Takamatsu

If you're the kind of traveler who finds Monet paintings suspiciously tranquil and secretly suspects museums are plotting against your sanity, the Naoshima Island Art Exploration might just win you over. Here, amid cherry blossoms and sea breezes, you'll stumble across Yayoi Kusama's iconic pumpkins, surreal enough to convince you she's in cahoots with Salvador Dali. Naoshima, an unassuming speck off Japan's Shikoku coast, has evolved from a sleepy fishing village into a whimsical playground for art lovers, architects, and those who simply crave stories that begin with, "You wouldn't believe where I spent the afternoon..." Go early-preferably in the mellow morning hours when sunlight hits Kusama's polka-dots just right-armed with sunscreen, good walking shoes, and an open mind. Reserve ferry tickets and accommodations at least three months ahead, and budget generously ($100-$150, depending on your art-appetite), because the installations are scattered across the entire island, cunningly designed to mess with your sense of direction. But embrace getting lost-it's half the charm. Whether you're an avant-garde devotee or a skeptical cynic just tagging along, Naoshima is absolutely worth it, if only so you can dramatically recount your encounter with giant polka-dotted pumpkins to friends back home and watch their eyebrows dance skeptically into their hairlines.

There are museums, there are hotels, and then there's whatever visionary genius (or deranged eccentric-take your pick) dreamed up the Benesse House Museum on Naoshima. Perched serenely upon this quiet, sleepy island set adrift in Japan's Inland Sea, it feels like what would happen if Tate Modern had a passionate fling with a seaside ryokan. Conceived by Tadao Ando-the minimalist architect who never met a concrete wall he didn't adore-the museum invites guests to literally sleep within whispering distance of world-class contemporary art, presenting the tantalizing risk of stumbling half-awake into a priceless Yayoi Kusama pumpkin or a James Turrell installation at sunrise. Practical advice? Book your stay months in advance, since the place has cultivated an obsessive fan base, and expect to shell out at least ¥30,000 per night (art and epiphany rarely come cheap). Pack your best black turtleneck for the chilly gallery strolls and sneak out of bed as dawn breaks for an eerily beautiful, absolutely Instagrammable morning light that makes even avant-garde nonsense profoundly meaningful. Is staying overnight within a museum strictly necessary? Probably not. But trust me, telling your friends that you spent the night wrapped in fine linens, mere feet away from a Basquiat-now that alone is worth it.