Epic One Day Boston Itinerary With Teens In Fall

Last Updated on March 13, 2024 by Nicole

My oldest daughter went to College outside of Boston. Over the years, I spent a fair number of days wondering around Boston either with her, or with my other 3 kids. We have eaten at some amazing restaurants, learned about early American history, and much to my teenagers’ delight, done some serious wallet cleansing shopping. After this last trip, I thought I would put together an epic one day itinerary with teens in Boston in fall. This itinerary is packed with the best things to do with teenagers in Boston in September, October and November.

Warning: This itinerary is heavy on eating, shopping and fun!

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Other Options

If you are keen to visit cool cities in the United States that will capture the attention of your teens, then you are in luck. There are lots from which to choose!

For other amazing destinations, please see:

• 10 Best Things To Do With Teens In Summer In New York;
• An Action Packed 3 Day New York City Itinerary In Summer With Teens; and
• Best 5 Day Itinerary In Winter In New Orleans With Teens.

Boston In Fall With Teens

Boston has a terrific vibe. It is great walking city. It is relatively flat with a lot of the major tourist attractions being an easy 30 minute walk between each other. There is a lot of interesting architecture, shops and history on almost every block.

Even though it’s a major city, Boston has a laid back feeling to it. Even in the centre of the city, you sense that people are busy, but not too stressed about it.

Accommodation and Transportation Tips In Boston

Two things about Boston that you should know before embarking on this fantastic one day Boston Itinerary with teens – Accommodation can be expensive and travel by car is a hassle. I have two recommendations.

Try to Stay Outside the City

On my last trip, we stayed at The Lodge at  Brandeis University.  Brandeis University is located in Waltham, a suburb of Boston. It is located on the Fitchburg line on the Commuter Rail and only takes 25 minutes to reach North Station in downtown Boston. There are lots of trains all day and into the night.

The Lodge offered 6 standard rooms at $90 USD (taxes included) and 2 suites at $120 USD (taxes included). Two of us stayed in a standard room which was comfortable with a nice bathroom, a fridge and microwave. I would stay there again.

Of course, if you have a decent budget, then there are several hotels in downtown from which to choose, including some Boston hotels with rooftop pools or Boston hotels with indoor pools for something extra special.

Avoid Travel By Car

There is nothing wrong with travelling by car. It is just not the most economical or timely choice in Boston. Boston has an excellent train and subway system that is inexpensive and much faster than travel by car.

Boston is an old city with a road system that does not always offer the most direct route to a destination. In addition, most travel within the city are on streets with only a couple lanes of traffic. There are highways but they circumvent the city or go underneath through tunnels, getting you to your destination through roundabout routes.

On several trips to Boston, I have been surprised by the cost of an Uber or a Lyft because the distance on the map does not represent the actual route a car has to take to get to that destination.

One Day Itinerary With Teens In Boston In Fall

Granted this one day Boston itinerary is jammed packed with amazing things to do. It is entirely possible to do all of it in one day – we did. But you can also spread out these activities over a couple days or long weekend. They are all fantastic things to do with your teenagers in Boston and a wonderful way to spend some time together in this beautiful city, especially in fall when the fall foliage begins to come out.

Start With The Boston Secret Food Tour

We did the Boston Secret Food Tour and it was fantastic. It started at 11:00 am a couple of subway stations away from the North Station and lasted for approximately 3 hours.

We spent most of our time in the North End of Boston, also called “Little Italy”, but also explored nearby Boston Public Market. 

Boston Public Market houses approximately 35 businesses that produce locally sourced ingredients or prepared meals or foods. It also offers public education, accessibility and affordable food for the community.

The cost was $65 USD for the tour. For the amount and variety of food that we ate, it was well worth the cost. You won’t need breakfast or lunch, and you won’t want an early dinner either! It was an absolutely fantastic tour.

North End

In Little Italy, we did the following:

• Had pumpkin ravioli with cream and pancetta (unbelievable!) and pizza at Bencotto.
• Had a coldcut, cheese, and muffaletta spread on fresh crusty Italian bread at Salumeria, one of the most popular Italian grocery stores in the North End.
• Tasted local beer and cider at the Golden Goose Market and Cafe.
• Finished off the tour with a freshly made cannoli at Modern Pastry, an old established Italian bakery with a long history of baking.

Boston Public Market

In the Boston Public Market, we did the following:

• Tasted honey at the Boston Honey Company. (Who knew that there were so many different flavours of honey depending on what flowers the bees pollinate???)
• Ate artisan nuts at Q’s Nuts. The flavours, like Mexican chocolate almonds or Cayenne Mango cashews, were insanely good.
• Ate a lobster roll at Red’s Best. The lobster was literally a few hours out of the ocean and exceptionally fresh.

Discover The Secret Shop

After the tour, head to Bodega, a short subway ride away. Bodega is an expensive and trendy men’s clothing shop. However, what makes this store a fun destination is that the store is hidden behind an intentionally scruffy convenience store. The only way to access the men’s clothing shop is to go into the convenience store and know where to find the door and how to open it. Once through, you are in a modern hip space that is fun to explore, even if you shake your head and say “no” to every single expensive thing your teenage son picks up.

Explore Boston Common

Hop back on the subway and head to Boston Common. This is a beautiful 50 acre park in the middle of Boston and the historical district. I don’t think any Boston itinerary would be complete without visiting Boston Common.

This is where we started our Freedom Trail tour on another trip to Boston, something that I would highly recommend doing if you have more than one day to explore Boston with your teen.

The Freedom Trail  is a 2.5 mile path that you follow which takes you on a journey into and through key moments of the American Revolution. You can do a self guided tour, a free walking tour, or paid tours. A self guided tour would allow you to spend a little bit of time on the Freedom Trail and then, get back on this one day Boston itinerary.

Regardless of whether you do some or all of the Freedom Trail on this day, I would recommend spending a little bit of time walking through this park. It is filled with trees and grass with lots of things for both kids and adults to enjoy.

Shop Along Newbury Street 

Just off Boston Common is Newbury street, a mile long street filled with gorgeous 19th century brownstones, shops and restaurants. The shops close to Boston Common are high-end and expensive, but don’t let that deter you. They are certainly beautiful to look at, but as you walk along and away from the park, less expensive yet cool boutiques start popping up. There are a few standard stores that you expect to see in every major city, but for the most part, these shops are small, unique and definitely fun to explore.

A perennial favourite of my kids is Nordstrom Rack Newbury, one block up on Boylston Street. I can’t remember ever walking out of that store without someone carrying a bag or two.

Treat Yourself At Georgetown Cupcake

By now, you might want to sit down and rest your feet so you might as well go and have a gourmet cupcake at Georgetown Cupcake on Newbury Street.

There are dozens of flavours from which to choose. The good news is that they are not too big, so you won’t have any problem rationalizing having another treat.

If you want to make friends, tune into the “fridge” cam in the morning to find the “Secret Flavour” of the day for a free cupcake and let your friends know. There is a limited supply so perhaps you should stop here in the morning on your way to the food tour. Just saying…

Eat A Late Dinner At Giacomo’s Restaurant

It’s dinnertime, right? Without a shadow of a doubt, one of the best Italian meals that I have ever eaten was at Giacomo’s Restaurant back in the North End. Be prepared to wait for your table, even with a reservation. I’d list all the must have entrees but there is no point. I have yet to eat anything that wasn’t mouth watering and utterly worth the wait.

Laugh At Improv Asylum

Also in the North End is the Improv Asylum, a comedy theatre featuring improvisation and sketch comedy. There are a couple shows a night that are family friendly (my 13 year old daughter had a blast), with a midnight show that is not! Tickets are well priced. It is a really fun way to bring your night and this epic one day Boston itinerary with your teens to a close.

***For a handy list of these Boston things to do, with links to relevant websites, and helpful hints, please fill out the form below and then click “Subscribe”.

Try A Cannoli At Mike’s Pastry

Ok. Almost bedtime…

Just in case your teenagers with hollow legs need a bedtime snack, walk about 8 stores down from Improv Asylum to Mike’s Pastry, for your final cannoli of the day. Mike’s Pastry is probably the most famous cannoli place in Boston. There is always a line up and only takes cash.

The cannolis are not any better than the ones from Modern Pastry (which funnily enough is across the street). However, what Mike’s Pastry offers are some amazing flavour combinations that you won’t find anywhere else. Plus, the cannolis are HUGE. Or at least it felt like that after the marathon day of eating, eating and more eating.

Last Word

What is the moral of this very fun one day itinerary in Boston with your teens? Wear comfortable shoes and pants with an elastic waistband!

You will spend most of your day eating and walking (and I think in that order) and doing both on one of the best Boston food tours. You will get to see a huge part of what makes Boston such a beautiful, welcoming and interesting city while eating your way through some extraordinary food.

For some strategies for keeping your teens off of their phones and social media while on your family vacations, please refer to my article Teenagers: 7 Ways To Limit The Effects Of Social Media On Your Family Holidays.

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