Working for an airline company has many benefits, including extremely discounted flights! Luckily for me my parents also get to partake in the flight benefits, meaning when my time came to utilize my benefits my dad and I hopped on a flight right to Boston, Massachusetts!
We spent only a short time in this wonderful city but boy did we pack it with all the adventures one could handle. We got to experience everything from sleeping in cars, one of the greatest historical walks in America, to a baseball lovers’ paradise at an under-the-stadium bar. I hope this Boston travel guide helps you know how to spend your time in this city.
With so many flights having longer layovers in Boston, this travel guide will help you not waste a minute and optimize your travel time! Let’s jump in!
Freedom Trail
If you are into history and want an excellent way to see the city the Freedom Trail is your answer! This 2.5-mile (4km) trail takes you through downtown and to the most important historical sites in the city. You will hit everything from one of the oldest gravesites in America, the home where the Boston tea party began, and even Paul Revere’s house. If you like American history you can’t miss this opportunity!
One of my favorite parts is the fact you can make this experience as cheap as you want. You can pay a fee to have a tour guide explain all the important stops. If you want the cheap option (and the option we chose.) You can follow the markers yourself and still have a grand time! The markers are easy to follow and there is enough information present allowing you full access to the same information you would get on a tour. Doing the walk yourself also allows you to skip over parts or stay longer at sites you love.
We did that with the very interesting graveyards and skipped over some other businesses we didn’t have a huge interest in. Overall this is a must while visiting the city and should be on every Boston travel guide!
Boston Commons
If you are visiting the Freedom Trail then you will want to pop into the Boston Commons! Sitting on 50 archers of land, the Boston commons is the oldest city park in America. It is a beautiful place to have a picnic, play at the park, or lay about and read a good book! It’s crazy when you are walking through the park and start to think of all the people who walked here before you. Again, if you love history you have to check this park out!
If you are driving and need a place to park there are parking garage entrances surrounding the park. It will take you to park underground, then when walking out you’ll come up and pop right into the middle of the park.
Different events are held here year-round so you can always check before visiting to see if anything is happening. When it comes to how long you need to explore this park I would say anywhere from 30 min -1.5 hours depending on what you want to do. If you are looking for a place to have a picnic you can spend the afternoon here. If you just have some time to kill then 30min would be enough.
Harpoon Brewery
After all that walking and exploring you’re gonna be hungry. My favorite place we went to eat was Harpoons Brewery! They are still within walking distance of downtown and sit right on the Boston Main Channel allowing for great views of the boats passing by! They had a ton of outdoor and indoor table games creating such a fun atmosphere to hang out in! We went around lunchtime and there was everyone from singles to families with younger kids enjoying the food and atmosphere.
Their prices are on the mid to low end for Boston. If you are into breweries you can take their tour for $20 where you will be rewarded with a glass to keep and endless drinks as long as you use that glass. For food they serve the best soft pretzels you will ever eat or amazing pizza. You can check out their full menu here.
The workers were all super friendly and you could tell they loved their job. They have a little gift shop area where they gave us free stickers and recommendations on where else to checkout. If you want a fun place to unwind and not break the bank Harpoons has you covered!
Quincy market
Now, this wouldn’t be a Boston travel guide without talking about Quincy Market! If you are looking for a super cute market to get lost in Quincy Market is for you. They have every type of shop here and are located right by the harbor for a stroll afterward. You can’t visit Boston without getting some lobster and this market has lobster served any way you could want! They have plenty of other food options as well for a delicious lunch by the harbor.
If you like shopping for little knick-knacks to take home you will be in heaven here as there are shops and street carts all over. Maybe you just want dessert? There are plenty of ice cream and candy shops around. This would make the perfect date spot to get some ice cream and stroll through downtown.
Even if shopping isn’t your thing there is still plenty to do here! If you like taking photos then this is a great place to come as there are so many little hidden gems to photograph. All the cute vendors unique to Boston, the historical buildings, and the boats make for a photographer’s playground!
If you need more help planning a trip don’t forget to check out this list to help you get on your way!
Fenway Park
If you like baseball you can’t miss Fenway Park! I’m not even a huge baseball fan but I still thought this was super fun! The best way to get here if you don’t have a car would be to jump on the T (Boston subway system) that runs through the city. It was super easy to navigate and there are stops all over the city to jump on and off. The price was also hard to beat as it was about $4USD from downtown Boston to Fenway Park and back.
Now you can catch an actual baseball game which is fun in itself or you can do what we did. There is a bar called Bleacher Bar located right on the side of the stadium. It is hidden under the bleachers with a look out right onto the field! You can stay as long as you like while buying drinks or food. The atmosphere is fun and filled with all sorts of people. It is a cheap way to feel a part of the fun without paying an arm and a leg for a ticket.
It is fun to just be around the stadium as there are a lot of great places to eat and hang out with all the fans. If you need help navigating the city or how to get here make sure to check out these helpful apps!
Boston Harbor
The iconic Boston Harbor is a can’t miss while you spend time in the city! There are so many places to go watch the fisherman and boats it’s hard to go wrong on the exact location. The harbor lines the city and provides plenty of bridges to cross the channels. They also have plenty of walkways that shoot out into the water to give you a close look. One of my favorite things my dad and I did here was get coffee and walk along one of the harbors.
For my history buffs, if you want to explore where the Boston Tea Party took place you can head on over to 306 Congress St. They have a great museum and you will be able to learn first hand what went on that night.
If you want to actually take a trip on a boat there are plenty of options for you! Boston Harbor Islands National and State Park Ferry Center would be a great option for finding cheaper ferry rides to nearby islands! If you want to see a full list of all their services and prices you can look here.
The other option is catching a whale-watching tour! I had friends who had a 12-hour layover in Boston and decided to take a whale-watching tour. They had the time of their lives and saw so many cool creatures!
Tatte bakery
Looking for a cute cafe to live out your Boston dreams? My dear friend recommended Tatte Bakery as a lovely getaway in the city! The coffee is top quality, the atmosphere comforting, and the prices not bad. They have multiple locations all over Massachusetts and in Washington D.C. If you are hoping to grab a quick coffee and stroll the historical streets they have you covered. Have some work to get done or need a space to concentrate, Tatte offers the best place to do so!
If you want to grab lunch and chat with friends they offer everything from sandwiches to salads. Any type of pastry you could want they also serve. On the weekends they even offer brunch which includes pancakes, eggs, and any sort of fancy toast you could want! If you are looking for a healthier option they do serve drinks with the base of beets or turmeric.
Overall this bakery and coffee shop is super well-rounded and fun to spend time in. If you just need a minute to relax after all the walking you’ve done you will not want to miss this spot! If you want to see their full menu and hours you can look here.
Seafood
Every good Boston travel guide needs a dedicated section for the best seafood! There are so many good places to go throughout Boston but I wanted to compile some restraints that weren’t going to leave you with a hefty bill.
If you want amazing clam chowder or the best lobster rolls you have to check out The Barking Crab! They are seated right on the water adding to the true Boston feel. The prices aren’t bad for the amount of food you get and the quality. They are easy to spot as you cross the bridge with their bright red and yellow tent and fun atmosphere pouring out onto the street! Location: 88 Sleeper St, Boston
Right across the bridge from The Barking Crab sits the cutest food truck James Hook & Co. If you want great seafood but don’t have a ton of time or want something less formal you will love this small shop! They have a small shop on one side of their lot and a small food truck on the other. Easy to spot with their bright red food truck and picnic tables outside, they make the perfect lunch spot! They are also right on the water perfect for watching the baots pass by! Location: 440 Atlantic Ave, Boston
Looking for more of a low-key bar feel? Summer Shack is perfect for a laid-back dinner! Famous for their lobster rolls they are a can’t-miss spot. After a long day of exploring this is the perfect place to show up and stuff yourself with all the seafood you could want. They are further out from downtown so you will probably want to drive but it just adds to the overall chill atmosphere! Location: 50 Dalton St, Boston
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