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Upscale Hotels on the Upswing

We have just arrived in San Francisco for the weekend, and the desk clerk at the game-themed Serrano Hotel invites us to roll the dice for an upgrade. We're allowed three tries; on my last I hit double fives. Yes! My friend Tracy and I check into a suite with an extensive menu of board games and a do-not-disturb sign that reads GAME IN PROGRESS. We play with the yo-yo, Etch-A-Sketch, and backgammon set that have already been provided. Also available: goldfish for guests who miss their pets. We head down the street to the Hotel Monaco, another of the Tenderloin district's many new boutique hotels, owned, like ours, by the Kimpton Group. The concierge lends us two goldfish. "Don't worry about feeding them," he says as I carry the bowl out. "They just ate."

Even looking as stern as I do in head-to-toe black and Armani glasses, I'm a joke target for good-natured tourists milling about on a Friday night. "Hey, are you gonna sauté or grill those?" one asks. "Don't take them into any sushi restaurants," another warns. Back at the Serrano's front desk, we sign out Operation and Mouse Trap to take to our room. "I just hope your fish don't get jealous," a clerk says.

We've been here only an hour and we're already done in by all the fun.

Not for long. We may be cynical, but Tracy and I are always looking for ways to amuse ourselves. We'd been working much too hard, so we'd decided to embark on a 10-day, entirely indulgent fun quest. Our plan: to travel through California, land of innovative entertainment, down to Mexico, availing ourselves of the imaginative new amenities offered at small upscale hotels.

We know just what we're looking for, too. Like so many travelers who came of age during the entertainment and technology revolutions, we want to telecommute, instantaneously, from anywhere we please, and to be pampered the way models are before they face the camera. We want fashion-forward food, perfect espresso, informed design, good lighting, authentic experiences in nature . . . oh, and limitless access to inner peace. And as vast as our expectations may sound, we don't want to be perceived as unusually obnoxious. After all, we're not alone: we're just your average double-clicking, channel-surfing, expense-accounting, style-obsessed, nature-savvy, art-conscious, high-strung, high-end, achingly ironic baby boomers being courted by hotels in the new millennium.

It's no wonder so many hotels are becoming fun houses of heady diversions and cosseting. At Miami's Albion and Beach House, both owned by Rubell Hotels, cryptic messages--STRANGERS LOOK IN YOUR EYES AND SEE BENEVOLENCE--are left on pillows before bedtime, along with trendy Chupa Chups lollipops from Spain. The Nob Hill Lambourne, in San Francisco, offers green algae shakes with a continental breakfast, and leaves vitamins as part of turndown service. And at the Atlantis, on Paradise Island in the Bahamas, there's a water slide (one of five) that sends guests flying via a clear tunnel through a shark-filled lagoon.

Bill Kimpton, owner of the Serrano (and other hotels, from Chicago to Vancouver), realizes that his more modest attempts to amuse guests may not work for the trendy, difficult Delano crowd. But like Delano owner Ian Schrager, Kimpton knows that, in a hotel lobby, comfort and discretion aren't always as alluring as novelty. "We make it easy for guests to come out of their cocoons and be playful," says Kimpton, who, because he's always felt intimidated by grand hotels, offers ice-breaking happy hours with tarot readings and massages. "When the psychologist Abraham Maslow studied self-actualized people, the common denominator he found was that, among other things, they were all childlike."

Indeed, we are feeling very childlike at the Serrano on our first morning. After waking up in a room that looks like a puppet stage, with red-and-yellow-striped curtains, we say good morning to our fish, eat chocolate, and play the Pokémon game attached to the TV. That evening in the lobby, a skinny jester is hosting a San Francisco trivia game. While I wait for a free 10-minute backrub in a corner, where people are drinking complimentary wine and carrying on as if they were at a high school reunion, two women let me cut the line. "We're nice because we're from Minnesota," one says.

"Is this the craziest place you've ever worked?" I ask the masseuse. "Not the craziest," she says, "but it's the happiest."

Ah, happiness. Every boutique hotel in San Francisco seems intent on promoting it. Chip Conley, whose Joie de Vivre hotels have inundated the Bay Area, says he's in the business of creating "identity refreshment"--promoting carefully crafted experiences for every picky visitor. Each of his 12 San Francisco properties is based on a magazine, from The New Yorker to Men's Health. Most overreachingly, perhaps, the Bijou, which takes its inspiration from Entertainment Weekly, has a front desk that looks like a movie theater concession, and a kiosk phone hooked up to the San Francisco Film Commission. Guests can call to get work as extras. "What better way to provide entertainment value?" Conley asks.

Costanoa, 50 miles down the coast, is "Outside magazine meets Vanity Fair," according to Conley. It's also a little Playboy, too. Because along with its high-end tents for camping, its luxury lodge, outdoor fireplaces, spa, hot tub, hiking trails, and horseback riding, there's some rather suggestive entertainment across the Pacific Coast Highway. Winter, it turns out, is elephant seal breeding time at Año Nuevo State Reserve. Costanoa, which mentions in its brochure that watching these massive homely creatures might induce affection in guests, offers hard-to-get tickets for guided viewings. "We call it our romance-and-adventure package," Conley says.

Unfortunately, we catch the seals on an off day. Except for two bulls engaging in a toothy contretemps amid a harem of placid females, these creatures aren't doing anything beyond lying around. They might as well be watching videos and smoking cigarettes, they're so listless. Valentine's Day, our guide explains, has already passed, and that's really the peak of the mating season. "Nature," Tracy remarks, "is more entertaining on TV."

Maybe wellness will be more fun.

We arrive at the Hotel Parisi, a small, Zen-elegant spot in La Jolla, to hear New Age music playing in the feng shui-attuned lobby. With an in-room yoga teacher and a psychologist on call (along with treatments at the nearby Chopra Center for Well Being), this discreet, high-end urban property is selling inner peace as entertainment.

So much for silly diversions like board games and dopey elephant seals. Here it's all about the ride inward. After having a yoga instructor named Tah give me a private lesson that's so coddling it's embarrassing ("Perfect" and "Good job" she keeps telling me, even though I'm being appallingly lazy), I have the pleasure of asking a licensed psychologist with a local practice for a session on my terrace. What fun--a shrink you can order in. And she's good, too; articulate and professional. She tells me that hotels distance you from daily routines, so they're good places to reflect on the meaning of life. She adds that many of the guests she counsels are suffering from the stress of success. This isn't my case, I tell her. My problem is that I'm having too much fun.

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