The Greater Boston metropolitan area is not only a hub for history but also renowned for its innovation.

Everywhere you turn in Boston – also known as the “Cradle of Liberty” for its pivotal role in the Revolutionary War– you’ll be reminded of its rich past. Just across the Charles River, in Cambridge, you can catch a glimpse of the future. Cambridge is home to some of the world’s most prestigious universities, including Harvard and MIT.

Boston also pride in its world-class museums and A-list sports teams like the Boston Red Sox, Boston Celtics and New England Patriots.

There’s so much to see and do in this fascinating city that you’ll need more time to truly experience it all. But for now, let’s make the most of your 3-night stay with this itinerary I curated for you. 

When to visit Boston

Shoulder seasons are probably the best time to visit. August can be very hot, while the winter can be bone-chilling cold. I visited Boston in December with my parents and we were all freezing… so make sure to bundle up. Personally, I would love to go back for the foliage season!

How to get to Boston

You can fly into Logan International Airport, drive, or get there by bus or train. I highly recommend the Amtrak train, as it was my first time traveling to Boston this way, and it was incredibly convenient. It takes about 4 hours from Penn Station to South Station , and you can find one-way coach tickets starting from $41. Trust me, it’s worth it!

Getting around Boston

Boston is a very walkable city. Additionally, you can also move around with Bluebikes ($2.95 for a single trip), take a taxi/Lyft/Uber, or hop on the subway – affectionately known as “the T” ($2.75 per ride, $12.75 for a 1-day CharlieTicket, or $22.50 for a 7-day pass).

Where to stay in Boston

  • For a 4-day adventure, Downtown is a great and affordable option.
  • If f you plan on visiting a lot of museums or spending time at the ballpark, considering staying stay in the Fenway-Kenmore area.
  • My personal favorite is Beacon Hill, one of the city’s most historic and charming neighborhoods. It reminds me of Brooklyn Heights, and, of course, it’s also pretty expensive.

My friend Laura Peruchi and I have been invited by Meet Boston, and we had the pleasure of staying at XV Beacon, a luxurious boutique hotel is located in Beacon Hill, just across from Boston Common, America’s oldest public park. 

Elegant and chic, this hotel was an absolute highlight of our trip! The rooms are spacious and very well designed, and equipped with all the comforts you could wish for. My room had a sophisticated sofa area with a fireplace and TV, a small cabinet with a mini bar and coffee station (with Lavazza coffee 😍), a cozy desk and an incredibly comfortable king-size bed dressed in Frette linens. Not to mention the Carrara (my home town!) marble bathroom with a Jacuzzi tub and and oversized rainforest shower head.

The service at XV Beacon is impeccable; they even took the time to fold my clothes! The cage elevators, rooftop deck with a stunning view of Boston, and modern fitness center (opening at 8 am) added an extra touch of luxury to our stay.

DAY 1 – Arriving in Boston

Get settled in and treat yourself to adelightful dinner at Lola 42, where you can indulge in Asian-inspired cuisine with a modern twist, inspired by countries along the 42nd parallel. Soak in the cool and eclectic vibes indoors or sit outside on the patio enjoying the waterfront view.

Fan fact: Lola 42 is run by Brazilians (like my friend Laura), and you’ll be greeted with warm and vibrant hospitality!

Day 2: History, Innovation and Museum Hopping

Start your day with a delicious breakfast and get ready for an adventure-packed day!

I had eggs, fruit and yogurt at Mooo…., the signature restaurant in our hotel known for its sophisticated atmosphere and modern decor. Not only was breakfast fantastic, but Mooo… is also renowned as one of the best steakhouses in Boston.

One of America’s oldest and largest used bookshops. It reminds me of a more picturesque version of Strand in NYC. The first two floors house a vast collection of general used books, while the third floor showcases rare collectibles.

🕒 Hours: Mon to Sat: 9am-5pm

Founded in 1634, it’s the oldest public park in the country. Do not miss Boston Public Gardens – America’s first public botanical garden – and the adorable Make Way for Ducklings statues, depicting a mother mallard and her ducklings. These bronze sculptures by Nancy Schön have become a beloved park landmark since 1987.

  • Beacon Hill (technically including Boston Common and extending northward)

Stroll around Boston’s most beautiful, picturesque and historic neighborhood: Beacon Hill. You’ll be mesmerized by its brick houses, antique lanterns, and cobblestone roads.

Fan Fact: Acorn Street is America’s most photographed street 📸

Ps. don’t you think 8 Acorn Street has the smartest door sign?

Did you know that the telephone was invented in Cambridge? Learn about groundbreaking research with a visit to the Massachusetts Institute of Technology (MIT).

We took a wonderful guided tour with Alissa Cordeiro, who shared fascinating insights with us. Here’s some of my favorites:

1. Cambridge is often called the Venice of America

2. The Great Bridge over the Charles River, connecting Cambridge to Boston, was built in 1660–1662, significantly reducing the walking distance from 5 hours to just 30 minutes!

3. MIT carries the Spirit of Leonardo da Vinci, not accepting boundaries between different fields of knowledge (they believe that everything is interconnected and that innovation happens through sharing information), considering Nature as a prime collaborator, and learning-by-doing.

4. Art and science are two sides of the same coin: they both require a tremendous amount of imagination.

5.  In October 1958, as a result of a MIT fraternity pledge, MIT students created “The Smoot“, a nonstandard unit of length equal to 5 feet 7 inches, which happens to be Oliver Smoot’s height.

Oliver, a fraternity brother, lay down repeatedly on the Harvard Bridge while his peers marked his height along the bridge’s span. To this day, the Harvard Bridge is measured in Smoots, with a total length of 364.4 Smoots plus one ear.

Housed within a 1929 Art Deco masterpiece that was once a Sears, Roebuck and Company warehouse. This unique indoor market, featuring an outdoor patio, offers a diverse selection of local food and drink concepts, all just a short walk away from Fenway and some of the best museums intown.

🕒 Hours:
Mon to Thur 8:30am -10pm
Fri 8:30am-11pm
Sat 9am-11pm
Sun 9am-10pm

Would you ever expect to find a 15-century Venetian palace with lush greenery in Boston? Click on the image to see the video on IG.

Traveler and eccentric Isabella Stewart Gardner purchased the building in the late 1800s to curate her extensive collection of American, Asian, and European artworks and object acquired during her travels. She hosted exclusive parties until her last days and, on her deathbed in 1924, declared that the museum should be open to the public.

You’ll be mesmerized by the museum’s skylit interior courtyard is adorned with beautifully arranged plants, flowers (curated seasonally), sculptures, mosaics, and masterpieces by renowned artists such as Rembrandt, Raphael, Botticelli, Titian, and more.

Time Out Market Boston manager Michael, recommended us to watch Netflix This Is a Robbery: The World’s Biggest Art Heist documentary that delves into the mysterious robbery that took place here in 1990.

Even today, the culprits remain unknown, and empty frames still hang on the walls, serving as a reminder of the unsolved crime… there’s a $10 million reward in exchange for information!

🎟️ Adults: $20, Seniors 65 and up: $18, Students: $13, Children under age 18: Free

🕒 Hours:
Mon, Wed, Fri: 11am–5pm
Closed on Tuesday
Thur: 11am–9pm
Sat & Sun: 10am–5pm

The Museum of Fine Arts Boston dates back to 1876 and houses an extensive collection of artworks spanning from the ancient Egyptian treasures to contemporary masterpieces and even the making of the children’s book Make Way for Ducklings.

Pro Tip: make sure not to miss the Monet collection and Edgar Degas’ Little Fourteen Year Old Dancer.

🎟️ Adults: $27, Youths 7–17: $10, Youths under 6: Free

🕒 Hours:
Sun, Mon, Wed, Sat: 10am-5pm
Closed on Tuesday
Thu & Fri: 10am-10pm

This 360° observation deck provides a sky-high vantage point of the city from atop the Prudential Centre.. On a clear day they say you might even catch a glimpse of New Hampshire!

🎟️ Adults Standard General Admission starts from $29.99

  • For dinner, we decided to return to Time Out Market Boston. If you have any restaurant recommendations, please share them in the comments 🤗

Day 3: Waterfront, Duck Tour and North End

Start your day with a visit to Tatte Bakery and Cafe! I fell in love with Tatte during my previous visits to Boston with Luca, and their pastries are simply irresistible.

The atmosphere exudes a chic, romantic, and Parisian vibe, making it super instagrammable. Don’t miss their croissants, french toast with housemade challah bread, croque madame, or breakfast sandwich with eggs, Vermont cheddar, and applewood-smoked bacon on housemade sourdough. I’m getting hungry just thinking about it!

Boston Harbor has played a significant role in the city’s history, and it has transformed into one of the most vibrant and lively neighborhoods to explore.

It reminds me of Dumbo for its former warehouses and industrial spaces now converted into sleek and fancy buildings. I recommend visiting the local Trader Joe’s to get a sense of how it looked in the past.

The juxtaposition of old and new creates a fascinating atmosphere, and the Seaport District is also home to the Institute of Contemporary Art.

Institute of Contemporary Art or Freedom Trail? At this point of your Boston itinerary, I’d suggest you to choose between these two options, based on what interests you the most… you’ll have an extra reason to visit again ☺️

This cutting-edge museum is a must-visit for contemporary art and architecture enthusiasts!

Designed by renowned architects Diller Scofidio + Renfro, the building itself is a work of art. Explore the thought-provoking exhibitions showcasing emerging and established artists from around the world, and don’t forget to take in the breathtaking harbor view from the second floor.

🎟️ Adults: $20, Students: $15, Seniors (60+): $17, Youth (18 and under): FREE
FREE THURSDAY NIGHTS: every Thursday from 5pm to 9pm. Advanced tickets – available at 10 AM the morning of – are recommended.

🕒 Tue, Wed, Sat, and Sun: 10am-5pm. Thu and Fri*: 10am-9pm – Closed on Mondays.
* The ICA closes at 5 PM on the first Friday of every month for First Fridays, a ticketed event.

During the summer, take the water shuttle (included in your ICA ticket) to the Watershed, located within the Boston Harbor Shipyard and Marina in East Boston at 256 Marginal Street. Open from 11am to 5pm Tue through Sun, with extended evening hours on Thursdays until 8pm (no Water Shuttle service). Closed on Mondays.

You can’t leave Boston without trying their clam chowder and Lobster rolls… and the Reelhouse’s Lobster rolls are incredible!!! If the weather permits, enjoy the stunning waterfront views from their outdoor patio. Even indoors, the view is still fantastic!

🕒 Mon – Sun: 11am – 1am

Perfect for all history lovers, and anyone interested in learning more about Boston’s crucial role in the American Revolution.

You can follow the trail on your own (like I did with my parents) or book a guided tour.

If you opt for a self guided tour, download the official brochure of the Freedom Trail and pick up a map and free guide at Faneuil Hall or the Boston Common Visitor Center at the beginning of the trail at 139 Tremont Street.

Start at the Boston Common and follow the narrow red brick line through the city. Each remarkable location is marked with a gold plate and there are plenty of informative signs along the way.

The trail is 2.5 mile long, and consider to walk for approximately 90 min to 2 hours, depending on how much time you want to spend at each location. Most sites are free to visit, and some do charge an entrance fee, such as the Old State House, Old South Meeting House, and Paul Revere House.

As you just learned during the Freedom Trail tour, the Faneuil Hall Marketplace was built in 1742, and is one of the most historic sites in all of Boston. It was here that the Sons of Liberty gathered to discuss independence from Great Britain. Inside the Hall, you’ll find Quincy Market, home to over 25 local eateries offering fresh seafood and sweet delights.

  • Boston Duck Tours – the tours launch from multiple location: Prudential Center, Museum of Science or the New England Aquarium at Central Wharf (where we embarked).

Hands down, this is one of the best adventures you’ll have in Boston!!!

I’ll describe it in the same way Michael, the Time Out Market Boston manager, introduced it to us (he provided us with so many tips on how to enjoy Boston… thank you again!): it might sounds cheesy, but trust me, you’ll love it. This tour turned out to be one of the highlights of our recent trip!

The ConDUCKtor will guide you to several landmarks while sharing both historical and less-known facts about them before splashing into the water. Don’t worry, you won’t get wet! Your “duck” will simply transform into a boat before splashing down into the Charles River.

Fun fact: you might even end up driving the boat – I did 😎 (click on the image below to see the video on IG)

  • North End, Boston’s Italian district.

I absolutely adore the charm of the North End! Covering just 0.36 square miles, it’s home to the oldest residential community – predominantly Italian by 1930 – and you can feel its colonial history permeating the streets.

If you haven’t done so (as it’s part of the Freedom Trail), make sure to walk along Salem Street, where you can visit the Old North Church, check out Paul Revere Statue, and explore the Paul Revere House at 19 N Square.

Wrap up your day with a plate of spaghetti alle vongole at Forcella, and enjoy the rest of the evening strolling along Hanover St.

Day 4: Brunch and back to the City

Savor your last day in Boston, with a delicious brunch at The Beehive, a hip and funky eatery and bar known for its world-class live music and rustic comfort food.

Afterward, make your way to South Station in time for your Amtrak train back to NYC. Please let me know how your trip went!!! I so look forward to reading your feedback, suggestions and recommendations 💖

If you have more time in Boston:

Dating back to 1912, Fenway Park is the oldest ballpark in Major League Baseball in America. Sports fans can’t leave Boston before taking a tour of this magnificent stadium, which is also home to the beloved Boston Red Sox.

Founded in 1636, Harvard is not only the oldest university in America, but also one of the most renowned educational institutions in the country. Take a stroll through its historic campus and immerse yourself in the rich academic atmosphere.

Opened in 1852, it’s the third largest library in the country, and it is famous for its stunning murals. Explore the vast collection of books and soak in the grandeur of the building’s architecture.

Across from the Boston Public Library and Old South Church in Boston’s Copley Square, you can also take a look at the finish line to the Boston Marathon.

  • Worcester Street, South End Historic District, Boston

If you have a passion for carriage houses, you don’t want to miss this super charming one (see more by clicking on the image below)

Immerse yourself in Boston’s vibrant theater scene by attending a performance by the Boston Lyric Company. Founded in 1976, it is the largest opera company in New England.

Laura and I had the pleasure of watching Rooted, an offbeat comedy about two sisters and a treehouse that inadvertently started a cult… it was a fun and memorable experience!

Is there anything else you think should be added to this Boston itinerary? Please share your thoughts and suggestions in the comments.

Brooklynite from Italy with infectious energy, Laura is a travel writer, photographer and creator. She shares NYC insider tips, unique experiences, and travel guides to inspire you to go after your dreams, live in wonder, and turn everyday life into Wow Moments.

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