I have officially fallen in love with Boston. My husband and I were able to spend almost a full week in the city and I have compiled this list of the best place to stay, the best place to eat, and the best things to do in Boston. I cannot wait to explore this city again some day!
First and foremost find a lovely place to stay. We hit the jackpot when we stayed at The Westin Boston Waterfront. My husband was attending his work conference there and we could not have asked for a lovelier place to lay our head at night.
The hotel offers all of the amenities you would imagine of a fine hotel, but it also offers extremely unique features as well. You can take a run around the city every weekday with members of the staff to get a unique and beautiful view of the Boston harbor. You can also rent the items you would need for this run for only $5 so your running shoes don’t take up your whole suitcase. Another fun feature was if you decide to skip a day of having your room cleaned up in attempt to be more earth friendly you can received $5 a day from their convenience store located right in the hotel.
I am pretty sure we chose the most beautiful time to be in Boston, and the city did not disappoint with it’s clear blue skies and charming sail boats. We loved being able to see the view of the harbor, it was really breath taking.
Another unique feature that you would not expect is their in house restaurant, M.J. O’Connors, has the best clam chowder we could find. I kid you not, my husband ate clam chowder at 5 different locations, including the well know location of “Legal Seafood” and he swears by O’Connor’s chowder. Check it out!
Any time I travel anywhere I will check with the concierge of the hotel for their recommendations for local attractions. I will also talk to the servers of our restaurants. “Tell me the secret places of the city. Where would you go first? Where would you eat? If you had a day off to explore the city what would you do?”
Explore Quincy Market
Our waitress from O’Connors suggested that I go to Quincy market on the the first day as I was exploring the city on my own and would be getting to the Freedom Trail and other historical monuments later with Paul when he would be out of his conference. Quincy market was the perfect place to start! Night or day there is almost always something going on! You will find live performers, delicious smoothies, souvenirs, chowder, restaurants galore, the original “Cheers” restaurant, and the Faneuil Hall Marketplace.
Faneuil Hall is the original place of trade in early america or the first “marketplace” of goods. This is a historical building and my best find here was access to their free walking tours of the Freedom Trail. The tickets are available 30 minutes before they begin and are first come first serve and completely free. There is a tour heading south and another tour heading north on the freedom trail so you will want to make time to do both. Each tour lasts about 60-80 minutes. I prefer walking tours with real people because you can ask questions and really get a feel for the passion they have for the history of the city. You can find more detailed information HERE. Or if you decide you want to look at the tour schedule when you get there just ask someone at the information desk located on the main floor of the building.
Walk the Freedom Trail
Whether you are heading down the south end or the north end of the walking trail you will be overcome with the beauty and history of Boston. One fun thing that I would suggest doing is watching a TV series that will help bring the story to life for you before you see the actual historical sites. Two of my favorites are John Adams and Turn:Washington Spies.
You will learn the true story of what happened to Paul Revere that fateful night while on your tour and why the well known poem is somewhat false. You will be able to step foot into the beautiful church where a lantern was hung, “one if by land and two if by sea.” You will see the site of the Boston tea party and step foot in the buildings where historical arguments raged on about who was right and who was wrong.
We loved seeing Paul Revere’s house and admiring the beauty of the trees that have seen a lot through the years. Take a stop into Captain Jackson’s shop to try a sample of homemade hot chocolate made spicy just the way the colonists liked it.
If you get the chance to speak with those who work at these historical sites make sure you do! I struck up conversation with a few and was surprised when they told me that so many file in and out, never stopping to ask any questions. I learned some very interesting facts that I am sure most don’t even think to ask.
Site of Boston Massacre.
Take a Duck Tour
If you only have a few short hours to spend in the city whether you are stopping through on a cruise ship or only have a short time, I would suggest you try a duck tour! These tours take you through the city and on to the water which makes for quite the adventure.
You could opt to do a hop on hop off tour which is a fun way to see the city if you have more time and you are not traveling with a baby.
We brought the car seat right onto the boat. There are no seat belts, but it made it a lot more comfortable for all of us. It was $10 to bring an infant, but that does reserve a special spot just for them which is nice.
Each travel guide on the duck tour has their own shtick and it can be a lot of fun. We had a hair-dressing pirate and he was very fun. He even let all of the kids on the boat take a turn at the wheel while on the water.
Eat a cannoli at Modern Pastry
You are most likely to hear about Mike’s pastry as it is a tourist hot spot. If you ask the locals where they go, they will tell you to make a stop at Modern Pastry. Oh my stars, this place is incredible.
We may or may not have tried three different desserts.
Visit the Museum of Science
If you have some time to spare you will want to come and get lost in the science museum. It is absolutely HUGE. I knew there was no possible way I could see all of it in the time I had and was advised to go to the Hall of Human science.
There are individualized tests that you can scan in with a wrist band to walk through your differences as a human. Think freeze time, arch in your foot, allergies, appetite, site, face recognition and more. You can then look at all of your data and see how it stacks up with other visitors that come to the museum.
My kids would have LOVED this if they were with me, but even Paul and I enjoyed the test too. You can then compare all of your data online by accessing your information through their website and your wrist band.
And if you are looking for a spot to nurse a baby this has got to be the nicest seat in the city…
Eat Italian food in the North End
There are so many incredible places in the North End to eat and I can’t tell you the top 10, but I can tell you that Antico Forno is the bees knees. We ate here twice and ordered their chicken parmesean both times! We also tried crab ravioli and their brick oven pizza. You cannot go wrong.
Don’t be surprised if your waiter’s first language is Italian and doesn’t speak English very well. This is the real deal and it is incredible.
Eat fresh sea food
Everyone told us to go to Legal Seafood. Everyone. I don’t know if we were there on an off night or what, but we did not love our food. I am guessing this was a fluke because even the locals said they love it…but the price tag was high and I did not love it.
With that being said, all of the sea food we ate every where else was lovely. One of our favorites was clam chowder from clam chowda in quincy market.
Go on a ghost tour
So this is completely non-traditional, but my husband and I love to go on ghost tours when we visit other cities. You get a completely different view of the city at night and it is also a great history lesson believe it or not.
On this history tour we talked about the witch trials that began in Boston preceding the Salem witch trials. We also covered prominent figures in Boston society when it was first being built, what happened to children who died from communicable diseases when they came over from other countries and got sick on the boats, a book made out of skin still kept in the local library, and legends of the oldest hotel in Boston which is still in operation.
Notice this picture is all crazy?! That’s what happens when you’re on a ghost tour and taking a picture! We loved our tour guide who has been on ghost hunters and a well respected ghost tour guide. You can check it out here. Use code HBWEB2016 for $3 off.
Visit the Aquarium
I was able to partner with the CityPass which is an awesome and affordable way to see the city. One of the venues on the pass is a ticket to the Aquarium. There were gorgeous fish, sting rays, otters, seals, and penguins. This would be a great place to spend the day.
Here are options available in the CityPass:
- Boston Harbor Cruises: One Long Wharf; ticket booth and look for CityPASS sign.
- New England Aquarium: Central Wharf off of Atlantic Ave.; take CityPASS/Express Line to ticket window #6
- Museum of Fine Arts, Boston: 465 Huntington Ave.; ticket desk of any entrance
- Museum of Science: Science Park on the Charles River; main box office
- Skywalk Observatory: Prudential Center at 800 Boylston St.; main level kiosk desk located in the mall or the 50th floor Skywalk front desk
Spend time at the Boston Harbor
One of my favorite afternoons was spent hanging out by the harbor. There were street performers, runners, people walking their dogs, and just enjoying the open air. It was lovely.
Take a ferry to Salem
I’ve always been intrigued by the Salem witch trials and with an hour long ferry ride you can take a round trip for $40. We were very lucky and just happened to catch the most beautiful sunset ever.
This museum was interesting. It basically does a quick depiction of what happened in the Salem witch trials and walks you through what led up to the hysteria in town. It is an old museum, but it gets the job done. Unfortunately we missed out on other museums that day because they closed early.
The memorials for the women lost in the trials can be found in the local cemetery. Their bodies are not here because they were buried by family in a secret place to keep their bodies safe.
I have to admit that one of my absolute favorite parts of coming to Salem was meeting this cat being walked by his faithful owner. He was a rescue pet and they made quite the pair!
Go to a Red Sox game
Now for the best part (in my husband’s humble opinion.) We attended a Red Sox game! A little secret you may not be aware of is the fact that you can get a tour of Fenway Park the day of the game and watch the team in batting practice. Keep in mind that you need to purchase these special tickets the day of the game and they are first come first serve. The tour begins at 4:00. We picked up our tickets that morning on our way to our Harvard tour and it worked out just right.
If you are going to the game with a baby…you are crazy. Okay, just a little. The seats are very close together and it can be REALLY loud. I’ll admit I underestimated the noise level just a bit.
Thankfully we were surrounded by nice people who liked us and our baby, but if you can leave the baby with a sitter that would probably be the best scenario.
There is a sports shop at quincy market made just for women, that is where I picked up my Red Sox shirt if you happen to be in the market for one.
Eat fresh ice cream from LuLu’s
Oh LuLu’s! Fresh homemade ice cream that will knock your socks off. This was the perfect treat in the north end. I love pastries and cake, but I really adore ice cream!
This was such a neat experience to see Harvard campus on a student lead tour. We were shown all of the historical buildings, and famous people who had lived there. We were also told what a day in the life of a Harvard student is like, and some funny stories about the students and alumni who have gone to school here.
Apparently there are some very strange things that happen to this statue as initiation for students that go to Harvard. The toe is considered lucky, but most of the students would advise you not to touch it.
We ate at Grendel’s right outside of campus. It was the perfect little stop for a sandwich and conversation.
Go on a harbor cruise
Another opportunity with the city go pass is to go on a harbor cruise. Learn all about the city from the shoreline. You can also go on a whale watching cruise or book a sailing trip!
Enjoy the energy of the city
There is so much to see! I hope you have enjoyed these ideas. There is something going on in the city almost always, so get out and enjoy it!
If you are staying at the Westin, make sure to talk with the concierge as they have the kindest staff and will point you in the right direction and help you get around town!
I have put this list of the best things to do with the idea that you may or may not be traveling with a baby. If you are traveling with a baby, here are a few quick tips that will help you with getting around the city.
Bring a stroller that will fold well but still allow for you to bring along the car seat. I say this because you may want to take Uber in and out of the city and will feel safest if you have a car seat to travel with your baby in the plane or the car. I cannot say enough good things about the new Britax 2017.
This car seat can be changed 12 different ways and also fold up quickly. You can add two seats and a kick stand to be able to accommodate three kids! I will be sharing more photos of how I will be using this stroller in the future as I have more kids to push around.
I hope you enjoyed this guide! Please let me know if you have any questions!
This post contains affiliate links. We may receive a small commission if purchases are made following our links.
A big thank you to Britax and The Westin Boston Waterfront for partnering with me on my adventures.