Tradewind Aviation and Martha’s Vineyards Winnetu Oceanside Resort a winning combination 

The last time I went up to Martha’s Vineyard, some months before the pandemic in the fall of 2019, it took me five hours by car to Woods Hole and another hour on the ferry to Oak Bluffs a schlep in anybody’s book. I could have got to Reykjavik, Iceland, more quickly. 

Two weeks ago, it took me precisely one hour and 38 minutes, from hopping a Splendid taxi in downtown White Plains to sitting down for dinner on the veranda of The Dunes restaurant at the splendid Winnetu Oceanside Resort, three miles outside elegant Edgartown, where I happily chowed down on an excellent supper of quahog chowder and Maine scallops with celeriac pure. 

This time around I took the sensible option, a Tradewind Aviation flight to the Vineyard from the spiffy Million Air private terminal at Westchester County Airport. The company operates private charters as well as scheduled services in the Northeast and Caribbean, with a handy summer shuttle service among White Plains; Newport, Rhode Island; and Martha’s Vineyard and Nantucket, Massachusetts. 

If you drive to the airport, a valet will whisk your car away and park it and have it ready and waiting for you at the terminal door on your return whenever that might be, all for the princely sum of $20. (Self-parking is also easy and free for up to 30 days.) Check-in, if you can call it that since there are no formalities to speak of, just the handing over of your bag if you have one is 30 minutes before takeoff. But you can wing it, so to speak, and show up just 15 or 20 minutes before your flight with impunity. 

So far, so blissful. Inside the terminal, a soaring edifice in stone and oak, with wonderful tree-branch chandeliers, Tiffany lampshades, cowhide-covered benches and beautiful, chrome propeller blade-like sculptures, there’s barely time for a cup of coffee and a glance at the fancy goods for sale a Tissot watch, anybody? A bottle of Poison? (by Christian Dior, that is) as  a ping on your cellphone tells you it’s time to board.  

Boarding entails a 30-yard walk to the waiting jet, as you clock your fellow passengers and try, at least in my case, to look nonchalant as if you do this every day of the week, while surreptitiously taking pictures of the plane as you pretend to be on the phone.  

That plane, an eight-seat Pilatus PC-12, is a gleaming piece of Swiss aeronautical engineering so beautiful to look at you could mistake it for a rich kid’s toy, only it flies like an arrow at 300 mph, cruising effortlessly at 20,000 feet. And if you’re that person after my own heart who can’t go 41 minutes without munching on something, you’ll want to sit at the back of the plane where the bags of potato chips, popcorn and other snacks are located, along with cold sodas and white wine. Otherwise you’ll have to ask the person at the rear to pass something forward.  

No sooner up than down, it seemed like only moment until our descent into the Vineyard. I looked at puffs of summer clouds from both sides now and thought about the sticky summer bumper-to-bumper traffic I had avoided, as the pretty island runway came into view and the baby jet touched down on the Tarmac with barely a kiss. 

Over at the Winnetu, Edgartown’s only resort hotel, as family friendly as it is grown-up and sophisticated, my second-floor West Chop suite comprised a neat king bedroom and bathroom with a large walk-in shower and luxury Dyptique products and a well-supplied kitchenette. The large living room with both a sofa-bed and an additional Murphy bed made it ideal for family accommodation. The room also featured a large terrace overlooking the gardens and pond, with the ocean just visible above the tree-line. South Beach, arguably the Vineyard’s finest, was just moments away.  

In the public areas, quirky design elements like pyramidical lamps, a penny-farthing bicycle, Staffordshire-type figurines on the mantelpiece and walls lined with old photographs of the estate and surrounding area make for a countrified feel. You’ll also find a pool table and of course a pool two of them, actually, as well as bocce, pickleball, tennis courts, basketball, table tennis, outdoor chess and programs for toddlers and older children. The on-site corner store will sell you breakfast on the hop, essential items you may need and many you will not. (I swear if I buy another branded baseball cap from a hotel shop I will have to move to a bigger house.) And the free hourly shuttle to Edgartown is a valuable amenity as is the (paid-for) daily water taxi service, which takes you into town meandering through sheltered Katama Bay. There are no resort fees. 

While Winnetu is not in any way a glitzy resort, which in any case would not sit well in this demure, family-orientated locale, it is an utterly delightful and wholesome one, managed with great sensitivity and concern for its faithful, annually-returning guests. 

Worth mentioning is that, while the Vineyard’s year-round population of around 17,000 many of them Westchester and Fairfield county residents, who relocated here during the pandemic swells to more than 150,000 in high-season, amazingly the island, especially the interior, never feels overcrowded. Even at full tilt, Winnetu, which also has private houses on its estate for sale or rent that benefit from all the hotel facilities, is large enough for guests to spread out and enjoy themselves.  

While year-round occupancy and the second-home market continues to increase, rentals on Martha’s Vineyard are also at an all-time high. From May 2022 to May 2023, 1,200 homes on the island were converted into weekly rentals, Matt Moore, Winnetu’s general manager, told me. Many of those renters are from the tristate area, and the convenience of flying up to the Vineyard from Westchester Country Airport with Tradewind, without so much as an airport body scanner to walk through, will be a boon.  

For my return journey, Winnetu’s affable bellman college sophomore Paul Forbes, who himself has long family associations with the island drove me back to the dinky Martha’s Vineyard airport, making good conversation all the way and filling me in on aspects of island life. With no check-in formalities at the airport, no TSA security screening and little fanfare, I was quickly aboard with my two fellow passengers, back in Westchester before I’d even finished my packet of Miss Vickie’s chips and white wine spritzer. 

Talk about the high life. Talk about cutting out the hassle. After an experience like this, it’s hard to come down to earth or to drive long-distance again. 

For more, visit flytradewind.com and winnetu.com. Travel Talk’s Jeremy Wayne is also a fully accredited IATA adviser with Superior Travel of New York. Contact him at jeremy@superiortravel.com.