• Rebecca Blackmon

Perfect Weekend Travel to Boston



Hey guys! One of my sweet friends Morgan recently took a trip to Boston, and was happy to share her weekend experience and her perfect Boston travel itinerary!


“What about Boston?”, I texted my best friend and best travel buddy. After a year of law school in the midst of COVID, I knew that as soon as I finished finals I would be ready to celebrate and celebrate BIG! My favorite way to unwind is to travel, especially somewhere I had never been before. So when the time came to research where my next destination would be, Boston stood out to me. As someone who loves good food, history, and the chance to spot Chris Evans in his hometown. I could not pass up the chance to visit such a cool place.


Weekend Travel to Boston - Where to Eat:

If you are anything like me, the first thing you’re going to research when visiting somewhere new, is where to eat - where to eat in Boston? Boston has no shortage of unique places to eat and drink. Here are the places we went:


Alden & Harlow

In Cambridge, Alden & Harlow had some of the best cocktails and appetizers we had during the trip. The portions are generous and were more than enough for the two of us to share while we sipped our seasonal cocktails. Not to mention, the view of the street at their outdoor tables set such a cute backdrop for a calm evening. Make sure to make a reservation ahead of time or you will have a bit of a wait as this is a popular spot for locals and travelers alike.


The Boston Sail Loft

You cannot go to Boston without getting some seafood. After a long day on the Freedom Trail, we winded down right on the water at The Boston Sail Loft. The view is good, but the food is even better. This is a perfect spot to eat before a trip on the ferry or before hopping on a water taxi to Charlestown.


Tiki Rock

At Tiki Rock, you will find neon lights, loud music, and tons of drink options. Tiki Rock really shined with their numerous unique cocktail options including quirky and fun cups each one came in. This is a great place to have drinks before dinner or a night out!


Caffe Dello Sport

Finally, do not miss the Little Italy dining scene on the North End. Every step you take in the North End, you will be met with a new Italian restaurant or cannoli shop. You absolutely MUST choose one and then follow up with cannolis for dessert. We chose to finish out each day of our trip with a cannoli and coffee at Caffe Dello Sport. This place was a hit, with so many dessert and beverage options, there is something for everyone. It stays open late and is the perfect place to end a long day of exploring in Boston.



Weekend Travel to Boston - Entertainment and Shopping:

While Boston’s history scene cannot be missed for history lovers, Boston has some great options for those who want a break from the revelry of tossing tea in the harbour. Of course, you can try and catch a Red Sox game, but don’t miss these two unique Boston spots!


Improv Asylum

By far the highlight of my trip, Improv Asylum is a comedy improv show that will have you rolling. With their quick-pace, witty jokes, and fun music, this show will catch your attention and hold it for the entire two hours you are there. (Bonus, the bar is stocked with some GREAT drinks- my choice was the Frose). This is the kind of experience that will fly by and you will hate to see it end. Buy your tickets ahead of time and plan for a fun night of laughter.


Converse Outlet

The converse outlet at the Lovejoy Wharf offers a unique opportunity for fans of Converse. The design lab at the back of the store is a hidden gem, where you can design your own shoes on the spot. It is a fun and unique experience that leaves you with a souvenir you will be proud to display after your trip.




Weekend Travel to Boston - Boston History Tour


Freedom Trail

Prior to going to Boston, we thought we would take a “self-guided” tour of the Freedom Trail. While that is an option, I would say the BEST way to get the most out of the city is by booking a tour in the Boston Commons. Our tour was through “History at Play”. Before this tour, I was of the opinion that I would be able to point out and read the plaques at the various historical spots without the help of a guide. What I quickly learned was that Boston is so packed with history, that you could easily walk by some of these spots and NEVER realize it.

I cannot say enough good things about our tour guide, Judith Kalaora. She was phenomenal, she walked us through the highlights of the Freedom Trail and not only provided the basics of each historical spot, she also had fun and quirky stories for the places in between.

History is so deeply embedded in the architecture of Boston. It is easy to pass by North Point Church without realizing it was the place where the phrase “one by land, two by sea” was coined. If you do nothing else, grab a guide for the Freedom Trail.

This tour took us through Boston and covered not only the high points, places like the site of the Boston Massacre, Samuel Adams Burial Site, and North Point Market, as we walked to each of these sites, The tour ended at Faneuil Hall right in front of North Point Market which was full of food choices and an opportunity to hop on the ferry and ride across to Charlestown to finish out the Freedom Trail at Bunker Hill.



Boston Ghosts & Gravestones

If you are a fan of the spooky or quirky side of history. Boston Ghosts & Gravestones is a light-hearted tour of the “darker” side of Boston. This tour gives a unique perspective of the city, because it’s the only way to see the graves of famous Bostonians under the cover of night. The tour guides are engaging and funny. It is a good family activity, despite it’s “spooky” aspect.


Boston Tea Party Ships and Museum

There are few experiences that will make you feel as patriotic as tossing tea into the Boston harbor. This museum was an immersive experience. The staff were all very knowledgeable and friendly. Although the ships were replicas, the staff made you feel like you really were a revolutionary. After the tour, head up to Abigail’s Tea shop and drink the same flavor tea that was tossed in the harbor.



Finally, if you are going to try out all of these awesome restaurants, businesses, and tours, you will need some transportation.



Weekend Travel to Boston - Transportation

Boston is a moderately walkable city, with some planning ahead of time, you can spend the day in one area while avoiding what can be a pricey Uber with a long wait time. If your feet get tired, Boston has cool options to the endless trek of long days exploring the birthplace of the American Revolution. You can ferry, water taxi, trolley, Uber, or ride a citi bike all throughout the city. We took advantage of each of those options. My favorite was the water taxi to Charlestown. It was inexpensive and gave a great view of the Boston skyline.




In conclusion, Boston is a fantastic place to visit. As COVID restrictions lift, there will be even more for this city to offer, from shows to concerts and revolutionary reenactments, Boston has something for everyone.








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