I like Andrew Strangeway a lot, but I’ve never met him. He’s the first person to land and sleep on all 162 of Scotland’s remote islands. The man clearly understands the pleasures of stepping onto a spot of land surrounded by water, though we don’t share every fascination. He’s obviously okay with a sleeping bag versus my insistence on high thread-counts in luxury hotels. I picture him eating a tin of beans warmed over Sterno, while I prefer to have a great chef in the picture.

Still, I am as powerless as he is to resist an island. In my case, it started with early trips to Hawaii and the Caribbean with my parents. Untethered from mainland reality, we always had a purer kind of fun, and that still holds true. Something about the limited elbowroom seems to concentrate and intensify life. Insulated by even a few feet of water, islanders are “us” and everybody else is “them”. Culture, food and language evolve in curious and mysterious ways so that inhabitants seem like a species all their own. Sardinia isn’t Italy. Santorini isn’t Greece. And I enjoy feeling a little less like my normal self when I’m in island mode.

Santorini, Greece

An island can be all about escape. Capri is the paragon. The Emperor Tiberius had the right idea early on, building not one but 12 villa retreats there. I imagine slaves rowing him out for the season, but the hydrofoil that whisks me there from Naples still leaves plenty of time to decompress. A convertible taxi with a blue and white stripped canvas top huffs up the switchback to the village of Capri. At the top, I prefer to hop out and walk. The going can be slow on the cobblestoned streets, and boutique windows beg for attention anyway. I plant myself at the beloved Grand Hotel Quisisana, where a few generations of celebs have hidden behind sunglasses beside the pool. My friend Gianfranco’s impeccable staff pulls off elegance with sly ease.

Capri, Italy

The secret to just about any island—and especially Capri—is to take your time. A majority of tourists only dip their toes in on rushed day trips. But settle in for a few days, and the place blossoms in ways most visitors can’t imagine. A stroll in quiet Capri at dusk is calming dolce vita. Lunch at the private beach club at Marina Piccola is the sort of barely restrained decadence I want from a fine island. I like to stroll up to the ruins of Tiberius’s grandest villa, where I can see much of the island’s rocky edge and be reminded how I’m afloat in a sea of contentment.

Guests taking picture in Montenegro

Sometimes, I crave an island for its very remoteness and a minimum of civilization. The Galápagos Islands fit that bill. Marooned in the Pacific off the coast of Ecuador, San Cristóbal is one of the largest in the archipelago. I am not a fan of cruise-by island visits. The point of an island is to be on it, and this one—for all of its amazing wildlife—is home to terrific luxury eco-resorts like the Golden Bay. By day, though, I am a latter-day Darwin, off to explore the rest of an island that hasn’t changed since the naturalist came ashore in 1835. Blue-footed boobies gawk at me on a lava trail walk, like they’re daring me to comment on their footwear. On a little calm-water kayaking excursion off the north coast, sea lions circle, splash and check me out. Snorkeling over the reef, I glance to the side and see that a marine iguana has adopted me as his buddy-system partner. It’s like an alien planet, but I come in peace and am welcomed accordingly.

Woman with tortoise in the Galapagos Islands

But if I could only visit one island for the rest of my life, it would have to be Hvar (pronounced “H-whar”) just off Croatia’s Dalmatian Coast. Hvar consistently makes the list of the world’s 10 most beautiful islands, and its gorgeousness is truly mind-blowing. I can stare at the indescribably blue Adriatic all day. When the lavender fields are in bloom, I love how their purple ribbons crest a hill and disappear into a silver-leafed olive grove. When, at the end of a country walk, a local olive grower pours me a long drizzle of his oil and nudges a plate of crusty bread my way, that is some kind of paradise. This is the breed of island where history is always close to the surface. My favorite hotel, the Adriana in Hvar town, is a former private villa tucked inside an arboretum. Yachts look just right here. Back in the day, King Edward VIII and Wallis Simpson sailed in to hide out before he abdicated the throne. I could give up a realm for Hvar, no problem at all.

Woman walking stairs in Hvar, Croatia

I’ll never beat Andrew Strangeway’s record of 162 islands in a single country, but I long ago lost count of how many I’ve landed on already. It may be that no man is an island. But it is just as true that no man is happier on an island than I am.