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Things to do in Boston when traveling by yourself!

Updated: Apr 8

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One of my favorite cities in the world, and I've been there several times because of the history, colleges, and food, Boston Massachusetts. I have visited as a solo traveler & with a friend and I feel that it is a great place for anyone that is a history buff. The Freedom Trail is a history buff's dream. Today we will explore, eat, and talk about all things to see and do if you are traveling by yourself in Boston near the Freedom Trail. Most are budget friendly or free along the Freedom Trail. (Except when you eat Italian in the North End, or a Lobster Roll near Quincey Market, they can be pricey).


Flying into Boston is great! It is neat to see through the airplane window, all the water, marshes, and tiny islands, I was not expecting it. Usually, it is cheaper to fly here and rent a car then most of the other cities in the Northeast. The only downside to the airport is finding the car rental spot. I was confused for a bit trying to find it and taking shuttles to go pick up my rental car.

Side note, fly into here if you are visiting southern Maine, New Hampshire, Vermont, or even Rhode Island. Trust me you will save some bucks by doing so. Plus, now there are cheap direct routes from any cities in the United States or beyond. If flying from Europe, I love the prices from TAP Airlines, and Norse Airlines. They are a great way to get into the country affordably. As for flying in the United States many airlines fly here as this is a large city, but one of the most affordable is Spirit Airlines. If you are from Charlotte North Carolina, click here for a blog I wrote on Spirit Airlines and their flight to Boston.

As for the solo travelers, I have always felt safe when walking the city. This is a great city for walking during the summer months, and I have never had any problems here. One of the best ways to see this city is to walk it. Take a walking tour with a group if you like, or walk it by yourself, it's up to you. There is even a self-guided tour with audio to help guide you to all the historical sites if you are walking by yourself. Check out the tours offered through a third-party vendor like Viator.

The start of the Freedom trail area

Beautiful houses and streets of Boston
Beautiful houses and streets of Boston

I just love walking in Boston, beautiful houses, the Freedom Trail, and several parks to choose from. All of this is free, and it covers basically 2 days or more depending how in depth you are or how fast you walk or if you get sidetracked by other places to see in the city. Most people can do more than me because of my bad knees and achy feet, but even though I am sore at the end of the day, it's worth it. One of the best things to do in Boston as a solo traveler is walking the Freedom Trail.

You are stepping back in time here to the American Revolution. Just think about how many historic figures walked these streets around 250 years ago. Samuel Adams, Paul Revere, Benjamin Franklin just to name a few.

Beacon Hill and the parks at the bottom of Beacon Hill

First Visit Beacon Hill, it is the best place to start a walk and you can continue on too many other places from right here. Grab a quick coffee or eat breakfast here. Just starting your walk around Beacon Hill, you will be overwhelmed by its beauty. Start behind the Massachusetts State House, or up Charles Street near Boston Common. The hill behind the State House is steep (but did you notice how impressive that building is with its gold dome). The brick streets, and the beautiful houses with flower boxes out front.

Words cannot describe how this neighborhood looks and feels. The Boston Brahmin, as it's known by, the architecture is Federal and Georgian in style and America's first professional Architect Charles Bulfinch is responsible for many of the homes in the area. Check out the Sunflower Castle on Mt Vernon Street, it is neat to see, and closer to 2 of my favorite eateries. There are several cute shops to check out too.

Random fact about picture above, The Massachusetts State House. In 1802 Paul Revere covered the dome with Bronze. Also, free guided tours inside the building happen every weekday from 10:30 to 3:30 at every half hour mark of the hour. That's 6 tours a day.

Food at Beacon Hill

  • The Paramount- (Pancakes, Bacon egg and Cheese sandwich, or Avocado Sunrise) most items are under $15 bucks and service is fast so you can get moving on with your day. Located on Charles Street. It may be closer for you to get to from Boston Common or Public Garden

  • Tate Bakery and Cafe- (Lamb Hash, or Croissant Sandwich for breakfast, Prosciutto and Fig Panini for lunch), also on Charles Street but farther on into the Beacon Hill area. Great fast service and the bakery part is amazing too.

  • If you are farther up near Cambridge Street, check out B Nutritious, Flour Bakery, The Tip Tap Room, or for lunch Anna's Taqueria.

As you come back down the hill and pass the State Building. you see a large park across the street on the right. Boston Common is massive, with a pond called the Frog Pond, a visitor center, Carousel, bandstand, and plenty of statues to see, as you walk around. Depending on when you are in Boston you can see live performances in the park too.

While in the park you can find some food, Earl of Sandwich is a great cheap place to eat, sandwiches, wraps, soups, salads and desserts. My favorites are The Original 1762 and the Buffalo Chicken Wrap.

Now before you cross the street to the park or after just as long as you stay near Beacon Street, 4 Blocks down Beacon Street, on the right is a TV landmark. the outside shot of the show Cheers. You know what I am talking about, the entrance to the Cheers Bar with the Stairs going down into the bar. (Neat huh!) Stop in this bar and rest your legs and grab a quick drink or bite to eat if you would like. But if you do, try the Sam Adams Brick Red, it is only sold in Boston and money made from the sale goes to the local community. Wish I could get it where I live.

Skyline view from The Public Gardens
Skyline view from The Public Gardens

After you leave Cheers, cross the street to the park, and you will see another park right beside Boston Common, Called the Boston Public Garden. There is a huge pond, statues (one of George Washington) and plenty of places to stop and look around. This is the park where Robin WIlliams and Matt Damon sat on a bench and talked in Good Will Hunting. You can easily find the bench because there are always flowers laid on the bench because of Robin Williams' death a few years ago. Bring some flowers if you like. This is the perfect place to enjoy some people watching and watch the squirrels play.

Also, side note, at the corner of Boylston Street and Washington Street is Chinatown, take a left out of the southern end of Boston Common on the Boylston and Washington is 2 blocks away.

Whichever Park you are in, Boston Common, or the Public Gardens, make your way to Boylston Street and turn left on Tremont. or back to Beacon Street, turn right on Park, then left on Tremont. Tremont is where you want to be at the edge of Boston Commons. At this point you have already seen 3 spots on the Freedom Trail. The State Building, Boston Common, and the Statue at the corner called Robert Gould Shaw and the 54th. (The first all-Volunteer African American Unit in the US Army). This is a good place to start the rest of the Freedom Trail, at the far-left edge of Boston Common on Tremont Street. Next stop is Park Street Church, and you can see it from where you are standing. This is where abolitionist William Lloyd Garrison made his first anti-slavery speech in 1818.

If you are wanting to spend more time near this area and forget about walking the rest of the freedom trail you can, there are plenty of places to see and visit. For example, the Boston Public Library is just a few blocks west of the Boston Public Garden on Boylston Street. Also, the Gibson House Museum is one block west of the Public Garden on Beacon Street. It is a great guided tour of an old Victorian home. Check out their website to book a tour in advance of your visit. If you hear the word “Back Bay” this section of Boston is also referred to as Back Bay East.

Aluity Insurance sells Allianz Travel Insurance
Aluity Insurance sells Allianz Travel Insurance

The Granary and Beyond

Now we continue on the Freedom Trail, the Park Street Church on Tremont Street, right beside the church is the famous Granary Burying Ground. Several famous people from the Revolutionary war era are buried here and even Mother Goose. Check out the graves of Paul Revere, Samuel Adams, John Hancock, and the parents and siblings of Benjamin Franklin. Continue on up Tremont Street and take a left on School Street (just a couple blocks away). On the corner is Kings Chapel, open daily to look around. The first woman to step off the Mayflower is buried in the graveyard in the back of the church, Mary Chilton. As you travel down School Street stop at the Boston Latin School (the oldest school in America, 1655) and see the Statue of Benjamin Franklin. Just a few steps down from there is the statue of Josiah Quincy III. (it's at the corner of City Hall Avenue. Turn left for a second to see Old City Hall, then turn back to School Street and continue on to the Old Corner Bookstore.

Across the street from the bookstore is the Boston Irish Famine Memorial and Reader Park check it out since it is on your way, and from there you can see the Old South Meeting House on Washington Street, The Old South Meeting House is where The Sons of Liberty walked out in 1773 and started the Boston Tea Party.

As a side note here, since I am talking about the real Old South Meeting House and the Boston Tea Party, there is a great replica on the Wharf. It is called the Boston Tea Party Ships and Museum. This is where they do reenactments, and you can see replicas of the ships that would have been in the harbor during the Boston Tea Party. It is not located on the Freedom Trail but is about a 13-minute walk from the real Old South Meeting House, and through downtown Boston. If you are interested but don't want to walk, take a taxi or Uber. You are already doing a lot of walking on the Freedom Trail so save those legs when you can.

The Old State House and Beyond

Boston- near Faneuil Hall and Old North Church
Boston- near Faneuil Hall and Old North Church

Walk north on Washington Street, if you need a stop there are a few places to stop along the way for food or drink or just take a rest. One of my favorites is right here on Washington Street. Falafel King, I just love it. Another one that is as good as the name says it is, B Good. You can stop at Starbucks, Dunkin or my favorite is The Well Coffee Shop for a quick coffee if that is all you need. (Sidenote take a quick trip down Water Street to see the Winthrop Building, then turn around and head back. Continue on Washington Street and take a right on the trail in front of the Old State House, (if you made it to State Street you went too far, but you are right beside the Old State House). Random Fact, did you know that from the balcony on this building in 1776 the Declaration of Independence was read out loud for the first time, causing a riot.

Continue onto Devonshire Street and take a left and you will come to the Boston Massacre site. Cross Devonshire Street and Congress Street at the same time and stop to look at the marker of John Winthrop's First House Site. Now cross State Street and walk north on the right side of Congress Street. On the same block you will see the Samuel Adams statue, Sam Adams Downtown Taphouse is where you want to turn right to continue the Freedom Trail.

Faneuil Hall and Beyond

Old State House
Old State House

If you miss the path like I did, just follow Congress Street to North Street (it's right there) and you can get anywhere from there. Faneuil Hall and Quincy Market is a huge area. Many little side streets to look at all the little stores close by. You can go inside and shop, and there are also tons of shops and places to eat all around this area. You can spend hours here just shopping, eating, and people watching.

By the time I got here it was late afternoon and there was music, vendors, and street performers. Look for the grasshopper on top of Faneuil Hall, the man that made it is buried in Copp's Hill Burying Ground (part of the Freedom Trail, just on down the trail).

The New England Holocaust Memorial and Union Oyster House are close by, go check them out as well. The Union Oyster House is the oldest Restaurant in the United States. There are several restaurants nearby that serve lobster rolls too, and if that sounds good, then I suggest grabbing one. Every time I am in Boston I have to have a lobster roll. Check out the Quincy Market while you are here in this area for some shopping and good food.  Nearby is the Armenian Heritage Park, The Greenway Carousel, and the Christopher Columbus Waterfront Park if you are looking for a place to sit and enjoy some people watching and flowers blooming in the summer.

If you decide that is enough of the Freedom trail for now and want to explore the Harbor this is the perfect place to start. The New England Aquarium is just a 6-minute walk from Faneuil Hall Marketplace. The aquarium is wonderful, and I guarantee you will enjoy watching the sea lions, penguins, and fish swimming in the tanks. The aquarium is at Boston Harbor, where you can enjoy a long walk on the Harbor Walk. The Harbor Walk will take all around the city’s harbors, South Boston and even further. I did not visit the aquarium and Harbor walk on the same day I did the Freedom Trail but could see how you can easily add this to a section of the Freedom Trail walk since it is so close by. There is just no way you can walk the entire harbor walk in one day, it is over 40 miles. If you are interested in reading more on this check out this blog I wrote on the Harbor Walk, and Fenway Park.

Paul Revere Statue and Beyond

After leaving the Faneuil area you will head a good bit north, it will be a bit of a walk from here. Paul Revere Statue, Paul Revere House, and Old North Church are what's next to see and you will be in the Italian area of Boston. All the Pasta, Pizza, and Cannoli's a girl can dream of are in this area. Travel up North Street, and you will pass through a beautiful garden called The Rose Kennedy Greenway and Wildflower Meadow. First you come to Paul Revere House, it's beside Rachel Revere Square and North Square Park. You can tour the house for $5.

Next take a left on Prince St, then a right on Hanover Street and you will come to the Paul Revere Statue on the left, but you will pass St Leonardo's Peace Garden on the way. At the Paul Revere Statue, walk through the Paul Revere Mall and you will come out at Old North Church, and the Saint Fransis of Assisi Garden.

After leaving the Old North Church, traveling down the Freedom Trail Road is Copp's Hill Burying Ground. It's not too far away to see. Many early Americans are buried here along with many Puritans. Robert Newman, who hung the lanterns in the Old North Church as a signal for Paul Revere to do his ride, is buried here. On one side of the Freedom Trail Road here is the Skinny House, check it out, it sure is skinny.

If you are willing to walk one block north towards the wharf from Copp’s Hill, you will be on Commercial Street and there is a park located here. On the edge of this park is a sign for the memorial of the Great Molasses Flood. This was a tragic and unusual flood that happened in 1919. Sticky Molasses flooded the area after a tank exploded. Can you imagine a 40-foot wave of Molasses coming towards you. I sure can't. Many people were injured and over 20 people died. It is a small plaque but interesting to see if you are a history fan like me.

After all the walking I had done at this point I gave up on the tour, I couldn't do anymore of the Freedom Trail in one day. Plus, I knew if I continued on, I would miss eating in Little Italy. There are still 2 more stops that are quite a large walk away, so I quit and got dinner and called it a day. I started fresh the next day and finished the trail. With Beacon Hill, Boston Common, and Public Garden before the trail, it was just too much to see in one day.

My favorite Italian restaurants in the North area where you are near Old North Church or Paul Revere House are located. (Heads up most are a little bit pricey up here, $20 to $30 a plate, some even $50 to $100).

Carmel Limo

Food in Little Italy near the Old North Church

Yummy pasta
Yummy pasta

*Lucia Ristorante- (Calamari Pirata). It's a little Pricey, but amazing. Located directly Across from Paul Revere Statue on Harris Street.

*Dino's Cafe-(Lobster Ravioli) Most menu items are under $20 Located on Salem Street,,,,, after you leave Old North Church walkout the back to Salem Street and walk south 3 blocks.

*Assiago- (Amalfi market Price) that tells you a lot about the prices here, but I love lobster. It is located on Prince Street near Leonardo's Peace Garden.

*Mike's Pastry- (Cannoli), The best Cannoli in Boston and desserts are always cheaper than most dinners anyway. Located on Hanover Street, just South of St Leonardo's Garden, and they have been open since 1946. Long enough to have perfected the Cannoli in my opinion.

*Rina's Pizzeria and Cafe- (Chicken Parm Ziti, Pizza by the slice, and Nutella Pizza) North on Hanover Street, on the right before you get to Paul Revere Statue. This is on the Freedom Trail. As you can tell I have been there often. It's Cheap.

Last part of Freedom Trail

I took an Uber to the USS Constitution the next day because of the distance between Copp's Hill Burying Ground, to the USS Constitution. is 1.2 miles and I knew I still had lots to see and walk to that day. Also, for those of you that hate bridges, you would have to walk over the North Washington Street Bridge which is over water. The USS Constitution is the oldest warship in US history, and you can tour for free. And the USS Constitution Museum is located there also, you can enter for a donation ($5 to $10) to learn more about the ship's history.

The last stop of the Freedom Trail Bunker Hill Monument, a tribute to the Battle of Bunker Hill, and only about a 5-minute walk away. Follow the signs that help you pass over the road that is a toll road to Tremont Street that takes you to Monument Square. Bunker Hill Monument was built in 1843, where the famous Bunker Hill Battle took place. The Bunker Hill Museum is located at the base, and it is free.


As a solo traveler you can explore this historic city by yourself and visit the same places that groups explore, but the best thing about it is you get to decide how long you can stay and explore some of your favorite spots. So, take a walk-through Boston, history buffs you will not be disappointed, Boston offers so much more to see and do than what this blog can hold, and I guarantee solo travelers will enjoy many other sections of the city that I have not touched on. So, get out there, explore the museums, and all the spots along the Freedom Trail, plus more. This is your vacation and Boston is the perfect place for a solo traveler.

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