The U.S. Department of Homeland Security has temporarily suspended Global Entry. We recommend allowing additional time for screening and customs when flying to/from the Caribbean. For any questions, please contact our team at 203-267-3305 option 1.
Nantucket Getaways: A Luxury Traveler’s Guide to Peak Season
Whether you come for the daffodils, the wine, or just want to breathe the sea air, Nantucket in peak season is well worth the trip, especially when getting there is as effortless as the stay.
The Quiet Side of The Bahamas: Things to Do in Eleuthera
Whether you choose to stay on Harbour Island or Eleuthera-proper, flights to North Eleuthera with Tradewind open up a truly tranquil vacation, with relaxation on pink sand beaches and adventures on land and sea. Read our four day itinerary for a range of things to do for a remarkable getaway.
A Guide to the Top Caribbean Islands
With an ever-evolving mix of cultures, landscapes, and experience, the Caribbean continues to call travelers back time and again. Tradewind’s comfortable scheduled and private charter flights provide an effortless connection to the region’s top islands, elevating the journey through this richly layered paradise.
New Flights to The Bahamas: Picture Perfect Islands to Visit
For travelers who value effortless access to paradise, three islands in The Bahamas come to mind: Nassau, Marsh Harbour, and North Eleuthera. Discover the hidden gems of these tropical destinations with a Tradewind scheduled flight.
Elevate Your Winter Escape: Charter Flights to Vermont’s Top Ski Destinations
With storybook villages, luxury ski lodges, and world-class terrain, the Green Mountain State is a skier's paradise. Plan your winter escape with a Tradewind charter flight to Vermont this winter season.
Next Stop, Nassau: What to Know Before You Fly
Flying to Nassau just got easier with Tradewind's new route, nonstop from Stuart, Florida. Learn more about entry requirements, what to pack and more for a seamless journey to The Bahamas.
Flying Private? Not Quite. But It Sure Felt Like It.
Flying Private? Not Quite. But It Sure Felt Like It: 36 Hours in the Bahamas With Kids How we skipped TSA, landed steps from the sand, and made a family trip feel like a
Discover Things To Do in Nevis: A Curated Luxury Itinerary
Discover things to do in Nevis with a curated luxury itinerary, exploring hidden beaches, historic streets, and lush landscapes, all accessible via Tradewind private flights.
Flying Private with Your Dog: Top Resorts & Travel Tips
Fly private with Tradewind and your beloved furry companion to the top resorts that allow dogs, from the Northeast to the Caribbean. Discover our top tips to flying private with your dog and get ready to explore the world with your whole family.
Anguilla Travel Guide: The Perfect Weekend Itinerary
From pristine beaches to gourmet dining options, Anguilla is the perfect escape for a weekend under the sun. Read our travel guide for a Friday to Monday itinerary following one of the many flights to Anguilla offered by Tradewind.
The Best Time to Visit Key West
Guests seeking a tropical escape without leaving the country need look no further than Key West. Every month is filled with music, festivals, or quirky events - the best time of year to visit Key West really depends on the kind of experience you want to have.