Best Stops in Boston

Boston is one of our favorite cities. We have been once in the summer and once in the winter and loved it both times. We covered some of Boston in our New England itinerary but I wanted to share all of our favorites in one place!

Best Stop in Boston

Favorite Restaurants

  1. Daily Catch: An amazing super small Sicilian-style seafood restaurant in the North End. This was my favorite meal in the city. There are only like 4 or 5 tables in the restaurant. They cook all the meals right next to you and serve the pasta in the pan they cooked it in family style. Johnny and I shared the fried calamari and clam linguine. Both were delicious,
  2. Panza: Another delicious Italian restaurant in the North End. We ate this for lunch both trips we were there. We ordered fried Calamari and chicken parmesan. During the summer we also ordered the lobster ravioli and winter we ordered the linguine all pescatore.
  3. Regina’s Pizzeria: Amazing Boston style pizza in the North End. We ate this twice in 1 trip. They are open late so it was a perfect late night snack.
  4. Bricco Salumeria and Pasta Shop: The best Italian sandwich in Boston. We just stumbled into this sandwich shop trying to find a snack for the train and found an amazing Italian sandwich. We were talking to a local and he said its the best one in Boston.
  5. Union Oyster House: Historic stop for New England Chowder. As America’s oldest restaurant, this place is a little touristy but I love their clam chowder. It’s the only thing we have ever ordered here. They also serve it with warm corn bread. It’s so good!
  6. Boston Farmer’s Market: Not technically a restaurant but they serve the cheapest fruit and vegetables we have ever seen. We stopped here to get snacks for the girls for the whole trip. Open Friday and Saturday only near the Greenway in North End.
  7. Boston Public Market: Another Market full of different local vendors. This market has more variety like coffee shops and many different restaurants. It’s a super cute, quick stop.

Favorite Sweets

  1. Mike’s Pastry: A very popular spot because the cannolis are the best in the city. We ordered a plain cannoli in the morning and it was so fresh and delicious.
  2. Bova’s Bakery: All the pastries you could every want. This place has so many amazing options. They also serve sandwiches and soups.
  3. Modern Pastry: We did not eat here but we did walk in and the desserts look amazing. I’m sure most of their treats are delicious.
Best. Stops in Boston

Favorite Things to Do

  1. The Freedom Trail: Starting the Boston Common, this is an amazing free activity to do. We only walked the trail in the Summer. My daughter loved following the trail. It brings you around to all the history stops of the city.
  2. Boston Common: We love just hanging out and walking in the park. There is a big park with great views of the city. There is a super cute little bridge in the park, perfect for photos. During the winter there was ice skating. During the summer there were events and plays. It is a great spot to find many things to do.
  3. Lawn on the D: We stumbled across this park when stopped at a brewery. This is only open during warmer months. It has so many outdoor activities. There are really fun activities like light up swings, corn hole, and Giant Jenga. The day we were there there was a live band and a bar set up. This was a great spot to spend evening.
  4. Boston Children’s Museum: This is a huge children’s museum. On Friday evenings it is $1 a person, so basically free. We could have spent another few hours here. My toddler loved it and so did we.
  5. Fenway Park: No trip to Boston is complete without stopping at Fenway to see a Red Sox game. It is an amazing experience. The place is amazing. The crowds are amazing, and the whole game is amazing. This is a must if you are there during the season. I believe they do tours and have concerts there as well but going to a Red Sox game is like nothing else.
  6. TD Garden: We have not been to a game here yet. Both times we were there the Celtics and/or the Bruins were away. We love experiencing basketball games in other places and this one looks like a great one! We do not have a hockey team in Louisiana so we love going to them when we visit other cities.
  7. Breweries: We love the craft beer scene right now because it is a nice place to hangout with adults and we can bring our kids. Our favorite in Boston is of course Trilium Brewing. All of their beers are pretty much amazing. Their new location is super nice. There is a hangout area downstairs and where they also sell cans. There is also a restaurant on the upper level of the building. We were there in the winter for this location. There is a really nice outside area that I am sure is amazing during warmer months. We also went to Harpoon Brewery. This was a really cool brewery that also served food. We like the New England Style IPA beer and they did not have really any of these at this brewery but it was a really nice place to hang out.
Best Stops in Boston
The Freedom Trail

Where to Stay

Boston is a pretty expensive city to stay in. On our first visit in the summer we booked a Priceline Express Deal hotel. It was around $180 per night for a 1 queen bed room. It was in the Back Bay Area. We stayed here to be walking distance to Fenway Park. We stayed in this Airbnb in the North End during our winter trip. It was in an amazing spot! It was one of my favorite Airbnbs I have ever stayed in. Easily walkable to all the restaurants I listed above. For $40 off your Airbnb stay click here.

Best Stops in Boston
Outside of our Airbnb

Getting Around

Boston is a very walkable city. We walked most of the places we visited. We did take an Uber or Lyft when it was dark just to be safe with our children. On our first trip we had car but really didn’t use it because parking was so insane. Street parking was very different than our city. In some areas you have to physically move your car every 2 hours. We just fed the meter after 2 hours but were still getting tickets and finally figured it out. We took the Downeaster Amtrak to Portland when we were leaving Boston. This was so easy with kids. It was only like $25 to get there for all of us. I highly recommend this if you are leaving the city.

Best Stops in Boston
Amtrak to Portland

Boston is such a fun city and is definitely a great stop even with kids. We are already looking forward to our next trip back! Let us know your favorite spots in Boston so we can stop next time we are in the city!

Best Stops in Boston

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