St. Thomas

Sliding through the labyrinthine waterways on the Virgin Islands Ecotours Mangrove Lagoon Tour feels like you're starring in your own surrealist documentary-half Jacques Cousteau, half Gilligan's Island. Set out early (think 8 a.m.) to beat the midday meltdown, or brave a twilight paddle if you're eager to spice things up with the elusive bioluminescent plankton that occasionally put on an extraterrestrial light show. Book at least two days ahead, especially during high season, and budget around 70 bucks per intrepid adventurer-well worth it for the chance to stalk juvenile sharks, sea turtles, and neon-colored fish hiding in and around gnarled mangrove roots as if playing an endless game of underwater tag. Toss sunscreen, eco-safe bug spray, and a waterproof camera or phone pouch into your backpack-the mangroves have an insatiable appetite for unsecured electronics. Sure, you're likely to get slightly sunburned, a little salt-stained, and possibly lose your sunglasses to a curious pelican, but paddling through this primordial maze is an evocative reminder of nature's wonderfully wild weirdness-if nothing else, you'll emerge salty-haired, smiling, and armed with a story that'll earn you at least two rounds of rum at the nearest beach bar.

Perched at the summit of St. Thomas' highest peak in Estate Cornwall, the mountain-top banana daiquiri isn't just a drink-it's a tropical rite of passage. Since the 1960s, thirsty travelers have scaled the island's leafy heights not for panoramic views alone-but to sip this rum-soaked masterpiece, whipped up with ripe local bananas and enough flair to make Hemingway suspiciously glance over from the afterlife. Arrive mid-to-late afternoon, when the cruise ship crowds have thinned and the sun paints the Caribbean sea in hues that justify your phone's camera upgrade. No need to overplan-two weeks' advance booking is sufficient-and budget around $10 for a generously boozy concoction served in a shamelessly kitschy souvenir glass you'll pretend you're too cool for, yet somehow bring home anyway. Bring along sunglasses, sunscreen, and a healthy dose of irony-but ditch any pretensions and your calorie-counting apps. Sure, it's touristy, overpriced, and unabashedly tacky, but sipping that daiquiri with the breeze in your hair, banana-infused nostalgia on your lips, and a slightly blurred vista of the Virgin Islands below is something you'll smugly recount at dinner parties for years.

If you're willing to drag yourself out of bed at an hour when only roosters and regretful partygoers roam the streets, heading to Drake's Seat sunrise view is worth every groggy misstep. Legend has it that the viewpoint earned its name from Sir Francis Drake himself, the dashing-but-not-exactly-loveable pirate and explorer who used this very vantage point in the late 16th century to scope out the merchant ships he'd soon relieve of their cargo. Today, instead of plundered goods, you'll find panoramic vistas of St. Thomas painted gold and crimson-a sunrise that almost makes you forgive Drake's thieving ways. Arriving about 30 minutes before dawn ensures you'll snag a prime spot-any later, and you'll jockey elbows with a sea of yawning tourists, selfie sticks in hand. Plan your sleepy-eyed pilgrimage a day ahead, pack caffeine, a sturdy camera, and perhaps a salty smirk-the legacy of piracy deserves just a touch of irreverence. Best of all, there's no fee: bring nothing more than a few bucks for the local mango smoothies sold roadside and a willingness to swap sleep for epic scenery. Even if you secretly loathe early mornings, this is one sunrise that'll give you bragging rights over every snooze-button devotee back home.

Water Island is the perfect antidote for travelers who find the usual Caribbean bustle a bit too rum-soaked and rowdy and crave instead an experience more akin to Robinson Crusoe-with cocktails. A brief ten-minute ferry hop from St. Thomas, this obscure little outpost-so laid-back it only became America's official fourth Virgin Island as recently as 1996-beckons with stretches of eye-wateringly blue water, gently rustling palms, and beaches so improbably empty you'll double-check whether you missed an apocalypse announcement. Arrive early, ideally mid-morning, to score prime hammock real estate near Honeymoon Beach, and pack essentials-sunscreen, snacks, and a cold six-pack-to avoid paying island prices (though splurging on a roadside fish taco or two is strongly encouraged). With ferry tickets around $15 round-trip (give or take, depending on how convincingly local you appear), it's an affordable detour, even for the stingiest beach bum. Plan at least a day or two ahead during peak season to secure your ferry ride or paddleboard rental, and set aside a budget of roughly $40-$60 per person for incidentals and inevitable beverage temptations. Sure, the island is petite and quiet enough to hear yourself think-possibly a frightening prospect-but the sheer novelty of doing absolutely nothing on an island few have heard of will dazzle your Instagram followers and horrify your productivity-obsessed friends.