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Recently, one of my best friends from college embarked on a spontaneous trip to Boston with me. Initially, I was hesitant to visit the east coast during February because of the extremely cold weather (30-40F); however, I’m glad I agreed to go because it was an unbelievable experience. Unlike California, I had the chance to first hand see “winter.” Boston, which is a lively city with historical buildings from the early 1600’s, is characterized by its stunning cobblestone floors, scrumptious lobster rolls, and new england clam chowder. All of my favorite things!

I enjoyed my time in Boston so much that I had to create a blog post and share all the best things to see and eat. With this Ultimate 3 Day Boston Itinerary, I will help you figure out the best time to visit Boston, where to stay, activities to do, sites to see, and restaurants to eat at. With that said, let’s begin!

Boston Weather Throughout the Year

boston weather
Photo Credit: Holiday Weather

From the graph above, it’s obvious that Boston experiences all 4 seasons throughout the year. Make sure to decide beforehand which season you want to visit Boston, as the weather varies dramatically from month to month. The summers can be sweltering hot, whereas the winters can be chilly and snowy.

What to Wear in Boston

beacon hill

The weather often dictates what clothing you should wear. During the days I was in Boston, the temperature ranged from 37F – 44F. Combined with the frosty arctic wind, I (aka the California girl) was freezing! Here is what I suggest you wear if you happen to visit Boston in the winter (Dec-March):

-long sleeve thermals

-thermal leggings to wear under your pants

-thick, warm jacket




-thick socks

-closed toed shoes (sneakers work)

-long pants

It’s not uncommon to see Bostonians and tourists wearing at least 4 layers to survive the cold winters.


Where to Stay

Photo Credit: Hotel Tonight

I highly recommend you stay in downtown Boston. Although hotel rooms are typically more expensive, you will be within walking distance to tons of restaurants, bars, and major attractions.

Hilton Downtown – Faneuil Hall Boston Hotel 

We stayed at this gorgeous 4 star hotel situated in the financial district and just a block away from the waterfront and Faneuil Hall. The room was slightly small, as most hotels in big cities are, but it was luxurious complete with all the main amenities. The room had a very comfortable king size bed, large bathroom, full size body mirror, a table, chair, TV, fridge, and two nightstands with chargers.

If you’d rather stay at a different hotel, try to find one located close to the major attractions including Quincy Hall, Seaport, Boston Commons, Freedom Trail, and Beacon Hill. You could probably spend a few days in downtown and not see everything it has to offer.

Getting Around Boston

Photo Credit: Hotel Guides

You’re probably thinking “Should I rent car? Can I walk to certain places?”

First of all, bring some comfortable shoes because you will be walking A LOT. Traffic in Boston is horrendous, especially during rush hour. With all the pedestrians walking around the city, it’s almost always faster walking to places than driving.

Parking in Boston is a real pain. Valet parking at hotels costs on average $50 per day. Trying to find parking at a restaurant or attraction? Mmm, it will be almost impossible. If possible, avoid renting a car because it is not worth the time driving in traffic and struggling to find parking. Instead, I suggest walking to all the major sites and lyfting/ubering to the farther attractions.

Boston Itinerary: Day 1

Faneuil Hall


 On Day 1, I suggest checking out the Freedom Trail, which starts in the center of downtown Boston, and has a red brick line leading visitors all around town to all 16 historic sites. Since it may be difficult visiting all 16 sites, you can split your trip into 2 days or pick and choose your must see attractions.

1.Start at Faneuil Hall

Faneuil Hall is the starting point for the Freedom Trail as it has a visitor center with readily available maps of the freedom trail and brochures for each specific site.

In addition to the visitor center, this hall also has small souvenir shops full of handmade goods and an authentic printing station where you can see how Bostonians printed paper back in the 1600s.

Lastly, it’s highly likely you will see at least one street performer. When we were there, we saw a drummer using plastic bins and tin bowls as a drum set. He was playing outside of Faneuil Hall when we got there around 11am and at 6pm that same day!


faneuil hall printing

2.Boston Massacre Site

In March 1770, the British army ruthlessly fired on an unarmed group of civilians, killing 5 people. This event broke out because of rising tensions from increasing taxes. Today, a medallion on the floor represents the site of the Boston Massacre site and remembers the brave individuals who sacrificed their lives.

Inside the building, there is a gift shop and museum to learn more about the Boston Massacre history.


3) Granary and Copps Hill Burying Grounds

granary burying ground

Granary Burying Ground is Boston’s third oldest cemetery and is the place where many well known historical figures rest in peace, including John Hancock, Benjamin Franklin’s parents, Paul Revere, and Samuel Adams.

granary burying ground

Copps Hill Burying Ground is named after William Copp, a renowned shoe maker. At this burying ground, you will find many crafts people and merchants buried here.

copps burying ground
burying ground

4) Boston Common

boston common

The Boston Common, built in 1634, is America’s oldest public park complete with acres of green grass, monumental statues, paved walking paths, a beautiful garden, and a large pond. During the winter, there is even an ice skating rink. You can easily spend an hour to half a day here just strolling around or having a nice picnic with your family and friends. The views of the many historical buildings surrounding the Boston Common are mesmerizing. This is for sure one of my favorite places!


boston common
Photo Credit: Mommy Nearest

5) Brattle Book Shop

brattle bookshop

Although this infamous bookstore is not a part of the Freedom Trail, it’s located just a few minute walk from the Boston Common on West Street.

Why is this bookstore so famous?

Well, I think the picture speaks for itself. As one of the oldest and largest used bookstores in America, it features a 3 story building full of general and antiquarian books, as well as an outdoor section of books. You can even find books for $1 or $2. What a deal!

brattle book shop

6) Paul Revere House

Visit the colonial 1680 home of Paul Revere, the well known midnight rider and entrepreneur who warned the Americans of the British people’s every moves.

Photo Credit: Boston University

7) Benjamin Franklin Statue and Former Boston Latin School


The Boston latin school is an immensely beautiful building and was the first public school in America for boys both rich and poor. A bronze statue of Benjamin Franklin, one of America’s founding fathers, stands right in front of the former latin school.

benjamin franklin statue

Places To Eat

mikes pastry
Photo Credit: Mike's Pastry
  1. Breakfast: Cafe Fleuri – Delicious breakfast choices at affordable prices.

  2. Lunch: Hot Eastern Delicious Szechuan Chinese Food. SPICY!

  3. Dinner: Giacomos Ristorante – One of the most popular Italian restaurants in the north end.  There is always a line, so get there or early or prepare to wait.

  4. Dessert: Mike’s Pastry – The quintessential cannoli pastry shop. Flavors include: chocolate, lemon, oreo, espresso, and more! They sell other pastries like cakes, cheesecakes, cookies, and cupcakes.


the grand boston
Photo Credit: The Grand Boston
    1. The Grand: A high end club located in downtown Boston that often has famous DJs such as Steve Aoki, Borgeous, and Dillon Francis. When we went to the Grand, we saw Borgeous live and it was amazing! Although the Grand has a really small dance floor, the LED screen and ceiling created a really cool, hypnotic vibe. 
    2. Royale Boston: A fun nightclub that offers both DJs and live music.
    3. Venu Nightclub: An international nightclub specializing in hip hop and latin house music.

Boston Itinerary: Day 2

beacon hill

Things To Do

1) Walk around Beacon Hill

Beacon Hill, one of the Boston’s most stunning and picturesque neighborhoods, is lined with Victorian style red brick houses, ivy growing on the walls, beautiful white doors, and cobblestone roads. Despite some steep hills, this historical area is great for a pleasant walk while taking in all the unique architecture.

Located right in Beacon Hill, the Black Heritage trail includes the Phillips School, Abiel Smith School, John Coburn House, John J. Smith House, and the African Meeting House. The 1.6 mile trail is a great way to learn about the many brave and intellectual men and women who lived in Beacon Hill during the 1600s.

beacon hill
beacon hill

2) Explore the Waterfront


The Waterfront is located in downtown Boston and has several wharfs with lines of small and large boats. There are a multitude of delicious seafood restaurants, an aquarium, and a number of paved walkways for strolling around and soaking in the gorgeous views of the blue harbor. If you are interested, there are whale watching tours such as the Boston Harbor Cruise that goes out into the Atlantic ocean to see whales, dolphins, sea lions, and sea birds.


3) Visit Bunker Hill Monument

The Bunker Hill monument was built 50 years after the “Battle of Bunker Hill” on June 17, 1775. This bloody fight between the British and New England soldiers took place across the Charles River, and resulted in 1,000 men wounded or dead. Today, a 221 foot tall obelisk stands in remembrance of the brave men who lost their lives on this tragic day. Read more about the battle here. 

bunker hill monument
Photo Credit: Billings Gazette

Places To Eat

florentine cafe boston
  1. Breakfast: North Street Grille – Popular brunch spot with delicious options

  2. Lunch: Bostonia Public House – Great food selection and bar in a lively, fun atmosphere.

  3. Dinner: Florentine Cafe –  Great Italian food in a romantic setting. I got the chicken parmesan and the portion was humongous!

Boston Itinerary: Day 3

harvard university

Things To Do

  1. Boston Public Library
boston public library
boston public library

Take a stroll inside the magnificent Boston Public Library, which was the first, free public library in America. I suggest spending at least 45 minutes exploring because there’s a lot to see including: historical murals, marble architecture, marble lions near the entrance, the many Bostonian study rooms, huge selection of books, cafe, and courtyard. The museum, upon stepping inside, has a very classical European vibe to it. Best of all, it’s free!

2) Isabella Stewart Gardner Museum

isabella gardner stewart museum

Located in Back Bay, this Venetian style palace turned museum, exhibits Isabella Gardner’s spectacular courtyard garden, architecture, tapestries, sculptures, and furniture. At $15 a ticket for adults, $10 for students, and free admission for those under 18 with a parent, it’s an affordable option to see one of the most revered American art collector’s home in the heart of Boston. Try to get there early because the line can get extremely long, even going all the way outside of the main entrance.

Tip: If your name is Isabella, you get in for free! If you wear Red Sox apparel, you get a discount.

isabella gardner stewart museum
isabella stewart

3) Explore Harvard University and Harvard Square

harvard university

Founded in the year 1636, Harvard University is one of the oldest and most prestigious universities in the world. With beautiful architecture, statues, historical gates, and landscape, it’s mesmerizing just strolling around campus. In addition, Harvard University has several intriguing museums that are great for the family, and a center called the Harvard Square, which essentially is a small town with tons of restaurants, stores, cafes, and bars. If you’re debating whether it’s worth it to go, do it! You can even pretend to be a student there, even for a fleeting moment.


harvard university
harvard square

Places To Eat

  1. Breakfast: Cafe Luna – A popular brunch spot very close to MIT. Reservations are recommended!

  2. Lunch: Luke’s Lobster –Amazing shrimp, lobster, and crab rolls!

  3. Dinner: Toro – Fine Spanish Tapa Bar. Get there early, make a reservation, or expect to wait an hour. There’s also a nice bar to get some drinks while you wait.



Although these days are jam packed with activities to do and places to eat, I hope you can visit at least some of these places listed in this 3 day Boston itinerary. 3 days is nowhere near enough to see everything, but it’s just enough to get a taste and feel of the city. 

If you haven’t already, check out my previous blogs on Stone Brewing World Bistro & Gardens: A Gemstone in the Heart of Escondido and 10 Best Things to do in Phuket, Thailand

Let me know in the comments below if you’ve been to Boston or plan on going to Boston anytime soon. I want to hear about where you’ve been and where you want to go. Thank you so much for reading and I hope you enjoyed this 3 day Boston Itinerary!