Shimmer Garage

A quick spur of the moment getaway is sometimes exactly what the doctor ordered. Read along to find out how to maximize 3 nights in Boston to its fullest.

Acorn Street, Boston, MA. July 2022

There are so many fun things to do in Boston. When you first thing of big cities, the list of what to see and do can be overwhelming. My husband and I booked this trip on Friday mid-morning and left Friday evening. After a whirlwind of not know what to do for my 3 day weekend, Boston happened to be the choice. Why? You may ask. The final deciding point for me was the Red Sox had a home game. Perfect. Growing up I watched baseball all summer long with my mom and sister. Now as I travel as an adult, I love to hit new stadiums and check out the “home team” field.

Stay: Hyatt Regency Downtown. We thought it was a great location. Easy to access from Lyft/Uber and there was a train station just a couple blocks away.

We ended up not using the train station while in town. We walked (30 miles in 2.5 days) and used Uber/Lyft and a ferry.

Day 1: After getting in super late due to travel delays, we decided we wanted to get as much in on our first full day. We ended up at Cafe De Jour and it was delightful.

We then chose to walk around downtown and hit the Freedom Trail. I HIGHLY recommend this. This trail is on a path through the city which takes you past various historical marks. I was absolutely blown away seeing so many neat things. The sites include: Boston Common, MA State House, Park Street Church, Granary Burying Ground, King’s Chapel and King’s Chapel Burying Ground, Boston Latin School/Benjamin Franklin Statue, Boston Massacre Site, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, USS Constitution, and Bunker Hill Monument.

Quincy Market was on the list to must sees and we ate at Regina Pizzeria and I snagged a coffee from Starbucks to keep going.

After the Freedom Trail, we hopped on a ferry to Salem, MA. It was neat to go through the harbor and hear some historical information. In Salem, we spent a couple hours looking through the town and seeing places such as the House of Seven Gables and the place where the witch trials took place.

We got an Lyft back to the city and found some stores to shop on Newbury Street. We then went to the Cheers inspired bar for some drinks and appetizers. We wanted to make sure we could pack in as much as possible and ending up walking back to other side of town to eat at Boston Burger Co. for dinner. They had so many flavors of burgers and toppings.

Day 2: We decided to let our legs rest a little and to sleep in just a bit. We hopped on over to Mikes Pastry and got some cannolis, brownie and cupcake. We decided since it was mid-morning we would walk to the Boston Tea Party Museum and go to Abigail’s Tea Room for a tea. After tea and exploration, we went to the Barking Crab for lunch. I definitely recommend this place if you are in Boston. The stuffed lobster was absolutely delicious. Since the Fan Pier Park was just a skip away, we decided to sit on the wall and enjoy some peaceful moments by the harbor. This made me realize that one day, I want to live in a harbor town and take my boat out on the weekend (but that’s a whole different story). Shopping was on the list again so we went to Washington Street to look around.

Next up was the Boston Red Sox and the NY Yankee game at Fenway Park. This was such a neat experience. The Red Sox won 11-6! We ended up walking right around 2 miles back to our hotel and really just enjoyed talking and walking the city.

Day 3. We had a mid-afternoon flight so we thought we would make use of the time as much as possible in the morning. We mapped out the famous Acorn Street and snag breakfast at The Paramount. After breakfast was a walk around Beacon Hill and the Charles River Esplanade. I grabbed a coffee at Caffe Nero.

Our time was up and we headed to the airport. 3 nights and 2.5 days of exploration was well spent. I have a feeling I will be back to Boston. It was such a charming and rich in history city. We hope you enjoy it as much as we did if you get a chance to visit.

-XOXO