16 August
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Our Agent’s Favorite Date Spots in Boston | By Maya Michalewicz

As proud Boston experts, our real estate advisors at Columbus & Over Group pride themselves in not only finding dream homes, but also knowing the city better than almost anyone else. So if you’re on the hunt for the perfect date spot, maybe try one of our agent’s favorites: 

Lisa Ha:

Hailey Henry – Downtown Crossing

It has an extensive wine list and nice intimate vibes. The 90s hip hop playing in the background that isn’t too loud, makes this a perfect date spot in the middle of Downtown Boston. The only downside is that the wait time can be long.

Charles River Esplanade:

If you’re looking for an outdoor date, you can never go wrong with grabbing a bottle of wine, cheese, and baguette, and heading over to watch the sunset on the Charles River Esplanade. 

Jamie Gaines:

Beehive – South End:

It’s a great place to go for a drink or a bite to eat and listen to live music. The eclectic, yet elegant interior makes it a fun and different date spot. 

Blue Bike:

Grab Blue Bikes and go across the river to the Harvard Bookstore and get ice cream for a perfect summer date!

Joe Castro:

Jillian’s Arcade – Fenway

AKA Lucky Strike– is a Fenway staple for a fun-filled evening! Grab a drink and explore the 3 floors of bowling, arcade, and more! The vintage-mood filled with good drinks and food make this a great upbeat spot. It’s located right behind Fenway Park, so you could even pair it with a ballgame and make it a whole day ordeal!

Jeff Hamilton: 

Borrachito – Seaport:

You’ll wow your date when you take them behind the Taqueria’s freezer door into a retro and playful elevated speakeasy in the heart of Seaport. Borrachito has amazing drinks and food at this Mexico City inspired bar. 


Prima – Charlestown:

Located in Charlestown’s 10 City Square is a new Italian steakhouse that has the perfect ambiance. Start your date in the back Rose Room for a pre dinner cocktail. The leather, subway tiles, and reclaimed wood make the space feel sophisticated and aged in a good way. It’s right off of the Freedom Trail, so you can go for a stroll after dinner.

Boston’s historical charm fused with its modern vibrancy offers couples a picturesque and entertaining place to make memories. From intimate restaurants and bars nestled in centuries-old neighborhoods to rooftop terraces with panoramic skyline views, to stunning public parks, Boston has it all. Is there a new place our agents should add to their list? Let us know!