Cuchi Cuchi
For bevies of dressed-to-the-nines bachelorettes and BFFs, a night at this dark-lit speakeasy may begin as female bonding, but fast-forward three margaritas later, and watch the mixing begin. 795 Main St., Cambridge, MA 2139, .
Eric Clapton
Twenty years later, Clapton is still la creme de la Cream. The Metro, Boston, MA .
Purgatory Chasm
A half-mile long and sixty feet deep, with caves for spelunking and clear spring water to drink. Sutton, MA
Boston University's FitRec Swim School
COURTESY PHOTO Cold water and newbie swimmers don’t mix. That’s why the pool used for kids’ lessons at FitRec Swim School is heated to a toasty 84 to 85 degrees, making it the perfect place for youngsters to learn how to make a splash with the help of Red Cross–certified instructors. 915 Commonwealth Ave., Boston, MA bu.edu/fitrec/aquatics.
Crane Estate
Your very own castle overlooking the sea. It's a reality at Ipswich's Crane Estate, a 2,100-acre tribute to natural beauty and manmade opulence that showcases water panoramas and one very regal Stuart-style manor. While several party spots are available, the showstopper is the Great House's rolling lawn leading to the Atlantic. 290 Argilla Rd., Ipswich, MA 01938, thetrustees.org/crane-estate.
Saltie Girl
One of the first restaurants to bring the concept of high-end tinned fish to our shores, this cheerful spot also excels in seafood of the uncooked variety. Opt for a dozen South Bays, or go all in with cobia, razor clams, and one of three varieties of sea urchin. There's no shortage of fish in these waters. 281 Dartmouth St., Boston, MA 02116, saltiegirl.com.
The Sunset Grill & Tap
Back when good beer selection meant both Bud and Miller Lite, these hopheads did their damnedest to broaden our horizons. A decade later, the bar stocks nearly 500 microbrews, including 110 on tap and three beer engines for those cask-conditioned ales. 130 Brighton Ave., Brighton, MA .
Oro
There's no better way to start a Sunday than at Oro, just a stone's throw from the water in Scituate Harbor. Your morning coffee will go perfectly with the Nutella-stuffed French toast and brûleed bananas, but if a bloody mary is more your speed, try it with the Waldorf chicken-salad sliders and fries. 162 Front St., Scituate, MA restaurantoro.com.
Lulu's Allston
It lures lively crowds with a 50-strong draft list bursting with smart selections, buzz-friendly fare (ranch-dusted tater tots!), a raucous soundtrack, and a patio bar with bocce lanes. 421 Cambridge St., Allston, MA lulusallston.com.
Barre Groove
They may not be traditional, but Alanna Perry’s barre classes incorporating mini trampolines, dancing, and even weighted pom-poms sure are a blast. The former New England Patriots cheerleader will have you jumping 360s and throwing your hands in the air before it’s even time for your first water break. 52 Province St., Boston, MA barregroove.com.
Kelley Square Pub
Photograph by Kelsey Cronin It’s easy to see what drew Vinny Paz and Tommy Lee Jones to this watering hole: Here, conversation flows and the beverage selection is ample (including the most affordable pour of Woodford Reserve we’ve ever seen). 84 Bennington St., Boston, MA 02128, kelleyssquarepub.com.
Shag
After a quick tête-à-tête, Brianna Coons shaped our unruly hair into something slick, taking into account our capacity for at-home styling (none). The best part? The chop grew out so evenly, it still looked fresh months later. 840 Summer St., South Boston, MA 2127, shagboston.com.
Ryan Wading Pool
The Ryan Wading Pool is our pick for the city’s best spray deck, where kids can clean up and cool off after a hard day’s summer play as they get soaked under the buckets that dump water from overhead. 350 River St., Mattapan, MA 02126, mass.gov/locations/ryan-wading-pool.
Lower Neponset River Trail
Embrace nature without leaving the city: With water-level views of the Neponset River and its salt marshes, this 5-mile nature walk from Dorchester to Milton just begs to be biked, walked, and jogged. Bring the kids and dogs along for outdoorsy family fun. Hallett Street, Dorchester , MA 02124, mass.gov/locations/lower-neponset-river-trail.
Bantam Cider Company Tasting Room
With pours spanning the cider spectrum—from the cherry-tinged Rojo to the farmhouse-style Sweet Scrumpy—Bantam’s taproom serves up a refreshing alternative to your typical neighborhood watering hole. Claim a standing table, and make a day of it. 40 Merriam St., Somerville, MA 02143, bantamcider.com.