Summertime in the U.S. brings patriotic holidays, family barbecues, and time-honored traditions like the beloved summer vacation. And what could be more American than planning a trip to a president’s favorite summer destination?
For hundreds of years, American presidents have taken advantage of Congress’ summer recess to indulge in some well-deserved time off, often returning to the same vacation home year after year. Just as the Kennedys are synonymous with Hyannis Port on Cape Cod, some of our more recent leaders have become associated with certain parts of the country—all of which are popular Tradewind destinations.
Read on to learn more about the four most recent presidents’ favorite vacation destinations—and how you can plan a trip there of your own.
Kennebunkport
The Bush home in Kennebunkport, Maine has long served as the summer home of not one but two presidents, both George H.W. Bush and George W. Bush. Walker’s Point Estate, as the home is known, sits on a heavily guarded peninsula just outside the coastal Maine town of Kennebunkport. The home has been in the Bush family for more than a century, with President Bush Sr. holding a special affection for the place—it was known as his “Summer White House.”
President Bush Jr.’s “Summer White House” was his Prairie Chapel Ranch in Crawford, Texas, but the former president still visits Kennebunkport several times a year—his daughter Barbara Bush married Craig Coyne there in 2018.
Flying with Tradewind Aviation is the ideal way to get to this area of Maine’s southern coast, as the Pilatus PC-12 can land at the remote municipal airport nearby, as compared to hours of driving or flying into Portland. Book a stay at one of Kennebunkport’s best boutique hotels: Hidden Pond or White Barn Inn, Auberge Resorts Collection.
Continue your trip by journeying down the coast to the quaint hamlet of Ogunquit for a drink at Barnacle Billy’s, where you just might spot some members of the Bush family—locals say they boat down to the waterside restaurant on occasion.
Martha’s Vineyard
Barack Obama spent time in Martha’s Vineyard seven of the eight summers he was in office, renting homes near Chilmark and on the island’s north shore. In 2019, the former president and his wife Michelle purchased a 29-acre estate on the coast near Edgartown, the largest city on the island. Obama’s Martha’s Vineyard home is nearly 7,000 square feet and boasts views of a barrier beach and the ocean.
Tradewind offers daily scheduled flights to Martha’s Vineyard from the New York area between May to November, which means planning a summer visit to the island couldn’t be easier. For those looking to fly on their own time, private charter is available to the Vineyard year-round from anywhere. If you want to be at the center of everything the island has to offer, stay at the Harbor View Hotel in Edgartown, which is within walking distance from Main Street’s restaurants, bars, and coffee shops. For a slightly quieter vibe, Nobnocket Boutique Inn is a lovely bed and breakfast in Tisbury. If you prefer a more luxurious and secluded experience, Faraway Hotels Martha’s Vineyard is the perfect choice, offering breathtaking oceanfront accommodations and exclusive amenities to make your stay truly unforgettable.
If you plan your visit around the Martha’s Vineyard African American Film Festival in August, you just might see the former president—the Obamas made a surprise appearance in 2022.
Palm Beach
Donald Trump often referred to his Palm Beach home as the “Winter White House,” as the former president spent significant time there before, during, and after his time in office. President Trump’s home in Florida, Mar-a-Lago, serves both as his vacation home and a private members club with golf, tennis, and dining. The 128-room mansion was built in 1927 for the heiress Marjorie Merriweather Post and purchased by Trump in 1985.
Tradewind continues to expand into Florida with a Southeast base coming in September 2023, and will offer private charters to Palm Beach in its Pilatus PC-12 from all over the state and the Bahamas. The Citation CJ3 light jet offers access to Palm Beach from Northeast destinations as well. The opulence of Mar-a-Lago finds its equal in the illustrious Gilded Age-era Breakers resort, while another option is the Four Seasons Palm Beach, renowned for hosting one of the finest restaurants in the area, Florie’s.
Nantucket
Nantucket is usually known as a summer destination, but President Joe Biden has long drawn attention to the island during the colder months. Starting in 1975, the Biden family has typically spent Thanksgiving on Nantucket, often making appearances at local shops and events such as the annual Christmas tree lighting. President Biden and his family returned to the island in both 2021 and 2022 for the holiday.
Tradewind operates scheduled flights to Nantucket from the New York area between April and early December and offers private charters from anywhere year-round. In the summer months, Tradewind flies to and from the island up to 25 times per day, making it by far the most convenient way to get to the remote island.
A summer trip to the island, with its plentiful beaches, outdoor restaurants, and classic warm-weather hotspots such as Cisco Brewers is always a good idea. Or, opt to channel the Biden family and visit the island in the fall, winter, or spring. If you’re considering a visit to Nantucket during any season, Greydon House is a must-visit boutique hotel, renowned for its elegant design and exceptional hospitality, providing an ideal blend of luxury and comfort for a memorable island getaway.
To learn more about Tradewind flights to Kennebunkport, Martha’s Vineyard, Palm Beach, Nantucket, and more, please visit our website. To receive a private charter quote, submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-203-267-3305 option 2.