Why leave your most loyal companion behind when they’re just as ready for takeoff as you are? Whether playing in the snow, jogging on sun-soaked sandy beaches, or hiking amidst fall foliage, exploring the world is more enriching when your four-legged adventurer is along for the ride. Dogs are more than pets; they’re family with whom we want to share the joys of discovering new places, new scents, and new adventures. That’s why Tradewind Aviation’s pet-friendly flights are beloved by jetsetting dog-owners.
Flying with your pet on Tradewind permits your furry companion to travel next to you in the comfort of the cabin, allowing for greater comfort and freedom of movement, with the added benefit of pets under 100 pounds traveling complimentary on Tradewind scheduled flights. Knowing your pet is safe and secure by your side offers great peace of mind, for travelers flying on both private or scheduled service.
On a private charter flight with dogs, you control the itinerary. Travel on your schedule, eliminate long layovers in crowded airports, and get to your destination comfortably, quickly and safely.

Tips for Traveling with Pets
- Make sure your pet is healthy and well-groomed.
- Have necessary documentation, such as a health certificate and proof of vaccinations. If flying internationally, check the requirements of your destination. For example, St Barths requires pets to have a microchip and rabies vaccination within a specific timeframe before travel; the Bahamas requires an import permit from the Bahamian Ministry of Agriculture, Trade and Industry. The US State Department site is a good place to start.
- Make a pre-travel appointment with your veterinarian to discuss recommendations for food, water, exercise, medication, and other helpful strategies.
- Bring a pet harness that can be attached to the aircraft’s seatbelt for your pet’s safety.
- Pack your dog’s favorite blanket, toys, and water bowl to make them feel comfortable while traveling and at your destination.
A number of resorts at Tradewind’s top charter destinations welcome guests and their four-legged companions. Check each hotel’s policy, as some have weight or breed restrictions, and inform them ahead of time that you’ll be bringing your pet. Here are a few that will make your furry friend feel extra welcome:

Northeast Resorts That Allow DogsÂ
Well-heeled dogs will love access to the great outdoors at The Point Resort in Saranac Lake, New York. Built a century ago by the Rockefellers during the Gilded Age, this Adirondack camp sits on a peninsula overlooking Upper Saranac Lake. Pet life jackets are provided for boating trips, and a signature welcome amenity is Bowser Beer, a non-alcoholic, non-carbonated beverage specially created for canine guests.Â
Twin Farms in Barnard, Vermont, is where lucky dogs can roam 300 bucolic acres of forest, meadows, and ponds while on a leash. It’s also great for hikers who want to explore miles of wooded trails accompanied by their canine companion. The resort hosts dogs up to 100 pounds in three of their freestanding cottages with screened-in decks—Log Cabin, Meadow, and Barn—which are perfect for savoring cozy mornings and fireside evenings, relaxing with your pup while enjoying views of the wooded surroundings.
If an English-style country garden is more to your dog’s liking, head to Nantucket. The Veranda House, part of the Nantucket Resort Collection, re-opened this year after a full-scale renovation. This historic property, which dates from 1684, retains key design elements like its namesake wraparound verandas with spectacular views of Nantucket Harbor. The Very Important Pet Program includes a curated guide to pet-friendly activities, complimentary dog walks, and a personal shopping appointment at Pawsitivity, a local pet boutique.

Southeast Resorts That Allow Dogs
Lunara Bay, a collection of waterfront estates with an exclusive marina, is just minutes from downtown Key West, Florida. It’s the perfect retreat for family gatherings and dogs who love to lounge outdoors. Large, fenced-in lawns offer space to roam, and there are private pools for dog paddling if yours is naturally inclined to swim. With a dedicated guest experience manager assigned to each estate, your pets’ needs will be efficiently handled.Â
Guests who book a Tradewind private charter to Key West and stay at least 2 nights at Lunara Bay will receive discounted rates on both air travel and accommodations, based on their travel window.Â
The Cove Eleuthera is a quiet Bahamian island resort with two private, white sand beaches and an abundance of natural wonders for you and your furry best friend to explore together. Hike the nature trail, stroll along the historic waterfront, go sea kayaking, and cool off with a swim in the clear, azure waters. A short boat ride away are the pristine pink sand beaches of Harbour Island, a favorite dog-friendly spot to explore (just be sure to keep them leashed). Cozy guest rooms stocked with a dog bowl and bed open to private patios and a tranquil landscape, making this a perfect choice for a laid-back Bahamian vacation both you and your dog will enjoy.
Montage Palmetto Bluff in Bluffton, South Carolina, goes above and beyond in pampering dogs with amenities like plush dog beds and custom-baked treats. Guests are greeted by four-legged members of the Canine Ambassador Program, and there’s even a gourmet pet menu available via in-room dining; ground Angus beef with rice and veggies is a favorite. Dogs can also enjoy services in the pet area of the onsite spa, and there’s plenty of real grass to play in and miles of trails for running and walking.

Caribbean Resorts That Allow Dogs
For French sophistication and island charm, St Barths is the ticket. Pets who crave calm surroundings will love Le Toiny where dogs are greeted by the resident pet master dachshund, Gladys. For feline lovers, cats are also welcome. The luxurious hillside resort has 22 suites, each with a private pool and an expansive terrace overlooking Toiny Bay. The concierge can arrange hikes, beach outings, and boat excursions for a truly memorable experience.
Your dog will live in the lap of luxury at Cap Juluca, A Belmond Hotel in Anguilla. Arrive by Tradewind private or scheduled service to a pet-welcoming, sophisticated environment. Spread across 179 acres along Maundays Bay, the best beach on the island, you’ll have picture-perfect views of the Caribbean from your villa, with private outdoor spaces ideal for relaxing with your best furry friend.Â
Scrub Island Resort, Spa, and Marina welcomes dogs and cats of any size to this private island sanctuary about a mile off the coast of Tortola in the British Virgin Islands. Accommodations have private patios and balconies where pets can enjoy the fresh tropical air. There are also pet-friendly grounds for walks and playtime, including scenic nature trails and beaches. The resort’s concierge team is available to assist with pet documentation for travelers from the U.S. to ensure a worry-free vacation from start to finish.
Tradewind Aviation private charter flights are available on demand, and with their pet-friendly policy, there’s no reason for anyone to miss out on the family vacation. Fly calmly with your loyal pet by your side and, wherever you travel, you’ll always feel at home.
To learn more about Tradewind’s private charter and scheduled flights, and booking your vacation, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 2. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1.