attractions to get it out of the way and see the "Historical Boston"
Anywhere you want to go is accessible by the underground train system which at first seems overwhelming but becomes second nature by the end of the day. We suggest heading to Boston's Historic North End where the historical Freedom Trail is located. This 1.5 mile trail hits almost every historical parts of the city and can take up to 4 hours to complete the whole trail at a fast pace.
Some of the highlights are Granary Burial Ground - one of the oldest cemeteries in Boston, displaying hand drawn grave markings.
Located around the corner is the Old State House - the site of the Boston Massacre. (Note the giant unicorn on top of the house.)
For food Little Italy is the only place to go. Stop by a small restaurant called The Daily Catch - an Italian seafood restaurant that is the size of a small living room, where patrons are forced to eat side by side. This is a cash only establishment so bring plenty ! While the dishes are a little pricey they keep you full and are served in large pots and pans. Be warned - there will be a wait.
(SIDE NOTE: There is also a location in South Boston that is bigger and takes credit cards.)
After you feel that you can't eat anymore - walk across the street to Mike's Pasty - famous for cannolis as big as your hands and come in a variety of flavors. They also serve cream puffs, lobster tails, gelato, cookies and more. The line is always out the door but it moves quickly so don't be discouraged.
Looking for a cheaper alternative to lunch? Or perhaps you want to grab something to go so you can picnic at the park?
Look no further than Monica's Mercato & Salumeria. This place always has a line out the door but they are serving up the most authentic and fresh subs you've ever eaten. I recommend the Italian of course. With a small coming in at $10 and a large around $16 these subs are perfect for sharing or munching on all day.
The trail ends at Boston Common's - the central park of Boston. This large, open area is outside the State House. From there we wandered to find dinner discovering the Theater District and Chinatown.
We ended up settling on Stoddards, an Irish eatery with vintage cocktails. The perfect meal to end the long day.
DAY 2: SOUTH BOSTON/UMASS
Power up with Union Square Donuts - with three locations you can find one close to you using the location finder via their website. They also have their doughnuts and doughies at various coffee shops throughout the area (SEE DAY 3)
Travel JFK Presidential Library and UMass. There is a free bus available outside of the rail station that I highly recommend, and prepare yourself for strong winds coming off the harbor.
With an affinity for learning about history and a love of retro items one could spend a whole day at the museum.
Don't forget to tour the outside of the property as well. JFK's sailboat sits outside of the museum and you can view home videos of JFK sailing with his son inside.
There is also a breathtaking view of the Boston skyline -
There is also a bottom level to the museum that hosts a rotating exhibit. During our time there we got to experience Ernest Hemingway "Between Two Wars."
South Boston is more commonly known as the business center - is deserted on the weekends, which gives tourists the run of the land. This side of Boston is the site of the Historic Boston Tea Party harbor which has a historical tour and replica of the ships.
The most popular tourist destination on this side of Boston is Harpoon Brewery - but make sure you get there early, the line tends to wrap around the building around noon and the tour tickets are sold at least two hours in advance.
But this gives you tons of time to feed your belly at Yankee Lobster before you guzzle all that beer. Within walking distance this tiny eatery with limited seating has a menu of nothing but authentic seafood that is caught in the harbor right outside of the restaurant.
I recommend the lobster roll or splurge for the 1 1/4 lobster - the prices will be some of the cheapest you can find in the city.
Next head to Harpoon Brewery - the oldest brewery in Massachusetts that brews a wide variety of beer. Their product is so good they only rely on social media and word of mouth as advertisement. They also have a cafe inside known for it's variety of pretzels that they bake from the spent grain they use in their brewing process, and donate the rest to local farms for cows to eat.
You can try every beer for two minutes with unlimited refills in their tasting room so brace yourselves. I recommend UFO Big Squeeze Shandy - which tasted like an orange wine spritzer and the UFO Razz, a raspberry beer.
This is also where the Boston Aquarium is located. Usually I don't hit up aquariums but my clients had year long passes and invited us! There is a great photo op outside the aquarium with all these amazing boats!
Looking for some more culture? The Institute of Contemporary Art is also in this area and is Free on Thursdays from 5-9pm. Go ahead and take in the odd art and don't forget to hang out on the deck for great views of the harbor.
DAY 3 & 4: HIPSTER BOSTON (BRIGHTON/ALLSTON/CAMBRIDGE)
I'm going to gush about Tatte Bakery for a second. With locations near Boston Common, Cambridge, and more (find locations via their website) This is one of my favorite bakeries in Boston.
They have the freshest baked goods, delicious coffee, and their TOAST PLATE is everything!! I've had almost everything on their menu and it is all to die for.
Don't miss an opportunity to stop in and grab snacks.
If Tatte is insanely busy or you just need an alternative try Lamplighter Brewing Co. / Longfellows This coffee shop/brewery combo has iced coffee flights along with beer! They serve Union Square doughies (doughnut holes) and make insanely delicious coffee. Their hop infused cold brew is not one to miss.
And right next door is Niche Succulent store - if you want to bring home a little potted plant!
Even after traveling to Boston three times I knew there was one place I wanted to see - the Isabella Stewart Gardner Museum. Yes - that was someone's house ! Can you imagine living in that. This woman collected great pieces of art, literature, and more and was actually the site of one of the greatest and biggest art heists in America. (read about that here)
You could totally spend a few hours looking through the 3 floors of artifacts and get caught up in the calming sounds of her solarium.
The Allston area of Boston is one of my favorite places. This run-down, hipster neighborhood is full of great resturants, tattoo parlors, artwork, and music venues.
And my favorite restaurant in Boston is HANDS DOWN - Lulu's !
I stumbled upon it one night after had drove 13 hours from NC to Boston. Whew ! The food is here AMAZING! So amazing that Andrew actually made this his weekly outing when he lived up there. I think he sampled everything on the menu and never had a bad experience. If I could get them to franchise in NC I would.
I heard that their brunch was not to be missed, so the last Sunday we were there we woke up early (they open at 10 am and it was PACKED when we got there at 9:45) The chef always has specials on pancakes and we just happened to walk-in during chocolate on chocolate! We also got their award winning "White Trash Hash" that I devoured. (Again can I just say how great this place is) and reasonably priced for Boston.