A day or weekend in Boston

Boston is the perfect city for a walking tour where most of the attractions are within walking distance of one another.  A perfect trip for history, architecture, museum, or urban enthusiasts.


You have 4 options to get in and  out of the city.

  1. Drive in and park
  2. Drive to a T station, park and take the T
  3. Drive to a commuter rail station, park, and take the commuter rail
  4. Fly into Boston Logan and take an Uber or the T to your destination

Depending on your comfort level with driving, public transit and how many people are traveling, each option has its pros and cons.

  • Drive in and park ($20 for family of 2; $20 for family of 4). Parking in the city can be expensive if you park in one of the touristy parking garages ($50+).  I’d recommend looking at www.spothero.com before you enter into the city to find affordable parking.  I typically use one of two garages in Boston:
    • Boston Common Garage- although this is right below the Boston Common and in a great tourist location, it is typically around $20. 
    • 660 Washington St. Garage- This garage is in Chinatown over near the theatre district.  It is easy on and off the highway and only about $25 (cheaper if going to a show). 

While you can find cheaper parking throughout the city, or even street parking if you are savvy, I find these two to be easy to get to and relatively affordable for their location.

The other word of caution is that Boston is not the most driver friendly city.  It has long historical roads so streets are not always in a grid format and can be difficult to navigate.  If you do not mind driving, then this would be the option that I recommend (and the one that I use).  You can find parking options that aren’t too expensive and it gives you the greatest flexibility to come and go as you please.

  • Drive to a T station, park, and take the T. ($20 for family of 2; $29 for family of 4)
    • There are several T stations that are in suburban areas that will have cheaper and easier parking than the inner city.  The T will cost $2.40 per person per trip and parking is typically $5-10 at the station.  This is a slightly more affordable option if there are only a few in your party and comes with less headaches.  However, where you park, will depend on which direction that you are coming from so check the T maps and parking options. The T gives you more flexibility than the commuter rail as trains run continuously from 5am-12:30am, whereas the commuter rail trains are far less frequent and will require advance planning.
  • Drive to a commuter rail, park, and take the commuter rail. ($30 for family of 2; $50 for family of 4)
    • This is a great option if you do not like to drive but live in the suburbs.  The commuter rail extends out as far as Worcester so you can often find one nearby with plenty of parking.  The commuter rail has a more rigid schedule and can be expensive with  Worcester to Boston at $13.25 each way per person plus the price of parking at the station.  However, there is a weekend deal that gives you unlimited commuter rail access for just $10 per person.   
  • Fly into Boston Logan
    • Boston is a major city and a hub for Jet Blue and Delta with several flights for United and American, as well.  Fares are relatively inexpensive and there is a T station at the airport that can take you any where you wish to go in the city. 


Boston is an excellent day trip, but it can easily be a long weekend as well, depending on what you would like to do.  If you do plan to spend the weekend in the city, I’d recommend going in the off season as most of the downtown hotels will be in the $300-500/nt range during the summer months but drop to $100-200/nt starting in November.  When looking for a hotel in the city, it is all about location as you will be spending little time in the hotel and most of the time adventuring around the neighboring area.  Boston is no different in this aspect and therefore I would recommend either staying on the Waterfront or in Back Bay.  These two neighborhoods are clean, safe, have close proximity to attractions and have plenty of nearby restaurants.


If you only have a day in Boston, I’d recommend this five mile walking tour.  This walk is relatively flat and gives you a mixture of history, architecture, museums, waterfront, and urban vibes.  The MBTA (T) system also runs throughout the journey, so if you wish to cut down on some mileage, you can hop on and off the subway for a quicker journey.

Start at the Arlington T stop which is on the corner of the Boston Garden. 

If you enjoy shopping, start your day by walking down Newbury St.  Enjoy higher end fashion, art, and home wares as you enjoy the beautiful brownstone architecture, keeping in mind that the further down you go (closer to Mass Ave), the more affordable things seem to get.

Then cut through the Boston Garden and Boston Common.  Stop to enjoy the many statues, gardens, street performers, and fountains throughout the area.  If it is winter, take a quick skate over at the Frog Pond in the Boston Common.

Next, it’s time to walk through Beacon Hill, which is the epitome of Boston with its beautiful brownstones, cobble streets, and large hills.  You can either walk down Charles St. to Pinckney St. to Joy St. or go straight though from Boston common down Joy St.  If you have not been, I’d recommend starting at Charles St. as there are many cute restaurants and shops and you will get a better feel for the neighborhood.

On the other side of Beacon Hill, you will approach Government Center walking through to Quincy Market and Faneuil Hall.  Stop at the Sam Adams Statue as you approach and enjoy some time walking through the shops and down through Quincy Market, stopping for a quick snack at one of the many vendors.  This area is beautiful at Christmas time, well lit for the holiday season making a great spot to do some Christmas shopping.  I recommend Pepper Palace or The Boston Pewter Company for those difficult people on your list.

Once you have done all the shopping that you can do, head into Boston’s Italian North End for lunch and a pastry (Mike’s Pastry or Modern Pastry) and while you’re there, visit some of the stops on the Freedom Trail as this is one of the most historic neighborhoods in the city, home to the Paul Revere House and Statue, Copps Hill Burial, and Old North Church.

Lunch spots:

  • Carmelina’s (sit down lunch)
  • Pauli’s (sandwiches)
  • Locale (sit down pizza)
  • Rina’s (more casual pizza)

After lunch continue down the Freedom Trail to get views of the waterfront and additional historic sites.

Finally, enjoy the evening down in the theater district.  Catch a show, shop in downtown crossing, enjoy a leisurely dinner or catch a Boston Harbor Cruise.  I lived in Massachusetts for over 30 years before I took the Boston Harbor Cruise and it was well worth it.  It is a beautiful view of the city skyline and the captain gives you a quick history lesson about the city.  We were lucky and got the true Boston feel as a man from Ireland was our captain for the evening.  The cruise takes about 90 minutes and leaves from the Battery Wharf area.  This also gives you the opportunity to have some of the best seafood in the country as you can eat right on one of the fishing piers.   If seafood is not your thing, not to fear, as there is something for everyone in downtown.

  • Get Dim Sum over in Chinatown (Bubor Cha Cha (casual) or China Pearl)
  • Mexican at Citrus and Salt
  • Live Jazz and Cocktails at The Beehive
  • Steaks at Grill 23
  • Seafood anywhere on the waterfront (Legal Harborside, The Chart House, Row 34)

Weekend Itinerary:

  • Red Sox game at Fenway
  • Jillian’s
  • Newbury St.
  • Boston Garden/Boston Common
  • Beacon Hill
  • Government Center
  • Quincy Market and Faneuil Hall
  • North End (Time for lunch)
  • Freedom Trail
  • Downtown crossing
  • The theatre district for a show or Boston Harbor Cruise

Friday Night

Head into the city Friday after work and catch a Red Sox game at Fenway Park.  There is no more Bostonian thing to do than enjoy a $10 beer in the country’s oldest stadium.  Whether you like baseball or not, this iconic evening will not leave you disappointed.   

If you have time before the game, stop in at either Cask n Flagon or Boston Beer Works to grab a beer and a bite to eat before heading into the stadium.  These places start to fill in early, so you’ll need to get there well before 6pm to get a table in time to make it to the game.  If you don’t have that much time, grab a sausage from Che Chi’s sausage cart outside gate E on Lansdowne St.

After the game, swing over to Jillian’s for a few games of pool or some bowling to end your classic evening.


See the Day trip itinerary for your Saturday


Sunday is a great day to complete your Freedom Trail walking tour with stops at the Old State House, Boston Massacre, The Great Spring, Old Corner bookstore, Old South meeting house, and Ben Franklin’s birthplace.  If you have some extra time, I would recommend spending it on the waterfront with either a trip to the Boston Aquarium or on a Whale Watch.  Both of these activities will take about 4 hours but are a great way to round out your trip. 

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