Thrifty Travel: Boston

Boston on the Cheap

Before moving to Boston, neither Johnny nor I had ever even stepped foot in the city. But it was love at first sight. We were moving from New York City, and I was expecting more of the same. But, no, no, no. First, Boston is pretty small. Since it’s one of our country’s oldest cities, I was expecting it to be big and sprawling. But you can walk all of Boston proper in just a few hours’ time. And almost all of it is easy on the eyes. I loved New York, but sometimes you had to search for the beauty. But Boston takes pride in its gorgeous history. The city is so well preserved, and each neighborhood has its own look and charm.

Since we’ve moved away, I’ve had so many people ask me what Boston’s like as they express that they’ve always wanted to go. And I always tell them the same thing: “Visiting Boston doesn’t have to be a big, expensive vacation! It’s just the right size that you can see all you want over a weekend.” And then I say, “Go, now. Spread your wings, little bird!” Okay, I wish I said that last part.

Johnny and I were on a tight budget when we lived in Boston (since we were still paying off our debt), but we still enjoyed the city without breaking the bank. I wanted to share the best of Boston on the cheap so you (and your wallet) can benefit the next time you head to Beantown.

MIke's Pastry

Fave Food Spots

Mike’s Pastry: $3-5/pastry

You can’t go to Boston without hitting up Mike’s Pastry. There’s always a line out the door. Johnny and I lived just a few blocks away, and we’d laugh every time we passed Mike’s because there was always a line. But it moves quickly, and it’s well worth the incredible pastries. My personal favorite? The lobster tail, which is basically one ginormous cream puff of heaven. Johnny and I would split it and still not be able to finish it in one sitting.

Galleria Umberto: $1.55/slice

Like Mike’s Pastry, Umberto’s is another place located in the North End (basically Boston’s authentic Little Italy). Galleria Umberto is only open for lunch, and you can’t arrive much later than 1:00, or everything will be gone. It’s cash only, and everyone who works nearby flocks there. Why? Because it’s the best tasting pizza you ever did eat. And the panzerotti (deep fried potato croquette)? A must!! Mmm. I miss that place big time.

Boston Hay Market

Open rain or shine every Friday and Saturday, Boston’s Hay Market is a one-of-a-kind open air market that sells fresh produce and fish. The prices are unbelievable. The best part? You can barter with the sellers. One rainy Saturday, Johnny and I were able to score 8 packages of strawberries for $2.00!


Fave Destinations

Public Garden: $0

Located right next to Boston Common (Boston’s largest park), the Public Garden is downright gorgeous. The landscaping is impeccably maintained, and you stumble upon one picturesque backdrop after the next. And if you’re feeling the swan boat ride around the lagoon, it’s only $3 a pop.

Freedom Trail: $0

The Freedom Trail not only covers almost all of Boston’s best destinations, but it also covers almost all of Boston, so it’s an absolute must. From Bunker Hill, to the site of the Boston Massacre, to Paul Revere’s House, to Boston Common, the Freedom Trail has it all.

Beacon Hill: $0

If you love historic neighborhoods that are drool-worthy in their beauty, take a stroll through Beacon Hill. The cobblestone streets are so quiet, and every home has its own history and character. If you can’t tell, Beacon Hill and I are in love.

Harvard: $0

If you’re in Boston, you have to see Harvard University, just a 20-minute subway stop away. It’s old, beautiful, and swarming with some of the best and brightest kids in our country. I loved strolling the campus and just soaking it all in.


Fenway Park Baseball Game

If you visit during baseball season, a game at Fenway Park is a no brainer. They just don’t make baseball stadiums like Fenway anymore. And I’m not even a big baseball fan. I mean, it’s over 100 years old — the oldest stadium in the country! And the atmosphere is electric, no matter where you sit!

Now I’ve gone and made myself nostalgic for Boston. If you’ve been eyeing a trip to Boston, it’s time to make it happen. And maybe this list will help keep your budget happy while you’re there!

Have you ever traveled to or lived in Boston? We’d love to hear what you’d add to this list!

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  • Reply Brian January 16, 2014 at 7:39 am

    I went to Boston a couple times because one of my best friends went to Harvard. That campus is pretty awesome. We did a lot of stupid things in that city like the time we went into one of the sketchier neighborhoods on St Patrick’s day not realizing it was St Patrick’s day

    • Reply Joanna January 16, 2014 at 11:50 pm

      Oh dear! I can imagine things could get pretty crazy in certain parts of Boston on St. Patrick’s Day! Glad you’re alive to tell the tale! 🙂

  • Reply Catherine January 16, 2014 at 7:42 am

    Boston is one of my favorite cities in the world! ive been twice and plan on going again. we just went to Boston/Plymouth this summer for 2 weeks. It reminds me of a much bigger version of my home in Halifax NS, very similar in many ways.

    • Reply Joanna January 16, 2014 at 11:52 pm

      Oh, I bet that was a great trip! Boston in the summer is perfection. I’ve never been to Halifax, but based on your description, it sounds pretty great!

  • Reply Heather January 16, 2014 at 9:19 am

    I went to Boston over Canadian thanksgiving a couple years ago, and I LOVED IT!! It is definitely one of my favourite cities.

    I spent very little money for that trip. I got a super cheap flight, and stayed in a small hotel that was reasonably priced b/c you shared bathrooms (I know some people don’t like that, but if I save $$, I don’t care – I also love staying in hostels).

    Everything I did was free. Even though it was early October, it was sunny and 30 degrees (Celsius!) the entire time so I spent it all just wandering the city – Boston Common, Georgetown, Beacon Hill, Freedom Trail, the waterfront, Harvard etc. I spent time just reading by the river. I went for a run along the river one morning. It was one of the best weekends away I had had in a long time.

    If you are considering it = GO!

    • Reply Joanna January 16, 2014 at 11:55 pm

      It sounds like you saw the best of Boston while you were there, Heather! That’s awesome you were able to get a cheap flight and accommodations. Aside from that, you barely need to spend a cent! And we loved running along the water while we lived there — nothing better!

  • Reply Becky @ RunFunDone January 16, 2014 at 9:19 am

    I’ve been to Boston once. I don’t remember much about it. I remember walking the Freedom Trail, and going to some sort of indoor farmer’s market-type-thing.

    • Reply Joanna January 16, 2014 at 11:55 pm

      Well then it sounds like you need to go again, Becky! 🙂

  • Reply Anna January 16, 2014 at 9:27 am

    I live here 🙂 And lordy almighty do I wish you guys still lived here! Baseball game date? I think so! I would add Ducali to the pizza place list, SO SO SO SO good. And, if you want to go out at night in Boston and not stand in the world’s longest line whilst looking longingly in at the bar that appears to only be 30% full, I would go to The Times. It’s an Irish pub that has a DJ on Friday and Saturday nights, there is no cover and never a line, and it is my go-to place to Beautious.

    • Reply Joanna January 17, 2014 at 12:01 am

      Definitely, Anna! You’re living the good life! It’s great to hear your favorite places. We never tried Ducali while we lived there, but we’ll be sure to add it to the must-eat list the next time we head back for a visit!

  • Reply Jennifer @ Budgeting in Baby January 16, 2014 at 9:33 am

    I have not gone to Boston but would love to go, especially for the historical aspects of the city. This is a great list and will keep these suggestions in mind for one day.

    • Reply Joanna January 17, 2014 at 12:02 am

      Yes, it’s a definite bucket-list city! Johnny and I still have so many other US cities we’ve got to check off our list!

  • Reply MelissaH January 16, 2014 at 9:41 am

    After walking around Harvard, a great place to hit up is Grendels Den. Their happy hour is nightly from 5:00 pm to 7:30 pm where all food on the menu is half price if you buy a drink!

    • Reply Joanna January 17, 2014 at 12:03 am

      Sweet! Thanks for the great tip, Melissa!

  • Reply Little House January 16, 2014 at 10:15 am

    Boston is a city I’d love to visit…in the summer! I absolutely adore compact, quaint old cities, they’re a stark contrast to sprawling Los Angeles (where I live.) Thanks for the tips!

    • Reply Joanna January 17, 2014 at 12:04 am

      Yup, it’s perfect in the summer and so very different from LA. That said, LA has some pretty great aspects, too! Johnny grew up there, and we hope to head there soon!

  • Reply Amanda @ Passionately Simple Life January 16, 2014 at 10:56 am

    I’m definitely going to have to try Mike’s pastry when I go in a few weeks! I’m all about those places that locals tend to know about and have lines out the door! That’s when you know it’s good!

    • Reply Joanna January 17, 2014 at 12:06 am

      How fun! Mike’s Pastry and Galleria Umberto are on the same street, so you could hit both places in one fell swoop! Have fun on your trip!

  • Reply NZ Muse January 16, 2014 at 1:54 pm

    My favourite memory of Bologna is waking up and going to the corner bakery every morning to buy fresh panzerotti stuffed with tomatoes and cheese. BLISS.

    We were only in Boston for a few hours last year, though it seemed like a very charming city. Crazy expensive though, which is why we didn’t stay in town and drove out of town to find cheaper accommodation!

    • Reply Joanna January 17, 2014 at 12:08 am

      Mmm. That sounds delish! Yup, you have to really search in advance to get good deals in our big cities!

  • Reply Alex January 16, 2014 at 5:25 pm

    We’re only a few hours away, so we try to do a weekend there at least a couple times a year. If we’re not staying with friends/family, we find the cheapest hotel rooms in the financial district. You are right, Boston is TOTALLY walkable, and if you really can’t hack it the T is super user-friendly. But for an extra few blocks’ walk it’s worth it to get the much less expensive rooms. (Esp. if you’re going Sat/Sun — folks that stay in those hotels are typically there on business, so it’s easy and cheap to snag a room on weekends.)

    Other ways we save:
    Bus in to save money (and hassle) on parking. You could also drive to a T stop just out of the city and park there.

    Splitting food at Quincy Market. It’s touristy, but if you’re going as a tourist, why not? But you really can split just about anything you buy there, and it’s plenty.

    Skipping the New England Aquarium. It’s probably something everyone should go to once, but for the money we prefer a trip to the science or children’s museum. Sometimes we just walk down to the waterfront and grab a drink out the outdoor bar and watch the folks boarding the tour boats, and then circle around and see the outdoor parts of the aquarium. Totally legit to do and you can still see the seal enclosure, walruses, and sometimes peek in and catch part of the shows. 🙂 🙂

    (P.S. The lobster tail is our favorite, too. And for cigar lovers, right next door to Mike’s is Stanza dei Sigari. One of our favorite haunts when it’s too darn hot. You can duck into their cellar and catch part of game and split a cigar. So fun!)

    • Reply Joanna January 17, 2014 at 12:15 am

      Great tips, Alex! Thanks for sharing. The first time we went to Boston, we took the Bolt bus (only $15 each way) from NYC, which saved us a boatload. And you’re right about the T… super simple to use!

  • Reply Kendal @HassleFreeSaver January 16, 2014 at 5:58 pm

    This is awesome, Joanna, thank you so much for posting! I haven’t visited Boston yet but I’d like to plan a trip with the hubs since his grandfather grew up nearby in Lowell, MA. My ideal vacations are ones where we visit locals who can show us their favorite spots and eateries, so this is the next best thing! Now I’m craving pizza and pastry – thanks for that, too!

    • Reply Joanna January 17, 2014 at 12:23 am

      No problem, Kendal! You guys would love it! Definitely go when it’s warm, since it’s a walking city. And how neat to visit a place where your husband’s grandfather grew up. Hope you get to go soon!

  • Reply sharon January 16, 2014 at 7:55 pm

    This post made me smile. I miss Boston, as I used to go there all the time as a kid. My ‘Italian’ grandmother lived on Hanover Street, right across from the Paul Revere statue. Back then, they would a feast in the street every weekend in the summer and we could see it all from my grandmother’s window. LOVE Boston!

    • Reply Joanna January 17, 2014 at 12:25 am

      Oh, I can picture exactly where you’re talking about, Sharon! I loved that little park where the statue was. That’s funny about the feast. Even still, almost every Sunday they do different saint’s parades/celebrations in the North End. We loved watching them out our window!

  • Reply Tushar @ Everything Finance January 20, 2014 at 11:45 pm

    I have never been to Boston, but I hear it’s amazing. Probably the thing I have heard most about Boston has been about the food and the culture. Sounds like a worthwhile city to visit.

  • Reply Hannah January 28, 2014 at 3:12 am

    Thanks for the tips! My husband and I, also some friends of ours are taking a roadtrip from Wisconsin to Boston for 5 days for St. Patrick’s Day and also to see Dropkick Murphys (our favorite band) in their hometown! I can’t wait, after reading this I’m even more antsy 🙂

    • Reply Johnny February 18, 2014 at 1:24 am

      Bostonians love their Dropkick Murphys. That sounds like an awesome roadtrip. Have a wicked awesome time!

  • Reply sarah February 2, 2014 at 10:15 pm

    i grew up in the south shore of mass, with frequent trips into boston and even a year of living in the city. while i defenitly prefer the suburban lifestyle, there is something special about saying you’re from boston. it’s a phenomenally spirited city. I love a good walk in fanuiel hall or down newbury street, even just for browsing!

    • Reply Johnny February 18, 2014 at 1:26 am

      There’s a certain energy and spirit about that city that’s hard to beat — especially after a Bruins or Red Sox game. We miss our walk and talks through the streets of the North End and Downtown.

  • Reply Kelly February 16, 2014 at 3:16 pm

    Thank you for all the ideas. My husband and I are headed to Boston in May to see our Detroit Tigers vs. the Red Sox at Fenway Park. I am extremely excited, as my mom is from Massachusetts. I am of Irish Decent, and my husband- Italian. I haven’t been to Boston since I was very little and my husband has never been. We have family in Agawam and Southwick, but plan on staying in or around Boston over the weekend. We will be visiting Mass. for at least 10 days. I’m also an amateur photographer, so you can imagine my excitement to be visiting such a beautiful place. We are planning on taking a trip to the Cape while we are there. Boston, Red Sox, Irish, Pastry, Cobblestone, Pubs, Fenway, Seafood, unforgettable memories await….

    • Reply Johnny February 18, 2014 at 1:31 am

      It sounds like you two were meant for Boston! I would have killed to have seen my Dodgers play in Fenway, but no such luck during the two seasons we were out there. It sounds like you’ve got the gist of your planning figured out. And I’m doing my best to not be extremely jealous. Enjoy your trip!

  • Reply Lori March 16, 2014 at 5:45 pm

    Hubby and I are spending 9 days in Boston in May. We already have our tickets to a Red Sox game, and we are knee deep in planning mode. This will be our first trip to Boston, and we are huge history/museum nerds. I can’t wait!

    • Reply Johnny March 18, 2014 at 12:14 am

      So jealous. We’ve been missing Boston a lot lately. No better park in America than Fenway. You’ll have a blast!

  • Reply Tori April 15, 2014 at 11:46 pm

    Lived in Boston while my husband attended law school. Absolutely loved it. We lived in Southie which is the Irish part of town and the only place to spend St.Pattys Day. Mike’s was good but we preferred Caffee Vittoria. You can’t go wrong though in the North End. Miss Boston every day since we left. Can’t wait until our daughter is old enough to take her there on vacation.

    • Reply Johnny April 19, 2014 at 10:35 am

      We’re in the same boat. Spring/summer really brings our Boston nostalgia. Walking around the harbor at night, games at Fenway, etc. But we’re hoping to be able to show our girl our once-temporary-home in a few years when she’s a little older.

  • Reply Amber May 22, 2014 at 11:06 pm

    Hey there! Great list, my husband and I are driving to Boston in a couple of weeks from New Orleans. We’re going there to see John Williams the film composer conduct the Boston Pops for a concert. We are beyond excited (we’re photographers and it looks like we’re gonna be way overwhelmed in historical beauty.) I was wondering if you could give any other suggestions on eateries that are inexpensive. For example, where’s THE best place to get a burger, that’s in the Public Gardens-Symphony Hall region of the city? We love American food, Tex Mex, and of course our seafood/cajun New Orleans cuisine. Any suggestions you could give would be so helpful. Also, what would you say would be the cheapest way to get back to our hotel room late at night (after the concert at the Symphony Hall) if we’re staying in the Crowne Plaza in Newton? Hehheh, sorry for the overload of questions. Thanks for any help you can give. 🙂

    • Reply Katie May 29, 2014 at 5:20 pm

      I am going to the John Williams concert as well! So excited!
      I live near Boston, and the best burger place I have been to is called the Green Street Grill-but it is in Cambridge, so if you are in that area it is worth a visit. It doesn’t open for dinner until 5pm FYI. It was seriously the cutest place, not too busy, adorable bar, great food, and clean/friendly staff.
      If you are traveling via subway, or as it is referred to, the T, you should get a plastic CharlieCard from a MBTA employee (they all have a few in their pockets or will go and get them for you, sometimes they give you a little guff over having to get you the CharlieCards but just be super nice and thank them a lot)-the card is free, and then you pre-load it with money on the self serve kiosk. If you buy the CharlieTicket-the paper version-each ride is $2,50, but if you use the CharlieCard each ride is only $2.00.

    • Reply Joanna June 4, 2014 at 3:04 pm

      Great tips from Katie! I agree wholeheartedly with what she said! Thanks for your awesome input, Katie.

  • Reply Jen September 15, 2014 at 3:56 pm

    Thanks for posting this! I’m FINALLY going to Boston after years of wanting this trip! Going with three others also on a budget who are also grateful for your post.

    We’re all excited just to be in such a historical place but not necessarily museum tourists. Do you think it is worth paying for most of the historic spots/tours or just enjoy the atmosphere?

    Thanks again for your advice!

  • Reply Emma Bail September 22, 2014 at 4:55 am

    Really love your post and your experience too.I am totally agree with you that Boston is such a city that anyone can fall in love with it in a first sight.I personally love to visit this city again and again.After reading your post i really can’t to visit Boston.Thanks for sharing your experience with us.Keep posting

  • Reply Celine June 23, 2015 at 9:15 pm

    I’ll be moving to either Boston or Cambridge in January as a Harvard grad. student. Do you have any tips for making the move? I’m a small-town girl and I’m fairly shy… Also, thanks for your post! I’m looking forward to seeing and visiting some of these places. 🙂

  • Reply T July 29, 2015 at 12:56 pm

    Thanks for this post. I enjoyed it. Myself and my fiancé are moving to Boston soon for 3 months. We’ll be using some of your tips- thank you!

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