Tampa

Slipping into the cool waters of Crystal River on a brisk winter morning to swim with manatees feels suspiciously like attending a slow-motion underwater tea party, where your hosts are lumbering, whisker-faced guests of honor who couldn't care less about your wetsuit-clad gawking. Once mistaken by delirious sailors for mermaids (you'd have to be spectacularly rum-soaked or vitamin-deprived to make that leap), these gentle giants float leisurely, munching seagrass and offering an occasional curious glance to visitors. Aim for the earliest tour available-morning inevitably brings clearer waters, fewer gate-crashers, and a better chance at an intimate encounter with these majestic marine mammals. Plan a few weeks ahead for much-coveted slots between November and March, and budget around $70 to $100 per person, a small price to pay for sharing space with creatures whose closest relatives are elephants (now that's some impressively quirky family lineage). Pack a towel, waterproof camera, and your dignity-though you'll inevitably lose the latter once a 1,200-pound sea potato gently bumps into your backside, sending your carefully curated Instagram pose sprawling. Ultimately, swimming with manatees isn't just a bucket-list item, it's a chance to briefly exist on manatee time-slow, peaceful, and blissfully indifferent to all your frantic human nonsense. And if that's not worth the price of admission, the story you're left with certainly is.

Forget Disney princesses-Florida has real-life, oxygen-sucking mermaids who've been defying logic (and probably OSHA regulations) since the 1940s at Weeki Wachee, a roadside oddity so delightfully kitschy it feels like Jimmy Buffett and David Lynch opened a theme park together. Weeki Wachee Springs, once a sleepy stop-off enticing weary travelers coaxed down U.S. Highway 19, quickly morphed into a Sunshine State legend, enticing generations of gawkers-Elvis Presley included-with its underwater ballet meets synchronized-swimming spectacle, all executed by impressively graceful mermaids breathing via submerged air hoses. Plan to arrive early-morning shows have fewer cranky kids and fewer cranky adults-and book tickets a few days ahead in peak summer months. A crisp Andrew Jackson ($13 for adults, $8 for kids) covers admission, leaving cash leftover for tacky souvenirs and fried delights near the gift shop. Pack sunscreen, sunglasses, and a hearty appreciation for retro Americana; bonus points if you wear a vintage Hawaiian shirt. Is it touristy? Of course. Slightly absurd? Absolutely. But worth every penny to brag at future dinner parties about the time you watched glitter-spangled creatures perform an underwater rendition of Hans Christian Andersen's tale-all beneath Weeki Wachee's crystal-clear, slightly surreal waters.

If you've ever wondered what it feels like to drive straight into a Jimmy Buffett song, a road trip to Florida's Key West is your answer-part tropical pilgrimage, part surreal journey through Americana. As you glide down the Overseas Highway, a feat of engineering audacious enough to make even Henry Flagler blush, you'll pass quirky rum shacks, pastel-hued seafood dives, and billboard warnings about rogue iguanas. Departing early in the morning is your ticket to both beating traffic and watching the sun spill golden chaos over the Atlantic, while dolphins show off just to spite the tourists who've tried (and failed) capturing them on camera. Wise wanderers book accommodations weeks ahead since inns fill faster than rum runners emptied glasses during prohibition. Set aside at least two or three days and a couple hundred dollars to properly sink into the rhythm of island time; pack sunscreen, swimwear, and an appreciation for Hemingway's peculiar taste in six-toed cats. Why bother with this sun-scorched pilgrimage? Because standing at the southernmost point, sipping something cold, and realizing it's not Cuba you're gazing at but your own strange, vibrant, perfectly absurd homeland makes for one hell of a good story-at least until the rum kicks in.