With more than 7,000 islands, islets, and cays, the Caribbean attracts sightseers and adventurers from every corner of the world. Besides the region’s ubiquity of clear waters and exquisite white sands that are unanimously favored by visitors, there are a

Four-legged family members are always welcome on Tradewind Aviation flights, but as every dog owner knows, hotels, restaurants, beaches, and stores aren’t always as accommodating. Here, find out how you can have the ultimate

When she has a morning or afternoon free to point her camera anywhere at all, Cary Hazlegrove checks the tide charts and heads to Little Neck at dead low. Twice every day, that breezy western stretch of

Only 13 miles of Atlantic Ocean separate a bubble of nearly autonomous New England charm from mainland reality. With its white-sand beaches, towering bluffs, and glacier-carved hillsides speckled with colonial cottages, Block Island is completely walkable, stretching just 7 miles

In anticipation of this year’s Nantucket Film Festival, accessible by Tradewind with daily scheduled flights and private charters to the island, we sat down with Executive Director Mystelle Brabbée to talk past, present, and

Compared to the bustle of New York City, some 110 miles away, Montauk really does feel like another world. The bohemian-chic neighbor of The Hamptons is home to beautiful Atlantic seascapes and stylish villages straight from your summer dreams, yet

The pilot of a plane nearing O’Hare Airport announces its “final descent into the greater Chicago area,” and the grammar mavens on board all wince. The error there is redundancy—either “greater Chicago” or “the Chicago area” would suffice. Adam Schaefer

For discerning travelers en route to the Caribbean, the transfer between a large-cabin charter jet and a final-leg turboprop can often lead to inconsistencies in service. In response, Tradewind Aviation and large-jet operator

“Our mother still doesn’t believe that we’re able to work together, because we spend so much time as rivals,” says Eric Zipkin, President of Tradewind Aviation. He and his brother, Vice President David Zipkin, founded the company

Blending tranquil stretches of white-sand beach with inspiring history, watersports, and spacious villas, few vacation destinations are as attractive for families as the beautiful Caribbean islands. Whether you’re seeking adventure, relaxation, or both, these three islands,

A breathtaking landing on the edge of the Caribbean may define a place for one pilot, while another could be drawn by unforgettable cuisine with a view of the Rocky Mountains. From seaside escapes to late winter respites, here are