Are you one of the 64% of parents who thinks the best way to spend time with family is by traveling together? If you said yes, then I bet you are in the process of scheduling another family vacation! There are so many places you can visit with the kids. And if they are all adults now, you have many other options. One of those options is to visit a city like Boston and check out the bars. Of course, Boston has quite a few incredible things to do too. You can walk the Freedom Trail, head out on a whale watching tour, or go shopping at Faneuil Hall. I can help you determine the best things to do in Boston for your family vacation. But today, I am going to focus on the best bars in Boston. This way you will know where you should go when you get thirsty during your busy days of making memories together.  

Visit the Best Bars in Boston 

Longfellow Bar 

The Longfellow Bar can be found just upstairs from Alden & Harlow in Harvard Square. This bar has a two-story lounge, as well as a seasonal roof deck. It is one of the best places to enjoy a drink with a view in the city.  

You can all order the basic wines and beer at this bar in Boston. However, it is the cocktails that this bar is known for. Try The Story, which is made with Jameson black barrel, yellow chartreuse, serrano, and peach. The chamomile honeydew vodka in the Sweet Creature is always a hit too.  

They have a small menu of foods that pair well with all the drinks. Consider the hickory smoked flat wings, grilled rosemary focaccia, or the Longfellow messy fries to start.  

The Warren Tavern 

You will need to escape the city for a little bit if you want to check out The Warren Tavern with your family. This is the oldest tavern in the state. It is located in Charlestown, which is right across the Charles River.  

Once you step foot inside, you will be following the footsteps of historical people like JFK, George Washington, and Paul Revere. Order your favorite brews and pair them with items like the short rib tacos or the Thai chicken lettuce wraps.  

Then sit back and relax, as you immerse yourselves in the lives of the locals.  

Sullivan’s Tap 

Out of all the best bars in Boston, there is one sports bar that is considered a must-visit. Sullivan’s Tap is also the oldest sports bar in the city. To say everyone in the city arrives here to watch a game may be an understatement. Arrive early if you want a seat for the game while on a family vacation in Boston.  

Oh, and remember, this is a Boston bar. So, any Boston team jersey is accepted. I would advise you to not wear a Yankees jersey unless you want to enjoy a ‘rousing conversation’ along with your drinks.  

The Tall Ship 

One of the more unique bars in Boston is The Tall Ship. You will find three large bars on the two hundred forty-five-foot ship moored on Pier One. There is also a patio next to the ship for those warm days when everyone wants to be near the water.  

Grab one of their magnificent cocktails or stick with a pint of beer. Just don’t skip the freshly shucked oysters in between games of cornhole with the locals.  

Fool’s Errand 

Fool’s Errand is one of the newer best bars in Boston. It opened to rave reviews in 2018. This bar used to be standing room only, but recently reopened with sixteen seats and an outdoor patio. During your bar visit, you can drink European cocktails and wine while indulging in bar snacks.  

Favorite menu items include the fancy pub cheese, burrata, and crispy pork empanada. Save room for the strawberry rhubarb shortcake or order a slice to go.  

Drink 

A visit to Drink in Boston will have you using your imagination when ordering a beverage. There is no menu at this cocktail bar. Instead, the bartender will ask you what you want or what your preferences are. The latter is perfect if you want to try something new but have no idea what that might be.  

As for the food, I suggest ordering churros. They are served with a warm chocolate dip. Although, if you want real food, the Drink burger and fries are the way to go.  

Daiquiris & Daisies 

You will discover both classic cocktails and creative drinks at this bar in Boston. One of the best things about this bar is you can spend as much time there as you wish. Quick drinks in between sightseeing are an option, as are long leisurely drinks throughout the afternoon or evening.  

I recommend the pineapple daiquiri, but the blueberry daisy, Big Papi’s salsa, and Pavarotti are all excellent choices too.  

Trillium Brewing Company 

There are a couple of different Trillium Brewing Company locations in Boston. Whichever one you choose to visit is fine since it is all about the beer anyway. I recommend starting with one of the seasonal brews or requesting a sampler so you can try as many as you can.  

Cheers Beacon Hill

Cheers Beacon Hill can be found on Beacon Street. It used to be called Bull & Finch. This bar was used as inspiration for the television show, which is why the name eventually changed. You can sit at the bar or a table with your family and pretend you are part of the Cheers family.  

This is the best bar in Boston for food, drinks, and making memories. Stop in the store before you leave to purchase a few souvenirs to remember your visit.  

These are some of the best bars in Boston. There are many others, and you may find your personal favorite as you wander around the city. I can leave you plenty of time for bar hopping, as I am personalizing your family vacation itinerary in Boston. You simply need to let me know how much time you need for these adventures.  

So, are you ready to have me create a personalized family vacation itinerary for your next trip to Boston or another destination?  

If you said yes, I would like to invite you to click here to schedule a personalized family vacation planning session with me. When you click on the link, you will be taken directly to my digital calendar to schedule a time that is convenient for you.  

Not ready for a personalized family vacation planning session yet? Sign up for my newsletter to continue to receive all the exciting travel information I share.