Boston on a Budget!

Earlier this year, my mom and I booked tickets for a fan convention in Boston, somewhere neither of us had ever been before. While the actress we had been planning to see cancelled the week before the convention, we still made the best out of our (very expensive) trip to the north!

While plane tickets weren’t too costly from Louisville, hotel prices were exorbitant. In the summer, low-end prices for brand name hotels often top $200 per night. This prompted us to try Airbnb for the first time ever....which we ended up regretting immensely. Not only did the Airbnb lack air conditioning, cable, and space, it was also outside of Boston. What we saved on hotel costs, we ended up spending on train tickets and Uber rides in and out of the city.

In the end, it would have been more cost-effective and definitely more comfortable to spring for a nice hotel in the city. Other than our accommodation arrangements, Boston was absolutely wonderful. When we weren’t at the convention, we visited Back Bay for shopping and sightseeing and the North End for delicious and authentic Italian food and even more sightseeing. 

We took advantage of the sunny and warm weather during our first day of the trip and headed to the Swan Boats near Boston Commons. The wait for the Swan Boats was relatively short, and the ride around the pond was calming and beautiful. The park is absolutely gorgeous, and the scenery makes for some fantastic photo opportunities.

The Boston Commons are just a few blocks away from Newbury Street which offers the best shopping in all of Boston. Here, you can find stores such as Kate Spade, Lilly Pulitzer, Chanel, Tiffany’s, and more! Since we're southerners, we eagerly ate at the oh-so-different Shake Shack there, and finished up the day by trekking it down to Fenway Park.

I had the lovely idea of eating at the Bleacher Bar, a small sports bar located on the outside of Fenway Park that has a large open wall that allows you to see what’s happening on the field. Unfortunately, my idea was sabotaged by a Billy Joel concert taking place that evening. The bar was absolutely packed.

The Bleacher Bar sounds like a lovely idea in theory, even if nothing is happening on the field, but I would recommend checking out if there is a game or concert before you go. However, we ended up at a Boston staple, Regina Pizzeria where the food was delicious and affordable, so no complaints here!

Our second day in Boston was mostly consumed by the fan convention, but when it was over, we were excited to fit in some good eats and sightseeing!


We found a wonderful Legal Seafoods right on the water near the Boston Aquarium, and had an authentic Boston meal: clam chowder, lobster rolls, and Boston Cream Pie. Legal Seafoods might be known as a chain to a lot of people, but it was definitely a different eatery for these southerners!

After we ate, we took an Uber back to our sad little Airbnb, and the night drive through Boston was absolutely beautiful. Driving in Boston seems insane and next to impossible for a tourist, so Uber was the perfect way to get around.

Our third day was again mostly taken up by the convention, but we had some more free time that evening. Eager for some more good food, we headed to Sullivan’s on Castle Island. We had some wonderful fish and chips, but they also offer inexpensive hamburgers, hot dogs, lobster rolls, and more. This is definitely a restaurant for eating outdoors- there is absolutely no indoor seating- so I would definitely recommend this place for a sunny day!

After our quick meal, we headed to Faneuil Hall, a place that many travel blogs had said to avoid because it is too “touristy.” However, we absolutely loved the shopping center. It’s a great place to get souvenirs and for sightseeing.

Our fourth day in Boston was undoubtedly our busiest! I was desperate to head to Wellesley to see the historic all-women's college Hillary Clinton attended.

We took the commuter train out to Wellesley which was an entirely foreign and strange experience for us, but it was definitely worth it! It was easy to find out which stop to take the train to and the transit employees were extremely helpful! Wellesley is an absolutely adorable and peaceful town. If you're in the mood for a relaxing, quiet getaway during your stay, Wellesley is perfect!

After we got back to Boston via the train, we headed to Boston’s North End. Not only is this the part of Boston where the Old North Church is located, it also has a large variety of authentic Italian restaurants to choose from. 

I did my research beforehand and found the most reasonably priced restaurant on the block. Bella Vista Ristorante is a small family business that serves up wonderful, authentic Italian food at a reasonable price. The food was delicious and better than any Italian food we'd ever had.

Afterward, we headed to the famous (and packed) Mike’s Pastry for some legendary cannoli. We packed it away to enjoy later and headed a few blocks over to the Old North Church.

Being inside the church and absorbing its history is a beautiful feeling. It's a must see for any tourist! After visiting the Old North Church, we headed back into the city to the Boston Tea Party and Ships Museum. Here, you can pay for the one-of-a-kind experience of throwing tea into Boston’s harbor like a true revolutionary! They also have a lovely Tea Room and gift shop that offers wonderful souvenirs.

Our fifth, and final day in Boston, was spent at Beacon Hill, a beautiful and historic neighborhood in Boston’s Back Bay. Walking the cobblestone streets in this neighborhood is truly like stepping back in time. The neighborhood is within walking distance of the famous Cheers bar and restaurant, so we stopped by for some amazing food before heading to the airport.

Boston is full of great, historic sites! I definitely recommend checking out the Old North Church, Boston Commons, Newbury Street, and Fenway Park. They're one of a kind experiences that you just can't find anywhere else! Have you tried any of these spots in Boston? Are there any other spots you recommend? Comment below!