Seven Healthy (And Active) Summer Date Ideas Around Boston

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


summer date ideas Boston

Photo by Amanda Lucidi

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).

Free Friday Flicks at Hatch Shell

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. Movies include films like Mary Poppins Returns, Spider-Man: Into the Spider-Verse, and Bumblebee. 

Boston Public Market

Produce at Boston Public Market / Photo by Olga Khvan

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, play catch, 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 or maybe even stock up on some fresh fruits and vegetables, if that’s your jam—who says grocery shopping can’t be a date?  

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. 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.

Blue Hills

Blue Hills Skyline Trail / Photo by Tessa Yannone

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.

The Night Shift Owl’s Nest on the Esplanade. / Photo by Tim Oxton/Night Shift

Log some miles and then cool off with a beer at the Owl’s Nest

First: If you’re both avid runners, kill two birds with one stone by turning date night into a workout and sync up for a run on the Esplanade. Or maybe, if you both need a little more competition hook up with one of these run clubs and make some new friends, while you’re also enjoying each other’s company. And if running isn’t your thing, take a stroll, roller blade, walk the dog, throw a frisbee, etc. The options are endless. Get creative.

Then: Head to Night Shift’s beer garden the Owl’s Nest right off the Dartmouth Street bridge on the Esplanade. There’s cold beer on draft, tables and chairs for lounging, and even corn hole. Honestly, what’s better than cooling off with a cold pour and views of the river?    

Outdoor rock climb and relax at the Street

First: Gear up for a climbing adventure, no experience required, and join Rock Spot climbing at many different places throughout the summer like Hammond Pond. The expert staff will bring all equipment necessary for a successful climb and safely belay and anchor all participants.

Then: Depending on where you are, 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.           

Spectacle Island

Spectacle Island / Photo by Tessa Yannone

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.

If you’re still looking for more ways to have fun in the sun, check out our summer bucket list.