Charlotte Amalie

Climbing up to Drake's Seat, perched smugly atop the lush Northside hills of St. Thomas, you're essentially retracing the steps (or rather, the bum-prints) of history's most notorious naval scoundrel, Sir Francis Drake himself-pirate to the Spanish, hero to the Brits, and an all-around master of maritime mischief. With dazzling views that stretch unapologetically across Magens Bay and the sapphire Caribbean, it's easy to imagine Drake lounging here, squinting down at Spanish galleons, stroking that legendary beard, and plotting his next audacious raid. Best visited in the breezy early morning or late afternoon golden hour (when cruise-ship hordes retreat, and your selfies won't feature an unwanted Hawaiian-shirted photobomb squad), Drake's Seat demands little more from your wallet than the willingness to tip the occasional street vendor, so a modest $10-$20 budget is more than enough. Pack a camera, a decent pair of shades, and an appreciation for slightly exaggerated pirate yarns, and show up spontaneously-after all, master spies rarely booked reservations. Even if maritime history doesn't float your boat, the panoramic payoff alone is worth the smug Instagram fame and bragging rights you'll gain for claiming you "occupied the pirate throne."

If your idea of an underwater adventure is less Jacques Cousteau and more Buzz Lightyear on a tropical bender, Coral World's Underwater Sea Trek in Smith Bay delivers brilliantly absurd fun. Strapped into a delightfully sci-fi helmet, you'll stroll leisurely along the ocean floor, channeling your inner astronaut-meets-mermaid while schools of fish eye you suspiciously, wondering how you ended up in their neighborhood. Aim for the mid-morning slot to dodge the crowds and secure the clearest views, and be thoughtful enough to reserve at least a week ahead-because let's face it, striding underwater in a bubble is popular enough to require some foresight. Make sure your swimsuit fits well enough beneath that goofy gear (wardrobe malfunctions underwater are awkward in any species), pack reef-safe sunscreen and a towel, and set aside around $100 per person-not cheap, but cheaper than therapy, and at least twice as entertaining. Historically, Smith Bay has seen pirates, explorers, and bold entrepreneurs, but perhaps none quite as daring-or as fashionably questionable-as you, trotting around beneath the waves like Captain Nemo after a rum punch too many. At the end of the day, even if aquatic power-walking isn't your typical go-to, it's worth the mild embarrassment and moderate dent in your wallet-if only so you can casually drop "that one time I strolled the ocean floor" into every dinner party conversation for the rest of your life.

Ah, the Skyride to Paradise Point-part aerial tramway, part floating Caribbean cocktail lounge-an adventure best tackled mid-morning when the cruise ship hordes are still preoccupied with buffet breakfasts and duty-free watches. Located above Estate Thomas, this quirky cable-car jaunt delivers you 700 feet skyward, dangling gleefully-if precariously-over lush greenery and turquoise swirls of harbor water, before depositing you atop a breezy hill with postcard views of Charlotte Amalie's bustling port and distant Virgin Islands. Plan your upward ascent at least a day in advance, not because it requires military precision (the whole thing screams casual island time), but to snag cheaper online tickets around $25-$30, saving cash for tropical cocktails or the inevitable souvenir coconut cup you'll proudly regret later. Bring sunglasses, sunscreen, and-let's be real-a fully charged phone for mandatory envy-inducing selfies. Sure, you could find more serious adventures or deeper cultural experiences on St. Thomas, but there's an irresistible charm in sipping rum-based concoctions while suspended above paradise. Trust me, even if heights make your stomach jump and sway more wildly than the gondola itself, the Skyride is worth the story you'll tell back home-preferably while holding a rum drink in your commemorative coconut mug.

If your idea of roughing it involves sand between your toes and rum cocktails under moonlight more than wrestling bears and filtering creek water, then an overnight at Cinnamon Bay on St. John is your kind of camping. Nestled on the postcard-perfect shores of the Virgin Islands National Park, this spot feels less like survivalist adventure and more like starring in a Jimmy Buffett song-minus the margarita-induced hangover (well, maybe). Historically speaking, pirates once marauded these waters, and while you probably won't find buried treasure, you will discover tranquil turquoise waves, rustling palm trees, and an oddly comforting chorus of tree frogs. Book your site a month ahead, pack your sunscreen, bug spray, and rum (of course), and aim to arrive mid-afternoon to secure a prime sunset-viewing vantage. Budget about $40 per campsite per night, and brace yourself: facilities are charmingly rustic-think showers that dribble with personality. But as you sit beneath an outrageously starry sky, listening to waves gently caressing this stolen little slice of paradise, you'll realize this quirky Caribbean camp-out is unquestionably worth it-even if only so you can brag later about camping somewhere pirates once buried rum barrels (or so you'd like to think).