A long winter weekend in Boston Massachusetts
To do a stopover on your way to or from your destination it does not have to be a stop advertised or a formal program by airlines. I have grown to really love breaking up long travel with a stopover somewhere and it is a good excuse to explore somewhere new you might not plan a whole trip to. When researching flights to the Azores I found direct flights from Boston, MA to Sao Miguel. Since I had never been to Boston, I decided to break up my flying and spend a few days exploring the city. To book the flights I just purchased them in two parts, I used Alaska Airlines to get me from Alaska to Boston and back and then booked a separate ticket on SATA airlines to and from the Azores. I gave myself three full days in Boston on the way to the Azores and then just one night near the airport on the return.
Early February might not be the ideal time to visit Boston, but with warm coats and a plethora of great museums to visit there is plenty to do and explore even in the cold. You just have to be flexible and realize that this might not be the same trip if you were planning just your ideal Boston itinerary and super focused on checking everything off that list. Stopover travel is great to just give you a taste of what a place has to offer, so you can decide if it is somewhere you really enjoy and might want to come back and explore when you have more time and more ideal time of year if you are hitting the location in the off season.
Day 1: Isabelle Stewart Gardner Museum, Fenway Park & Boylston Street
Have breakfast at Tate Bakery. There are several throughout the city, so just find the one closest to you. The food is incredible and they have some great unique coffee choices as well. It is the perfect start to the day.
Spend an hour or two wandering the Isabelle Steward Gardner Museum. There is lots of beautiful European, Asian and American art on display here, but even the building is an impressive work of art. The building was built in the style of a 15th century Venetian palace with beautiful grand rooms and a nicely manicured garden in the courtyard. There is also a nice cafe on site where you can get coffee or lunch before heading out in to the cold.
From the museum walk through the back bay fens gardens towards Fenway Park. E if it isn’t baseball season it is still cool to checkout the classic old stadium. There are tours of the stadium or in the stadium there is a bar called the Bleacher Bar, which has a glass roller door you can look out on to the field from. Enjoy the atmosphere and get some food and drinks here.
Next you can head over to Boylston and Newbury Streets, which is just a short walk. You can stroll and look at the cute shops along the streets. Pop into Eatly to browse all the great Italian foods and goodies. There are tons of different food spots here and also lots of items to bring home.
While you wander stop in the Boston Public Library and wander the halls until you find Bates Hall. It feels straight out of a Harry Potter movie or something, with its grand arched ceiling and massive rows of tables all with little green lamps. The old part of the library is a great spot to wander and check out all the old architecture. Not far from the library you can also pass by Trinity Church another incredible piece of old Boston architecture.
After a bit of relaxing, we went to dinner at the Union Oyster House, which is considered America’s Oldest Restaurant. Of course no trip to Boston is complete without eating a lobster roll and what better place to do it than this old classic restaurant. I went for the warm roll with butter on a cold winter Boston day.
Day 2: Museum of Science, Beacon Hill, and Little Italy
In the morning hop a taxi to the Museum of Science and spend a few hours wandering the exhibits. If the science museum isn’t what you are looking for there are tons of other museums in Boston. Others that look fantastic, but I didn’t have time to go to are: JFK Presidential Museum & Library, The Museum of Fine Arts, The Havard Museum of Natural History, and the Boston Tea Party Ships and Museum.
After the museum you can walk towards Beacon Hill neighborhood stopping at Flour Bakery & Cafe for a great lunch and coffee or just a sweet treat. Then wander the Beacon Hill neighborhood famous for its cute brick buildings and Boston charm. Charles Street is the main drag and has lots of cute little shops, cafes, and restaurants. A few of my favorite stops where the Beacon Hill Books & Cafe and Covet consignment store.
As you continue walking you’ll hit the Boston Commons Gardens. If it is extremely cold like it was when we were there, the ponds in the park may be frozen. We stopped to watch a number of people play hockey on the frozen ponds in the park, probably not something you see even once a year.
Head to dinner at Lucia Restaurante in Boston’s little Italy. There are tons of incredible Italian restaurants in Boston and I am not sure you could go wrong with any restaurant choice in little Italy. We loved this spot's homemade pasta and desserts and cozy atmosphere. There are also lots of great cocktail and wine bars in the neighborhood as well you can head to after dinner for a night on the town.
Day 3: The Freedom Trail & Donut Tour
The freedom trail is a two and a half mile long path through Boston that passes by almost 20 historically significant places in the city and at least walking part of it is definitely a must in Boston. There are tours of the full trail or you can download maps on your phone and just walk it yourself, stopping in the little museums and churches along the way.
After doing most of the freedom tour in the morning we met up with our guide on the Underground Donut Tour. Boston is where Dunkin Donuts started and has some of the most donut shops of any city. The tour was fun, filling (so many donuts) and very informative. We went two four quite different donut shops and also learned some of the history on the city along the way. At each shop we tried part of a couple different donuts, so we were very full of sugar by the end, but all of them were delicious and some unique flavors. I highly recommend the tour as a fun option that gives you a unique perspective of Boston’s culture and history.
After the tour continue walking more of the freedom trail and grab food if you are hoping for something with a little more sustenance. We spent the afternoon hanging out at the Green Dragon Tavern to keep with our old school Boston vibe. The basement of the original Green Dragon Tavern was used as a meeting place for many groups during the America Revolution. It is believed the Boston Tea Party was planned at the Green Dragon and that Paul Revere left for his great ride from the tavern. The original building was destroyed, but there is a new Green Dragon Tavern in the same area.
Day 4: Stroll the South End, Brattle Book Shop & Democracy Brewing
We again went to Tatte for breakfast, there was just so much on the menu to try, we couldn’t help going back. I think I could spend every day eating there trying different things on the menu and not get bored with the food. Then it is time to walk off that breakfast and stroll more neighborhoods. Boston has so many old neighborhoods it is fun to just wander, you’ll come across parks, churches, and fun colored front doors. We spent the morning strolling the South End walking through parks, past amazing churches and admiring the old brick buildings.
Then made out way up to Brattle Book Shop, a charming old book store that sells old and antique books and has a whole section outside. We spent at least an hour looking at the books outside and then on the many floors inside. They have a great collection including many rare books. Then we stopped at Democracy Brewing for a late lunch and a good beer. It is a fun building with old library or study room vibes. There is exposed brick and big wood tables and booths.
