On past trips to Hawaii, Joel Stein stayed in touristy areas and never made it to the exotic landscapes he’d glimpsed from afar. This time, he booked a trip with a company that offers incredible insider adventures.

Every time I’ve been in Hawaii, I’ve felt like I was on the set of a faintly depressing film about the ’70s. Sure, I’d catch glimpses of the black-sand beaches, the volcanoes popping out of dense jungle and those gorgeous, extraterrestrial-looking plants—but they were always overpowered by my hotel’s boxy wooden structure and avocado-and-orange color scheme. Why, I wondered, would a place this naturally beautiful want to conjure up America’s darkest decade?

Determined to get closer to the beauty I had seen only from the airport shuttle van—and to taste the Hawaiian food and culture I knew only vaguely from hotel luaus—I signed up with Pure Kauai and Pure Maui, two parts of a company specializing in personalized vacations. Pure has gotten attention lately for hosting celebrities like Matt Damon. The company’s founder, Phil Jones, was about to start a luxury-vacation-planning business in Los Angeles when he met his future wife, who lived in Kauai. Together they built Pure, a firm that, in addition to setting guests up in the villas and condos it manages, matches them with a team of private chefs and local experts like surf instructors, yoga teachers, masseuses and hiking guides.

All Pure clients are assigned hosts, who steer them to secluded island spots. Our Kauai host, Bryce Toney, met me and my wife, Cassandra Barry, at the airport and put leis around our necks. Strung with plumeria, which smelled like honeyed peaches, the flower garlands relaxed me in a way that made me understand that a lei has a purpose other than making me feel like a jerk. Bryce drove us to the North Shore of Kauai, where the few tiny towns are dotted with adorable hippie coffee shops and surf stores.

The center of Kauai is jungle that gets more rainfall than just about anywhere else on earth, and the North Shore coast alternates between rocky cliffs and wide beaches. Our house, inside a gated community, is appropriately called the Hawaiian Romantic Cottage: one room, with a queen-size bed that faces windows looking out on our own private view of a cliff and the ocean. I have never felt so much pressure from a room. We also have an enormous backyard with a hammock, a giant Flintstone-esque table, and a rocky path down to a tiny spit of beach. Once we managed to get there, the beach was empty except for a few teenage surfers and a 72-year-old fisherman named Eddie, who gave us a lift back to our gated community—where we, of course, ran into a family out walking their pet goats. Hawaii was starting to seem like a children’s book written by someone who took a lot of drugs in the ’s60s.

That night, we sat in our house eating a pizza topped with delicate, sweet smoked ono fish and capers from Kilauea Bakery & Pau Hana Pizza, a local hangout that also makes sourdough bread. We ate the pizza with a bottle of crisp Maui Blanc pineapple wine, which was by far the best non-grape-based wine I’ve ever had (i.e., we still didn’t finish half the bottle). Looking out at the moonlit ocean, Cassandra and I felt like we were the only people in Hawaii. In the right decade.

The next morning, a private chef came to our house and made us lemon-ricotta pancakes with fresh mango and pineapple. He also packed us turkey-and-hummus sandwiches on sourdough to take on a hike, after which I asked Bryce to show us some of the food that locals actually eat. He hooked us up at the Hanalei Liquor Store, the best place to get Spam musubi—sushi-like, teriyaki-spiked Spam and rice wrapped in nori—that are delicious in a way I won’t attempt to defend.

I spent the afternoon at a river, practicing stand-up paddle-surfing—the sport made hip by surfer Laird Hamilton and those ab-tastic pictures of Jennifer Aniston—in which you stand on a board and use kayak-type oars for balance and speed (or for making a big splash every time you fall). For dinner, Bryce dropped us off at Bar Acuda, the one great restaurant on Kauai. Chef Jim Moffat, named an F&W Best New Chef in 1996 when he cooked at 42 Degrees in San Francisco, took a yearlong surfing trip to Kauai with his family in 2003 and stayed there. Frustrated by the island’s lack of decent restaurants, he opened this cozy, casual, poorly named, tapas-style place. (Surfers seem to be even bigger suckers for puns than hair-salon owners.) "It works around my schedule, not the other way around," Moffat says—which means that Bar Acuda doesn’t serve lunch and is manned by sous-chefs when the late-afternoon surf is rad. The restaurant offers seasonal dishes from the local-organic school: Tender, bright ahi tuna carpaccio was touched with onions, a splash of balsamic vinegar and tiny bits of habanero that never overpowered the fish. One enormous sea scallop, just barely cooked through, came wrapped in grilled pancetta amid a ring of roasted garlic and lentils. It’s not easy to get good wine on the North Shore, so our glasses of a great Argiolas Vermentino, Turley Zinfandel and many other Moffat selections were, perhaps, overappreciated. That night, a bit drunk, Cassandra and I let the Hawaiian Romantic Cottage down.

We woke early to take surfing lessons, which I dreaded, since my general take on the ocean is that it’s cold and full of things that might touch you unexpectedly. So, as cool as our instructor, Ian Vernon, with his long hair and perma-giggle, may have been, his lesson on the beach about riptides and currents left me panicked. But once we paddled out, with the tropical water and my wet suit keeping me warm, and he pushed me off into my first tiny wave—and I actually stood up—I was hooked by the feel of being pushed along like an amusement-park ride. I truly believe that no one other than Ian could have gotten me standing nearly the whole time, and reluctant to leave the water after an hour.

Later, we drove to the parking lot at Hanalei Pier to eat at a taco truck some islanders had told me about. Pat Grenz, a gentle, bearded surfer from Colorado who once cooked at Bar Acuda, opened Pat’s Taqueria because he had always wanted to run a place that serves the food he loves: fresh mahimahi tacos. Even better, to my taste, were his carne asada tacos. He marinates the beef in teriyaki sauce and chili powder, and it comes out rich and juicy. The truck is open only from noon to 3 p.m.—which leaves Grenz with plenty of time to surf.

Spoiled by having Bryce fulfill my every whim in Kauai, I was now warmed up for Maui, a short flight away. Our new hosts—Ryan Siebring, president of Pure Kauai’s year-old spin-off Pure Maui, and his colleague Mindy Robertson—lei-ed us up at the airport and showed us around. Maui is more developed than Kauai, but the beaches are better: expanses of white-sand coves and tropical plants. Our house, Ahihi Bay Hideaway, sits on its own bit of rocky coast. Listed at $7.2 million, it’s the only rental house in the area’s nature preserve. All mahogany and glass, it has a saline pool carved out of volcanic rock and a two-story cylindrical aquarium. Huge windows slide away completely, opening the ground floor out onto the coral reef where we did some amazing snorkeling, spotting two giant sea turtles and fish that looked like the spawn of neon signs. The house is owned by Napa Valley vintner Fred Constant, who had left some bottles of his Constant Cabernet Sauvignon, which were big yet balanced—and, best of all, not made from pineapples.

Mindy took us to a hiking trail marked only by barbed wire, which was pushed down so you could step over it. She ran shoeless through thick bamboo like a mad monkey, leading us over cliffs with rope ladders and gnawing on guavas, which she shared with us. This, I thought, was the Hawaii I always knew existed, like the jungles in Apocalypse Now if Coppola had been shooting a Disney movie. After passing three small waterfalls, we swam through a river to a fourth, giant fall.

Exhausted, we got a late lunch at the Flatbread Pizza Company in Paia (a branch of New England’s Flatbread Company), where the ovens are stoked with mesquite-like kiawe wood. We sat at a communal table amid heavily tattooed surfer hipsters, and after eating a mesclun salad piled with arame seaweed and tossed with a ginger-tamari vinaigrette, we shared a mess of small, thin-crusted pizzas. The Mopsy’s Kalua pork pie—with mango barbecue sauce, Maui-grown pineapple, Surfing Goat chèvre and kiawe-smoked free-range pork—was awesomely Hawaiian.

With a whole new attitude about ocean activities, I woke up early the next morning to go outrigger canoeing with guide Jake Abeytia, who races for a local club team. When I told Jake I wanted lunch somewhere that wasn’t packed with tourists, he pointed me to the Eskimo Candy fish store for containers of poke—delicious one-inch cubes of raw ahi mixed with scallions, soy sauce and sesame oil. Owner Jeff Hansen, who looks like a yacht captain from, yes, the ’s70s, has been selling seafood to restaurants on Maui and Kauai since 1987; Bar Acuda is one of his customers. Five years ago he opened this small, reasonably priced spot on a side street in Kihei so he could sell to locals. It’s a take-out joint with a few tables where you can eat seafood chowder, crab cakes or seafood pasta piled high with shrimp, scallops, clams and whatever fish Hansen thinks looks best.

I needed that break from all the poshness, especially since I was about to experience the most outrageous part of our vacation, the one Pure had been talking up even before I arrived: AquaCranial Therapy. A New Agey massage, it was to be administered by the technique’s inventor, Rebecca Goff, who spends her summers in Tonga swimming with whales. Better yet, I learned she was going to give me something called cetacean resonation, her new whale-swimming-based therapy. I felt like the king of Atlantis.

As Goff explained what was about to happen, it became clear that AquaCranial Therapy was no mere head massage in the water. "Craniosacral therapy disorganizes the electrical field so that it reorganizes more coherently," she told me. I then spent 20 minutes in the ocean with my head in an airplane neck floatie, as she spun me, rocked me like a dolphin in the womb, and tapped a crystal tuning fork against my forehead and feet. Afterward, she told me there was a lot of tension on the left side of my heart. "Whatever you’sre doing," she said, "stop." This totally freaked out my electrical field. When we got back to the car, Ryan and Mindy asked me how it was. Could I tell these nice people who had been working so hard to make me happy that the only effect it had on me was to make me feel weird? I could. And I did. And they, ever the perfect hosts, laughed and told me that everyone is different. I wanted to replace everyone in my life with hosts.

For our last night, Cassandra and I stayed home. We took a dip in the pool while private chef Scotty Olival cooked dinner with ingredients he’d gathered that afternoon from a garden near the organic café he used to run. We had lobster (Scotty claimed he’d caught it with his hands) mixed with mango in summer rolls and with kabocha squash in a bisque. He served an ono-and-ahi carpaccio as good as Bar Acuda’s, and blended cashews and coconut into a thick dipping sauce that went perfectly with his skewers of grilled prawns and Maui beef. Sitting there, full and contented, I knew I’d finally been won over—after family disasters on cruises and bus tours—to the idea of letting someone else plan my vacation for me.

Joel Stein is an op-ed columnist for the Los Angeles Times and writes about food, pop culture and sports for Time magazine.