Union Island

Dragging yourself up Mount Taboi-Union Island's undisputed rooftop-is the sort of activity people smugly mention at dinner parties, casually dropping altitude numbers like they're recounting a heroic conquest rather than an exhausting, sweaty scramble through tropical foliage. Start your trek early, around daybreak, both to dodge the Caribbean sun's malevolent mid-day wrath and to experience that smug sense of superiority as you watch everyone else below still fumbling sleepily through breakfast. Plan ahead-a few days should suffice-to sweet-talk a local guide or at least secure decent directions; wandering blindly into the island's interior is just asking for your very own Robinson Crusoe moment. Budget? Surprisingly easygoing: a few Eastern Caribbean dollars to tip your guide and a pocketful extra for celebratory cold beers afterward should cover it nicely. Pack water, lots of it, and don't forget bug spray unless you have a masochistic fondness for itchy souvenirs. As you collapse triumphantly atop Taboi, gazing down on a surreal, panoramic patchwork of sapphire-blue sea and emerald-green islands scattered about like tossed dice, you'll realize the blisters and curses uphill were worth every step-if not for the glorious Instagram bragging rights, then surely for the sheer joy of recounting your epic ordeal to unsuspecting acquaintances for years to come.

Perched precariously atop a wobbly reef of discarded conch shells, Happy Island is precisely the kind of place your sensible aunt would warn you against-making it all the more irresistible. Conceived by local visionary (or mad genius, depending on your cocktail count), Janti Ramage, this buoyant boozy oasis off Clifton Harbor serves as both testament to human ingenuity and joyous disregard for conventional island architecture. Charter a water taxi late afternoon (ideally around sunset to bask in the perfect amber glow-Instagram will thank you) and stash away at least $30-$50 cash for a respectable buzz and generous tipping opportunities. Leave your dignity onshore; bring sunscreen, sunglasses, and an open-minded willingness to embrace spontaneous dance-offs with sailors who've been anchored too long. Book ahead if you're traveling at peak season, or live dangerously and charm your way aboard last-minute. Even if booze-laced ocean breezes and sashimi-fresh ceviche don't impress you, the sheer audacity of building an entire island out of lunch leftovers-an act of Caribbean-level recycling ingenuity-certainly will. This isn't just a bar; it's a floating, rum-soaked rebellion-worth every penny and every wave-induced wobble for the story you'll enthusiastically embellish for years to come.

At Chatham Bay, you're not just enjoying seafood-you're attending a sumptuous aquatic conspiracy. Imagine yourself sprawled indolently on powdery sands, as local grill-masters coax lobster and red snapper into smoky perfection on rudimentary grills fashioned from repurposed oil drums, the aroma intoxicating enough to inspire scandalous envy among distant sailboats bobbing offshore. Arrive by mid-afternoon, long after the sunburned cruise day-trippers have packed up their selfie sticks, but early enough to secure prime beachfront real estate; spontaneity is delightful, but calling ahead a day or two will save you from tragic crustacean deprivation. Toss in some cash-around $30 to $40 per head-for seafood so fresh, it practically swims onto your plate on its own initiative. Pack a towel, bug spray, and just enough rum to convince yourself you dance like a local when steel drums kick in. Sure, there may be prettier beaches in the Caribbean (though few), or finer dining experiences globally (undoubtedly), but where else can you boast you've savored charred mahi-mahi beneath a star-studded sky, toes buried deep in sand once frequented by smugglers and pirates? Even if seafood isn't your thing, come for the palpable hint of rebellion lingering in Chatham Bay's air, stay for the feast, and leave with a salty smile and a story that's almost certainly exaggerated-but deliciously unforgettable.

If your idea of paradise involves smacking into jellyfish while frantically adjusting your snorkel mask-you're in luck. Sailing to Tobago Cays Marine Park is a journey worth braving sea spray and sharing space with overly optimistic amateur pirates. Nestled in the Caribbean's Grenadines, these sandy specks of island bliss look suspiciously like they've been Photoshopped onto the ocean. Historically a hideout for pirates and smugglers (so bonus points if you spot treasure chests or bottles of rum), today they offer something equally outlawish-unbridled close-ups with sea turtles who seem slightly annoyed by your selfie-stick wielding enthusiasm. Plan your escape for early morning, when turtles are feeling sociable and tourists still lie comatose from last night's rum punch. Book your sailboat or catamaran at least a week ahead, and expect to shell out around $120 per person, a fee that's less "pirate pricing" and more conservation contribution. Essentials include sunscreen potent enough for albinos, waterproof gear for Instagramming your bravery, and cash to tip your captain, because trust me, they deserve it after navigating your overexcited antics. Even if you spend most of the day sputtering through your snorkel, wind-torn and sunburned, bragging rights come guaranteed: after all, how many people can casually drop lines about swimming with endangered reptiles and surviving marine park shenanigans over their next meal?

If your idea of nightlife involves fewer cocktails and more cosmic existentialism, skip the fancy bars and head straight to Fort Hill on Union Island, where the Milky Way puts on a dazzling nightly cabaret free of hangovers and questionable karaoke. This tiny Caribbean haven, blissfully free of light pollution and tourist hordes, has hosted generations of navigators, pirates, and dreamers staring skyward for guidance, treasure, or existential comfort-sometimes all three. For optimal celestial drama, show up late-midnight is prime viewing-and bring a blanket, binoculars, and a flask of something potent, because staring into the universe's infinite abyss tends to make one thirsty. Plan at least a couple days ahead, watch out for moon cycles (new moon nights are ideal), and budget around zero dollars-since the universe, thankfully, hasn't figured out how to charge admission yet. Sure, at some point you'll realize you've come a long way to lie on your back staring at space gas billions of miles away, but trust me: getting humbled by the immensity of the cosmos is worth every bit of your existential dread-and if nothing else, it'll earn you one hell of a story next time someone brags about their fancy resort vacation.