Dream of managing an island hotel?

The dream: quitting your hamster-wheel job in a grinding city to run an enchanting hotel in the tropics, where the daily routine includes ocean swims and cocktails at sunset.

The nightmare: The pool is undergoing repairs, and the guests are hot and desperate to swim; the hotel's snorkel equipment leaks and must be replaced; and a hurricane is brewing offshore.

"This is not a job, it's a lifestyle," says Bob Gevinski, 40, who put his life as a freelance photographer in Boston on pause in October 2007 to manage the Hix Island House on the Puerto Rican island of Vieques. "When I was a guest here, I thought, 'How can I extend this feeling or make it part of my life?' "

Many people share this fantasy: the never-ending vacation that comes with a paycheck. They mull the idea of trading in long commutes, 7.5 hours of desk time, Dilbert bosses, and plain old monotony for a life of simple pleasures and unusual challenges. They imagine escaping, yet not fully dropping out.

Yet what is the reality of running Hotel Paradise? After a weekend spent shadowing Gevinski, I learned that the truth lies somewhere between dream and nightmare.

I met Gevinski at my sister's wedding, where he spent most of the time behind the lens, orchestrating our poses and propping up our smiles. Months later, I received a mass e-mail from him, in which he detailed his life-changing plan: "For the next two years, I've committed myself to a sleepy island in the Caribbean. I'm taking the time down here to manage one of my favorite hotels," Gevinski wrote about his career upheaval, the second in four years.

Gevinski, who once worked as an ad sales manager at CBS television stations, later explained how he landed this gig.

As a photographer, he frequently shot destination weddings on the tiny isle once controversially inhabited by the U.S. Navy and now an open secret of white sand beaches and lush landscapes. He stayed at the Hix Island House three years in row, befriending owners John and Neeva Gayle Hix, who divide the calendar between Vieques and Toronto.

The couple needed a manager to run the place and sent out a letter that tapped into the fantasy: "There must be someone who has the dream to run a hotel in the Caribbean?" Gevinski's sister responded, but eventually she and her husband started to crave mainland life. They returned to New York, passing the keys to another couple before Gevinski took over.

"He is very fortunate," says Joe McInerney, president of the American Hotel and Lodging Association. "You usually need experience.

"A manager has to be a jack-of-all-trades," McInerney adds. "He is the host, but he also cleans the rooms when there's a no-show. He does the accounting, the marketing, the managing and the operations. He does everything."

Gevinski met me at the tiny airport with stubble on his tanned face, his shorts and T-shirt wrinkled and worn after a day of labor. It was October, a slow month, and the staff of five was finally shifting its attention to repairs and renovations that had piled up during the high season, which runs December to April. The top chore on Gevinski's list was resurfacing the pool.

On the short drive to the hotel, along bumpy roads draped with thick vegetation, we compared afternoons: Mine involved a delightful 20-minute flight from San Juan cushioned between puffy clouds and the calm Caribbean Sea; his consisted of an islandwide scavenger hunt for an O-ring. Gevinski desperately needed an after-work drink, but he was still on the clock.

"It's Friday night. I figured I'd go get some beers," he shouted from the bottom of the deep end after we had dropped off my bags. "But no, I am putting on bonding agent."

Only two guests were staying at the 13-room property that night, Paige and Meg Finnegan, honeymooners from Chicago. More specifically, newlyweds who wanted to swim. (The hotel has two pools, one on the main property, the other at La Casona, a house often booked for special occasions. When not being rented, this area is usually off-limits to other visitors.)

Besides the usual responsibilities of a manager, the Hix Island House places additional demands on Gevinski. The 15-year-old hotel, which originated as a private home for Hix, an architect, and his clothing-designer spouse (all of the bathrobes and nightshirts are by Neeva Gayle), hews to an eco-design that many might find challenging. The buildings are built of gray concrete slabs, which hold up well against the elements but have a bomb-shelter look. In addition, the loft-style apartments lack window screens, and some of the rooms are missing an entire fourth wall. Ergo, guests may find bugs and lizards in their quarters, or a small rainwater lake forming by their slippers.

To his relief, Gevinski does not have the pressures of an amenity-filled resort. There's no on-site bar or restaurant: Guests either eat out or cook-and-cocktail in their studios, which come with full kitchens and breakfast fixings. There's no fitness center - only the pool (which is better suited for lazy laps than for heavy workouts), yoga sessions in an open-air pavilion, and on-call masseuses, who knead visitors in their rooms or in the gardens. The front office sells island necessities, such as bug spray and water, but few items worth taking home.

Some of the manager's jobs are done behind the scenes: Gevinski tossing frayed robes into the stockroom, painting a corroded refrigerator door, rejecting overripe grapefruits before they land in guest-room fruit bowls.

"Yes, it's nice to think about putting up a hammock in the field, but what's more important is removing a soap container with rust or finding hair in the shower," he said. "My job is to protect the hotel's reputation and keep the customer happy."

What would make this weekend's guests happy would be completion of the pool repairs, a job that was running behind schedule and prompting Gevinski to frequently update the Finnegans on its progress.

Not tomorrow, but hoping for Sunday, or Monday morning, before breakfast.

Gevinski rose at 6 a.m. Saturday to check on the band of pool workers who should have been two hours into their task. (One of the many adjustments Gevinski had to make was the changeover to Caribbean time; everything is slower here.) Instead, the men, looking half-asleep, sipped coffee, smoked and idly chatted in the dry depths of the pool. Gevinski paced around, looking for the crew's employer, who eventually showed up and set his staff in motion.

Not long after, Gevinski moved on to his next duty - checking e-mail for reservations and queries - but he had to hurry. Yoga was starting soon.

Two alternating yoga instructors provide morning lessons to guests and island residents. Today's session was taught by Jen Dehner, who moved to Vieques from California nearly 12 years ago and also sells jewelry.

"Expand from the heart and look to the future," Dehner intoned, as legs lifted and bent over knees, and heads rested on opposite shoulders.

"Oops, I forgot to open the pool at the main house," Gevinski whispered, realizing in mid-pose that he hadn't unlocked the gate to La Casona, preventing Meg and Paige from using his pool while theirs was filled with workers.

The rest of the day mainly consisted of "doing the rounds" and "checking up on people." Did all of the rooms receive a loaf of fresh bread made by Leti, one of the housekeepers? Were the kitchens restocked with coffee, ketchup, eggs? Did Alex, a local boy who travels to work on horseback, mow the entire lawn? Were the bananas ripe for picking? Did anyone feed the skinny stray dog starving for love and food?

"You plan to do these things," Gevinski said as he surveyed the rooftop cactus garden (in need of weeding), "but you never know what's going to happen. So you really can't plan more than half a day."

Whatever was going to happen was going to have to wait, because as the sun started its evening drop, Gevinski made a quiet break for Sun Bay Beach, a curved strand walled in by sea-grape trees and coconut palms.

"I haven't been to my favorite beach since last November, and it's only three miles away," he said, admitting that he often settles for Sun Bay because his hotel cell phone works there. Midway through his walk along the water's edge, a cloud of mosquitoes swarmed his head. He raced back to the car and drove off, his rare escape rudely interrupted.

Sunday is hardly a day of rest for a hotel manager, and Gevinski's seventh day started ominously: "I dreamt that I didn't turn off the pump, and the pool shed was on fire." No inferno, but plenty of chores. On top of the usual work, he had to head to the supermarket near the town of Isabel II to buy food and drinks for an impromptu happy hour. Also on his shopping list was new snorkel gear, after the Finnegans brought the hotel's faulty equipment to his attention.

Indeed, responding promptly to guest requests was one of the first lessons he learned. "The first year, you make mistakes. The second, you learn from those mistakes and do better," he said after plunking down hundreds of dollars for new fins, masks and snorkels. "The third, you are doing things perfectly."

But when you have a pool to fill, hors d'oeuvres to assemble, a dog to feed, inventory to restock, reservation requests to answer, and an approaching hurricane to contend with, you might start missing that cubicle on the 17th floor. Or not.

"There are moments of panic," Gevinski admitted, "but at the end of the day, I never say, 'I wish I were doing something else, I wish I were in a skyscraper in New York City, working the phones.' " Then, he drove off toward the hotel, because his guests needed him, and he needed them.

The Finnegans finally swam in the guest pool, two days before they had to return to Chicago. Gevinski is considering staying on at the Hix Island House for a third year, or perhaps managing a hotel in another country. Returning to Boston is also an option, however slim.