How to See the World and Indulge in Dog Love Too

Pets Sitters in Paradise
By Jill Draper, January 2020, Updated June 2021
Pet sitters travel the world

Kai and Kana in Kauai, Hawaii

After the family dog died of old age and their two sons started careers, Gregg and Amber Russell faced a quandary common among retirees: Should they look for a new dog and enjoy the fun and companionship dogs offer? Or should they remain pet-free so they could travel wherever and whenever they choose?

Lucky for them, they found a way to do both: as pet sitters for the well-to-do in places as various as Hawaii, southern Spain, the Caribbean islands, British Columbia, New York City and more.

The Russells don’t get paid for pet sitting, nor are they reimbursed for airfare, but they do live in style in interesting locations, usually with the use of the family car and, sometimes, maid service. “We feel like we hit the jackpot,” says Amber.

Recently, for the fourth time in nearly as many years, they spent a month in a gated community on Kauai, Hawaii’s fourth largest island, known for its secluded beaches and dramatic scenery. When their stay begins, Amber jots down the household’s schedule: the gardener comes on Fridays and the housecleaner on Saturdays, followed by the koi pond caretaker, who shows up every two weeks. Meanwhile, Gregg feeds a dozen colorful koi their daily rations, skims leaves and palm fronds from their pond, and scoops up any poisonous king toads with a longhandled grabber. After feeding and walking Kai and Kana, the resident Aussies, they set out a treat dispenser and ask Alexa for background music (the dogs are partial to classical, country or soft rock), then head to the ocean to play in the surf or relax on the beach.


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“I go through about three books a week,” Amber says. “I could easily live like this.”

And so they do, seeking out petsitting jobs up to six times a year in places on their travel wish list. Summer months are off-limits; they love the mild weather in their hometown of Portland, Ore., and Gregg likes to tend their large home garden. But after mid-September, they’re ready for adventure.

The Russells pay a $90 annual fee to list their profile on (other sites offer similar options). Depending on the platform, the focus may be large—North America, Europe or Australia/ New Zealand—or country/ location-specific. Ambitious pet sitters are known to wake up in the middle of the night to check for real-time notifications posted by homeowners halfway around the world, but some sites combine opportunities into one or two daily lists.

The most popular sites have thousands of registered sitters, and competition can be fierce for plum assignments. “If we’re one of the first to apply, our odds are probably 75 percent,” says Amber. “If not, they go down quickly.” Of course, the selection process swings both ways. Some listings don’t come with the use of a car, and others fall during an area’s rainy season —those, she usually ignores.

To be selected, the Russells rely on their experience, professional backgrounds, client reviews, security clearances (TSA Precheck status and driving records, for example) and word of mouth. After caring for the Kauai Aussies, they were invited back to the neighborhood by a homeowner across the street to care for a pair of Maine Coon cats. And while some sitters maintain their own website with an introductory video, photos and testimonials, the Russells upload this type of information onto their “Trusted Sitters” profile. In the beginning, they paid to be listed on additional sites, but now they find enough matches on one.

They’ve had some standout experiences: strolling through traditional villages on the Greek island of Paros, where clotheslines often sport long-tentacled octopus hanging to dry before cooking; floating in a hot-air balloon over the Rio Grande in Albuquerque; taking high tea at Butchart Gardens in Victoria (courtesy of their client); and visiting all manner of beaches, biking trails, old forts, churches and castles.

Typically, they venture out after the animals are fed and walked, returning in five or six hours. Restaurants are less expensive for lunch than dinner, which works well with their budget. For month long stays in Hawaii, they frequent the local library and volunteer at a church food bank. They’ve also toured a neighbor’s winery, been invited to a swanky New Year’s Eve celebration, and oohed-and-aahed at 85 votive candles floating in a pool at a backyard birthday party.

The pets they care for are part of the fun. By late afternoon, the Aussies are eager to chase Frisbees on the lawn before joyously twirling around at the prospect of a top-down ride in their owners’ Mini Cooper. On California’s Catalina Island, the preferred mode of transportation was a golf cart; the Basset Hound in their care enjoyed riding shotgun. In British Columbia, a chocolate Lab and a mixed-breed rescue dog were enthusiastic hiking partners on green-canopied trails through old growth forests.

“We’re truly animal lovers. If we didn’t travel so much, we would have a dog for sure,” says Amber. “Once we’ve satisfied our desire to see the world, we will.”

In addition to dogs, they’ve looked after cats, fish, chickens, a parrot, two steers and a tortoise. Some of their charges require special services; Gregg has learned how to wield a mallet to pound raw, bone-in chicken, and Amber can administer medicine and vitamins.

They usually arrive a day or two early to learn animal and household routines directly from the homeowners, making sure to locate the breaker box, water cutoff and fire extinguisher. If they’re borrowing the family car, the Russells offer to drive the homeowners to the airport and pick them up when their trip ends. They often prepare a “welcome back” dinner, set aside the junk mail and do small chores.

Of course, there are the occasional downsides. Pet sitters face their own piles of mail and maintenance projects when they return home, and they may find themselves out of the loop with friends. The assignments also can take an unexpected turn. When a hurricane shut down a Caribbean job, the Russells stood to lose their airfare until they convinced an agent to eliminate the change fee.

Little things can go wrong, too. In a Greek town where few spoke English, Gregg asked a barber to use the same clipper number he liked in the U.S. The Greek numbers did not match, however, and he exited the shop with a shockingly short buzz cut. It helps to have a sense of humor, says Amber.

The Russells still enjoy an occasional organized tour— the typical whirlwind trip with a hotel change every two nights—but they like the slower pace of exploration that pet sitting allows. “It’s been a good lifestyle for us,” says Gregg. “We’re hooked.”

Photo by Jill Draper

Jill Draper is a Kansas City, Mo.-based freelance writer and editor specializing in features, news articles, profiles and blogs.