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The Perfect Itinerary for a Weekend in Boston in 2024

The Perfect Itinerary for a Weekend in Boston in 2024

With a plan to hit of the city’s best and most interesting highlights, a single weekend in Boston is all it takes to fall in love with this historic, action-packed city. 

You’ll discover the most worthy spots for history, food, drinks, shopping, and gorgeous waterfront views in our 48-hour Boston weekend itinerary. 

What Can You Do on a Weekend in Boston?

Boston's Back Bay skyline with the Charles River and sailboats in the foreground as one of the stops on a 48-hour weekend Boston itinerary

Michael Sean OLeary/Shutterstock

The beauty and history of this waterfront city makes it seem like a weekend just won’t be enough to fully enjoy Boston, but that’s not the case! 

With the right planning and ideas for the most impactful spots to hit, you can turn a weekend in Boston into an action-packed trip that truly connects you to this fascinating city. 

There are scenic spots to see in the city’s famous pond- and path-filled parks, historic sights and markers that make a stroll feel like a scavenger hunt, and sunset cruises through the harbor that detail the city’s history. 

Boston’s culinary scene will bowl you over with delicious breakfast to dinner options throughout the different neighborhoods. Leave room for a few sumptuous snacks and drinks in between! 

The extensive beer history here traces back to the 1800s. You can’t go without touring the Samuel Adams Brewery or enjoying local craft brews on draft at pubs and restaurants around the city. 

Public and presidential libraries that belong on the cover of Architectural Digest and fascinating neighborhoods with cobblestone streets and family-owned shops should be on your list, too. 

The question isn’t really “What can you do on a weekend in Boston” — it’s more like “What can’t you do on a weekend in Boston?”

48-Hour Itinerary for a Delightful Weekend in Boston

Got 48 hours to spend in bustling Boston? That’s plenty of time to hit the highlights and see what makes this historic city – founded in 1630 and the birthplace of the American Revolution – great.

Spend a weekend in Boston to get familiar with its extensive and captivating history, taste the distinctive local flavors in seafood and internationally-inspired cuisine, and take in the beauty of its waterfront parks and paths.

So how do you spend a weekend in Boston without feeling like you’ve wasted time or left out any of the best stops? Use this 48-hour itinerary to see and do it all in a weekend.  

Day One: Freedom Trail, Boston Harbor, and Harbor Cruise

George Washington statue in Boston Public Garden surrounded by colorful tulips is a spot to visit on the first day of a weekend in Boston

Jorge Salcedo/Shutterstock

  • Boston Public Garden
  • Boston Common park
  • Freedom Trail walking tour
  • Lunch at Faneuil Hall Marketplace
  • Boston Museum of Fine Arts
  • Boston Tea Party Ships & Museum
  • Boston Harborwalk
  • Sunset historic Boston Harbor cruise
  • Dinner and drinks at Boston Public Market

Start your first morning at Boston Public Garden, a Victorian-style hideout right inside the city with its own lagoon. Take a Swan Boat ride April-September and see real resident swans on the water.

Look for Ether Monument and Make Way for Ducklings statues as you walk and admire the foliage and flowers through seasonal transitions! 

Right next to it is Boston Common park (established in 1634), a crash course in the city’s extensive history and a gorgeous spot to continue your weekend trip walking along its storied paths. 

The Boston Common Frog Pond is a tranquil space in the park, surrounded by a cafe, carousel, summer splash pool, and huge lawns where yoga classes and city movie nights take place. 

Grab a coffee from the Frog Pond Cafe and set out on the 2.5-mile Freedom Trail walking tour to spend your first morning in Boston getting to know the city through 16 historic stops (most are free).  

You’ll see the Massachusetts State House, Park Street Church, historic markers at the Granary Burying Ground from the 1600s, and 330-year old King’s Church and Burying Ground.

Continue on to see the Benjamin Franklin statue in front of the Boston Latin School – the oldest public school in the nation – where the founding father was once a student. 

Pop into the Old Corner Bookstore next and the Old South Meeting House where the Boston Tea Party began.

The Boston Massacre site is a chilling thrill for true crime fans. Next is Faneuil Hall, the site of America’s first Town Hall meeting.

It’s now a marketplace home to shops and great options for lunch (like Wicked Lobstah for a classic lobster roll and Monkey Bar for dessert).

Angled view of the Paul Revere House on the Boston Freedom Trail for a Boston weekend itinerary

Paul Revere House on the Boston Freedom Trail/Zack Frank/Shutterstock

After dining on lobster rolls or chowder like true Bostonian, continue on the trail to see the city’s oldest structure, the Paul Revere house. 

The USS Constitution, “Old Ironsides,” sits in the Charlestown Navy Yard and the final stop, the Bunker Hill Monument, commemorates the famed battle of the Revolutionary War.

The Boston Museum of Fine Arts makes an excellent afternoon stop. Head over to the Boston Harbor to see Boston Tea Party Ships & Museum that brings some of the history you’ve learned on the Freedom Trail to life.

If you’re museum-ed out, stroll (or rent a bike) along Harborwalk, tracing the edge of the water and seeing more of the city.

You can book a 90-minute sunset Boston Harbor cruise to hear about the city’s history from the perspective of the harbor. It culminates in a traditional cannon salute!

As you head back after sunset, you’ll be ready for a delicious dinner and celebratory beers or dessert at the Boston Public Market.

Piled-high sandwiches at Beantown Pastrami Company and tasty brews at Boston Beer Alley make this a great place to savor the rest of your evening before a jam-packed day tomorrow! 

Day Two: Harvard, Libraries, Back Bay, North End, and Sam Adams Brewery

View of the John W. Weeks Bridge in front of the Harvard University campus in Boston during springtime, open for student-led guided tours during weekend trips to Boston


  • Breakfast at Bagelsaurus
  • Walking tour of Harvard University
  • Harvard Museum of Natural History
  • Brunch at Tatte Bakery & Cafe
  • Tour Fenway Park
  • Boston Public Library
  • Back Bay historic homes and shops
  • Lunch at Atlantic Fish Company
  • Tour the North End “Little Italy” neighborhood
  • John F. Kennedy Presidential Library and Museum
  • Tour and taste at Samuel Adams Brewery
  • Dinner and cocktails at Brassica Kitchen + Cafe

Waking up for your second day in Boston is even better when you start with a delicious bagel and schmear or breakfast bagel sandwich at the cult favorite Bagelsaurus. 

Book a student-guided walking tour of Harvard University to see one of the nation’s most prestigious universities up-close with a 70-minute campus walk-through.

If you’re up for it, you’ll enjoy a tour of the Harvard Museum of Natural History ($15 admission) next. It’s filled with interesting science collections and a great way to spend the late morning. 

It’s the perfect opportunity to stop by the beloved Tatte Bakery & Cafe on Harvard Square for an incredible brunch and coffee or a filling, Boston-style lunch.  

Head across the Charles River to check out America’s oldest ballpark and home of the Boston Red Sox, Fenway Park. You can take a 1-hour guided tour of the stadium (get tickets in advance).

The Boston Public Library is massive and impressively designed. It was America’s first public library and its cathedral-like interior is the perfect place to catch your breath and enjoy a cup of tea in the lounge. 

Just east is the Back Bay neighborhood, filled with historic brownstones on Newbury Street, trendy restaurants, interesting shops, and bars that you’ll want to spend a couple of hours enjoying. 

Pull up a chair at Atlantic Fish Company in the popular sidewalk section, where you can taste fresh seafood with great views of the city. You’ve got to try the famous Shellfish Tower and New England clam chowder! 

Bike chained to a fence at dusk in the Boston North End Italian neighborhood with colorful, lit shops around the cobblestone streets for a guide to spending a weekend in Boston

A lone bike chained to a fence on a quiet night in Boston’s Italian North End, April 25/James Kirkikis/Shutterstock

Next up is checking out the historic and captivating North End neighborhood, Boston’s Little Italy.

Cobblestone streets, boutiques, excellent restaurants and bars, and a distinctly European feel will make it one of your favorite parts of Boston.

Be sure to head to the Italian bakery, Modern Pastry, to build your own cannoli, taste the freshest biscotti and pizelle, and grab a 4-piece torrone pack to go! 

After that, it’s time for the John F. Kennedy Presidential Library and Museum for exhibits and memorabilia creating snapshots of President Kennedy’s life and achievements. 

Head west to Samuel Adams Brewery to taste the famous beer and enjoy a tour detailing the brewing process for just $10. Tours start as late as 6:30 and take 45 minutes. 

You’ll finish up the evening at the eccentric-yet-upscale Brassica Kitchen + Cafe for European-inspired seafood and fresh, local favorites like Koji Risotto and delicious cocktails, beer, and wine. 

Things to Consider

Weeping willow trees by the pond in Boston Public Garden on a beautiful spring weekend in Boston

ESB Professional/Shutterstock

Making the most of your weekend in Boston starts with a great itinerary that hits all the highlights, but if you keep these tips in mind, you’ll enjoy your trip even more. 

  • Mix, match, and customize your plan. If some of the stops in this itinerary don’t strike your fancy, don’t hesitate to swap some different spots in! This is intended to be a great starting point for a weekend Boston trip, but there’s a lot packed into each day. For a more relaxed trip, consider removing a few stops to leave extra breathing room. 
  • Get out and walk. Many of Boston’s neighborhoods are extremely walkable and you’ll discover even more shops, museums, historic markers, and restaurants this way. When you have the opportunity to get out and walk, do it! You’ll enjoy Boston from a more local perspective. 
  • Consider making it a 3-day weekend trip. If you can schedule a little more time in Boston, you’ll be able to space your stops out a bit more and see more of this captivating city. Some of the neighborhoods, the downtown area, and university campuses can easily take up more of your time as you wander through. 
  • Ask for local recommendations. While these are our favorite Boston attractions and stops, you’ll never regret asking a local for their favorite restaurants, neighborhoods, and stops around the city. Boston is a big city and there’s much more than you could ever pack into a 48-hour trip, but it’s worth venturing out for something great! 
  • Find a great, centrally-located hotel. Wondering where to stay in Boston? Making base camp downtown, in the North End, or in Charleston area will keep you close to the stops on this weekend itinerary and put you near all the action. We love the Bostonian Boston downtown and Boston Marriott Long Wharf in the North End.

Frequently Asked Questions

Historic brownstone apartments lining the brick paved streets in the Back Bay neighborhood during a laid-back fall weekend in Boston

Jorge Salcedo/Shutterstock

You’ll supercharge your weekend in Boston when you know the answers to travelers’ most-asked questions! Take a look at the FAQs below to study up.

Is Boston good for a weekend trip?

Boston’s best attractions are in a relatively small area, making it an excellent city for a weekend trip packed full of cool stops and experiences.

As the 3rd most walkable US city, it’s perfect for strolls through downtown historic sites or along the harbor. With prestigious universities, some of America’s oldest buildings, and great food options, Boston is always good for a weekend trip.

How do I spend a perfect weekend in Boston?

The perfect weekend in Boston starts with leisurely walks through its public parks and ponds, walking tours past historic sites and the harbor, and visits to its unique museums like Harvard’s Natural History and the Museum of Fine Arts.

Add in a fresh lobster roll or clam chowder, brews and tour at Samuel Adams Brewery, and a couple of hours to check out the bustling North End (Little Italy) and Back Bay neighborhoods to make your weekend complete.

How to do Boston in 3 days?

You can easily do Boston in 3 days with an idea of what interests you most. History buffs shouldn’t skip the museums, guided Boston Harbor cruise, and Freedom Trail 2.5-mile walking tour to 16 historic sites.

Foodies and culture vultures will want to make time to visit the neighborhoods with lots of character, restaurants, and shops in the North End and Back Bay’s Newbury Street. Everyone can appreciate the beautiful library, downtown area, and Fenway Park.

Is 2 days enough in Boston?

Two days is enough time to see Boston’s highlights and get a good feel for the city. To pack as much into a 2-day visit as possible, start your days early and schedule your stops strategically to avoid back-tracking across the city.

What is the best month to go to Boston?

October is the best month to go to Boston overall. It’s when the fall foliage is at its peak, temperatures are mild and cool, fall festivities are in full effect, and walking through the city is absolutely perfect.

Seeing Boston decked out in natural orange, gold, purple, and red is stunning and really adds to the historic charm of this old American city.

So, Ready for a Weekend in Boston?

Boston weekends are far from lazy – there’s a lot to see and do in the bounds of this prominent and historic American city. Following a pre-planned itinerary like this one will help your trip go smoothly. 

Make sure to pack comfortable shoes for walking and a jacket or coat for cooler temperatures in the fall, winter, or early spring.

Bring an appetite to fill up on lobstah, chowdah, brews, and all the littleneck clams you can bear! Don’t be surprised if you find yourself ready to return in a matter of months – or even sooner.