A Boston Tour Guide by a Bostonian

I was born in Boston and have spent my entire life living in the Greater Boston area.  I lived in the city on and off when I attended Northeastern University and then spent 20 years working first in the Financial District and then in the Seaport District.  I pulled together this tour guide from the viewpoint of a Bostonian.  When someone tells me they're planning a trip to Boston and asks what they should do and see, the following is what I recommend.  

This list is not meant to be all inclusive.  Boston is small and walkable, but it's a major city and naturally, there is a lot to do here.  I have not included any bakeries, restaurants or the like made trendy by Instagram.  I'm not saying that those places are lousy.  When someone reads this three years from now, I want it to be relevant.

This is Boston as it has always been.



What To See and Do

The most convenient way to see the city and learn its history is through an organized tour.  I would suggest either Boston Duck Tours or Hop-On Hop-Off Trolley.  The Duck Tours are extremely popular and I would definitely recommend them if you have kids with you.  When I worked on the corner of Devonshire, Congress and Milk, my office was on the 4th floor and both of these tours would roll by my window.  Duck quacking and trolley ringing are completely normal city sounds to me.

Freedom Trail

The Freedom Trail is a marked 2.5 mile route through 16 historic points of interest in the City.  Walk as much or as little as you'd like.  You can even break this up over several days.  Note that you can book (and pay for) a tour but in my opinion, this is something you can do on your own and save some money in the process.

To see my blog post from when we walked part of the Freedom Trail with the girls, click here.

If you're a runner, there is a Freedom Trail 5K.  You run from site to site and stop at each for a few minutes.  All running abilities are welcome.  



Fenway Park

For baseball fans, seeing a game at historic Fenway Park is a fun outing.  Did you know you can also tour Fenway Park?  A few years ago, I toured Fenway Park with a group of co-workers and it was extremely interesting.  There's historical significance to Fenway so don't think you have to be a huge baseball fan to enjoy this.



Boston Public Library

Boston Public Library was established in 1848 and was the first free large municipal library.  If you're in the Copley Square area, check it out.  The building dates back to the late 1800s and it's amazing.  (The Boston Marathon finish line is right out front too.)

Boston Common and Public Garden

The Commons and Public Garden are located right next to each other and if you're in the city, I highly recommend taking a walk through both.  In the Public Garden, you'll find the Make Way for Ducklings statues and Swan Boats.

Where to Eat

There are so many places to eat in Boston but I want to focus on one particular area - Boston's North End.  The North End is not only Boston's Little Italy; it's Boston's oldest residential community.  Here you'll find tasty Italian restaurants along with historic buildings and sites.  

We love going out for pizza in the North End because, really, the pizza close to home just can't compare.  Okay, okay.  There are some excellent pizza joints outside of the city.  Our favorites include Town Spa in Stoughton and Zack's in Randolph.  Unfortunately, neither are close enough for convenient pick-up.  

Galleria Umberto

Simply referred to as Umberto's by locals, this counter service shop serves up Sicilian-style slices along with calzones and arancini.  When I worked in the Financial District, my co-workers and I would eat lunch here at least once a week.  It's that good.  They are only open for lunch, closing mid-afternoon when the food runs out, which means everything they serve is fresh.

This family owned and operated business began serving pizza in the mid-1970's.  The two brothers who work the counter know all their regular customers and go out of their way to give you the best service.  My friend really liked the corner pieces of pizza so if the owners saw us in line, they'd grab a new pizza and pull the corner slices for him.

Tips:  It's cash only and most crowded during the noon lunch hour.  It's not unusual for the line to snake out onto the sidewalk.  They are closed for one month (usually July) in the summer for vacation.  

Pizzeria Regina

This pizzeria opened in the North End in 1926.  Regina's pizzas have a thin crust with the proper ratio of cheese and sauce.  It's a hugely popular restaurant so get in line early.  It seems like there's always a wait too.  

To see photos from visits to Regina's, click here and here.



Sweet Stuff

For dessert, you'll want to visit either Modern Pastry or Mike's.  You can't go wrong with either.  I have photos and talk a little bit more about the difference between the two in this post here.  

Notes from a Bostonian

Faneuil Hall

I wanted to bring up Faneuil Hall because while it has historical value, it mostly seems like a tourist trap.  Take away the historical significance and it's really just a bunch of eating spots and stores, much of which you can find at home (Gap, Loft, etc.)  Now, if you want to shop for souvenirs, then, yes, this is a good place to visit.  There are quite a few shops selling souvenirs.  If you find yourself sightseeing and you're hungry and you want to grab something to eat, go right ahead and get some food.  Personally, I would not recommend Faneuil Hall as a place to spend a ton of time unless you are into shopping.   Note that it is on the Freedom Trail.

The building labeled as Quincy Market houses all the food kiosks.  If you do eat here, these are my recommendations:

• Pizzeria Regina - Not exactly the same at the original in the North End but close enough.
• Boston Chowda Co - Really tasty bread bowls, go for the clam chowda.
• The Chipyard - Freshly baked chocolate chip cookies.
• North End Bakery - I used to pick up a cannoli from this bakery whenever I was craving one but didn't want to trek to the North End.  

Working in the Financial District and, for a period of time, directly across the street from Faneuil Hall, I can tell you that it can become extremely crowded here, especially during the warmer months.  There are solicitors, street performers and school groups.  If you grab food from a kiosk, your best bet is to head upstairs to find a table.  It's okay to stalk people who look like they're wrapping up their meal.  It's an accepted practice.

Museums and Aquarium

As I mentioned above, this guide is not intended to include everything available in Boston.  However, I do want to mention there are many museums located throughout the city, as well as the aquarium.  Interest can be very specific depending on the type of traveler though.  Some people don't like aquariums, some people think looking at art is boring, some people don't have children.  If you do decide to visit one of the museums or the aquarium, try to plan for a non-busy time.  When is it busy?Warmer months, especially June through August, weekends, Massachusetts school vacation weeks and holidays.

Parking Tip

Parking in a garage, as to be expected, is expensive.  If you are staying outside of the city and want to drive in over the weekend, check out the Garage at Post Office Square.  Because it's in the Financial District, it offers reduced rates for weekends and weekdays after 4:00.  It may take you an extra five to ten minutes to walk to your destination but I think the savings is worth it.  For example, this is where I park when I bring the girls to see The Nutcracker.  It cost me $9 versus the $25 parking garages near the theater were charging.  I also park here for events at The Garden.



This is on Pinterest if you like to save posts there.