Donald Trump has previously questioned the wisdom of going on holiday. “Don’t take vacations,” he wrote in his 2004 book, Think Like a Billionaire. “What’s the point? If you’re not enjoying your work, you’re in the wrong job.” But the former US president’s numerous trips over the years suggest he had a change of heart. And his extended family are also partial to a relaxing break. From Florida to New Jersey, Paris to Dubrovnik, here are some of the Trump family’s top holiday hotspots.
Turquoise water, white sand and one of the Caribbean’s largest coral reefs… no wonder Canouan Island (one of 32 islands that make up Saint Vincent and the Grenadines) is where the world’s billionaires come to unwind. It’s also home to Raffles Resort, where Donald Trump hosted his Million Dollar Invitational 54-Hole Golf Tournament.
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Tiffany Trump celebrated the end of her midterms by holidaying at The Cove, a luxury resort on the island of Eleuthera in the Bahamas. She posted a snap from the 2016 trip to social media, showing her standing in front of a golden crescent of sand and turquoise seas. The resort – which has two private beaches – is described on its website as an “off-the-beaten-path hideaway [that] makes you feel like you’ve washed ashore on your own private Caribbean island.”
It’s easy to see why Ivanka Trump picked Cayo Espanto – with its white-sand beaches and private, seafront villas – for her babymoon. Ivanka was six months pregnant with her third child in 2015 when she and her husband Jared Kushner visited the exclusive resort, located three miles (5km) off the coast of San Pedro, Belize. As well as world-class cuisine, the private island getaway offers guests a host of activities including scuba diving, fishing and luxury yacht tours.
Donald Trump bought Mar-a-Lago, a resort and national historic landmark in Florida's Palm Beach, in 1985. As President, he used the 1927 Moorish-style building to host foreign leaders like President Xi Jinping of China, calling it the “Southern White House”. He also made frequent weekend visits to the lavish estate while he was in office. Given it's one of the largest mansions in the state of Florida, with 126 rooms in all, it’s no wonder he chooses it to be his primary residence now.
It's easy to see why the Trump family pay regular visits to their 5-star hotel in Oahu, Hawaii – towering above Waikiki’s white sand beaches and stalk-skinny palm trees, the venue has an infinity pool overlooking the Pacific Ocean, a Hawaiian-style spa and a state-of-the-art health club. Donald Jr. and his then-wife Vanessa celebrated their 10th wedding anniversary there in 2015. He uploaded a photo on Instagram with the caption: “The view from our @trumpwaikiki room was so good it was hard to leave.”
Ivanka and her husband Jared took their three children to Hawaii to celebrate both Hanukkah and Christmas in 2016. The family reportedly stayed in a private villa at the Four Seasons Resort Hualalai on the Big Island of Hawaii. The two-storey Presidential Villa has lavish indoor and outdoor living spaces with unobstructed sea views, direct beach access, granite bathrooms and a private spa.
With its luxury hotels and mountain lodges, world-class skiing and a county airport that’s perfect for arriving by private jet, Aspen, Colorado, has long been popular with the rich and famous. Donald Trump has visited Aspen in the past, while his daughter Ivanka headed there for a summer break with her husband in 2021. The pair reportedly stayed at the Snowmass area's Wildcat Ranch – a 7,000-acre ranch complete with a boating lake, horse riding trails and a rodeo arena.
One of Donald Trump’s flagship hotels, this luxurious Manhattan pad has a prime location on the edge of Central Park. Its suites have floor-to-ceiling windows with superb views, and the sweetest suite features two bedrooms, elegant furniture and handcrafted crystal chandeliers. No wonder Donald Trump – a native New Yorker – stays here when he’s in town.
Virginia is one of the top wine-producing states in the US, and the Charlottesville area has more than 40 wineries – including one owned by the Trump family. Tucked away beneath the Blue Ridge Mountains, the 1,300-acre Trump Winery is one of the largest vineyards on the East Coast. You might spot a Trump sipping award-winning sparkling, white and red wines in the tasting room. Eric Trump is among the family members to have visited on numerous occasions – and now serves as the vineyard's president.
Tiffany Trump’s mother, Marla Maples, was born and grew up in north Georgia, home to towering mountains and roaring rivers. So, little wonder that Tiffany has spent the Christmas holidays there. In 2016, she headed to her mother's birthplace of Whitfield County, 35 miles (56km) west of Chattahoochee-Oconee National Forest. She posted a photo to Instagram showing a Christmas tree and festive table on Instagram, with the caption: “Merry Christmas and Happy Holidays!”
Both Donald Jr. and Eric are keen hunters – the pair have gone on shooting trips together in numerous locations, including West Monroe, Louisiana. Donald Jr. posted a series of photos on Instagram showing him with friends dressed in camo with rifles slung over their shoulders and holding up carcasses of animals. Louisiana is popular with duck hunters – its creeks and swampy backwaters attract thousands of ducks between September and January.
Hunting destinations appeal to Donald Jr. who has a game book including elephants, leopards and crocodiles. Closer to home, Iowa has vast swathes of land open to public hunting. Donald Jr. joined the Governer’s Annual Deer Hunt in southern Iowa’s Appanoose County in 2016. At the same time, his dad was also in the state to try to harvest votes for the Iowa caucuses.
A more low-key destination, New Jersey has 127 miles (204km) of beautiful beaches, oceanfront towns and Atlantic City’s impressive Steel Pier. Its amusement rides and go-kart track has attracted celebrity riders, which include Ivanka and her family. In 2016, she posted a photo of Jared and Joseph smiling in a bumper car. New Jersey is also where Donald Trump enjoys downtime at his golf club in Bedminster.
Golf may be the main sporting passion of most of the Trump family, but Lara Trump is a big tennis fan too. The wife of Eric Trump visited the International Tennis Hall of Fame in Newport in 2015. Housed inside a former casino, it has a museum, grass tennis courts, indoor tennis facilities and a theatre. It’s located near other Newport highlights, including The Elms (a replica French château) and Fort Adams State Park, a huge coastal fortification.
A sunny boat ride in North Carolina sounds like a great way to enjoy the Christmas season. Eric Trump shared a holiday snapshot in 2016 of his wife Lara and their two dogs sailing off Wrightsville Beach. Ideal for active beachgoers, Wrightsville offers everything from kayaking to surfing, and the surrounding area is dotted with hiking trails… and golf courses. No wonder it’s a Trump holiday hangout.
Ivanka Trump enjoyed a spot of sightseeing in the beautiful city of Dubrovnik with Wendi Murdoch back in 2016. She posted a snap of herself with the ex-wife of media tycoon Rupert Murdoch, showing them posing in front of the terracotta rooftops of the historic Old Town. The tour was taken during a summer mini-break away from the kids. Her husband, Jared Kushner, also came along for the ride.
Ivanka Trump and her husband Jared Kushner headed to Tel Aviv for a low-key holiday in 2022. The couple was spotted on a night out in the city wearing casual clothes and holding hands after enjoying a meal at the beachside restaurant Manta Ray. The restaurant specialises in seafood and mezze dishes, such as deep-fried calamari, shrimp with vodka and grouper cubes served on black lentils.
The Greek island of Mykonos holds a special place in Tiffany Trump’s heart. It’s where the daughter of the former US President met her husband, billionaire fiance Michael Boulos – and the pair have enjoyed many holidays on its sunny shores. The glamorous isle has become like a second home to Tiffany, who has visited a number of times since meeting Boulos there in 2018, including as a guest of Lindsay Lohan who owns a beach club on Mykonos.
Ivanka chose Egypt for a family holiday after announcing her exit from politics in 2022. The former White House senior advisor took her husband, Jared Kushner, and their three children to see the Pyramids for the first time. Their trip – which coincided with Thanksgiving – saw them ride camels in the desert, visit mosques and tour Giza to see its Great Sphinx. Ivanka posted snaps on Instagram, commenting: “So special to explore the beauty of Egypt for the first time with my family!”
The Trump family reportedly booked an entire floor at a £22,000 ($26,700)-a-night 5-star Corinthia Hotel in London for their first state visit to Britain back in 2019. Ivanka, Don Jr, Eric and Tiffany stayed in the plush hotel, whose A-lister guests have also included Beyoncé and Jay-Z, George Clooney and Rihanna. The Royal Penthouse Suite has its own lift, private spa access and a walk-in wine cellar.
Donald Trump jetted into Scotland for a golf holiday in 2022, visiting the luxury Turnberry golf resort in Ayrshire, which he bought in 2014. The 5-star resort – which Trump spent £200 million ($243.5m) renovating – was where he stayed on his first official visit to the UK back in 2018. It’s made up of three sites – a golf course, a golf academy and a 5-star designer hotel. According to the Trump website, Turnberry is “enchanting and exceptional… delivering an old-world luxury experience”.
With sweeping views of the Aberdeenshire coastline, Trump International Scotland is an award-winning golf course with a 5-star country hotel and fine dining to boot. The former President bought the Menie Estate (a former shooting estate) in 2006, later saying: “we are going to build the greatest golf course in the world.” It opened six years later, and Trump visits his beloved golf course on most of his Scotland visits, including on a week-long trip in 2022.
Donald Trump and his wife Melania enjoyed the lavish surroundings of his plush Doonbeg resort during his Irish visit in 2019. Trump bought the hotel – which boasts an 18-hole championship golf course – in 2014 and it now employs around 300 people during high season. The four-bedroom suites are the largest, featuring ocean-view window seats, grand fireplaces and bathrooms stocked with Natura Bissé toiletries.
Tiffany Trump enjoyed a luxury ski vacation in the French Alps with her husband Michael Boulos. The couple jetted off to the glamorous resort of Courchevel, which is known for its chic shops, plush accommodation and fine restaurants (along with its world-class skiing). Tiffany’s mother, Marla Maples, joined them for the holiday, posing with her daughter in selfies with snow-covered mountains and a Giorgio Armani store behind them.