My oldest daughter goes to College outside of Boston. Over the years, I have spent a fair number of days wondering around Boston either with her, or with my other kids. We have ate at some amazing restaurants, learned about early American history, and much to my children’s delight, done some serious wallet cleansing shopping. After this last trip, I thought I would put together a one day Boston itinerary. This itinerary is packed with things that we have all loved.
Warning: This itinerary is heavy on eating, shopping and fun, and light on history and education…
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, it feels like people are busy, but not too stressed about it.
Accommodation and Transportation Tips
Two things about Boston that you should know before embarking on my one day Boston Itinerary: accommodation can be expensive and travel by car is a hassle. I have two recommendations.
Try to Stay at The Lodge at Brandeis University
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 cost is $6.75 per trip.
The Lodge offers 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.
Avoid Travel By Car
There is nothing wrong with travelling by car. It is just not the most economical or timely choice.
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. Highways circumventing the city or underneath in tunnels are also limited by direction and lanes. On previous 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 Boston Itinerary
1. Boston Secret Food Tour
We did the Boston Secret Food Tour. It started at 11:00 am a couple of subway stations away from the North Station. It lasted for approximately 3 hours. We spent most of our time in the North End of Boston, also called “Little Italy”, but also explored relatively new Boston Public Market, just across from Little Italy. Boston Public Market houses approximately 35 businesses that produce locally sourced ingredients or prepared meals or foods. It also offers public education, accessibility and affordability of food for the community.
The cost was $65 USD. 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.
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.
2. 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.
3. 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 one day 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. The Freedom Trail is a 2.5 mile path that you follow which takes you on a journey into and through the American Revolution. Regardless of whether you do the Freedom Trail or not, 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.
4. Newbury Street
Just off Boston Common is Newbury street, a mile long street filled with gorgeous 19th century brownstones that are filled with 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.
5. Georgetown Cupcake
By now, you might want to sit down for a pinch 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… For a little bit of fun, tune into the “fridge” cam in the morning to find the “Secret Flavour” of the day for a free cupcake. There is a limited supply so perhaps you should stop here in the morning on your way to the food tour. Just saying…
6. 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 Little Italy. 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.
7. Improv Asylum
Down the street 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 the one day Boston itinerary to a close.
***For a handy list of these activities, links to their websites, and helpful hints, please fill out the form
8. Mike’s Pastry
Ok. Almost to a close…Just in case your teenage son with the hollow leg needs a bedtime snack after this epic one day Boston itinerary, walk about 8 stores down 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.
What is the moral of this one day Boston itinerary? 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). 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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