5 Day Boston Itinerary

 5 Day Boston Itinerary

Boston, and the surrounding area, is full of pivotal historical sites, beautiful parks, delicious food and interesting museums.  Spending 5 days exploring Boston and the area around it will allow you enough time to try a bit of it all.  Here is our ‘5 Day Boston Itinerary’ perfect for seeing the best of Boston and the surrounding area. 

5 Day Boston Itinerary Overview

  • Day 1: Walk the Freedom Trail, Quincy Market
  • Day 2: Lexington/Concord, Tour Harvard 
  • Day 3: Day Trip to Portsmouth
  • Day 4: Boston Tea Party Museum, Boston Public Market, North End
  • Day 5: Explore Salem 

Note: This itinerary is best set-up for arriving the day before and leaving the day after (this is what we did).  Alternatively, you could fly-in very early on day 1 and fly-out very late on day 5.  If traveling with littles, we do not advise this though.  Set yourself up for success and arrive the day before and leave the day after if you time allows. 

Disclosure: This article contains affiliate links. That means that, at no cost to you, we may get a small commission if you purchase through these links. This helps us keep providing travel resources for you! 

We took this trip when our daughter was 2.5 years old and our son was 8 months old.  For more information on exploring with a baby, please see our Top 10 Baby Travel Tips, How to Hike with a Baby, 5 Top Baby & Toddler Flying Tips and Flying with a Baby posts. 

Day 1: Walk the Freedom Trail, Quincy Market

On the first day of your 5 day Boston trip, walk the Freedom Trail.  This 2.5-mile trail takes you through the city to 16 different historical sites that were vital during the Revolutionary War and other historic events.  Walking this trail is a great way to see a lot of historical landmarks located in Boston in a relatively short time frame.  It’s also a great first day in Boston activity because it will help orient you to the downtown area.  On this trail you’ll see

  • Boston Common (Boston Public Garden Adjacent to this)
  • Massachusetts State House
  • Park Street Church
  • Granary Burying Ground
  • King’s Chapel Burying Ground
  • Benjamin Franklin statue and the former site of Boston Latin School
  • Old Corner Bookstore
  • Old South Meeting House
  • Old State House
  • Site of the Boston Massacre
  • Faneuil Hall (Quincy Market across from here)
  • Paul Revere House
  • Old North Church
  • Copp’s Hill Burying Ground
  • USS Constitution
  • Bunker Hill Monument

Be Your Own Guide

 5 Day Boston Itinerary

Download the Freedom Trail Brochure for more information on each spot on it.  We printed off this brochure and then took turns reading about the historical sites when we arrived at each while walking the trail.  You can alternatively take a guided tour of the Freedom Trail (offered by many different companies).  We opted for time independence, the ability to spend as little or much time at each spot as we wanted and the ability to deviate from the path as we desired.  We highly recommend this option as we spent a lot of time at Boston Common and then the adjacent Boston Public Garden (not part of the trail).  The Freedom Trail is easy to follow too.  Locate the brick path that marks the trail (2 bricks, sometimes painted) in the middle of the sidewalk (picture centered above of what the bricks look like) and simply follow it.  

 5 Day Boston Itinerary

We’d recommend budgeting at least 4 hours to walk this trail with breaks.  The most efficient way to walk it is to start on one end, walk to the other end and then Uber back to the beginning (if you need to get to your car).  We opted to start in the middle of the trail at Faneuil Hall/Quincy Market.  We first went southwest towards Boston Common, and then we retraced our steps back to Faneuil Hall/Quincy Market for lunch.  Then, we continued on the trail Northeast to the North End/Bunker Hill before retracing our steps back to Quincy Market.  It took us about 7 hours to walk the trail, but we walked it back and forth (started and ended at the same point) and took quite a bit of time to explore many spots just off but not on the Freedom Trail.  

Close to Freedom Trail Highlights

Some of our favorite stops while walking the Freedom Trail were not actually on the Freedom Trail but just off of it.  Hence why we think being your own tour guide of this trail, especially with how well the trail is marked, is your best option.  

Boston Common Park and Boston Public Garden

We spent a lot of time at Boston Common Park (part of trail) as well at the adjacent Boston Public Garden (not part of trail).  Boston Common Park is the oldest public park in the US.  It used to be a pasture for sheep and then a training ground during the Revolutionary War. Now it is a park where many famous people have spoken including Martin Luther Jr. and John Paul II.  It has a lot of open green space and paths.  There’s also a playground and a carousel at this park (not in operation during our visit though).  

 5 Day Boston Itinerary

Likewise, Boston Public Garden, across the street from Boston Common Park, was one our favorite places to explore in Boston.  This park is home to statues of the ducks from the Classic Robert McCloskey Make Way for Ducklings book.  Our daughter loved visiting these ducks SO much.  She ‘fed’ and hugged each.  She also had her stuffed cow ‘play’ with them.  The simple statues were such a hit.  At Boston Public Garden, there are also the iconic swan boats you can ride in the pond here (although not in operation during our spring weekday visit).  Further, if you are a fan of the show Cheers, you can hit up the Cheers Bar while here as it is right across the street from the park on the north side.  

Marlborough Street and Commonwealth Avenue

Some picturesque streets to explore, just east of the park, include Marlborough Street and Commonwealth Avenue.  These streets are lined with pretty townhouses and a tree-covered path even runs through the center of Commonwealth Avenue.  We actually visited these on another day (when we watched the Boston marathon) but easily could have added onto the Freedom trail.  These streets have all the northeast charm and are the perfect spot for a leisurely stroll.  If staying in the city center of Boston, we highly recommend being as close to these streets, Boston Common and Boston Public Garden as possible. 

Quincy Market 

About midway along the trail, the Quincy Market (not part of the trail), just adjacent to Faneuil Hall Marketplace (on the Freedom Trail), was another spot we enjoyed.  It is a good stop for a relatively quick and inexpensive bite to eat.  The market is filled with many different food vendors so everyone can get whatever type of food their heart desires.  We all opted for different specialty pizza slices from Regina Pizza, a Boston original pizzeria.  There was also an entertaining electric violinist in the main dining area and many other small specialty shops in the market.   As travelers who like people but not crowds, beware that this market is rather busy though. 

Greenway Carousel

Not far from Quincy Market is another one of our toddler’s favorite Boston spots, the Greenway Carousel.  This carousel is unique in that it is filled with animals native to the area.  It has whales, sea turtles, squirrels, rabbits, foxes and owls.  Our toddler got a real kick out of riding on both the fox and rabbit (and her stuffed cow got to ride too).  Each ride is only a couple dollars.   See our Boston with a Baby or Toddler post for more toddler and baby friendly Boston ideas.

Logistics Tip

If planning to drive into Boston and start/end your day at Quincy Market (like we did), you can park at the Boston Harbor Garage.  It is pricey ($44 a day) but very convenient and the price is on par with the other structures in the area.  If you arrive before 8:30 am though, parking will only cost you $25.  If you do not mind walking a little farther and are visiting on a weekend, park in this uncovered lot for only $5 (you will not find parking cheaper anywhere else in Boston, weekends only). 

Dinner at Paramount

If looking for a great dinner spot with super tasty food and tons of variety, head to Paramount in Beacon Hill. This restaurant has been open since 1937 and is well liked by locals and visitors.  As a party of 8, we each got something completely different but everyone liked it.  Even Natalie’s Dad, who may be the harshest critic, enjoyed it.  

Day 2 of 5 Day Boston Itinerary: Lexington/Concord, Tour Harvard 

On day 2 of your 5 day Boston itinerary, head to Lexington and Concord in the morning and then tour Harvard in the afternoon.  


Lexington is the spot where the Revolutionary war started on April 19, 1775.  On this day, Paul Revere rode from Boston to Lexington to warn the town that the British were coming.  The Revolutionary War then started here when the Redcoats arrived.   

 5 Day Boston Itinerary

The main historic attraction in Lexington to visit is the Lexington Green where the first clash between Minutemen and Redcoats happened.  Before walking around the Lexington Green, stop in the Lexington visitors center for a map that explains the Lexington Green sites.  We were able to walk the green at our own pace this way. Including our visit to the Visitors Center (fun souvenirs and some historic displays), we spent about an hour here.  There is also the Buckman Tavern Museum (where Minutemen prepared for the Redcoats arrival) you can tour.  Although we have not toured it ourselves, the general consensus from everyone we talked to is that the museum is not worth the cost of admission.  

Tip: Check to see if reenactment occurs during your visit.  We were visiting Boston around Patriots Day (April 19th, commemorates the start of the Revolutionary War) and there were several reenactments in the area.  Sam and Natalie’s Dad attended one at the Lexington Green.  It was a unique, and likely once in a lifetime, experience that any history buff would enjoy.  


Concord is only 5 minutes away from Lexington.  Like Lexington, it is another hub of key historical sites.  Here you can walk across North Bridge, the site of the Shot heard around the world, and watch the 30 minute “The Road to Revolution” presentation at the Minute Man Visitor Center.  If only doing these activities, budget an hour here.  If looking to spend more time in Concord, you can also walk 5-Mile Battle Road Trail that connects Meriam’s Corner in Concord to Lexington, visit The Old Manse (house that Ralph Waldo Emerson and Nathaniel Hawthorne both called home) and visit the Sleepy Hollow Cemetery (not “The Legends of Sleepy Hollow” Cemetery but where famous authors mentioned above are buried).  


 5 Day Boston Itinerary

In the afternoon on day 2 of your 5 day Boston trip, after visiting Lexington and Concord, head to Harvard for a guided tour of the first college founded in the US in 1636.  It’s very interesting to learn about this historic and prestigious college.  The college campus itself is beautiful as well with many historic brick buildings.  Harvard offers free guided tours daily.  We took the 3 PM tour.  Sign up the Friday prior online with the link above to the tour you want to take.  The tours do not book up instantly but be sure to set an alarm early in the morning on the preceding Friday to book the tour time you want to take to ensure you get the time/date you want. 

Day 3 of 5 Day Boston Itinerary: Day Trip to Portsmouth

On day 3 of your 5 day Boston itinerary, take a day trip to Portsmouth, New Hamshiphere.  Portsmouth is a charming New England port city about an hour north of Boston.  It is actually the 3rd oldest town in the US and is filled with colonial architecture.  Portsmouth’s downtown area has many local boutiques and restaurants.  Market Square, the center of this picturesque downtown, is easy to locate with the tall white steeple North Church as the focal point.  Start your visit to Portsmouth at Market Square as it is a good stepping off point for exploring the rest of the downtown area by foot. We spent the morning walking on brick lined streets and checking out the different local shops. 

Portsmouth Activities

Beyond the downtown area and local shops, this town has many other highlights including the parks, museums and waterfront eateries.  We enjoyed lunch at the River House.  Here we were able to dine on the waterfront and have some really delicious seafood (the best of our trip).  We then headed to waterfront Prescott Park.  This simple park has some walk out piers and some nice green space.  

Right next to this park is the open air Strawberry Bank Museum.  Although closed during our visit (open May-October), we were able to see some of the preserved historic buildings on the outside of the grounds.  Right across the street from some of the buildings of this museum is a park of swings (the highlight of our visit to Portsmouth for our toddler).  To round out our visit to Portsmouth, we drove across Memorial Bridge into Maine (we were able to be in 3 states in one day with only an hour of driving).  

Stop at a Local Ice Cream Stand

On your way back to Boston (set GPS to avoid tolls), be sure to stop at Lagos Ice Cream, a homemade ice cream stand with the BEST ice cream.  If you know us in real life, you know we take our ice cream very seriously and this ice cream was SO good.  There were about 50 flavors to choose from here. We tried the Funky Panda which is a vanilla based ice cream with caramel, oreos and coconut.  It was delicious and seriously the best ice cream we have had in a long time.  Important note–only cash is accepted.

Day 4: Boston Tea Party Museum, Boston Public Market, North End

On the 4th day of your 5 day Boston trip, head back into downtown Boston in the morning.  Today your first stop will be the Boston Tea Party Ships and Museum.  At this museum, you’ll take a 75 minute tour of the Boston Tea Party ships and learn more about the history of the events leading up to and after the Boston Tea Party.  The actors that put on this tour really make it fun and engaging. You’ll even get to throw tea overboard into the harbor at one point.  This museum is open 7 days a week 10am-5pm (tours about every 30 mins) and costs $34/person.  You can make reservations in advance online but it seemed like there was plenty of availability on most tours to join as a same day/walk up add on. 

Parking Tip: If visiting on a weekend and driving into Boston, park in this uncovered lot for only $5 (you will not find parking cheaper anywhere else in Boston, weekends only). 

Boston Public Market for Lunch

After visiting the Boston Tea Party Museum, walk to the Boston Public Market for lunch.  This market is filled with local vendors and different food options.  Seafood, donuts, bagels, middle eastern food, etc.  This market was quieter and less bustling than Quincy Market, which was a welcomed change of pace. 

North End for Cannolis

After having lunch at the Boston Public Market, head to the North End for dessert.  The North End of Boston is the Italian district with all the best Italian restaurants and pastry shops.  Get a Cannoli from both Mike’s Pastry and Modern Pastry.  Many local Bostonians debate which shop has the better Cannoli.  Natalie votes Modern and Sam votes Mike’s.  Toddler votes both as “really good”.  You’ll have to try both to see which one you like better yourself! 

Day 5 of 5 Day Boston Itinerary: Explore Salem 

On the last day of this 5 day Boston Itinerary, head to Salem, the infamous site of the Salem Witch Trials in 1692.  This city is steeped in history and New England Charm as well.

Spend a ½ day or full day exploring this spooky city.   Start your time in Salem by stopping into the Salem Visitors Center.  Here, the staff will be able to tune in to any local happenings that day and give you a map.  From here, head to the Salem Witch Trials Memorial, about a block away north of the visitors center.  This simple memorial has stone benches for each victim of the witch trials.  During these trials, 19 people (14 women and 5 men) were killed.  Reading how each person died (most hung, one pressed to death) really drove home what happened here in the 17th century.  

Essex Street and McIntire District

After visiting the Salem Witch Trials Memorial, head north a couple blocks to stroll down Essex street.  This street is filled with many local and spooky themed stores.  Halloween really is a year round season here.  On Essex street, you’ll also be able to stroll past the Elizabeth Montgomery Bewitched Statue and the House of Seven Gables.  This house was made famous in Nathaniel Hawthorn’s book.  You can go inside of it but the consensus is that it is not worth the admission cost. 

 5 Day Boston Itinerary

From the House of Seven Gables, continue west on Essex street.  You’ll walk past the medieval appearing First Church in Salem and the historic Ropes Garden and Mason.  From here, head south on Chambridge street to Chestnut street.  Chestnut Street is part of the McIntire District in Salem.  This district is filled with some of the finest pre-twentieth century homes in America.  Many of Salem’s most important citizens, including Nathaniel Hawthrone, lived in homes here. Each house has a sign on it indicating the year it was originally built and any historical figures who lived there.  Walking up and down this street was our favorite part of our visit to Salem.  You can also head north and explore Federal Street to see more of these picturesque homes.  

Local Ice Cream, Coffee & Parks

After walking around Salem, head back downtown to get coffee and/or ice cream at two local shops, Odd Meter Coffee Co. and Melt Homemade Ice Cream,  only one door apart from each other.  The homemade carrot cake ice cream at Melt was the perfect afternoon treat.  After this we headed to Salem Common Park where there was a nice playground for our toddler to play on.  If looking for a less bustling option to end your time in Salem, head to the lighthouse at Winter Island Park.  

We found Salem easy to navigate ourselves and appreciated being able to explore at our own pace.  If you’d prefer a guided tour, there are plenty of those too.  The visitors center will be able to tune you into any tours going on the day you visit.  

Where to Stay in Boston

On your 5 day Boston trip, we recommend staying in a central location a bit north of the city center.  A central location outside of the city will make day trips shorter and will be more cost effective than staying in downtown Boston.  We recommend staying at the High Rock Home in Lynn, about a 30 minute commute north of Boston. This condo’s central location, ample square footage, back patio, family friendly amenities and helpful host all made our stay great.  Read more on why we’d recommend this Airbnb in our Where to Stay in Boston as a Family post.   

We hope this guide helps you plan your 5 day Boston trip.  Anything you’d add to our guide? We’d love to hear your feedback and questions.  Please leave us a comment!

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