Tresco

Clinging stubbornly to a granite outpost on the windswept shores of Tresco, Cromwell's Castle is less a quaint historical attraction and more an architectural middle finger raised defiantly toward an invading world. Built in 1651 under the grim shadow of Oliver Cromwell's Puritan ambitions, this fortress wasn't exactly designed for postcards-it was intended to keep Dutch invaders out and, presumably, damp, miserable soldiers in. But today, this squat, weather-beaten guardian provides visitors with jaw-dropping panoramic views across the Scilly Isles, so picturesque they could make even Oliver Cromwell's stony heart flutter. To truly soak in the surreal maritime splendor, arrive early in the morning-before the day-trippers invade-to enjoy the ruins in moody solitude. Budget nothing-entry is refreshingly free-but come prepared with sturdy boots, a waterproof jacket, and a flask of something strong that Cromwell himself would likely disapprove. A little planning goes a long way: check the tides and weather forecasts the day before and brace yourself for brisk walks and gusty sea air. Visiting Cromwell's Castle might not drastically alter the trajectory of your life, but there's something undeniably satisfying-bordering on smug-in casually regaling friends back home with stories of your pilgrimage to a 17th-century fortress built by humorless Puritans in the middle of nowhere.

If you've ever dreamed of aquatic shenanigans akin to swimming with puppies-except these puppies weigh two hundred pounds, have whiskers, and glide effortlessly beneath the waves-then snorkeling with Atlantic grey seals in the Eastern Isles is your absurdly delightful ticket. These playful creatures, once hunted heavily for their fur and oil but now thriving, seem to harbor no grudges; indeed, they'll curiously approach your snorkeling mask as though you're the next quirky thing to trend on Seal Twitter. Aim for early morning excursions, when the waters are crystal-clear, the tourists haven't yet swarmed, and the seals are feeling extra sociable after their breakfast feast. Book at least a few days ahead and budget around $80-$100 for a two-hour splash session-bring towels, a reliable underwater camera, and your best aquatic dance moves (seals appreciate a flair for drama). Even if you're skeptical about trading dry land and dignity for flippered fumbling, there's no denying the priceless bragging rights of returning home boasting, "Oh, nothing big-just spent the morning as honorary mermaid royalty, hanging out with seals."

There's something gloriously absurd about island hopping around the Scilly Isles, a scattering of stubbornly British islets clinging like crumbs to England's southwestern apron. Picture yourself aboard a rattling boat-part ferry, part bathtub with an engine-gently spray-slapped awake as you bounce between islands named like eccentric British uncles: Tresco, Bryher, or St. Agnes. Arrive early, preferably catching the morning sun as fishermen grumble lovingly into their nets, and plan at least a day or two ahead unless you enjoy the islanders' amused smirks at the new arrival stranded dockside. Pack cash (£30-£50 should suffice), snacks, a sturdy hat, sunscreen, and a waterproof jacket, because there's nothing Mother Nature loves more than surprising overconfident tourists. Historical oddities abound-from shipwreck-laden shores whispering tales of maritime misadventures to smugglers' hideaways straight from a Stevenson novel. Even if your sea legs fail and your sandwiches turn soggy, remember this: nothing makes better pub chatter than recounting how you braved the unruly tides just to sip tea and nibble scones on remote islets most folks can't even pronounce.

Camping out on Bryher Island isn't just about roughing it beneath a reassuringly waterproof canvas dome-it's more like being gently slapped awake by Mother Nature herself, in the nicest possible Bryher-esque way. Glamping here, amid the brine-kissed winds and stubbornly rugged terrain of the tiniest inhabited isle in the Scilly archipelago, manages to marry rustic charm with just enough plushness to keep your inner hedonist from fleeing home to Netflix. Historically, Bryher's been the quiet neighbor, overshadowed by its flashier siblings, but that's exactly why it's perfect-come dusk, the lack of human buzz grants you a star show that makes Galileo look unimaginative. Plan at least a month in advance, nab a canvas abode with proper bedding (thank heavens), and arrive by late afternoon-ideally with a bottle of local gin, a jumble of cozy layers, and astronomy apps ready. Budget around £100-£150 per night, a modest fee for the chance to smugly recount at dinner parties the night you casually counted constellations under Bryher's arrogantly unpolluted skies. Even if the stars hide behind clouds, the memory of sipping your gin beneath a weather system that could spontaneously decide to gently soak your socks is exactly the sort of tale worth exaggerating endlessly.