Six Healthy (And Active) Summer Date Ideas Around Boston

Kayak on the Charles River, hike at Blue Hills reservation, and definitely skip the movie theater with our summer date guide.


Spectacle Island

Spectacle Island / Photo by Tessa Yannone

When the summer months are brief and you’re trying to soak up every free minute you have outside, a traditional date of dinner and a movie is not going to cut it. Save the indoor activities for the rest of the calendar year, and soak up all the sun you can with your someone special. Who knows, you may just find your next favorite shared hobby (that doesn’t involve The Office and take out pizza).

Rent a kayak and watch a Friday night movie outdoors 

First: Rent a kayak (single if you’re competitive, double if you really love/trust each other) from the Allston/Brighton Paddle Boston location and paddle down the Charles to the Kendall Square boathouse where you can drop the kayak and walk across the Longfellow bridge to the Esplanade.

Then: Take advantage of the Hatch Shell’s free movie screening every Friday night at sunset during the summer. August’s movie lineup includes Beauty and the Beast and Thor. 

Free Friday Flicks at Hatch Shell

Swim at the Mirabella Pool and snack at the Boston Public Market 

First: Head to the Mirabella pool in the North End, where you can buy a day pass for $3 and lounge by the water, throw a football in the water, or heck, have a cannon ball contest—we won’t judge. Or even bring some goggles and a cap and swim laps.

Then: Stroll down Hanover, stop in for a cannoli (to split, of course) and save your appetite for some snacks at the Boston Public Market. Make your rounds and grab a salad at Mother Juice and a fresh chocolate drink, stone ground right in front of you, at Taza Chocolate. Maybe even stock up on some fresh fruits and vegetables, if that’s your jam—who says grocery shopping can’t be a date?  

Boston Public Market

Produce at Boston Public Market / Photo by Olga Khvan

Pedal to Harvard Square and cool off with some frozen yogurt 

First: If you have a bike, great. If you don’t, rent one from the Nashua Street Blue Bikes station or the one next to TD Garden and hit the Esplanade, heading west to Harvard for a leisurely four-mile cruise next to the river.

Then: Ditch the bike at the Bennett Street docking station off of the Harvard Street bridge and walk up to Harvard. Cool off with a Freeze from Pressed Juicery on Mass. Ave., which is their take on soft-serve. It’s completely plant-based and free from dairy. When you’re done, if you have the stamina to ride back, pick up the bikes where you left them. If not, the Harvard Square T stop is a short walk away.

Grab a cup of Joe before hiking at Blue Hills Reservation  

First: Take this date out of the city (yes, you need access to a car for this one) and visit Legacy Place to engage in some small talk, if it’s one of your first dates, over a cup of coffee at Caffè Nero. Or if you’re hungry, load up with some fuel for a long hike with a Cava bowl or B.Good salad and smoothie.

Then: Drive the short 10 minutes to the Blue Hills and take the skyline trail up to an overlook of the city of Boston. Be sure to have your hiking shoes on and bring some water—the hike is very hilly with many rock faces and roots to climb over. If you’re car-less, Middlesex Fells to the north of the city can be accessed at the end of the Orange Line with a short bus ride.   

Blue Hills

Blue Hills Skyline Trail / Photo by Tessa Yannone

Outdoor rock climb and relax at the Street

First: Gear up for a climbing adventure, no experience required, and join Rock Spot climbing at Hammond Pond. The expert staff will bring all equipment necessary for a successful climb and will safely belay and anchor all participants. Their next adventure is on September 2, but if you can’t make it, try rock climbing at their indoor facility in Southie.

Then: Take a stroll down the Street at Chestnut Hill and recharge with herb brushed tuna or a falafel from Tender Greens. Re-hydrate with a smoothie from Juice Press and kick your feet up at the Green.           

Adventure on the Harbor Islands and pack a picnic 

First: Purchase a ferry ticket for $20, and hop on and off at the different Harbor Islands. If you time it just right, you can hit Spectacle, George’s, Peddocks, and Lovells all in one day. There are almost five miles of trails on Spectacle as well as the highest point in the Harbor for great views of the city. Peddocks, the largest and most diverse island, features a network of trails, historic structures, unique geologic features, and even solar energy installations.

Then: When you’re sufficiently tuckered out, head to one of the many beaches, lay out a towel and enjoy a picnic on the beach and a dip in the water.