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A Packed Boston Itinerary: 3 Days for First Timers

A Packed Boston Itinerary: 3 Days for First Timers

I recently had the opportunity to visit Boston, Massachusetts, twice–and I absolutely love it! I like how much time people spend outdoors, the food is excellent, and there is SO much to see and do. While this three-day Boston itinerary doesn’t cover everything there is to do in the city, it will undoubtedly get you started. Have fun!


Boston Itinerary: Day 1

The first day of my Boston Itinerary will have you learning about the history of the city, having lunch at the largest food hall in New England, exploring a quintessential Boston neighborhood, and more. Wear comfortable shoes, because we’re walking all over!


Breakfast at the Friendly Toast

The Friendly Toast is a New England restaurant chain founded in 1994. Its scratch kitchen serving creative dishes, bar mixing up one-of-a-kind drinks, and nostalgia factor make this the first breakfast stop on your Boston itinerary.

Friendly Toast’s all-day brunch menu is full of cleverly named dishes, like Some Like It Tot, Friendly Toast Benny, Brunch-Burg! Right Ahead, and the Medley Crue. Plus, the Friendly Toast offers gluten-free, vegan, and vegetarian options.

Closest location to Boston Common: 35 Stanhope St


Walk Around Boston Common

Boston Common is America’s oldest park, established in 1634. Since then, it’s been a place for free speech and public assembly. 


Today, Boston Common’s 50 acres make up a thriving greenspace, complete with trails, ballfields, monuments, memorials, a playground, fountain, bandstand, carousel, and Frog Pond (used as a spray pool in the summer, a reflecting pool in the spring and fall, and ice-skating rink in the winter).

The park hosts a variety of events throughout the year, too.


Take the Freedom Trail’s “Walk Into History” Tour

The Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.

Immerse yourself in this city’s remarkable past by taking the Freedom Trail’s Walk Into History tour. Departing from the Boston Common Visitor Information Center, this 90-minute, one-mile walking tour highlights the diverse history at 11 of the 16 official Freedom Trail Historic sites. And it’s led by an 18th-century costumed guide. 

Tickets are $17 for adults and $8 for children (ages 6-12). Senior and student discounts are available.


Lunch at Quincy Market

The Freedom Trail Walk Into History tour ends at the iconic Faneuil Hall Marketplace, home to Quincy Market—the largest food hall in New England. Quincy Market has various food options, including fresh seafood, pizza, pastries, and international eats from 25+ local eateries.


Two of my favorite finds are the Lobster Roll at Boston & Maine Fish Co. and the Lobster Mac and Cheese Pie from Boston Chowda.


Shop Faneuil Hall Marketplace

Faneuil Hall Marketplace boasts 40+ specialty push carts and name-brand stores. From locally owned stores to toys, Boston souvenirs to shoes, you can find it all here. As one of the most popular things to see in Boston, I had to add it to this Boston itinerary.


Other points of interest nearby include the incredibly moving New England Holocaust Memorial, Boston Public Market, and Massachusetts State House.

Explore Boston’s North End

Boston’s North End, known for its Italian food offerings and pastry shops, is home to some of the city’s oldest buildings. It was settled by Puritans from England, after all.

While you’re in the North End, stop at the remaining Freedom Trail sites: Paul Revere House, Old North Church, Copp’s Hill Burying Ground, Union Oyster House, Ebenezer Hancock House, North End Park, and the Paul Revere Statue.

When you’re finished in the North End, pick up a slice of pizza for dinner. There are a bunch of pizza spots, but I’ve had good slices from Sal’s and Regina Pizzeria.


Wander Around Beacon Hill

In my opinion, Beacon Hill is the quintessential Boston neighborhood. Its narrow, cobblestone streets are lined with boutiques, restaurants, gas streetlamps, and picturesque Federalist-Era architecture.

Stores that I enjoy stopping in are Beacon Hill Books & Café (the most charming bookstore), Whitney and Winston (children’s), Helen’s Leather, and Gus & Ruby Letterpress (stationery). 


Boston Itinerary: Day 2

If you didn’t fall in love with Boston on day 1, you should today. After visiting America’s first public botanical garden, you will explore the Back Bay neighborhood, take in the Museum of Fine Art, and see the iconic Fenway Park.


Enjoy the Public Garden

Day 2 of your Boston itinerary begins right beside where day 1 started—at the Public Garden.

This was America’s first public botanical garden, established in 1837. The Victorian-era Public Garden has meandering paths decorated with statues, fountains, and beautiful flowers, trees, and plants. You can even ride on a swan boat while you’re there.


Explore Back Bay

Famous for its picturesque rows of Victorian brownstone homes, Back Bay is a beautiful area. In addition to stunning architecture, you will also find trendy restaurants and a plethora of shopping opportunities.


The most famous shopping street here is ‘Newbury’. You can find big-name apparel stores, such as Betsey Johnson, Burberry, Chanel, Lilly Pulitzer, Ted Baker London, and Valentino. Additionally, you can find health and beauty, home decor, and pop-up shops on Newbury Street, plus a multitude of art galleries.

There’s a lot to discover in Back Bay!


Lunch at Atlantic Fish Co

While exploring Back Bay, I stumbled upon Atlantic Fish Company and had a great meal there. The restaurant has been serving Boston fresh seafood since 1978, sourced from the harbor every morning.

The food is great, but the complimentary bread is worth the visit alone. So tasty!


Discover the Boston Public Library

You don’t have to be an avid reader to enjoy the Boston Public Library, which is why it has earned a spot on this Boston itinerary.

Established in 1848, the Boston Public Library is a pioneer of public library service in America–it was the first large free municipal library, the first public library to lend books, the first to have a branch library, and the first to have a children’s room.


Back Bay is home to the Central Library in Copley Square, which encompasses two buildings. The historic McKim building (opened in 1895) is known for its classical serenity and elegance. You will find artwork by Daniel Chester French, John Singer Sargent, and the iconic Bates Hall reading room here.


The Boylston Street Building (opened in 1972) features a 21st-century library space, broadcast studio, and innovation center. There’s even a café inside! 


Visit the Museum of Fine Art

Next, you will head to the Fenway-Kenmore area of Boston.

The Museum of Fine Arts Boston tells the story of the human experience through its 500,000 works, showcasing ancient artistry, modern masterpieces, local legends, and global visionaries.


Exhibitions and galleries on view at MFA Boston include Monet, Strong Women in Renaissance Italy, Mummies, Wedding Fashions and Traditions, South and Southeast Asian Art, Tiny Treasures, and Hamilton Palace Dining Room, to name a few.

There’s so much to see at this incredibly thoughtful museum that you could spend hours browsing all the displayed items. General admission is $27 for adults, $10 for youth (ages 7-17), and free for children ages 6 and under.


Visit Fenway Park

You can’t come to Boston and not see Fenway Park! Home of the Boston Red Sox, it’s referred to as “America’s Most Beloved Ballpark”.

If you’re visiting while the Red Sox are playing at home, absolutely consider seeing a game. But if not, a quick glance of the stadium will have to do.


Finish Traversing the Fenway-Kenmore Area

Finish day two of your Boston itinerary in the Fenway-Kenmore Area. The neighborhood is full of locally owned restaurants where you can stop for dinner and shop for Boston souvenirs.

Grab dinner from one of its many restaurants, such as Fenway Johnnies, Citizen Public House & Oyster Bar, Saloniki Greek, or Wow Tikka.


Boston Itinerary: Day 3

I may have saved the most fun for last. Today, visit my favorite spot in Boston (Castle Island), tour a Presidential Museum, play mini golf at Puttshack, and end the day with an incredible seafood meal overlooking the harbor.


Watch the Sunrise at Castle Island

Castle Island is a 22-acre land-bound island on the shore of Dorchester Bay and the Boston Harbor in South Boston. You can walk, bike, swim, picnic, and watch planes take off and land at Boston Logan International Airport. Fort Independence, the oldest fortified military site in British North America, sits on top of Castle Island.

The scenery here is absolutely beautiful, claiming a spot on your Boston itinerary.

Accessibility Note: Beach wheelchairs are available at Carson Beach and Pleasure Bay 


Breakfast at Flour Bakery + Cafe

Led by James Beard Award-winning pastry chef Joanne Chang, Flour Bakery + Cafe has multiple locations in the Boston area.

While the restaurant serves numerous tasty treats, breakfast items include homemade scones, muffins, cinnamon rolls, seasonal pop-tarts, and croissants. You won’t want to miss this stop on my Boston itinerary!

Closest location to Castle Island: 19 Drydock Avenue


Tour the JFK Presidential Library and Museum

The John F. Kennedy Presidential Library and Museum is dedicated to the memory of the 35th president of the United States. It is located on a ten-acre park overlooking the sea that JFK loved and the city that launched him into greatness.

The JFK Library and Museum conveys his enthusiasm for politics and public service through 22 permanent exhibits and some special exhibitions covering JFK’s life from boyhood to his legacy today.


The museum includes a collection of 30,000 artifacts (including gifts from world leaders, furniture, clothing, artwork, and family memorabilia), giving visitors a look into JFK’s life and the time he lived.

Tickets for adults are $18, youth tickets are $10, and children 12 and under are free. They offer discounts for students and Veterans, too.


Visit the Seaport Area

The Boston Seaport is a 21st-century neighborhood designed for the way people live today. After a decade of development and $22 billion renovation, culture, industry, and community converge here. You can find it all at the Seaport, from dining to shopping, art, and parks.


One of my favorite shops in the Boston Seaport area is Little Words Project. You can make your own adorable beaded bracelet in-store, aimed to spread kindness and positivity. Other stores include Bluemercury, L.L. Bean, rag & bone, Sephora, Stonewall Kitchen, and Warby Parker.

For lunch, stop in one of the Seaport’s many restaurants–like Bartaco (one of our favorites in Nashville), Tuscan Kitchen Seaport, The Barking Crab, Taste Bakery & Cafe, or Legal Sea Foods-Harborside.

If you’re looking for a quick lunch so you can keep exploring Boston, Shake Shack is always our go-to.


Play Mini Golf at Puttshack

Puttshack is the world’s only upscale, tech-infused mini golf experience. Their Trackaball technology keeps score for you as you play, and the whole place has a fun vibe. Each hole offers a unique challenge; you can earn or lose points depending on your play.

I played Puttshack Boston’s Emerald course, and my favorite holes were #2 (you had to answer a trivia question with your shot) and #4 (like a giant, interactive pinball machine).

In addition to mini golf, Puttshack also serves globally inspired-food and craft cocktails. Puttshack Boston is open to players of all ages until 8 PM when guests must be 21+. One round of mini golf is $18 per person or $10 for children 12 and under.


Dinner at Boston Sail Loft

End your time in Boston with a fantastic meal from Boston Sail Loft. Serving arguably the best clam chowder in town, the restaurant offers fresh, classic New England seafood and fantastic views of the Boston Harbor.


Additional Boston Activities

Are you looking to pack even more fun into your Boston trip? Here are some additional activity suggestions.

Enjoy Boston’s Greenspaces

Boston is FULL of greenspaces. Seriously, there is one on every block. Sit and enjoy, read a book, or walk around one of Boston’s many parks.

Use this list to find the parks in each Boston neighborhood.

My two favorites are the Charles River Esplanade (beside Beacon Hill and Back Bay) and Rose Kennedy Greenway (between Quincy Market and the North End).


Walk Harvard’s Campus

While you’re in Boston, stop by America’s oldest college and one of the country’s most prestigious universities–Harvard.

Harvard’s campus traverses the Charles River from the heart of Cambridge to nearby Allston. Be sure to stop by the Harvard Yard, aka the heart of campus; it’s where you will find red-brick buildings, Johnston Gate, and the John Harvard Statue. Harvard also offers free, student-led public walking tours, but registration is required.


Tips for Visiting Boston

Our Boston itinerary is packed full of things to do: I reiterate, wear comfortable shoes.

I have done most of these activities by driving and by taking rideshare. Parking is limited (and expensive) throughout the city, so I recommend using a rideshare and walking when you can.


Spending more time in the area? Take a road trip to Providence, RI!

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