36 Hours is Plenty of Time to Savor The Best of Boston, Here’s How

weekend in boston

Spending weeks exploring a destination sounds nice, but that’s a time luxury few of us have these days. The great news is that there’s no prerequisite amount of time required to visit a new city. In fact, we think 36 hours is ample time to get fairly well acquainted with Boston, and we’ve got plenty of suggestions on how to do just that!

Weekend in Boston? Here’s What to Do

Finish Up The Workday, and Head on Out!

A weekend trip can mean heading out after working a half day or finishing up a full day of work, and then hopping in the car, a train, or on a plane. Boston is a relatively short drive from many east coast cities, a couples hours in a train from New York City and a quick flight from nearly anywhere! No need to take those precious vacation days if you don’t want to, yet.

Friday Evening

Say you arrive in Boston around 5 or 6 p.m.; you’ve still got plenty of time to try one of the city’s acclaimed restaurants, catch a show, or take an evening stroll through the Back Bay. Boston is one of America’s most walkable cities, and we highly recommend you hit the pavement!

  • Dinner Recommendation: Beacon Hill Cheers – Yes, you read that correctly, we’re talking about the very pub that inspired the show.
  • Get Out Your Giggles – For a show suggestion, we recommend heading to one of Boston’s comedy clubs! Check out ImprovBoston Theater or The Comedy Studio.  

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weekend in boston

Saturday Adventures

Waking up in Boston, with a full day ahead of you to explore, is such an incredible feeling! Herein lies the only real challenge of the weekend, narrowing down what to do, see, and eat all day long. Rough life, right? Here are some ideas to get you started:

  • Breakfast: The Friendly Toast in Copley Square
  • Outdoor Adventure – Especially if this is your first time in Boston, you won’t want to skip the Freedom Trail!
  • Lunchtime Eats: The Butcher Shop – A tribute to European boucheries, located in Boston’s South End, this is more than Butcher Shop, it’s a neighborhood wine bar and restaurant!
  • Afternoon Meandering: Isabella Stewart Gardner Museum– Perhaps our favorite museum in all of Boston, or the world for that matter, is the Isabella Stewart Gardner Museum. Without giving too much away, this is the house of philanthropist Isabella Gardner and is filled with her eccentric art collection.
  • Step Back in Time For Dinner at: Lucky’s Lounge – A Frank Sinatra-themed bar that will make you sing with pleasure! Every single Saturday evening there is a tribute jazz band from 7-10 p.m.

weekend in boston

Savory Sunday

Though these are your final hours in Beantown, we hope you savor every drop! Wake up slowly after sleeping, breathe in the sights and sounds of the city as you make your way to brunch, a city-wide obsession. Your taste buds will begin to water as you walk into Boston Chops. If you’ve still got some time before your train, plane, or drive, there’s one final stop you should make. Pop into the world-renowned Museum of Fine Arts! There’s always a new exhibit to peruse, and plenty of permanent exhibits for your eyes to devour.

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After 36 hours in one of the most architecturally gorgeous, culturally vibrant, and cuisine rich cities in the nation, how do you feel? Well, you can answer that after you get back! We’re willing to bet you’re going to feel fantastic, especially after two nights of stellar sleep and luxury surroundings at Copley Square Hotel.

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