Oak Bluffs

Throw yourself-quite literally-into cinematic lore at Martha's Vineyard's infamous Jaws Bridge, the sun-blasted span in sleepy Sengekontacket immortalized in Spielberg's shark thriller. While technically discouraged (though enthusiastically practiced), leaping from this modestly nerve-wracking height-a deceptively humble 15-foot drop into salty, chilly water-is a rite of passage for adventurous souls desperate to add a dash of Hollywood bravado to their vacation stories. Mid-afternoon is prime time, when sunburnt spectators gather and cheer, offering a perfect balance between liquid courage at lunch and sunset selfies afterward. Plan your leap spontaneously (overthinking will doom you), pack a towel and waterproof bravado, and budget nothing but your dignity. Why bother braving bridge-jumping jitters, nagging park officials, and unseen aquatic life lurking mockingly in your imagination? Because, dear friends, it's not every day you get to tell friends at dinner parties you survived a plunge off the set of cinema's hungriest shark story.

There are few things more satisfying-or oddly competitive-than beach plum foraging along salty island shores. To the uninitiated, beach plums might look like oversized blueberries on steroids, lurking rebelliously among wind-whipped dunes and salty scrub brush. Native to the coastal sands of the Northeast, these tart little fruits once inspired colonial homemakers to whip up tangy preserves and liquors so robust they fueled rebellions, tavern brawls, and questionable romantic escapades, often in the same evening. Today's beach plum hunt-best undertaken early in the morning before sunburned tourists swarm-requires a graceful balance of timing and cunning; arrive too late in the season (late August into early September is prime), and you'll find that some enterprising grandmother has already cleared the bushes bare. Pack sturdy shoes, a good hat, a bucket or two, and enough grit to brave thorny bushes and territorial seagulls. Budget nothing except your dignity-though sacrifices may include scratched forearms and sand-filled shoes-and savor the smug satisfaction of transforming tart, wild-picked fruits into homemade jams or cocktails that'll awe friends and frighten enemies. Even if you fail spectacularly and emerge berry-less, sunburnt, and covered in sand flea bites, the tale of your foraging misadventure alone will boost your salty street cred for seasons to come.

Paddleboarding at State Beach is the nautical equivalent of yoga class-tranquil, graceful, and deceptively humbling. Trust me, you'll start out thinking you're the next Magellan, only to discover your balance skills are more reminiscent of a tipsy toddler. Early mornings are your sweet spot: beat the Instagram hordes, commune peacefully with curious dolphins, or at least avoid plowing into the afternoon amateur hour. Historically, paddleboarding has Polynesian roots, practiced for centuries by indigenous explorers who likely didn't drop $7 lattes before taking to the waves. Plan to reserve your board ahead of time-especially on weekends-unless your idea of a fun Saturday includes haggling with overly tan rental dudes. Budget around $25 to $40 an hour; a small price to pay to propel yourself across glassy waters and pretend you're not sucking in your stomach when fellow beachgoers glide by. Bring sunscreen, water, and a waterproof phone pouch, unless the prospect of dropping your new smartphone into Poseidon's locker is your form of gambling. Even if your paddling career is brief, and your dignity sinks faster than Titanic fanfiction, paddleboarding at State Beach leaves you with an unbeatable combination of mild adrenaline, solid core exercise, and a story that makes you sound infinitely cooler at brunch.

Golfing at Farm Neck Golf Club feels less like a mere round of golf and more like crashing an exclusive party where the guest list includes presidents and pop-culture royalty. Set against Martha's Vineyard's postcard-perfect backdrop, this place practically whispers "You're welcome" with every ocean breeze rustling through the impeccably manicured fairways. Tee off around early morning-no later than sunrise-for the glorious pleasure of outsmarting the casual celebrities still nursing their artisanal coffees and hangovers. Book a tee time at least two weeks ahead if you want a shot at the coveted weekend slots, or risk languishing with the crowd who thought they could charm their way in last-minute. Budget-wise, prepare to part ways with around $200 per person, a price tag that isn't just green fees-it's bragging rights, pseudo-prestige, and permission to casually drop names mid-conversation. Pack your clubs, sunscreen, extra balls (the rough has a mischievous appetite), and just enough reverence to respect the tradition, yet enough irreverence to appreciate the absurdity of chasing a tiny ball in the footsteps of presidents. Because whether your swing is Tiger-level graceful or closer to Charles Barkley comedy, golfing at Farm Neck is worth it-even if only for the priceless ability to say, "Obama sliced it right here, too."

The Martha's Vineyard Museum might initially sound about as thrilling as a cardigan convention but, surprisingly, delivers quite the historical kick-less 'stuffy artifacts behind glass' and more 'juicy tales of whaling exploits and shipwreck drama.' Located in Vineyard Haven, a place so charmingly nautical that you half-expect a boat captain named Ishmael to pass by muttering about sea monsters, this museum covers it all-from maritime adventures to rebellious residents who'd rather not join the mainland party. Go in the morning-before the day-trippers swarm in-and plan your pilgrimage at least a week ahead if it's high season, unless you relish long lines filled with overly confident yacht dads explaining maritime navigation to eye-rolling teenagers. Budget $20 for admission, plus another tenner or so for the requisite post-museum seafood snack (fried clams are the unofficial currency here). Pack your patience (tourists move at glacial speeds) and your sense of irony (because you're voluntarily paying money to see whaling harpoons and faded portraits of stern-looking sea captains). In the end, though, this quirky island gem pulls you in precisely because of its idiosyncrasies-a reminder that history, especially when it's salty, scandalous, and seriously maritime, always makes for one hell of a story.