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Where to visit in Downtown Boston

Updated: Jan 24, 2022

You’d be “wicked smaht” (something Bostonians say often) to follow this guide to visiting Boston. This is your ultimate guide to doing Boston on a Budget.


Oh Boston. I am not a city girl, but Boston changed this for me. Boston was hands down the cleanest and safest bigger city that I have ever been to. There were many late nights walking back to our hotel in the dark, and we didn't feel the slightest bit unsafe. Everyone also was SO NICE, which I was surprised by (well unless you bring up Tom Brady, then you never know how the rest of the conversation is going to go).


Bostonians Love their Sports:


Tour Fenway Park, or see a Red Sox Game:

We ran out of time and unfortunately couldn’t make it inside Fenway (to my husband’s great disappointment). But my mother in law and sister in law were able to make it, and said it was the best part of their entire trip to Boston. They do offer tours which you have to buy tickets for ahead of time, or check their game schedule and catch a game.

You can book a tour directly here. I would also suggest checking groupon for deals on these tours, but avoid TripAdvisor as they often cost extra with fees.


See a Patriots Game:

While we were in Boston, the Patriots had a home game against Tampa Bay (and their beloved Tom Brady). We did not attend the game, but the streets were wild. We watched many people yell at each other across the street for wearing the wrong jersey, or refer to one another as a traitor for following Tom Brady. The energy was so fun to be a part of, and I don’t even watch football! (Well not by choice, I actually watch A LOT of football while my husband has it on and I blog beside him lol).


Watch the Celtics swish some hoops:

This was another activity we didn't get to take part in, but I would have loved to do! Basketball is definitely more my jam than other sports. (But I do love my home team most, the Utah Jazz). Either way, some game day treats and a nosebleed ticket never fail to bring some fun and good memories. The stadium is also right downtown and easy to walk to, which is a plus!



Good Food = no possible bad outcomes


An essential stop: Mike's Pastry

Before I begin telling you why you ABSOLUTELY MUST go here while in Boston, I will tell you something even more important: BRING CASH. Even though it is 2022, they only take cash. Not even Venmo or Apple pay. We made the mistake of standing in line for a good 20-30 minutes before we got to the front and were told they only took cash, which we didn't have on us. Thankfully, while standing in line we met the sweetest couple from Indiana who paid for our treats! Talk about an act of service. (Someday I'll go more into this, but I truly believe traveling often is the quickest way to realize there are so many good people in the world, and to gain a better empathy & understanding towards one another. Also, to make lifelong friends all over the world!) Anyways, let's get to the point. The Cannoli and Cheesecake at Mike's are divine. Mouth Watering. Honestly, I will leave it at this. Wait in the line, it is WORTH IT. And again, bring cash.


Eat at the North End Italian District:

You honestly can't go wrong with any pizza or pasta from the Italian District, located near Mike's Pastries. I highly recommend stopping along the way for a bite to eat of any classic Italian dish!


History lives on:

Okay okay hear me out... before you press the snooze button on History, I promise this will be the most interesting and exciting history lesson you will ever learn. Getting to stand where such monumental moments in the United States History occurred is mind boggling. Don't sleep on the history of Boston!


The Freedom Trail:

You really have two good options when it comes to the Freedom Trail: Take a Duck Boat tour, or walk. My mother in law and sister in law opted for the Duck Boat tour, and my husband and I walked it. So let's compare the two and find the best option for you! The Duck boat tours are literally a duck boat on wheels with a tour guide that takes you around each of the 16 stops. Great way to see the entire city along the way, and saves you some energy from walking the entire way. The only downside is that you can't hop on and off of the ride, so you often just drive past your stops. It also is about $46/per adult and $31 per child, whereas walking it is free. You can prebook your tickets here. If you do opt to walk instead of take a tour, you absolutely need to download the Freedom Trail app. It is about $7 on the Apple App Store or Google Play Store. This is what we did while walking, and we learned so much. This is also a great way to make sure you don't get lost. Another tip to avoid getting lost, is that there will be a brick "trail" so to speak all along the sidewalks of Boston. If you follow this, you are on the right path. Some of the stops on the trail include the burial place of John Hancock, Paul Revere,Samuel Adams, and the victims of the Boston Massacre. It honestly felt like holy ground to me, to stand where such brave men lay who played such essential roles in creating the country of Freedom we are privileged to live in today. I am thankful to these men and women for the life I live today. Other stops along the way include Boston Commons, Massachusetts State House, The Park Street Church, The Kings Chapel & Burial Ground, the site of the Boston Massacre, The Paul Revere house (that does $5 tours before 4 p.m.), Bunker Hill, the USS Constitution, and so many more monumental stops.



The USS Constitution:

This was one of those accidental finds where you strike gold. We got here at the end of the freedom trail probably around 5:00 P.M. when they were closing. They weren't doing tours for the day anymore so we peaked our heads over the gate. One of the guards saw us and invited us in to help do the Evening Colors with the Navy Crew Stationed there. My husband jayk got to fire off the cannon for the evening colors! It was so cool, and our favorite memory from Boston. My tip would be to get there right before evening colors as they close, or to at least try to get there for a tour of the boat during the day.


Bunker Hill:

Bunker Hill is another stop along the Freedom Trail that felt like hallowed ground. It was just getting dark when we arrived and the monument was lit. We laid on the lawn for a few minutes and just gazed at it in silence. It was almost reverent.


Take a quick detour to Salem:

I'll link my guide to salem HERE so you can see all the best things to do! It's a quick 30 minute train ride from Boston from the North Station.




Transportation:

Your options for transportation in Boston are Public Transportation by train or bus, Uber/Lyft, or walking. My recommendation: Opt for public transportation and walking. Uber/Lyft adds up FAST. There are some areas you can't walk to due to the waterways and layout of the city, but when you can walk or take public transportation, do it. Get a Charlie pass for $14 and it covers all trains and busses which is great for hopping all over the city or to Salem for a day. If it is the weekend get the $10 weekend pass that includes all unlimited transportation for only $10 over the entire weekend! I would download the MBTA app, it is the easiest way to figure out the train and bus system. The T train is the best for getting around the city.


Stays:

I've said it before and I'll say it again, I am team Hampton Inn or Hilton until I die, with Airbnb following close behind. We stayed at a Hampton inn and a Hilton in Boston. We stayed at the Hampton Inn Boston Logan Airport Chelsea first. It was very nice, but don't be fooled, it isn't right next to the airport. It's a 20-25 minute Uber/Lyft from the airport. There was a free continental breakfast that was actually fabulous with many choices! But, our second stay, The Hilton Boston Logan Airport was literally on the Airport Campus. The Hilton was one of the most stellar hotels I have ever stayed at. The staff was so kind and continually offered us upgrades without us asking. The view of the city and airport is beautiful! There is not a complimentary breakfast offered here. I recommend checking Expedia or Hotels.com for rates on both of these, and Joining the Hampton/Hilton rewards program.





Don't forget to pack:

*I do make a small commision off of these links and appreciate your support*


Wrangler Rolling Duffle Bag:

A good carry on with FOUR wheels (tipping with two wheels is so last year)



A cute hat for the Instagrammable pics:


A good quality backpack that doesn't scream tourist:



All in all, thank you for being here. Please reach out if you have any questions or comments. Share this post to spread the Boston love!


Safe Travels to you and yours,

Lenny

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