Where to Go for the Holidays—And What to Know Before You Go

This year, planning for the holidays is markedly different, as we all navigate the challenges of social distancing and Coronavirus travel safety. Yet the new normal also offers several advantages if you’re still looking to take a trip between now and the new year or this winter. Here, we break down what you need to know for planning a holiday trip during Covid.

Contact Indagare or your Trip Designer for more information on coronavirus travel safety, including the destinations that are open to travel, new Covid-19 hotel policies, the safest routes or transportation options available, future trip-planning advice, inspiration and ideas.

Indagare Members can also see our curated list of Indagare’s favorite destinations open to U.S. passport holders now: Coronavirus Travel Information: What’s Open To Americans

Caribbean Villa and Yacht Rentals Have New Terms (And Some Old Ones)

In a welcome move, many villa and yacht owners in destinations throughout the Caribbean have altered their contracts to allow cancellations or credits for rescheduled visits due to international border closures. And there’s often a new addendum in the contracts to cover the possibility of regulations changing while you’re on the ground.

What hasn’t changed though: the ubiquity of minimum night-stays. As with previous holiday seasons, hopeful travelers must be comfortable with anywhere from five-day to week-long bookings, depending on the villa or yacht owner.

Seasonal Ski Pass Holders Will Get Big Perks

Across the country, ski areas are establishing new capacity limits on the slopes, and most have moved to an online reservations system which will limit the number of lift tickets per day. In most cases, priority for reservation slots will go to seasonal pass holders and members of multi-resort passes. Epic, the pass for 34 ski areas including Beaver Creek, Park City, Stowe, Vail and Whistler, is giving its members a full month in advance to reserve days during peak season before opening up sales to non-pass holders. Many of the resorts affiliated with the Ikon Pass have yet to announce their final plans. What we know so far: Big Sky, Jackson Hole and Taos will require advanced reservations (including for Ikon members), while Deer Valley, Killington, Mammoth and Stratton will let Ikon holders on the slopes without making advanced reservations. No news on whether the same will apply at other Ikon mountains like Alta, Aspen and Snowmass, which are all finalizing new protocols. But we will be on the lookout for you.

You Might Need to Take a PCR Test Before You Go

If you’re planning an international trip for the holidays, you will likely need to take a Covid-19 PCR test to enter the country. Most countries require the test be administered within 48 to 120 hours prior to either departure from the U.S. or arrival in the foreign country (language varies on government websites), so timing your test to account for travel time can be crucial.

And for those making interstate domestic trips to the Northeast from other parts of the country, showing proof of a negative PCR test will nullify the required 14-day quarantine. (Hawaii’s regulations are still among the most stringent, and it’s unclear whether they will be lessened by December. At this time, the state requires—and enforces—arrivals to quarantine, regardless of test results.)

Contact Indagare and your Trip Designer to help you figure out the best testing options near you.

Your Special Meals & New Year’s Eve Will Look (Slightly) Different

One of the hallmarks of the season is the large dinner and celebrations, and many of our favorite destinations around the world throw annual parties in which guests can mingle. This year, of course, that will look different. For cold-weather destinations, it remains to be seen whether indoor gatherings of any kind will be safe or permitted. Most of the United States currently allows indoor dining, but at a reduced capacity, making early reservations even more essential should you decide to plan a dinner for your group. Another option for those who prefer to avoid indoor, multi-group dining: restaurants throughout the summer have improved their take-away capabilities, and will likely offer catered holiday menus that travelers can eat in their own accommodations, if there’s a kitchen.

In warmer climates, the emphasis will be on the outdoors. Mexico’s Cuixmala, for example, is still planning its yearly candlelit New Year’s Eve bash, complete with a mariachi band at the poolside dinner followed by fireworks, beach bonfires and dancing. What will be different: to allow for social distancing, Cuixmala will be expanding the area for dining and dancing from previous years, and is looking into other steps which will ensure safety.

Certain Destinations Are Filling Up: Here’s Where You Can Still Go

Fewer destinations open to Americans means fewer options for holiday vacations. On top of that, many of our most-booked properties have reduced overall guest capacity to maintain social distancing. The takeaway: options for hotels the weeks around Christmas and New Year’s are limited this year.

Here’s where we still see availability at our favorite hotels in destinations that let in U.S. passport holders. As of September 15, all hotels and resorts mentioned below have availability—ranging from a single guest room to a multi-room villa—throughout the period between the days leading up to Christmas and January 2, 2021.

Contact Indagare to secure exclusive perks and preferred rooms when booking your holiday travel.


Turks & Caicos
One of the Caribbean’s dreamiest clusters of islands, Turks & Caicos beckons beach lovers to its white sands, balmy waters and glamorous resorts. Where to Stay: COMO Parrot Cay is an exclusive resort on its own island—a 35-minute boat ride from Providenciales (“Provo” to locals)—which evokes the castaway beach feel associated with the Maldives or Bali. Its gorgeous private villas with butler service and stunning water have earned it a loyal following, including from high-profile celebrities.

St. Barth’s
While France is still closed to Americans, those searching for a little je ne sais quois can still head to St. Barth’s, which mixes French culture—and cuisine—with a laid-back tropical ease. Where to Stay: Cheval Blanc Isle de France is set on one of the most beautiful beaches in the Caribbean. The LVMH property has been closed for months, but is reopening its doors in time for the peak season on St. Barth’s. We’re also still seeing villas at Hôtel Le Toiny, at the far southeastern end of the island. Each of its secluded villa suites has a private terrace with a pool and stunning views down the hill to the sea.

Canouan Island
Tiny Canouan, part of the St. Vincent & the Grenadines, is a refreshingly quiet Caribbean escape with powder-white sand, turquoise waters and a lush, mountainous landscape. Where to Stay: Mandarin Oriental Canouan commands the perfect location on Canouan: a quiet curve of hillside that looks out over Godahl Beach. In contrast to the extraordinary emerald-blue ocean, the décor of the hotel’s suites and villas is an intriguing mix of cool grey marble, pale ceilings and walls and hot pink accents.

This ultra-scenic (and convenient) East Coast getaway is just a two-hour flight from Boston and New York. Peak season, especially to enjoy Bermuda’s pink-sand beaches, ends in November, but December is still a great time of year for golfing and sailing. Temperatures hover in the 70s, and you’ll likely have the beaches all to yourself, though the water will be too cold for swimming. Where to Stay: Rosewood Bermuda sets the bar for luxury in Bermuda, and finished a major renovation in early 2018. Perched on the edge of a cliff, its British colonial manor house feel provides a distinctive sense of place. For a departure from that British colonial aesthetic, consider The Loren. It’s decidedly modern, with a glass-enclosed lobby and floor-to-ceiling windows that open onto terraces overlooking the resort’s private beach and the sparkling Atlantic beyond.


New England
In search of cozy? New England delivers historic charm and quintessential winter weather. Think wood-burning fireplaces, hearty (though frequently innovative) cuisine, lots of perfect corners for reading. Where to Stay: At Vermont’s historic Woodstock Inn, with roots dating back to the 18th century, rooms—all of which underwent renovations in 2018—feel like a friend’s comfortable country home. The property also has its own ski resort, the alarmingly named Suicide Six. Despite the frightening moniker, the small mountain is family-friendly and a fun place for kids to get their first taste of skiing (More serious skiers can spend the day at Killington, just a 25-minute drive away.)

Smoky Mountains
America’s most-visited National Park is virtually empty come the winter months, and temperatures usually hover in the comfortable range for brisk walks through gorgeous forests and up the region’s gentle peaks. Where to Stay: Blackberry Farm is sold out for the weeks surrounding the holidays, but its younger sister-property, Blackberry Mountain, still has some availability. The smaller, more health-focused property has cozy, stylish rooms and villas, along with a great culinary program.

Colorado’s most exclusive resort town, Aspen draws ski-bunnies to its chic shopping and après ski scene as much as to its slopes—which, when combined with neighboring Snowmass, offer more than 200 miles of runs and trails. Where to Stay: Aspen’s most coveted address, The Little Nell offers stylish rooms, a slopeside location and superb service. The ski-in, ski-out hotel at the base of Aspen Mountain blends contemporary New York apartment vibes with Western touches such as “barn door” closets that slide open and wrought-iron hardware or horse photographs by Michael Eastman.

Jackson Hole
This laid-back Wyoming town has some of America’s most dramatic landscapes, and mixes cowboy town with cosmopolitan hub. Grand Teton National Park’s peaks are just five miles north, and the town’s own mountain lets daredevils ski on black diamond runs with a vertical drop of more than 4,000 feet. Where to Stay: On a hillside 10 minutes from town, Amangani’s sleek, understated interiors allow the region’s spectacular landscapes to be the star.

It remains unclear whether Hawaii will continue to require a 14-day quarantine, but there are certainly few more beautiful destinations to spend two weeks. Where to Stay: If self-isolation is still enforced, finding the right villa with services like in-home grocery-delivery available—not to mention a fabulous pool—is key.


Pacific Coast
Along Mexico’s Pacific Coast, jungle-topped hills cascade into the sea, and outdoors enthusiasts enjoy activities ranging from hiking and biking to horseback riding and surfing. Where to Stay: About 100 miles south of Puerto Vallarta, Cuixmala is bold, lavish and entirely unique. The late billionaire Sir James Goldsmith bought the 25,000-acre parcel of coastline and fashioned his family’s own private reserve (complete with zebras). Initially closed to visitors, the property now belongs to Goldsmith’s children, who have opened Cuixmala as a hotel with rooms and villas for rent. On our Radar: Opening November 1, One & Only Mandarina is the newest luxury hotel in the region.  We’re eager to see its treehouse-chic suites and villas, which will have private pools and an appealing indoor-outdoor layout set in a jungle above swimmable shores.

Los Cabos
Cabo is an easy flight for West Coasters looking for sun, surf, sand—and some seriously luxurious resorts. Each winter, it also hosts one of the world’s great natural spectacles, as upwards of 20,000 gray whales venture down the Pacific Coast to the warmer, protected waters off of Baja. Where to Stay: The newly opened Four Seasons Los Cabos is a beautifully designed resort along the region’s undeveloped East Cape, more than an hour away from the main hotel corridor between Cabo San Lucas and San José del Cabo. The main draw here: a two-mile-long calm, swimmable beach (you can’t swim in the ocean at most resorts in Cabo).

Riviera Maya
On the Yucatán Peninsula’s eastern shore, Mexico’s Riviera Maya is a gorgeous swathe of coastline, with white sand beaches backing onto lush tropical forests dotted with eco-adventures (cenotes!) and Maya ruins. Where to Stay: Rosewood Mayakobá is built around a network of lagoons and mangrove-lined canals which lead to a beautiful beachfront pool and swathe of sand. Every suite comes with private plunge pools and rooftop patios or a private garden.


December in the Galápagos means idyllic temperatures, perfect for seeing the archipelago’s unique wildlife, including sea turtles and iguanas—the latter of which are particularly colorful during the holidays because it’s mating season. Where to Stay: Indagare members have created life-long memories aboard Galápagos yachts, which navigate between the islands and offer the most options for animal spotting and activities. We have several favorite boats for private and semi-private sailings, some of which still have open cabins.

Costa Rica
Costa Rica is an adventure lover’s paradise, with verdant coastlines on both the Caribbean and Pacific, plus a mountainous, jungly interior. Where to Stay: Nayara Springs, set at the base of the Arenal Volcano, is a secluded, adults-only lodge that offers quiet, natural surroundings, excellent service and a melodic soundtrack courtesy of the local tropical birds. Activities include volcano tours and horseback rides to a nearby waterfall.


Up-close encounters with endangered mountain gorillas, coupled with the resilient spirit of the people and the beauty of the landscapes make Rwanda a truly singular destination. This year, the country enacted new safety precautions limiting the number of visitors per gorilla trek to protect everyone involved—guests, guides and gorillas—making for an extremely private safari experience.  Where to Stay: Volcanoes Virunga Lodge has some of Rwanda’s best views, with 10 chic, free-standing bandas overlooking the Virunga volcanoes, the sweeping Musanze Valley and lakes Ruhondo and Bulera. We also love Bisate Lodge, whose dreamy thatched suites are nestled against a lush hillside near Volcanoes National Park, and Magashi Camp, with six tented suites perched right at the water’s edge of a lake on a private concession of Akagera National Park.

After rains in the beginning of the month, late December sees Kenya—home to the Maasai Mara Reserve and its abundant wildlife—at its greenest. Described as “the cradle of humanity,” the country’s magnitude is palpable in its savannah landscapes and vibrant tribal cultures. Where to Stay: There is still (limited) availability at Angama Mara, one of Africa’s most elegant safari lodges. On a rugged escarpment, its rooms’ sliding glass doors open to balconies with expansive views overlooking the Mara below. Daily game drives usually include spotting lions, leopards, elephants, buffalo and black rhinos. Indagare Intel: Melissa is currently in Kenya scouting a new property we’re excited about. Stay tuned for more!


If you have a few weeks of time, the charming countryside and villages of England’s bucolic Cotswolds region could make for a relaxed, Earl Grey-fueled holiday. Where to Stay: The UK requires international visitors to self-isolate for 14 days, so finding the right home rental—with private outdoor space and the opportunity for grocery delivery—for the first two weeks of your stay, is essential. Contact Indagare for one of our preferred England country homes.

Other options we love with similar quarantine policies: Ireland, Scotland

You won’t be lounging on the beaches or diving into the Adriatic from a yacht in December, but winter has its own charms in Croatia. What you’ll see: historic towns and villages, a burgeoning wine region and the terraced, aquamarine waters of Plitvice Lakes Natural Park—all blissfully free from summer crowds. Where to Stay: Contact Indagare to help secure a countryside villa, which makes a great home base for exploring Croatia’s interior, as many of our favorite hotels are already booked.


Late December sees balmy temperatures and pleasant sea breezes in the Maldives, a cluster of more than a thousand atolls off the southern tip of India. Where to Stay: In a country known for its luxurious hotels, Soneva Fushi has set the standard since it opened in 1995. The carbon-neutral resort, on its own private island, was an early pioneer in barefoot chic, and offers Robinson Crusoe-style villas set along its white-sand beaches.

French Polynesia
French Polynesia epitomizes the term “far-flung,” with crystal clear waters, lush and varied tropical landscapes and gorgeous beaches. And while December can be rainy, the downpours are usually sporadic and shouldn’t interfere too much with the day’s activities—namely swimming, scuba diving, snorkeling or simply lounging. Where to Stay: The Brando is one of the world’s most awarded hotels, and for good reason. Formerly Marlon Brando’s private island paradise, it’s now an eco-luxury resort, with sumptuous villas set along two beaches and exceptional service from its staff, most of whom are local.

Contact Indagare or your Trip Designer for more information on coronavirus travel safety, including the destinations that are open to travel, new Covid-19 hotel policies, the safest routes or transportation options available, future trip-planning advice, inspiration and ideas.

Indagare Members can also see our curated list of Indagare’s favorite destinations open to U.S. passport holders now: Coronavirus Travel Information: What’s Open To Americans

– Peter Schlesinger on September 16, 2020

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