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East Coast Road Trip: A Day in Boston!

Welcome to my 14-day series on our East Coast Road Trip where I share our adventures along the way, how we’re doing this on a budget, honest reviews of attractions & restaurants we visit, and money-saving tips and ideas. If you missed it, read Day 1 here, Day 2 hereDay 3 hereDay 4 hereDay 5 here, Day 6 hereDay 7 here, and Day 8 here.

Okay. It’s official. I have fallen madly in love with Boston.

As in, I think I want to move to Boston. Or at least rent an apartment in the North End and visit for a week every month. (Hey, a girl can dream, right?? ;))

The coffee shops. The open air restaurants. The quaint streets. The scenery. The smells. I almost felt like I was back in Rome!

On Day 9 of our trip, we slept in and the drove to downtown Boston where we got all-day parking a block from Boston Common for just $15.

A few notes about parking and traffic:

  • Since we were visiting on Sunday, a local hotel offered all-day valet parking for just $15! From what I could tell — and what I heard — visiting on the weekends means that parking is much less expensive than it is on weekdays.
  • You can read more about parking in Boston here. (Locals: is that list accurate? I wasn’t sure.)
  • We also found that the roads were easy to drive and navigate (however, keep in mind that we are used to Nashville traffic!), traffic wasn’t really heavy like we expected, and was nothing like NYC. So it was no problem for us to drive into the city instead of taking the subway into the city. However, we were there on a Sunday, so I think that made traffic a lot lighter.

After visiting the Boston Common, we headed out to walk the Freedom Trail. We LOVED how there was such an eclectic mix of modern and historical.

We were pleasantly surprised to notice how much cheaper the prices were in Boston compared to the prices we’d been seeing in NYC and DC! (For instance, tourist-y t-shirts were $10 and water bottles were $1.)

We loved getting to spend time at the Old South Meeting House, the site of the Boston Massacre, and Faneuil Hall.

We went to the Rose Kennedy Greenway halfway through our day and then came back to it near the end of the day because our kids loved it so much!

One of the things my followers on Facebook had told me that we had to do was to check out Mike’s Pastry’s and Modern Pastry. It seems like there might be a sort of friendly disagreement between locals as to which shop is the best.

Some locals said we HAD to go to Mike’s and others said we HAD to go to Modern. And most of the locals had a strong opinion as to which one we should go to! So we decided to go to both. 😉

We went to Modern first. The line was out the door and they had quite a huge selection of options but they line moved so fast that we had barely made our decisions of what we wanted to get by the time we got up to purchase. Note: They only accept cash.

Mike’s was PACKED. As in, there were 6 (?) long lines out the door, you couldn’t really see what they offered (though it was clear there was a LOT of cannoli options!) because there were so many people in front of the display cases.

While Jesse waited in line, the kids ate what some of we bought at Modern Pastry… which was probably completely against the “rules”, but they were hungry and the wait was long! 🙂

We got a cannoli and a scone at Mike’s and they were both so yummy!

We also walked to see Old North Church and Park Street Church.


And then we walked over the bridge to the USS Constitution. We LOVED getting to go on board this ship and couldn’t believe how they let people just walk around and touch almost everything!

A few things I wish had known ahead of time:

  • It’s a long walk to get to the USS Constitution from Boston Common — especially if you do it at the end of walking the Freedom Trail. Silas was pretty worn out, but he loved the ship.
  • It’s free to go on the ship. The museum (which we didn’t go to) is a suggested donation of $5-$10 for adults, $3-$5 for children, or $20-$25 for families.
  • The ship is not open all the time. Sometimes it is closed for repairs. You’ll want to check before going to it. (I’d hate for you to make that long trek for nothing!)
  • You have to show your ID to get on the ship and your bags are searched.
  • They allow you to bring sealed food and water bottles on the ship. (Or at least they let ours through without mentioning that it would be a problem!)

We walked back to Boston Common from the USS Constitution and saw Paul Revere’s house on the way.

We stopped by a SweetGreen to grab some salads to split for dinner and then had a picnic at Boston Public Garden where we fed the ducks and marveled at how perfect the weather was and how beautiful the evening was. This park is very worth visiting!

We hadn’t expected to stay in Boston until after dinner time, so my phone died for the last hour of the day so I wasn’t able to get all the pictures I would have liked to of the park, but we would highly recommend it.

We then headed back to our car around 7:30 p.m. and drove to New Hampshire (our first time there!) to be able to say that we’d visited the state and then headed to Albany, NY for the night and then it’s onto to PA!

To be continued…

Have you been to Boston before? Any suggestions for the best free or inexpensive places to visit there?

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  • Laura says:

    We live 1.5 hours away from Boston, on NH’s southern border and love to visit Boston. The Boston Children’s Museum is $1 every Friday night. This museum is geared toward younger elementary ages I would say. Also, Bunker Hill is free and a pretty good view of the city, after you climb all the stairs! Not as good a view as the Skywalk on Prudential, but the Skywalk costs, so Bunker Hill is a good alternative if you need to be cheap! Boston Harborwalk is a pretty and interesting walk along the harbor. A walk through Chinatown is also interesting.

    • Stacy says:

      Laura – is it usually insanely busy? I want to take my kiddos to the children’s museum but have been putting it off.

      • Laura says:

        We went to the Children’s Museum last September and it really wasn’t bad at all. Maybe because it’s offered every Friday night it wasn’t busy? I also thought Sep may have been a good month as ppl are getting into school life and routines and maybe aren’t thinking so much about outings at that time..

        • Beth says:

          Hi! I live just a few miles north of Boston? The Children’s Museum is busiest in summer, over vacations and during weekends. If you’re a stay at home mom or mom with a flexible schedule, I highly recommend going on a weekday and see if your local library has passes for deep discounts.

    • Thanks so much for these great tips!

  • S.T. says:

    I absolutely love these posts of your vacation. Thank you and keep them coming!

  • Teresa says:

    It’s too bad you didn’t have time to visit NH more than just a drive through! There’s so much to do and beautiful scenery… Mt Washington, the Flume Gorge, the seacoast, etc!

  • Darla Weaver says:

    We live in Boston and love it! We’ve lived here since Febuary (my husband is an ESL teacher at a refugee/immigrant center) and all 12 of us have fallen in love. We have 9 sons, 1 daughter with the oldest being 17 and the youngest 11weeks and they all love it. We live within walking distance of the subway and also a 5,000 acre nature reserve so it’s the best of both worlds. We’re foodies so our date nights are great with all the different food options. The Boston Public Library is also a great place to visit. We don’t know how long the Lord has us here but we’re enjoying it to the fullest.

  • Melissa says:

    We loved our trip to Boston and did the Freedom Trail and all the historical stops you mentioned as well as stopping at the Make Way for Ducklings status in the Garden (our kids loved that as we had read the book many times before) and seeing the Boston Children’s Museum. We have been to many Children’s Museums across the country and this is definitely one of my top 3. It was AMAZING and although it was a bit pricey, I thought it was worth the splurge and might be a part of a museum reciprocity programs offered throughout the country. It would be worth checking out for sure!

  • Jen says:

    I’m originally from New England and this post makes me miss Boston! So which did you like better, Mike’s or Modern? I think the selection is better at Mike’s but I’ve had a few Bette things at Modern.

  • Julie says:

    I’ve never been to Boston , but if I ever go, I want to see the Make Way for Ducklings statue.

  • So glad I stumbled upon your blog! We are visiting Boston next week and we plan to visit the national park sites and walk the Freedom Trail. Your tips and notes are super helpful, love all your photos too. Thank you for sharing this!

  • Monica says:

    Will you be visiting Philly? I loved living there for 4 years. I’ve heard that it’s similar to Boston, so I would love to hear your take on that! Loving the road trip posts!

  • Steph says:

    We are headed to Boston for an overnight over Labor Day weekend. Would love to find out how to book an affordable hotel–what website you use or if any users have a hotel they highly recommend. Traveling with a 7, 5 year, and 6 month old. I’ve been to Boston and done the Freedon Trail and Harvard. What are the most sees for a one day extravaganza?! Thanks!

  • Marla says:

    I just wanted to say that this post made me so homesick (I’m from MA but moved to GA over ten years ago and just don’t get home enough). The North End and Mikes/Modern are great, but I wish you’d also had time to eat ICE CREAM. There’s nothing like ice cream in New England. Sigh. Oreo from JP Licks…..yeah. Also, if you ever get back, cross the river and go to Cambridge and Somerville too. Hope you enjoyed your brief trip to NH as well! 🙂

    • Oh! I don’t thin any of my readers recommended ice cream on my social media posts where I got a bunch of suggestions from locals as to what to do/visit/eat in Boston. Otherwise, if enough people had recommended it, we totally would have tried to make it happen!

      • Libby says:

        New Englanders eat more ice cream per person than any other region of the country! The small ice cream shops are GREAT. I’m pretty sure that ice cream with mix-ins was started in Boston in the 1970’s by Steve Herrell (sp?).

  • Stacy says:

    I can’t believe everything you fit in to your one day here in Boston! You did more in one day than I’ve done in the 10 years I’ve lived here… ok, maybe not but it seems that way. Also, it’s a trek from the Common to Charlestown. No wonder your sons feet hurt. Next time head down toward Copley Square – there’s a beautiful fountain there and while I’m not a Christian Scientist, the church has an amazing reading room that is definitely worth checking out. Also, you could have checked out Fenway 😉 Next time though.

  • Hannah says:

    I’ve been enjoying all your vacation posts, from your photos of each place your family visited, to your description of packing, preparations, and meals.

    Your Boston pictures brought back good memories of when my family and were there 8 years ago. All the quaint streets and historical landmarks were memorable. It was a city I’d love to go back to one day!

  • RO says:

    You make everything seem so fun! I think during the summer that every city in the US needs to have water shooting out from the sidewalks. I’ve never seen a bakery get so crowded, so both places you visited must have some really yummy food. I know I should, but after eating all that goodness, I would have had to hang out around a park bench for at least 2 hours. You guys have some serious energy. Hugs…RO

  • Jeanine says:

    I’m so excited! Silas has a Pirates shirt on, (Is he a fan??) and you’re visiting my home state next! Can’t wait for your next post!

  • Jessica says:

    Three words for your next visit, dear Crystal:

    Mike’s City Diner!

  • Phil says:

    The bakery boxes for both Modern and Mikes pastry are made right here in Chattanooga, TN

  • Kimberly in NC says:

    What is the person making on the lathe?

    And totally off subject of your vacation, but I’ve noticed your blue nail polish several times in pics and want to know what brand it is and what tips to making it last? I hardly ever paint my nails because it almost immediately chips. Yours looks good and I assume you did them yourself?

  • So fun! I’ve never been to Boston, but I’ve always wanted to take my girls. Especially now that I’m homeschooling. Thank you for the pictures, and including us on this unforgettable journey!

  • Christine says:

    I don’t know how you do all that walking in sandals!!! I’d be miserable! I have to wear sneakers!

  • Beth says:

    Following your trip has been so fun. Love all the money saving tips too. I’m a long time follower of yours and love that you visited my state and my favorite city❤️ Looks like you found most of the must-do’s and accomplished a lot! The Rose Kennedy green belt was an above ground highway most of my life. The transformation when they took it down and moved the highway underground has been amazing. Looking forward to reading about your next stop!

  • Carol says:

    These pictures bring back memories! I love Boston and all of its history. We took a trip to New England five years ago and did the Freedom Trail, Mike’s Pastry, and the ship tour. Thanks for sharing!

  • InbaL says:

    I would highly recommend visiting Cambridge too, and taking a tour (free) of Harvard and MIT campuses, and then crossing the Harvard bridge for great views of the Charles River and Boston and walking the Esplanade and the lagoon in Boston.
    You can also rent a kayak in Cambridge and go on the Charles River and into the lagoon!

  • Shelley says:

    I lived in Boston for 7 years and enjoyed all the places you visited! We live about 2.5 ours away now and go back as tourists every once in a while and always struggle with parking. I checked out the link you posted which is helpful but what hotel did you park at for the $15 valet parking on the Sunday?

  • Lauren G says:

    Just want to let you know that I love these posts! I am an east coaster and its neat to see your take on all of these sites. Would love you to take more long family vacations!

  • Bobbi says:

    Thanks for sharing! I’m going to Boston soon and this has me SO excited for the trip!!! I was there once 10 years ago and going this time with my husband. We are going to Fenway and a concert as well as some of the places you went, Crystal. We are also going to Cheers! We had 2 glasses from there and one broke, so excited to get a replacement. Thanks for your post!!!

  • Monica says:

    Best way to get over to Charlestown (and the Constitution) is to take the Shuttle Boat from Downtown across the harbor. It is located right next to the aquarium – near the greenway – and cost the same as taking the T. It is always fun to be out on the water instead of walking. I work in Charlestown and love taking the shuttle boat!

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