Fun Weekend in Boston (3-Day Boston Itinerary)
Visiting Boston for a few days? We just went and had an amazing time! I’m excited to share with you all of the fun things we did during our weekend in Boston!
This 3-day Boston itinerary is perfect for visitors looking to experience the best of the city’s history, culture, and charm.
From walking the iconic Freedom Trail and exploring the historic neighborhoods of the North End, to taking in the views along the scenic Boston Harbor, this travel guide offers the perfect mix of sightseeing, dining, and local flavor.
Whether you’re planning a weekend getaway or a short city break, this itinerary covers all the top things to do in Boston in 3 days.
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Day 1
Day 1: Historic Boston & Freedom Trail
On day one of this 3-day Boston itinerary, we will focus on the American Revolution history sites and the downtown area.
Boston Commons
You will want to start your morning at the Boston Common. This is America’s oldest public park. Lots of the tours will start in this area. You can book ahead of time or on-site.
Freedom Trail
I was so glad we booked a tour of the Freedom Trail. It was awesome to have a guide to tell us all of the amazing history behind the different sites. The tour lasts about 2 and a half hours.
We were able to visit the following sites:
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- King’s Chapel & King’s Chapel Burying Ground
- Old South Meeting House
- Old State House
- Boston Massacre Site
- Faneuil Hall Marketplace
- Paul Revere House
- Old North Church
Lunch
A great place to backtrack to is Quincy Market. You can try clam chowder in a bread bowl at Boston Chowda. You can also get that famous banana pudding at Magnolias (we did this in New York!) So good!
If you have a less adventurous eater, there is also Pizzeria Regina and the Dog House.
After lunch, I would choose either heading to the USS Constitution or the Tea Party Museums. Both are so cool.
We opted for the USS Constitution. This ship was built in 1799. It is still a commissioned Navy ship. It was used in the War of 1812.
This ship was so well constructed that it has lasted over 200 years!
You will get to tour the ship. There is a museum that is very interactive and fun for kids.
For Dessert, head over to Mike’s Pastry or Modern Pastry.
Evening Out
I highly recommend dinner in the North End. There are lots of Italian restaurants. I’m talking homemade noodle and all. So So Good.
You can try out places like Carmelina’s, Giacomo’s, or Mamma Maria. We decided to go with Carmelina’s. It was amazing!
We had been told by many people that Modern Pastry is the better choice for cannolis, so we got a cannoli and a pastry there.
Sunset Cruise
If you have time after dinner, you could go on a Harborwalk along the waterfront. If you are really adventurous, the last sunset cruise leaves at 7:30 pm.
Day 2
Day 2: More City Adventures
There is so much to see in Boston. Day 2 will hit some of the things we missed on day 1.
Breakfast
Boston is known for its brunch places. We were able to try a few.
We had Little Luna and Cafe Beatrice. They were both amazing. At Cafe Beatrice, we tried some pastries and the breakfast tacos.
I highly recommend the breakfast tacos at Cafe Beatrice. The best thing at Little Luna was the French toast. I highly recommend both restaurants.
Harvard and Longfellow House
We decided to explore Harvard. You can book a campus tour or just drive around. We took a short walk to visit the Longfellow House – Washington’s Headquarters National Historic Site.
It was once the home of poet Henry Wadsworth Longfellow, and it also served as George Washington’s headquarters during the Siege of Boston.
The home is beautifully preserved and offers guided tours filled with literary and historical depth.
One thing I will say is that the tour is long! It is a lot of standing. I loved learning, but I felt like the tour should have been 20 minutes shorter.
After visiting this site, I would pick one or two of the following activities:
- Fenway Park (Historical tour or see a baseball game)
- Tea Party Museum or USS Constitution (If you didn’t do it on day one)
- Food Tour
- Boston Harbor Boat Tour (Codzilla, Duck Boat, or Sightseeing Tour)
- Plimoth Plantation (If you are traveling with kids)
We loved taking our kids to Plimoth Plantation. It was so fun for them. You will have so much fun no matter what you choose!
Dinner in Boston
There are so many amazing restaurants in Boston. We went to the Puritan. It was really good. They had a variety of different options.
Day 3
Day 3: Day trips from Boston
If you have access to a car and would like to get out of the city, there are some amazing sites near Boston to check out.
Lexington And Concord
I was so excited to take a day trip to Lexington and Concord (about 30–45 minutes from Boston). These picturesque towns were the sites of the first battles of the American Revolution.
We were able to walk the Battle Green in Lexington, visit Minute Man National Historical Park, and reflect at North Bridge in Concord, where “the shot heard ’round the world” was fired.
There are historical houses all along the road where you can pull off and take tours.
In Lexington there are amazing tours that visit the following areas:
1. Buckman Tavern
Why it’s historic: Militia gathered here before the Battle of Lexington.
Tours available: Yes, seasonally (spring–fall); guided or self-guided options.
Highlights: Restored interior, Revolutionary War exhibits, and period artifacts.
2. Hancock-Clarke House
Why it’s historic: Paul Revere stopped here to warn John Hancock and Samuel Adams on April 18, 1775.
Tours available: Yes, guided tours only.
Highlights: 18th-century furnishings, personal stories of the Revolution.
3. Munroe Tavern
Why it’s historic: Used as a British field hospital during the retreat from Concord.
Tours available: Yes, often in combination with the other Lexington homes.
Highlights: British perspective of the Revolutionary War
In Concord
1. The Old Manse
Why it’s historic: Home to both Ralph Waldo Emerson and Nathaniel Hawthorne.
Tours available: Yes, offered by The Trustees of Reservations.
Highlights: Literary and Revolutionary history, original 18th-century features.
2. The Wayside: Home of Authors
Why it’s historic: Home to Louisa May Alcott, Nathaniel Hawthorne, and Margaret Sidney.
Tours available: Seasonal National Park Service tours.
Highlights: Focus on literary and family life in the 19th century.
3. Orchard House
Why it’s historic: Home of Louisa May Alcott and where she wrote Little Women.
Tours available: Yes, guided tours year-round.
Highlights: Original furnishings, Alcott family belongings, focus on daily life.
Visit Salem
Cape Cod
Cape Cod is a perfect day trip from Boston, offering a refreshing escape filled with coastal charm, sandy beaches, and classic New England scenery.
Just a 1.5 to 2-hour drive away, or you can take a high-speed ferry, Cape Cod invites visitors to explore quaint seaside towns like Sandwich, Chatham, or Hyannis, enjoy fresh local seafood, walk scenic beaches, and even spot lighthouses and seals.
Whether you’re in the mood for relaxing by the water, biking along the Cape Cod Rail Trail, kayaking, ziplining, or browsing local shops, it’s an easy, relaxing getaway from the city.
Are you Ready For A Fantastic Weekend in Boston?
Whether you’re a history buff, foodie, or just looking to experience classic New England charm, Boston offers the perfect blend of culture, adventure, and walkable city fun.
In just three days, you can explore the Freedom Trail, enjoy world-class museums, savor delicious local eats, and soak in waterfront views, and even have time to venture out of the city!
From cobblestone streets to iconic landmarks, Boston is a city that leaves a lasting impression and plenty of reasons to return. Enjoy your weekend in Boston!
I know you will have so much fun on your weekend trip to Boston. If you don’t have 3 days be sure to check out my 1-day in Boston itinerary!
If you have more time on the East Coast, check out all of the amazing East Coast historical sites, East Coast National Parks, or other East Coast Family Vacations I have you covered.
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