Boston is one of the oldest (and prettiest) cities in the US, speckled with historic sites, stunning buildings, and lovely parks. There are so many great walks to take, interesting places to see, and amazing (sea)food to be had, so it can get quite difficult to choose between all of it. Lucky for me, I have local Bostonian friends to help me prioritize…
Where to stay:
Intercontinental Boston in Back Bay is a great upscale hotel with extremely comfortable rooms and amazing city views. It is conveniently located, and (like with all Intercontinentals) the service is excellent.
How to get around:
Walk or take Uber. Boston’s fresh air makes it really pleasant to walk everywhere, but there can be far between places, so Uber is a convenient and very affordable alternative.
Where to eat:
Mike’s Pastry in North End has been making an unbelievably wide variety of cannoli since 1946 (when I first walked in, I thought “it really can’t be necessary with that many options”, but then 10min later I happily contended that “yes it can”). It is quite an experience to see this busy bakery shop in action, especially when you’re battling to keep your choices down to just a few (good luck with that).
La Burdick in Back Bay makes great coffee, handmade chocolates, and various desserts. Even though the chocolates and desserts may be a bit on the sweet side for breakfast, they should definitely be stocked up for later.
Top of the Hub in Back Bay is a great place for lunch and/or afternoon drinks. The food is very good (of course a bit pricier due to the location), but the views of the city are just simply spectacular.
Legal Harbourside in South Boston is a large three-floor restaurant right by the water with great views, both from the downstairs patio (more casual) as well as the upstairs patio (less casual). It is nice and calm during (early) lunch and gets increasingly busy as people trickle in for happy hour drinks and dinner.
Yankee Lobster in South Boston is a fantastic little hole-in-the-wall spot for indulging in lobster rolls and other local seafood specialties.
Yvonne’s in Downtown is a very special (hidden) place with amazing decor and atmosphere. The food and drinks are delicious, and the experience as a whole is really just quite unique.
Toro in South End is a happening tapas place with many delicious small dishes and a great, local atmosphere.
Ristorante Pagliuca’s in North End is a casual restaurant that serves authentic (southern) Italian food. One should definitely go for their lobster ravioli as well as their tiramisu, espresso, and limoncello.
What to eat:
Lobster, lobster rolls, lobster bisque, crab, crab rolls, crab cakes, and clam chowder (you really must have it all)! Though Boston really rocks its seafood, it is also quite impressive with its Italian food, Puerto Rican food, and local BBQ.
What to do:
Do a Duck Tour. This funky-looking bus takes you around the city on land and in water (it does both). I would normally never get into a tourist bus or boat, but this tour is really quite good, and you get a nice overview of all the historic landmarks.
Stroll around Boston Public Garden, a lovely, green area right next to Boston Common with pretty trees and flowers. On your way to the park, you may notice passing that bar where everybody knows your name…
Stroll around Boston Common, a large green park with great views of the surrounding city. It is a wonderful place to enjoy an afternoon on the grass reading a good book.
Walk (part of) the Freedom Trail, especially from Boston Common to Faneuil Hall. This portion takes you past various interesting historic buildings and quaint areas, and when you get to Faneuil Hall, you can always go inside to check out the market.
Go for jazz night at Wally’s Cafe, a very cool local jazz club that has great jazz musicians as well as enthusiastic audiences.
What not to do:
Don’t be shy to go outside of Boston. Areas such as Cambridge or Roxbury are also super interesting to explore.