Get Away on a Canine Caribbean Vacation

As we continue to emerge from the protracted pandemic, two things are clear. First, our dogs have been all too happy to have us home. Second, we really need a vacation.

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Luckily, as we enter winter, several Caribbean destinations offer attractive options to bring Fido along for a much-needed beach getaway. Let’s look at a few U.S.-controlled islands, as, for Americans, these present the least hurdles to a delightful, dog-friendly vacation.

Of course, first off is getting there. Not surprisingly, where a dog is permitted to spend a flight depends on his size. Though rules can vary, typically only dogs that fit in a carrier under a passenger seat can fly in-cabin. Considering the cozy conditions of most planes, that means only the smallest dogs — 20 pounds maximum, and often less — qualify for coach (See sidebar). Expect to pay an extra $75 to $200 each way. Many airlines restrict the number of animals per flight, so book early.

Puerto Rico

To enter Puerto Rico, dogs must be microchipped, vaccinated within six months of visiting and, within 30 days of entry, a licensed veterinarian must complete a destination-specific Pet Passport ($20 at

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Pet-friendly lodgings abound in Puerto Rico, with everything from luxury resorts like the Fairmont El San Juan to budget-conscious options like Ponce’s Solace by the Sea Hotel accepting four-legged guests. Of course, direct rental sites like Airbnb and Vrbo also list pet-friendly accommodations.

Dog-friendly beaches near busy San Juan are limited, but Hobie Cat Beach (don’t worry: cat connotes “catamarans,” not felines) in the Carolina neighborhood is a gem. Shorelines in less densely populated areas generally have no restrictions. And besides the beach, Puerto Rico offers two things no other U.S. island can.

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First, northeastern Puerto Rico’s El Yunque National Rainforest is the largest of any Caribbean island. Capped by the 3,500-foot Luquillo Mountains, its 200 inches of annual rainfall cascade back to sea level via wondrous waterfalls. It’s an unparalleled place for a nature hike. It’s a jungle, so watch out for ticks, snakes and predatory animals.

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Second, Puerto Rico features a road dedicated to all things pork. Hey, it’s vacation … set the doggie diet aside for a day with a pit stop-filled tour down La Ruta del Lechón, about an hour’s drive south from San Juan.

Puerto Rico also is ideal for the aspiring dog owner, offering opportunities to mix sun and  fun with voluntourism and, perhaps, meet a soon-to-be forever friend in the process.

The bad news: Puerto Rico has a notorious stray problem, with some 500,000 satos — Spanish for “street dog” — roaming the island. The good news: The most gratifying part of a Puerto Rico vacation can be punctuated by a wet kiss or two hundred. Rescue organizations like The Sato Project accept assistance preparing dogs for “freedom flights” off the island to forever homes on the U.S. mainland. Puppy love is a regularity. “Many volunteers become forever families for a sato,” says founder and president Chrissy Beckles.

U.S. Virgin Islands

Dog-friendly St. Croix allows dogs on its Cane Bay beach. Dogs can be unleashed on the beach unless it is turtle-hatching season, and then all dogs must be leashed.

To enter the U.S. Virgin Islands, a dog must have an official health certificate stating his area of origin, accompanied by a certificate showing vaccination for rabies within the past 12 months. (It is recommended that they also be microchipped.)

St. Thomas is the USVI’s most popular island and, despite trending upscale, moderately priced dog-friendly accommodations can be found — and many don’t charge an extra fee. lists a surprisingly wide range of options, including affordable Airbnb and Vrbo rentals. For a more traditional hotel setting, the Emerald Beach Resort is affordable, right on the water and fido-friendly. (Note: Confirm with a property that it is pet friendly, as policies do change.)

Besides the beach, St. Thomas has a number of calm, picturesque waterways, including mangrove lagoons. Some kayak operators will permit dogs to come along on tours. A local tour operator called CaribbaConnect is a solid source to plan such an excursion.

Puerto Rico’s rescue organization The Sato Project accepts assistance preparing dogs for “freedom flights” off the island to forever homes on the U.S. mainland. The author’s own dog, Vector, is a Sato dog.

While all Caribbean islands have strays, the USVI’s issues were exacerbated by 2017’s Hurricane Irma. Out of that storm’s rubble emerged St. Thomas’ Off the Rocks Rescue, which collaborates with shelters across the USVI and finds homes primarily in New England. Volunteers are welcome to help clean cages and socialize with recently rescued dogs and cats and potentially find a more permanent playmate.

There is also Pets with Wings, a program under the Humane Society of St. Thomas, that transports homeless animals to rescues and potential adopters on the U.S. mainland. Flight volunteers accompany the rescue pets through the airport and flight and deliver them to a rescue representative at the mainland airport. Check out these adventures on the PWW’s Facebook page.

Nearby St. John is less pet-friendly. Hansen Bay Beach, while lovely, is among the island’s few dog-friendly public beaches.

On Saint John’s western shore, south of the island’s famous Honeymoon Beach, the St. John Inn on Cruz Bay Beach is a charming boutique hotel just minutes from outside dining and other fido-friendly attractions. Notably, the property is just a 10-minute walk to the lush Virgin Islands National Park.

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For those with more wanderlust, a better bet may be St. Croix, the southernmost of the chain’s major destinations. The north end’s Cane Bay Beach, as well as Sunset Beach (by the Pink Condos) on St. Croix’s west coast, are especially dog-friendly.

After the beach, take your pooch on a nice walk through Christiansted, the USVI’s most historic and pleasant town. It’s also where many of the island’s most compelling dog-friendly hotels can be found. Whereas Puerto Rico is tropical, much of St. Croix’s landscape is desert-like. For a great hike, drive to Point Udall — the easternmost locale not only in St. Croix but all of U.S. territory — and revel in the rarity of a beachfront desert. That includes cacti — so paw protection is highly recommended.

As with any trip, especially during COVID, make sure you call hotels and airlines for updated rules and regulations.

Flying With Larger Dogs

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Dogs that cannot fit in a crate below a passenger seat must fly in the cargo hold, and are treated … well, sort of like luggage. While this is an option, we at Dogster generally recommend against it given this type of travel’s history of adverse events. Especially if your dog has significant separation anxiety — or gets easily frightened by jostling — flying with your large dog may not be the best idea.

Also, not all airlines allow animals to travel as cargo (including jetBlue and Southwest), and several, including American, United and Delta, have suspended their programs due to COVID-related changes. Check with individual airlines for availability.


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