Fortunately for Fido, a winter escape to the U.S. Virgin Islands has few requirements—no quarantine is required for healthy, vaccinated pups, and only standard health paperwork is needed. Spend your mornings splashing in the turquoise water at Cane Bay Beach and Sunset Beach, an idyllic stretch of sand that welcomes dogs off leash from October through March. When hunger strikes, head to the Lost Dog Pub and Pizza in Frederiksted for a slice and a pint. Then, take a sunset stroll at Grapetree Beach to enjoy a colorful game of fetch by the sea with your furry travel mate. After dinner, put your paws up at The Buccaneer, where sweeping views of the ocean and rows of palm trees act as a constant reminder that, thankfully, you’re a long way from home!

Cabo San Lucas, in Mexico, attracts visitors year-round for its Pacific views, laid-back vibes, and winter temperatures above 80°F. Take your pup on a walk along the beach on the southernmost tip of the Baja Peninsula during low tide and discover the iconic Land's End Arch. Let Fido splash around in the shadow of one of Cabo’s most treasured natural landmarks.

After his day on the beach, let your best friend be pampered at Las Ventanas al Paraiso, A Rosewood Resort. The resort’s dedicated team of dog butlers lavishes pups with first-class service, including morning and evening walks, soothing massages, and private “doga” classes. Furry guests also receive a portable Pet Cabana that will keep them shielded in shady comfort as they lounge on the resort’s pristine beaches.

Snowbirds and snow-pups alike flock to the Florida Keys for warm breezes and dog-friendly adventures. The southernmost islands in the United States provide snowbirds with a welcome respite from the rasping cold of winter. Tour the stunning azure waters and get a diver’s view of the sea life beneath the waves on a Key Largo Princess Glass Bottom Boat. Dogs on the tour are greeted with a water bowl and plenty of pets. Then spend the night at the Baker's Cay Resort Key Largo, where Fido will receive his very own engraved dog tag and a personal invitation to attend the daily yappy hour, featuring a special pet menu just for him.

Puerto Rico’s capital offers the perfect blend of beaches, culture, and canine-friendly charm. Start at Hobie Cat Beach, one of the island’s most welcoming shoreline spots for dogs. In the morning, wander the stretch of sand freely together and paddle in the water. In the afternoon, walk the cobblestone streets of Old San Juan and bring Fido to run and play in the expansive green space outside El Morro, one of the island’s historic fortresses. Spend your evenings at the Verdanza Hotel, where the pet-friendly rooms come stocked with pet beds, water bowls, a toy and a welcome treat. The hotel even has its own Paws Park, an outdoor dog park with an agility course.

Say aloha to sun-soaked shorelines and surf-town vibes in the Hawaiian Islands. In Honolulu, Fido can learn how to stand up paddleboardSUPDog Hawaii at SUPDog Hawaii. The company offers lessons, so you can SUP with your pup in the warm Pacific waters. Next, visit Kahala Beach with your dog for an expansive white-sand beach where you can swim and stroll while taking in the views of Diamond Head. Then, unwind with your surfer “Dood” at The Surfjack Hotel & Swim Club, a trendy hotel in the heart of Honolulu. Pups of all sizes are invited to enjoy a relaxing stay in a bright and airy room with its very own private lanai. Dogs are free to join their owners throughout the hotel’s common areas, including by the pool and in the lounge area. Be sure to keep your eyes peeled for Surfjack’s canine concierge, a French Bulldog named Jack, during your stay.

In recent years, Chiang Mai has developed into the backpacker’s mecca of Thailand. Experience tuk-tuk rides and street markets with Fido, and be sure to snap his picture in front of the historic temples. Local dog owners recommend a walk around Huay Tung Tao Lake during your visit. There are several pet-friendly trails surrounding the water, along with an array of sculptures against a backdrop of rolling hills.

Ketawa Pet Friendly Hotel is the perfect place to spend the night with your pooch while you’re visiting this laid-back city. The rooms are equipped with a pet bed/tipi and bowls. As the name suggests, the hotel welcomes four-legged guests with open arms and a cafe that sells treats, wet and dry food, toys and bowls. Let your canine tourist dive into the pet pool, meet the eight house dogs, and book a grooming service. If you want to embark on any activities in the city that aren’t as open to dogs, you can leave your pup in the safe hands of the hotel staff.

Year-round sunshine and postcard-perfect beaches make The Bahamas an ideal pick for pups who love the sea breeze. Take a walk with Fido to Cabbage Beach on Paradise Island, a beautiful place to lie back under the shade of a palm tree and listen to the waves lap the shore. Canine companions can run and play off leash as long as they are under voice command. For a delicious meal and refreshing cocktail, head to Hillside House where pups are permitted at outdoor tables. When the sun sets, retire to The Colony Club Inn & Suites, a popular and budget-friendly hotel in the heart of Nassau.

For pups who prefer lounging to leaping, the Dominican Republic’s private beaches and shaded cabanas are a dream come true. Enjoy a lazy vacation with your small dog in one of Eden Roc at Cap Cana’s private suites with your own private pool. Pets receive a plush dog bed and bowls to make their stay as relaxing as possible. Ride around the resort in your private golf cart together, sunbathe on the beach, and experience classy service throughout, including day beds and shady umbrellas for dogs to snooze under in comfort. Eden Roc’s “Bone Appetit” menu for dogs will ensure Fido is well-fed, too!