Our Boston Trip Tips {+Secrets!}

Boston. When we got off the plane, I was asking myself why in the world we decided to come to Boston in the first place. I had surprised Joel for his birthday after crunching finances to make it work.  I like…sorry…love going to new places. It wasn’t necessarily on my list, but I thought it would still be fun. I had no idea how much I would end up falling in love with that city! It has so much to offer! I’m going to tell you exactly what we did, how we did it, and how to make it work on a tighter-than-tight budget!

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First of all, Boston is supposed to be one of the most expensive cities to travel to in the US. I beg to differ.  Like I said…tight budget, love to travel. If you are looking for a luxury trip to Boston, you have stumbled across the wrong blog, darling.  If you love traveling for the culture, cheap eats, and are only at your hotel for a bed, then you have arrived!

I am going to share the key points of our trip and how we managed it.

1.) Getting There FOR FREEEEEEE! Y’all. We are SOLD on the Southwest Rapid Rewards credit card.  Two years ago we signed up for this credit card.  You have to stalk their website and wait for the sign-up bonus to go up to 50,000 points.  I don’t claim to be a credit card rewards expert (yet), but I have done my research, y’all! I will talk much more about credit cards and how to make them work for you in an upcoming blogpost! But for now, just know they pay you if you do it the right way! (Extra, extra! BOTH of us flew for FREE to both Boston AND New York City on just our sign-up bonus!!!!!!!!) HELLO!)

2.) Stay/Sleep I want to reiterate right now that we are not luxury travelers. We love culture, experiencing new places, and we are usually not there for chocolates on our pillows but to explore! That being said, we decide (for each individual trip specifically) what we will settle for stay-wise.  We know us, and we know what kind of trips we are taking when we plan them, and they differ from trip to trip. When we planned our trip to Bean Town (which, I found locals don’t like the traditional nickname),  we knew we literally just wanted a place that was warm, that would be semi-centrally located, and had a bed we could fit on.  We started looking around and realized quite a few hostels, have private rooms with full beds.  Yep, its like a dorm where you usually have to use the bathroom in the hallway with everyone else on the floor, but like I said, warm, location, bed! Again, if thats not you, turn around. Committed adventure travelers only. ; ) I found this GREAT place called 40 Berkeley in Boston’s Southend, which is a historic, clean, beautiful, quite place to stay with tons and tons of gorgeous brownstones! It was, also, only a few blocks away from the subway! Score! The room itself was not anything over the top, it was just what we wanted and the right price.

3.) Must Do’s/See’s We are the people that will seek out every high-entertainment, low-cost experience that will make out trip the best possible! And Boston is a gold-mine for these sort of activities.

Freedom Trail This is definitely a highlight for anyone that loves history!  However, I’d go as far as to say this is a highlight for ANYONE! First of all, The Freedom Trail takes you along every historical site in Boston.  It winds through miles of the historic city.  You can absolutely find a tour that will point out the places of interest. We are not these folks.  We want to have the freedom (see what I did there?) to stop off and check out anything and everything along the path! So, instead, we bought a little book chalk-full of great information that took us along the trail to everything we wanted to see, and if it didn’t happen to peak our interest, we moved on.  If we wanted to stop and eat clam chowder on the street, we did! To us, thats the the only way to go! But, the trail takes you all around to see every site possible.

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Fenway Park Personally, Joel and I love baseball! One of our travel goals is to see a game in every stadium in the US. However, I don’t care if you are a Yankee Fan through and through, or you’ve never seen a baseball. Fenway itself is a great story!  We went in early December, after the season had come to a close, so we went on a tour. Honestly, I’m glad we took the tour. Don’t worry, we’ll be back for a game. Boston is a place we’ll be back to several times!

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Sam Adams Tour Its free, and it includes plenty of sampling of their current selections! (Don’t forget to keep the receipt!)


4.) Boston Eats We do a little bit of research before we go, scanning blogs and Pinterest looking for the well-known hole-in-the-wall treasures.  But we hold those plans extremely loosely.  Our favorite thing to do when it comes to restaurant hot-spots is hearing it straight from the horse’s mouth.  Ask the LOCALS! Duh! I mean who would really know??? So here is the list of places we went, most of which were recommended by, yep, Bostonians.

     Regina’s When we go anywhere new, or anywhere just out of town for that matter, Joel has to sniff out the best hamburger. But me, I have to seek out the finest slice of pizza.  Regina’s is in an adorable neighborhood.  You really can’t find an ugly neighborhood in Boston, though. We went for dinner, and the line did go out the door but was not terrible.

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    Doyle’s (Jamaica Plain)This place was amazing! It had a great Irish atmosphere.  The people working were extremely friendly.  Doyle’s was the first bar to carry Samuel Adams and still has one of the largest selection of Sam Adams beers around.  I had one called Brick Red. It was delicious, but I haven’t been able to find it anywhere else. So you know it’s selective!  **SECRET TIP**The Samuel Adams tour is great! And FREE!! But here’s the tip. Go take the tour first, then take your ticket from the tour to Doyle’s afterward.  If you order a drink in Sam Adam’s specially crafted glasses (which are pricey), you get to take it home for free! Woo! Another perk of talking to locals!

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      Bova’s (Little Italy) **Bova’s is another secrete tip in itself!** This was another exceptional discovering by talking to the locals! The Freedom Trail takes you straight through Little Italy. I could have spent a couple of days just hanging out there. It’s such a quaint, adorable part of Boston. We had to find ourselves a cannoli, of course.  Everything online will tell you that you should go Mike’s Pastry.  However, you’ll be waiting for a long while to get something that you can get right around the corner, with no wait , at Bova’s.  And they were delicious!

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    Mr. Bartley’s (Cambridge) Like I said before, Joel needs to find his perfect patty. So we went on the hunt and found Mr. Bartley’s while we were on our way to Harvard.  The burgers were more than worth the trip out to Cambridge.  The seating is a little cramped and communal, but to us it just added to the charm. Also important, they only take cash! Do yourself a favor, and don’t go to Boston without going to Cambridge. Gorgeous!


**Just a little tip… Joel and I are straight-up foodies.  We like to eat as many different of the go-to eats as we can when we travel to have that extra cultural, local adventure.  Instead of having the traditional 3 meals/day, we will split meals wherever we go and move on to the next foodie-fave a little while later.

Boston is one of those places that makes every stranger feel like they belong there.  Remember this, also.  Bostonians have a rep for being harsh. EVERY person from Boston we came across was so incredibly kind and wanted to help.  Being from the south, we expect kindness to look a certain way…hospitable, chatty, engaging.  These people were sincere, went out of their way to make sure we had what we needed, and really cared, even with the little chattiness they offered. Love it.

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Boston really is a city that has everything for everyone. I’d totally recommend everyone go at least once…but, I’ll warn you, you’ll want to go back! I’d love to hear about your Boston trip! Let me know what your favorite places and eats were, or if you have tried these recommendations, then I’d love to hear your thoughts! If you have any questions, just comment! Happy traveling!


23 thoughts on “Our Boston Trip Tips {+Secrets!}

  1. I went to Boston a couple years back and loved it! Never really noticed the lobster smell… But glad to hear that there are lodging options that are decent and work on shoestring budgets.


  2. Reginas!!! I’m so glad you mentioned that place, it’s delicious. My husband/in-laws are from Boston and so is my Step Mother, so I have deep ties to that magnificent city. I’m glad you came to love it just as much. You need a clam strip roll next time you go back, my husband has long debates over if it’s better than a lobster roll! Can’t wait to see where you travel to next.


  3. Hi Michelle! Oh, thats great! I love meeting people that know the city. We hope to go back over and over again! How fun that you have family there!! Yes, we LOVED Regina’s! I will definitely have to try the clam strip roll next time. 😀


  4. My Boston travel tips for next time (learned from locals of course!) Mike’s Pastries & La Famiglia on the North End for Eats, Newbury comics for endless isles of music and movies, and the chance to chill out by the ocean upon exciting! …thanks for the heads up about the credit card through SW (need!)


  5. BAH! Boston is at the top of my places to go list. I teach 8th grade US history and we spend like 3 weeks talking about the American Revolution so actually seeing all the places I teach my students about would be AH-MAZING!! I’m going to Washington DC this summer, so hopefully next summer I can Boston. Looks like y’all had a blast! 🙂


  6. Glad y’all had a good time! Boston is on our list of cities to go visit. But about that Southwest card!? I’m sold!! Can’t wait to read your blog posts to come!



  7. oh, then it would totally be perfect for you!!! It’s extremely cool to see all those places in person! I’m actually going to DC this summer, too! So you’ll have to let me know what not to look for if you get there before I do! Thanks Kathleen!! 😀


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