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7 (COVID-Era) Dream Trips, Planned by Experts

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Dream trip: a private 13-bedroom house and island in Maine, planned by Black Tomato

Courtesy of Clapboard Island

Dream trip: a private 13-bedroom house and island in Maine, planned by Black Tomato

Stay flexible and keep your sense of humor: It is possible to take a dream trip during COVID.

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Right now, returning to a city hotel close to home might be enough of a “dream trip.” 

Julie Danziger, managing partner of Embark Beyond and New York resident, recently checked into NYC’s Equinox Hotel in Hudson Yards with her three children. “Opening the door with a key card was almost like seeing the Great Barrier Reef,” she joked. It doesn’t take much to feel like you’re escaping these days, and more and more families are taking advantage of hotel “schoolcation” setups (all with good Wi-Fi, naturally) to get away.

But for many travelers, including AFAR’s readers, getting even farther away—on an international trip—is on the horizon. We surveyed more than 1,000 readers and found that 86 percent plan to travel internationally in 2021–2022 and 66 percent are currently planning their next trip. And as COVID tests and canceled flights become part of the challenge of taking a far-flung trip, using a travel advisor may save you time and headaches.  

If your 2020 dream trip has been deferred, here’s some inspiration for when the time is right, with lessons learned from the experts. 

That beach holiday we all need right about now

Dream villas and hotels in Cabo San Lucas, Mexico 

Mexico never closed its air borders to Americans, and Americans are booking a lot of travel to Mexico, according to Danziger. “Mexico in general has been hot because it’s easy to get to, it is (literally) hot, and they don’t require negative COVID tests like two minutes before the trip,” she says. “People don’t want to scratch their heads trying to figure out if they can visit a place. And with Mexico, there are fabulous hotels, amazing service, incredible value, and it’s easy to understand how to go.” Land borders are still closed, though, and there are enhanced precautions like temperature scans and additional questioning at some international airports. COVID-related safety restrictions are in place in most resorts. 

Danziger recommends an “off-the-charts” villa in Cabo called La Datcha, inspired by a traditional Mexican hacienda, with 10 bedrooms, brightly colored furniture and artwork, a full gym, and several dining areas overlooking the ocean. 

Jennifer Wilson-Buttigieg of Valerie Wilson Travel says it was “wonderful to book the stunning new Zadún, a Ritz-Carlton Reserve in Los Cabos, not only to see Los Cabos welcoming Americans, to support new openings,” she says. The hotel opened in November 2019. 

For a taste of Baja beyond the hotel and resort world, Kate Doty from GeoEx recommends its Boundless Baja itinerary, which explores an “often-overlooked” part of Mexico—including two UNESCO Biosphere Reserves: the Sierra de la Laguna Reserve and the desert islands of Espiritu Santo Reserve—and Baja’s animal wildlife and scenery. 

A few months in St. Bart’s with your whole family 

In St. Bart’s, the beloved Eden Rock hotel, part of the Oetker Collection, sits literally on a (large) rock, surrounded by sandy beaches and turquoise blue water. After undergoing a big renovation after Hurricane Irma destroyed much of the property in 2017, it reopened to acclaim last year. Now, it’s reopening again on October 22, a few months after St. Bart’s reopened for tourism in June. 

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The ultimate multigenerational COVID-era trip now includes private house rentals for months at a time, and you can get a killer one through Eden Rock’s rental arm. “If you book a house, obviously through your favorite travel agent, via Eden Rock Villa Rental, you get access, lounges, and breakfast courtesy of Eden Rock Hotel,” Danziger says. “It’s like staying at the hotel without staying at the hotel. Now if only I could get Eden Rock to do this for me at home. I could use one of their croissants at home.” 

One of Embark Beyond’s clients rented a large villa through Eden Rock Villa Rental for two months. They have four older children with their own families and each week, a different child will come visit with their spouses and families. With four kids, each kid gets two week-long trips—not a bad deal. 

Private islands and beaches in French Polynesia 

Cocktails at sunset. Clear blue water. A private island in the South Pacific. You can still experience this magic, though it’ll take some work.

Where to start? Rachel Hays, an advisor with All Star Travel Group, recommends the Brando on Marlon Brando’s French Polynesian island, Tetiaroa, where she booked Los Angeles–based clients for two weeks in July. “The Brando is a private island resort with 35 villas on white-sand beaches, and they had a wonderful time,” she says. Will Kiburz, vice president of Coronet Travel, also booked two weeks for a couple, split between the Four Seasons Bora Bora and the Brando in August. (They were originally scheduled to travel in May.) 

Complications from needing COVID testing within a certain timeframe, customs paperwork, and multiple flight cancellations all presented problems to solve, handled by him. “It takes the right kind of client, in my opinion, to be traveling during COVID,” he says. “You can’t have the attitude that you ‘have’ to make or do anything. They have to be flexible.” 

At the last minute, Kiburz had to fly the couple from their home in St. Louis through Los Angeles just to be tested. Kiburz researched the testing requirements by the French Polynesian government and called it “mind-boggling”—pages of test results it accepts or doesn’t. The paperwork showing the results couldn’t have any reference to “rapid test,” even though it had to be a rapid test to meet the arrival conditions. He used his network of hotel contacts in L.A. to get connected to a clinic in Beverly Hills, and although the doctors confirmed they could make it happen, he made sure his travelers knew that the testing was not guaranteed. In the end, “everything went perfectly.” The clients flew first class on Air Tahiti Nui—though their flights were also cancelled and rebooked multiple times. But when they landed back home, they thanked him for everything, saying the trip was fabulous. 

Pro tip: Walker says the direct flight back to Los Angeles from Papeete always departs late in the evening, so they always book a day room for clients at the InterContinental Resort Tahiti, a five-minute drive from the airport, so they don’t have to wait all day at the airport. 

Honeymoons don’t have to be (very) delayed

(Some of) Africa awaits 

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Honeymooners are turning to countries like Tanzania, Rwanda, and Kenya that are open to Americans. “We just booked a really cool two-week honeymoon with a great new company called Africa Roam [which only works with travel advisors],” says Josh Bush, owner of Avenue Two Travel in Villanova, Pennsylvania. “The couple will be doing everything privately, including staying at Segera Retreat, a boutique property on Kenya’s Laikipia plateau. They will even spend a night in the bird’s nest–style open-air sky bed. From there, they will stay at tented camps near the Mara River to see the migration and crossings in private vehicles. They will travel to Rwanda and Singita for gorillas and golden monkeys in between visits with local communities at each location.” The agency also arranged activities such as mountain biking and hot air ballooning, all with privacy in mind. 

Kate Doty is booking travelers on Rwanda and Kenya private safaris. She calls its custom Kenya private safari the “quintessential dream safari,” beginning in Amboseli with views of Kilimanjaro and herds of roaming elephants, moving on to the Lewa Wildlife Conservancy and Sirikoi Lodge, experiencing the heart of the Maasai Mara in luxury tents, and ending at the pristine Diani Beach on the south Kenya coastline, where you can walk for five miles in either direction, snorkel, and dive.  

Adventure closer to home 

New England in the fall is still a dream during COVID  

Experiencing New England in the fall has always been a dream trip. Katie Cadar, director of leisure sales with TravelStore, has been planning getaways for two couples who normally go far-flung. “But with COVID, they are now taking a two-week driving trip to see the leaves change, small towns and villages, national parks, and the beauty of New England in the fall,” she says. Among the highlights: stays at the Woodstock Inn and Resort and Cliff House Maine, hiking around Mount Washington, and visits to the Ben & Jerry’s factory, the Farnsworth Art Museum, and Millay House Rockland. Plus, lots of great meals booked throughout the two weeks.

Black Tomato adventure from a private island base in Maine 

A private seaplane to Acadia National Park, met by an expert guide; a full-day yacht charter cruising up the Kennebunk River to the Dolphin Restaurant for views and dinner; lobster fishing, waterskiing, sailing—all of these dreamy adventures were part of an ultimate late-summer escape to Maine, planned by Sunil Metcalfe, sales director and travel expert at Black Tomato. The clients (a couple and their beloved dog) took over Clapboard Island in Falmouth for a COVID-sensitive and private experience at a recently refreshed (gob-smacking) 13-bedroom, nine-bath home. The island also has gardens, rocky beaches with calm coves for swimming, walking trails, kayaks, and a 450-feet zipline that you can use with staff supervision and a signed waiver—plus seriously speedy Wi-Fi for staying connected.

For the stay, they arranged COVID testing for not only the guests but also everyone who staffed the property, including housekeepers, a private chef, and island manager. “Everyone felt safe and free from anxiety, so they were fully able to embrace the travel experience, despite the uncertainty of the times,” says Metcalfe. “The clients also wanted to stay fit, so we designed a pop-up gym with a treadmill, yoga mat, weights, and more.” Not to forget the furry family member—Metcalfe arranged for a fence and dog gates for their dog.

An NYC staycation, with “Zoom school”

Danziger’s trip to Equinox Hotel in Hudson Yards reminded her how great a city break can be, especially if the city closest to home is New York. “It’s a novelty now,” she says. “I was in awe of the magic.” For Danziger and her three school-aged children doing “Zoom school,” a change of scenery overlooking the Hudson River was exactly what they needed. During the day, they booked a meeting space with great Wi-Fi where the kids spread out, did “gym class” by running to the top of the Vessel, and ordered room service for lunch. “The dream can be closer to home,” she says. “People may want to ease back into travel, and staying local is the perfect way to do that.” 

>>Next: 5 Luxury Travel Habits That Surprised Us 

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