8 Great Summer Dates in Boston

Before you agree to meet that cute guy from Tinder, or see that pretty girl from OkCupid, plan the best date possible this summer! Here’s 8 Great Summer Dates in Boston for the best spot to have fun and enjoy the sun. These are cheap, outdoor date ideas that will sweep her off her feet a bit more than your usual Netflix-night-in. Bring on the romance with these incredible date ideas!


1. Boston Pedal Boats on the Charles River

Take advantage of the humidity by pedaling around the Charles River in a couples paddle boat! This cute, fun idea can be cheaply rented for either 30 min or an hour. Check out the amazing views of the city from your boat, and after walk along the Esplanade to Harvard Square for a date-night to remember. Wednesday through Friday, take full advantage of this adorable first-date activity.

boston pedal boat



2. The Bleacher Bar at Fenway

One of the hottest spots in Boston, the Bleacher Bar is located right below the bleachers in center field of Fenway Park. Eat, drink, and watch the game without paying premium prices for Fenway Park tickets for a one-of-a-kind baseball experience and an even more unique date night.


3. Shakespeare on the Common

Commonwealth Shakespeare Company has performed free fully-staged productions of Shakespeare plays on the Boston Common since 1996. Bring your date to a fantastic performance of King Lear from July 22nd to August 9th this summer! This will be Commonwealth Shakespeare Company’s 20th season of Shakespeare on the Common, so it would be a shame to miss this incredible opportunity to show-off your artistic side to an unsuspecting date! After, go get some ice cream or walk around the Common at night for a romantic and fully-entertained evening.


4. Kayak and Sail on the Charles

Since 1946, Community Boating Inc. offers sailing and kayaking on the Charles River from 10:00AM to 5:00 PM seven days a week. Take an adult sailing class with your date, or just plain impress them with your kayaking skills this summer! With a fantastic view of the city, the Charles River is a definite destination spot for outdoor activities for you and your date.


5. Boston Bike Tours and Rentals

Go on a bike tour with your date with Boston’s Urban AdvenTours! Take a city view tour, or a night ride with your date around Boston or Cambridge, offered everyday. This amazing outdoor date idea is definitely one to take advantage of, so use this fun and active date to kick off a fantastic date night!

6. Harvard’s Arboretum

Go on a romantic walk throughout the Arnold Arboretum at Harvard University! With a plethora of plans and flowers to brighten up your day, this date idea will definitely have your date smiling ear-to-ear. This free, outdoor activity is open everyday and is a great precursor to a perfect date night.


7. Fenway Park Walking Tours

Bostonians are definitely reverent of their historic Fenway Park, so take your date on a unique walking tour of the best place on earth! This one-hour walking tour will be a great start to a great evening with your significant other; not only do you get to ogle at the perfection that is Fenway, but your date will appreciate your deep love of all things Red Sox.

8. Boston Harbor Cruises

With 329 weekday departures, Boston Harbor Cruises are a great way to get to know the city and your date! Go for a whale watch, take a ferry to the Cape, or get on a dinner cruise!

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