Boston &

The North Shore

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Boston & The North Shore

Boston

Where To Eat

Eastie

Santarpio's ♡* (East Boston - near the airport): If you land at Logan Airport and want the best pizza in town, paired with an old school gritty Boston experience, head to Santarpio’s. It’s 1 mile from the airport. If you go during peak meal times, be prepared to wait.

Rino's ♡ (East Boston - near the airport): My favorite Italian restaurant of all time is Rino’s- also not far from Logan Airport. Old school, massive portions, hole in the wall, homemade pasta spot. Get the raviolis, they’re the size of your head. If you go during peak meal times, be prepared to wait.

Donna's (East Boston - near the airport): The perfect greasy spoon breakfast spot. I’ve been going here since I was a kid with my Nonna - she still goes every Friday. Perfect breakfast spot on your way to/from Logan Airport!

Downtown & Seaport

Tony C's (Seaport): Great place to watch any sporting event. Right on the water in Seaport (really nice view). Great food & atmosphere.

Strega (Seaport): There are a few Strega’s in the Boston area. We like the one in Seaport as its on the water & has great views. Excellent Italian food, great atmosphere and service.

Legals Harborside ♡ (Seaport): Each floor of Legal’s Harborside is a bit different atmosphere. The roof top is great for drinks, views & apps. If you sit inside, its a great restaurant for a nice dinner/date night but is also family friendly. This is also in Seaport right on the water front. Their food is excellent - a local/boston chain. I love their clam chowder!

Nico Ristorante ♡ (North End) : Excellent restaurant in the heart of the North End. They have high quality food & great seafood dishes. Highly recommend

Neptune Oyster (North End) : I am embarrassed to admit I have never made it here before but had to include it in my Boston recommendations. Wait times are typically ~2 hours. I only hear the best things about Neptune including their warm Lobster Roll…

Mike's Pastry ♡♡ (North End): Best cannoli in town - just do it. There is always a line but it’s worth it & moves fast.

Caffe Vittoria (North End): If you don’t want to wait in line at Mike’s Pastry, head over to Caffe Vittoria for a cappucino & cannoli. My sister and I love this little cafe. I didn’t know until recently that it was the first Italian Cafe in Boston. We used to drive in all the way from Nahant just to sit in here for coffee & a snack.

Things To Do

Where to stay: If I were visiting Boston for the first time, I’d stay in either Back Bay, Boston Commons, Seaport or The North End.

Faneuil Hall : Its fun to walk around and shop at Faneuil Hall - there is a ton of  shopping, food, history etc. Very touristy but fun to do/see for an hour

Newbury Street/Back Bay ♡ : Great for shopping (a mini/quaint Michigan Ave, cute restaurants/cafes you can go to) , really pretty buildings and old walk ups! 

Boston Commons: Great/beautiful park to walk around - a lot of duck tours start here as well!

Duck Tours: The most touristy thing to do in Boston - I went as a kid and thought it was the coolest. Fun family friendly activity…

Freedom Trail: I did this in Middle/High School so the details are fuzzy - I do remember it is very educational and it takes you all around Boston to the most historical sites! You can do a guided tour or do it on your own with a map (I always prefer guided!)

Red Sox Game ♡♡ : If you’re in town during a Red Sox game, definitely try and catch a game. The stadium and energy are like no other stadium. Before the game, head to one of the bars around the stadium (or even inside the stadium)

  • Bleacher Bar ♡: This bar is super unique as its situated in the outfield of Fenway. You don’t need a game ticket to enter but can see the field from inside the bar. Good bar food and perfect spot for pre-game drinks!

  • Cask'n Flagon : Great sports bar about 2 blocks from Fenway. Get there early, it gets crowded.

The North End (“Little Italy”) ♡♡ : The North End is a very unique and beautiful part of Boston. It is Boston’s “Little Italy” - complete with a ton of tiny Italian cafes , restaurants and shops. I love walking around eating & shopping in the North End. I have been to many restaurants in this neighborhood with my family growing up and sadly don’t remember all of their names. I will say, with the competition and quality of Italian food that the North End has to offer, no restaurant that is subpar would last in this part of town.

Charles River: If its nice out- walking along the Charles River is really pretty. Sometimes there are concerts @ the Hatch Shell (along the Charles) - so definitely look up their schedule if you’re in town during the summer.

Sam Adam's Brewery ♡ : really fun and cool learning about the history of Sam Adams. There is also a free trolley that will take you to Doyles Pub after the tour, its really cool and 100+ years old (all the Kennedys’ have been there and you get a free Sam Adams glass if you get a beer there) -- its in Jamaica Plain, worth going (a little out of the way//20-30 min train ride)

Harpoon Brewery ♡ (Seaport): Great local brewery. If Sam Adams is too much of a trek, I recommend doing this brewery tour instead (better location). Harpoon does several tours a day at a very reasonable price. You can enjoy their taproom as well for beer flights & baked pretzels / snacks.

Harvard Square: Cambridge is really pretty (all old red brick buildings and sidewalks). Cool area to walk around/eat, you’d have to take the train there from downtown Boston.

Encore Boston : Massive Casino in Everett MA - opened recently (Summer 2019) - I hear its exactly like the one in Vegas and is a blast. I haven’t been quite yet.

The North Shore

Towns to Visit

If you head to the North Shore, 2 worthy stops along the way are Kelly's Roast Beef ♡ or Dryft Revere ♡ on Revere Beach. Kelly’s is a famous roast beef spot (Boston’s equivalent to Portillo’s in Chicago) - either get a jr roast beef 3 way & fries or a lobster roll! Dryft is also on Revere Beach if you’re looking for a nicer, trendy, sit down restaurant with great food, cocktails & ambiance!

Nahant: This is the town I grew up in - tiny beach town (1 sq mile) about 15 miles north of downtown. Very family friendly town with a ton of beaches. Only 1 restaurant and 1 sub/pizza shop in town. I don’t recommend a day trip as parking is non-existent for non-locals however, could head to the public beach along the Causeway (Long Beach) - I think its $5-10/day for parking. It is probably best to opt to stay at an Airbnb to explore the island a bit.

  • If you’re looking for an Airbnb for a relaxing beach weekend, my parents have an Airbnb upstairs from their house. It can sleep up to 6 people and is literally steps from 2 beachs (Short Beach & Doggie Beach).

  • Seasides: Great quick take out/delivery spot for a pizza, steak & cheese, mozzarella sticks or a greek salad. It is right by short beach so you can get food to go & enjoy it on the beach

  • Tides : Sports Bar/Family Friendly restaurant. Good spot right as you enter the island. One side is a family friendly sit down restaurant, the other is more of a sports bar. Great views of the beach. They have everything from burgers & fries to salads, wraps, pasta dishes etc.

Marblehead : gorgeous beach town on the North Shore. It’s really nice to walk around ,eat , shop etc in Old Town. The neck has massive houses (which is nice for a drive around the Neck :) -- not necessarily a ton to do but if you/re trying to get out of the city, could be a nice little day trip!

  • Favorite Restaurant: 5 Corners Kitchen ♡ Great for lunch or dinner. Super cute with an excellent menu

Salem : If you go in October, it’s a huge destination for Halloween ♡♡. A lot of shops, restaurants & haunted houses etc for Halloween.  A cool town even not during October/Halloween. You can take the train there from about (about 40min-1 hour from Boston).

  • Favorite Restaurant: Dube's Seafood ♡ : Old school New England hole in the wall, fried seafood spot

  • Finz ♡: Nicer, upscale seafood restaurant on Pickering Wharf

Gloucester is an old fishing town (from the Perfect Storm) with incredible seafood!

  • The Causeway ♡♡: best seafood in the North Shore if you ask me. Get the fish chowder, steamers, mussels, lobster roll and/or lobster mac & cheese.  Its a hole in the wall but probably one of my favorite restaurants of all times. If you go during peak times, be prepared to wait.

  • Nichols Candies ♡: On your way into Gloucester (right off the highway), you’ll see Nicols Candy - its been around since the early 1930’s. I can’t head to Gloucester or Rockport without stopping in for some homemade chocolate & penuche fudge. I’ve even driven 45 minutes up there with my family just to get some fudge.

Rockport is a beautiful town on the water with a lot of local artists, restaurants, cafes, ice cream & fudge shops.

  • Bearskin Neck ♡♡ : is the part of Rockport that is worth spending the day at. The town is a bit seasonal and closes down in the fall ( a lot of the restaurants are only open during spring/summer/ early fall) so I would double check places before going all the way up there because they could be closed just an FYI!

  • Roy Moore's Fish Shack Restaurant : Right as you enter Bearskin Neck , Roy Moores Fish Shack is on the left- great seafood option for lunch or dinner.

* ♡ = a favorite

♡♡ = a must do