by Eric Barton | June 3, 2019

A Writer’s Journey: How to Travel Florida in Style with your Dog.

Once shunned at most resorts, pups finally get Five-star treatment at Florida’s finest hotels.

The author, his dog, Lucky, and wife, Jill, at the W Fort Lauderdale. They overlook a sunrise on a modern looking balcony.
The author, his dog, Lucky, and wife, Jill, at the W Fort Lauderdale. Photography by Mary Beth Koeth.

We were lounging under an ancient sea grape tree, with tiny spotlights of morning sun barely fitting between its leaves, as big as dinner plates. The gentle Florida Bay waves lapped, the water as clear as a vodka shot. The dog, now 13, almost equivalent to a centenarian, with her blonde fur frosted white, snored between us on a beach towel, a placidity we wanted to go on forever.

Suddenly the pup popped her head up, her gray-covered snout picking something up. She can’t hear a delivery man’s knock, and maybe her eyesight is shot too, but she’s still got a terrific sniffer. She creaked her bones to a standing position and scampered, as much as an old girl can, off between the knotty knees of mangrove roots. She returned holding a prize, a gnarly coconut the size of a Nerf football. Her tail knocked excitedly into our chairs as she dragged her new toy through the sand. 

She tired herself out even before we could get the camera app open. But this was, without question, the most energy we’d seen from her in a year’s time. It was also a moment that justified taking her on a three-day road trip to the Keys, a trip planned solely so she could have a final vacation designed just for her.

Back in 2007, when my wife, Jill, and I first got our pup from a Chesapeake Bay retriever rescue group, polite people didn’t take their dogs on vacation. Or at least that’s the impression we got from employees and fellow guests the first time she plodded through the lobby of a decent hotel, the Sheraton on the Country Club Plaza in Kansas City. People like to describe thin dogs as skin and bones, but she barely had that, mostly just four oversized paws and topsail ears propped on 35 pounds of skittishness. 

Pamper your pooch welcome basket
See our List of the Top-15 Dog Friendly Hotels in Florida: Where Pooches Get Pampered.

Jill and I  named her Lucky. Peanut butter and boiled eggs filled her out, and then we took her along on regular road trips. As a rescue from an Arkansas pig-farm-turned-puppy-mill, she didn’t know how to climb stairs, walk on a leash or ride in a car. Even the shortest trips would equal anxiety and a roll of paper towels. The vet suggested giving her a new association with traveling, and so we took her and a tennis ball to the park daily until the back seat became her favorite spot. Months later, we set out on an epic trip through the Southwest, and she whined with excitement past the rainbow monoliths of Colorado. 

Eric playing with his dog, Lucky, in a hotel room.
Eric and Lucky have become hotel snobs. Photography by Mary Beth Koeth

If she could talk, she’d brag now about the 27 states she’s visited. Arizona via Amarillo. Up to New Hampshire to swim in never-warm lakes as deep as the mountains they mirror. Twice yearly to North Carolina, where she’d whimper incessantly as we closed in on Asheville.


We found that, living in Florida, we’re flush with reasons to take a road trip with our Lucky. On Lovers Key near Fort Myers, a wooded path leads out to a Gulf-side beach that looks untouched by time, where there’s a dog park full of brackish splash pools and a slow walk out to deep water. With sand as soft as powdered sugar and waves that almost always remain chill, St. Pete’s Fort De Soto was worthy of a day’s drive with a wet pup in the back seat. Then there’s Key West; the dog beach at the end of Vernon Avenue might just be a tiny spit of land, but afterward you’re still in a town where bar and restaurant patios seem more complete with a dog underneath you.

Those trips used to mean roadside motels, or, if you were lucky, an Aloft, like the one in Tallahassee that became a respite for so many South Florida dogs and their owners hours before Hurricane Irma. Many modest hotels might be dog-friendly, but you can only take so many microwaved Holiday Inn cheese omelets. Something’s changed recently in the hotel industry, though, and at properties where anyone with a leash in hand might once have been evil-eyed by bellboys, we’re now given luxury doggie gift baskets and offered special packages including, and this is a true story, a limited-edition W Hotel dog bandana. In Winter Park, which has a good argument to be the state’s friendliest city for dogs, the boutique Alfond Inn attracts pet owners with a package that includes a session with a professional photographer and prints to take home later. Gloria and Emilio Estefan’s place in Vero, the Costa d’Este, also rolls out the canine red carpet. A pet suite comes stocked with toys, treats and a plush doggie bed brought in from a local boutique.

In Amelia Island, we discovered that the Atlanta families that mob the place in the summer disappear when schools reopen. We snagged a beachfront villa for a couple hundred bucks and opened the French doors to find nothing but the dune between us and the beach. Even under a wintery sky the color of primer, we spent a day doing nothing but lobbing a tennis ball on a beach so big it’s a long walk just to reach the water.

At 13 years old, Lucky might be more than 90 in human years, so sometimes she needs a little extra help with the stairs.
At 13 years old, Lucky might be more than 90 in human years, so sometimes she needs a little extra help with the stairs. Photography by Mary Beth Koeth

We probably should be sending holiday cards to the cleaning crew at the Westin Cape Coral, where we returned from a day of paddleboarding through the estuaries behind Pine Island. We made our way up to our room with a life-jacketed pup, using towels from the pool and a pocket full of pilfered mini shampoos to bathe away the brackishness.

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The most welcoming resort we’ve found so far was on our latest road trip, to the newly refurbished Baker’s Cay in Key Largo. It’s not just that pets are allowed, but also that the pups can go everywhere, on that stunning beach lining the property, into the modern-coastal lobby, and even into every restaurant, including the fine dining one perched above the mangroves. After the pup played on the sand and slept between our chairs for most of the day, she joined us that night for dinner, winding clumsily between chair legs as we ate fresh catch.


It was barely five days after we returned home to Fort Lauderdale from that trip that Lucky needed an emergency vet visit. Maybe playing with that coconut and dragging behind us around the Baker’s Cay property was just too much for the old girl. She spent a night and most of a day panting, in considerable mysterious pain, unable to lie down, and no test seemed to diagnose what was wrong. “She can’t spend another night like that,” the vet said with some necessary finality. It seemed like maybe she had taken her last road trip.

But then she turned things around, energy returning over the next week, even chasing the ball one time for a Facebook video. This summer, we’re taking her with us again to Asheville. Along the way, we hear there’s a fine B&B in St. Augustine, and old dogs are welcome.