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  • Writer's pictureChristine

Boston Travel Tips

A view of the Boston city skyline from our hotel room in Cambridge.

We have lived in the Philadelphia area for almost 20 years now. While we go up to New York City a couple of times per year, we have never been further north into the New England area. That includes Boston. We talked about going there several times, but never made it work.

So, when we decided to attend the Levitate Music Festival in Marshfield, MA, I got the idea that we could add a few days to our trip and spend them in Boston before heading down for the festival. After spending some time there, I wish we had made the effort to visit before. This trip was our first to the area, but definitely not our last!

Here is some information and tips that I gathered during our recent visit to Boston.


Boston is both the capital and the largest city in the state of Massachusetts. With a population of almost 675,000, it is the largest city in New England. The greater Boston area has a population of around 4.8 million people, which makes it the 10th largest metropolitan area in the country.

While the Boston area has a large population, the city itself is quite manageable. I found it very easy to get places, the downtown area was very walkable, and it was very manageable to see all the main sites in a couple of days.

Tip #1 – Getting Around: Boston is a typical “big city” on the east coast, and driving anywhere (particularly in the downtown area), can be a challenge. In addition, parking in downtown is scarce and expensive. You can easily get around Boston without a car. While we didn’t use it, their mass transit system (the subway is known as the “T”) is available. We found it easiest to just get an Uber anytime we wanted to go somewhere that was too long to walk.

Tip #2 – Weather: We were in Boston over the 4th of July holiday, and the weather was beautiful. It was a few degrees cooler than we had it in Philadelphia, and definitely less humid. However, in speaking to some of our friends that are locals, the weather is brutal in winter. Boston gets hit often with a lot of snow. In fact, when a Nor’easter hits the coast, Boston can get several feet of snow dumped on them. I would suggest not visiting in winter unless you bring a shovel and winter boots!


When we did the drive from Philly to Boston, we discovered that it wasn’t as bad as we thought it would be. The trip took us about 5 ½ hours and was quite scenic.

Tip #3 – Driving to Boston: If you are driving from Philly to Boston, plan the timing of your trip accordingly. You will have to pass through NYC to get there and cross the George Washington Bridge, which can be a traffic nightmare. We drove up to Boston on July 3rd, and I’m guessing a lot of people were not working and taking an extended holiday, so traffic was light.  We still hit some traffic on the bridge.

Boston is also linked to the Northeast Corridor on Amtrak, so getting a train between any of the major east coast cities – Boston/New York/Philadelphia/Baltimore/DC – is easy and they run frequently. Taking the train will help you avoid traffic, as well as eliminate having a car with you to worry about.

If you are coming from further away, Logan Airport is Boston’s main airport. It is located in East Boston. There is also a cruise ship terminal in Boston, so there are a number of cruise lines that make stops there.

Tip #4 – Getting Around in Boston: For several reasons, if you can avoid having a car in Boston, that’s a good plan. If you are flying in or coming in by train and will be mostly in the center of Boston, skip renting a car and just take public transportation, a taxi or an Uber. Boston is not laid out on a grid, so not only is traffic an issue, but it is not very easy to figure directions out.


Like any major metropolitan area, hotels in the downtown area of Boston can be quite expensive. While they are convenient to stay in, the cost might break the bank on your travel budget. Depending on your need to be in the city center, you may want to consider staying outside of the city. The hotel rates definitely go down the further away from the city center you are located.

Tip #5 – Consider Staying in Cambridge: If you want the convenience of being close to the city center area, but don’t want to pay the higher hotel rates, consider staying in Cambridge. Located just across the Charles River, you can walk, take a short cab/Uber ride, or take public transportation from Cambridge into Boston quite easily. We stayed at the Courtyard Boston/Cambridge ( and I was very happy with the hotel and the location. It’s right on the Charles River, so I was able to get up every morning and run/walk the trail along the river. There are a lot of things to do in Cambridge, itself. It was also very easy to get anywhere in Boston we needed to go.

Tip #6 – Check the Fine Print About Parking: Because parking is a premium in both Boston and Cambridge, almost every hotel will charge you extra to park your car – even if you are a guest at the hotel. When I was searching hotels in Cambridge, every hotel charged $40/day for parking on top of the hotel rate. The parking charge is not always noted clearly on the hotel’s website or if you are booking through a third party site, so be sure to do your research and call the hotel if you aren’t sure. Sometimes a deal is not as good as it appears when you find out there is an extra daily charge to park your car.

As mentioned above, we found Uber to be our best option for getting around the city. We parked our car at the hotel when we arrived, and didn’t move it again until we were leaving. Uber drivers are plentiful in the area. We never had to wait longer than 5 minutes for a car, no matter where we were in the city.  The costs for all of our Uber rides was very reasonable. There are also plenty of taxis around in the city center area.


Boston is possibly best well known for its Freedom Trail, which includes several sites that played a crucial role in the American Revolution, including the site of the Boston Massacre, the Boston Tea Party, the Siege of Boston and Paul Revere’s midnight run. The Freedom Trail is a 2.5 mile route through the city, that will take you to all of the key historic sites. You can start the Freedom Trail at Boston Common, and follow it all the way to the USS Constitution. There is also a visitor’s center at Faneuil Hall. Check out for more information.

One of the sites on the Freedom Trail. In front of this building is where the Boston Massacre occurred.

Tip #7 – Visiting the Freedom Trail: You can pay for a ticket and join one of the public walking tours that cover the Freedom Trail. If you book online, tickets are $12 for adults, $10 for seniors/students and $6.50 for kids. However, if you aren’t looking to get deep into the history and just want to see the sites, it’s easy to follow the trail on your own. Start at either Boston Common or the USS Constitution and look for the red brick path in the sidewalk. That path follows the trail, and will take you to each location. You can also download the app for $4.99, which will allow you to still get all of the information about the various sites, but do the trail at your own pace.

Tip #8 – Visiting Faneuil Hall: Faneuil Hall is a large market that contains lots of different shops and places to eat (think of a mall food court on a larger scale). If you decide to go there, be aware that it is very “touristy”. Depending on when you go, it can be very crowded. Additionally, food there is expensive. My husband really wanted to have a lobster roll, and all the prices we were seeing were around $25 for one.

Faneuil Hall is one of the stops on the Freedom Trail, and has lots of shops and restaurants.

If you are a baseball fan, be sure to book a tour of Fenway Park. You can buy tickets on-line at The tour lasts a little over an hour, and takes you all through the stadium. You get to sit on the oldest seats in any major league baseball stadium, sit on top of the Green Monster, and even go inside the press box. There is also a very cool display at the end of the tour with lots of baseball memorabilia. Tickets are $20 for adults and $14 for kids. It’s definitely worth checking out.

One of the views of Fenway Park you will have on the tour.

You get to go behind the scenes at Fenway Park on the tour, including into the visitor’s locker room.

Tip #9 – Visiting Fenway Park: If you have a tight schedule, be sure to buy your tickets online in advance and book a specific time. They also offer tours on game days, but our tour guide told us that those tours sell out fast, so plan ahead if you are going to a game and it’s something you want to see.

If you like to run/walk/bike, check out the Charles River. It divides Boston from Cambridge, and both sides have a very nice paved path that runs right along the river. I ran the path every morning while I was there, and it was always busy with people.

The trail that runs along the Charles River on the Cambridge side.

No stop to Boston would be complete without visiting the bar that served as the inspiration for the popular television show “Cheers”. Located in the Beacon Hill neighborhood, the bar is actually called the Bull & Finch Pub. However, you can have a beer in a “Cheers” branded mug, and shop for all of your “Cheers” gear in their gift shop.

Tip #10 – The T.V. Set Bar: When you go in the bar, signs will direct you up to the top floor to see the television set bar. Honestly, other than having some lighting installed to make it look a little like a t.v. set, I’m not sure why they call it that. It doesn’t look anything like the bar on the show. Unless you want to see the gift shop (which is right next to that bar), skip the steps and just have a quick beer at the lower bar.

On the Cambridge side of the river, be sure to check out the campuses of Harvard and MIT. The Harvard Square area has lots of shops, bars and restaurants right near the Harvard campus. Kendall Square is a similar area near MIT’s campus.

One of the buildings on MIT’s campus.

One of the buildings on Harvard’s campus.


Boston is known for its beer, and we visited a lot of breweries while we were there. Some of my favorites are as follows:

Aeronaut Brewing Company: This brewery is located in Somerville, which is a short drive outside of Cambridge. Not only is their beer excellent, but their facility is worth visiting. We went on a Thursday night, and they had a really great jazz trio playing live music. While they don’t serve food, they had a food vendor there who you could purchase food from. There was also lots of space with beer hall style tables set up, where people were talking, playing board games, etc. They also had a commercial kitchen area, where it looked like they did cooking classes. Worth checking out for the beer and the music. You can get more information at

Lord Hobo: We went to their beer bar in Cambridge. This is not somewhere that tourists would typically go. The bar is a little dark and the bartenders are “interesting”. But, their beer was great and we got great service. While we didn’t try the food, their menu looked amazing as well. This is a place I would hang out at late at night, drink beer, and hang with the locals. Check out their information at

Trillium Brewing Company: This was probably some of the best beer we had on the trip. They have a retail only store on Congress Street in Boston. They also have a beer garden in Boston at Atlantic Avenue and High Street, that is only open in the summer. Their taproom is located in Canton, which is a 30-40 minute drive outside the Boston city limits. If you can’t make it out to the taproom, try the beer garden to at least get a taste of their beers. For more information, go to

Night Shift Brewing: Again, you have to travel a bit outside of the city limits, but the beer here is worth the trip. Located in Everett, Night Shift has a large taproom as well as an outdoor patio space. They feature food trucks, as well as different events including live music. Check their website at for more information.

Mead Hall: While this place doesn’t make their own beer, you can find almost any beer you want here. They have 100 beers on tap, including lots of local beers. The bartender was very knowledgeable and helped us make our selections. Located in Cambridge, it’s worth a stop. Check them out at

Just some of the beer taps at Mead Hall.

We also had some great food while we were there. Here are a few of my suggestions:

Orinoco: This was definitely my favorite restaurant in the Boston area. We visited the location in Harvard Square in Cambridge. It’s a little tough to find. There is a very small sign on the street, and the entrance to the restaurant is down a little alley. They serve South American food that is all fresh and is absolutely delicious! The service was great and the prices were very reasonable. This is definitely a find if you are looking to be a bit more adventurous, and try something local and off the beaten path. Menus and information on their other locations can be found on their website at

Mike’s Pastry: If you have a sweet tooth, you have to visit Mike’s Pastry. Known mostly for their cannoli, my husband also had a piece of Boston cream pie that he said was amazing. They have three locations – Boston, Cambridge and Somerville. The one in Boston can get pretty busy, so if you are staying in Cambridge and are in the Harvard Square area, stop in there. There was no wait when we walked in. You can eat your cannoli there, or they will box them up for you to take home. You can see all of the different goodies they make on their website at

All the different types of cannoli they have at Mike’s Pastry.

Cambridge Brewing Co.: If you want to combine good food and good beer, check out Cambridge Brewing Co. Located in the Kendall Square area near MIT, they have some very good beers and a great menu. We ordered a couple of appetizers, and were so full that we weren’t able to eat entrees. I will put this place on my list when I return, as their pizzas looked delicious! They have a great outdoor patio space, and were dog friendly outside. Check out their menu at

Have questions about Boston and the surrounding area?  Have you been there and I missed one of your favorite places?  Comment below or e-mail me at 

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