Articles

Best Winter Vacation Ideas for 2020-2021: 25 Trip Ideas from Antigua to Zambia

As temperatures drop, we’re turning our attention to the places to be this winter, even if our getaways might look a little bit different this year. To help you plan your winter vacation—for 2020, 2021 and beyond—we’ve rounded up our favorite destinations that are currently open to American travelers for a much-deserved escape somewhere cozy, seaside, stylish, tropical, stimulating or serene—whatever you find yourself needing in the months between November and March. While the après ski set may be going private this year, and our favorite holiday markets remain out of reach, there are plenty of festive experiences—and incredible hotels and resorts—to put these winter vacations on your radar: sundowner cocktails in the Serengeti, beach reads on your own jungle pool deck, a long day on the slopes or in the surf and mind-blowing meals at some of the world’s best restaurants. From a new resort on Mexico’s Riviera Nayarit to behind-the-ropes access at the Pyramids of Egypt, here are 25 reasons to start planning your next winter escape.

Contact Indagare or your Trip Designer to start planning winter vacations for this year and the future. Beloved destinations like the ones below are booking up quickly. Our team can match you with the accommodations and activities that are right for you and provide information on coronavirus travel safety, destinations that are open to travel, Covid-19 hotel policies, transportation options, private villas and charters and more. 

Winter Vacations for Sun and Scene Seekers: The Caribbean

The Caribbean has long drawn couples, families and friends for easy warm-weather getaways, thanks to its powdery white-sand beaches, warm turquoise waters and pampering resorts—but every island has its own atmosphere and specialties. For a jet-set scene, St. Barth’s is not to be missed—with top hotels including the legendary Le Toiny (which offers 14 freestanding villa suites and a 72-hour cancellation policy), the contemporary, buzzy Le Barthélemy Hotel & Spa (reopening October 28), Cheval Blanc St-Barth Isle de France (reopening October 29), Eden Rock and Le Sereno. With just a 3.5-hour direct flight from New York, travelers looking for a more romantic, secluded atmosphere should visit Turks & Caicos, where they can retreat into the private pavilions at the sleek and serene Amanyara (which offers open-air pavilion rooms with direct ocean access, as well as free-standing villas with infinity pools) or the exclusive villas at COMO Parrot Cay, while Grace Bay Club offers separate accommodations and pools to keep both couples and families happy. Another top family-friendly option, also accessible via direct flights from the U.S., is Antigua, where the all-inclusive Jumby Bay (reopening November 7) offers a private island location, friendly atmosphere and top-notch amenities on a spectacular beachfront—while the island’s first luxury hotel, Curtain Bluff, guarantees personalized service and a host of activities (including squash, waterskiing, snorkeling, kayaking, tennis and more) that are well-suited to families with older children.

Entry Requirements & Covid-19 Safety: As of October 28, the Caribbean Islands that are currently open to Americans include St. Barth’s (flying via San Juan), Turks & Caicos, Antigua, the U.S. Virgin Islands, Saint Vincent and the Grenadines (including Canouan and Mustique), the Bahamas, the Dominican Republic, Barbados, St. Lucia, Bermuda, Puerto Rico and St. Maarten. Consult the islands’ respective U.S. Embassy websites, as well as the link below, for specific information regarding entry and Covid-safety requirements, which vary from island to island. Many islands require proof of a negative Covid-19 RT-PCR test for entry, and some enforce self-quarantine for U.S. travelers at their chosen resort or villa accommodation.

Related: Indagare Caribbean Islands Matchmaker: The Best Caribbean Islands Open Now for Every Traveler

Winter Vacations for Nature and Wellness Devotees: Belize, Panama and Costa Rica

The Central American nations of Belize, Panama and Costa Rica are home to lush jungles, white-sand beaches and azure seas that protect astounding biodiversity. Here, ancient ways of life survive in modern culture, emphasizing a spiritual harmony with Mother Earth—known in Costa Rica as “pura vida”—that manifests itself in a plethora of outdoor activities that will get your blood pumping and a holistic, nature-based approach to healing, nutrition and wellness. Creating a haven for true disconnection and restoration, a handful of singular eco-lodges—like Belize’s Blancaneaux Lodge and Turtle Inn (both reopening November 1), Panama’s Islas Secas (reopening mid-December) and Sweet Bocas and Costa Rica’s Kasiiya Papagayo (reopening December 15) and Nayara Springs—offer intimate, outdoor-centric settings, with just a few standalone accommodations (ideal for social-distancing) and mindfulness, beauty, spa, adventure and fitness programs.

Entry Requirements & Covid-19 Safety: As of October 28, Belize, Panama and Costa Rica* are open to U.S. citizens. Panama requires that travelers book accommodations at approved Gold Standard hotels (the Indagare-preferred hotels mentioned above fall in this category); download the Belize Health App and input the required information no more than 72 hours prior to landing in Belize; and present proof of a negative Covid-19 PCR test taken within 72 hours of arrival in Belize. You may also choose to submit to testing upon arrival if you are unable to bring this proof; no quarantine is necessary once proof of negative results is confirmed (source: Belize Tourism Board). Panama requires proof of a negative Covid-19 test (PCR or Antigen) taken within 48 hours prior to traveling to Panama; alternatively, you will be required to take a test at the airport at your expense ($50.00) (source: U.S. Embassy in Panama). *Costa Rica is currently only open to U.S. citizens who can present a valid driver’s license or state ID from 24 states, including the Tri-State Area, New England, D.C. and California. As of November 1, Costa Rica will be open to all U.S. citizens who provide proof of the proper insurance to cover Covid-19 related medical treatment and quarantine lodging while in Costa Rica, as well as a completed health pass form. A negative Covid-19 test is not required (source: U.S. Embassy in Costa Rica).

Related: Kasiiya Papagayo: Finding La Pura Vida at Costa Rica’s Newest Eco-Resort

Winter Vacations for Multigenerational Families: American West

For a trip that’s closer to home, but still offers a robust array of outdoor and wellness activities—as well as a luxe set of hotels and restaurants and wide-open, snow-dusted vistas—the ski towns of the American West could be the solution you’ve been searching for. While Aspen, Vail and Deer Valley will suit those looking for a bit of glamour, Jackson Hole, Big Sky, Beaver Creek and Sun Valley are known for their easy charm—as well as top-notch slopes. Indagare-adored properties like Montana’s The Ranch at Rock Creek, Colorado’s Dunton Hot Springs and Utah’s The Lodge at Blue Sky will satisfy the non-skiers in your group with horseback riding, ice-skating, private movie theaters, spa treatments and more.

Entry Requirements & Covid-19 Safety: As of October 28, U.S. citizens are able to travel freely between states. However, there may be certain protocols or restrictions in place, depending on what state you live in. For instance, as of October 27, New York residents are required to self-quarantine for 14 days if they have traveled to Colorado, Montana, Utah, Wyoming and other states (source: New York State Government Website). Please consult your home state and destination’s government websites prior to making travel plans and take all necessary safety precautions, including mask-wearing, sanitizing and social-distancing, when traveling between states.

Related: What Skiing Will Look like During Covid

Winter Vacations for Outdoor Adventurers: Rwanda and Namibia

If you’re looking to get far, far away from your own backyard, both Rwanda and Namibia offer temperate weather and the chance to immerse yourself in nature, privately. While Rwanda’s strong response to the pandemic means that you will be able to trek to see the endangered mountain gorillas—a major highlight of the itinerary—at a time when the forests feel virtually tourist-free, Namibia continues to be one of the least-densely populated countries in the world, with huge open spaces and great swaths of silence stretching over desert dunes. A retreat to our favorite luxury safari lodges—like Rwanda’s Bisate Lodge, Magashi Camp and One&Only Gorilla’s Nest and Namibia’s Little Kulala (reopening in November), Hoanib Skeleton Camp (reopening in November) and Serra Cafema (currently closed)—will include days scouting for lions, elephants and rhinos; the chance to engage with local communities and culture; dining under the stars; and connection with the beating heart of Africa.

To quote Indagare Founder Melissa Biggs Bradley on the impact of traveling to both of these places—of Rwanda, she has said: “Go see for yourself how a country can rebuild after a massacre; you cannot help but feel hope for humanity;” of Namibia, she has written: “The silence isn’t just something you hear; you feel it. The open skies and unbroken horizons seem to reach into forever in a way that shifts perspective.” Melissa is returning to Rwanda this month to lead two Insider Journeys. There are still a few spots left! Learn more here.

Entry Requirements & Covid-19 Safety: As of October 28, both Rwanda and Namibia are open to U.S. citizens (Namibia is confirmed to be open until at least November 30). Travelers to Rwanda must complete a passenger locator form prior to departure and, upon arrival, present a negative PCR Covid-19 test certificate for a test taken no more than 120 hours before their initial flight; a second PCR Covid test is required upon arrival, and travelers must self-quarantine in their chosen (and approved) hotel, until they receive negative results (approximately 24 hours). Travelers must also present negative results from a third PCR Covid test, taken in Rwanda no more than 120 hours before departure, in order to exit the country (source: U.S. Embassy in Rwanda). Travelers to Namibia must present a negative result from a PCR Covid-19 test taken no more than 72 hours prior to boarding their flight to Namibia; they must also submit a health declaration and health surveillance forms and provide details of their itinerary to port officials upon arrival (source: U.S. Embassy in Namibia). Travelers to both Rwanda and Namibia may be required to submit to health screenings at the airport.

Related: Join Our 2020 Insider Journey to Rwanda!

Winter Vacations for a Mix of City and Country: London and Hampshire

If your winter vacations preferences err on the side of cozy, London, its surrounds and the Cotswolds are open to travelers who are willing to self-isolate for 14 days upon arrival. If you have the time to spare, we recommend holing up at an idyllic country estate like Heckfield PlaceBelmond Le Manoir aux Quat’Saisons or Cliveden House, or else your own private rental, where you will have plenty of time to make your way through The Holiday, Love Actually, Pride & Prejudice and perhaps even a Harry Potter marathon. Then, transfer back into the city for socially-distanced afternoon teas at such locales as Claridge’s and Sketch—whose winter decorations are absolutely over-the-top (in the best way)—trips to Harrods and the National Gallery (open for advance-bookings only) and meals at our favorite restaurants.

Entry Requirements & Covid-19 Safety: As of October 28, the United Kingdom (including Northern Ireland, Scotland and Wales) is open to American citizens. Travelers from the U.S. to England must complete a passenger locator form and self-isolate for 14 days upon arrival, and they may be contacted to verify compliance. Travelers do not need to present a negative Covid test upon arrival, and there are no curfews or restrictions on interstate travel in place (source: U.S. Embassy and Consulates in the United Kingdom).

Related: The Best Afternoon Teas in London

Winter Vacations for Wine Lovers: Croatia and the American South

Entry Requirements & Covid-19 Safety: As of October 28, Croatia is open to U.S. Citizens. American travelers will not have to self-isolate or quarantine if they present proof of a negative PCR Covid-test taken no more than 48 hours prior to arrival at the border; arriving with an expired PCR test will allow for a shortened period of time in self-isolation, pending a negative result of a local PCR test. Those who do not provide a negative PCR test upon arrival will be ordered to quarantine/self-isolate for at least 7 days prior to taking a local PCR test (source: U.S. Embassy in Croatia). As of October 28, U.S. citizens are able to travel freely between states. However, there may be certain protocols or restrictions in place, depending on what state you live in. For instance, as of October 27, New York residents are required to self-quarantine for 14 days if they have traveled to Virginia, Arizona and other states (source: New York State Government Website). Please consult your home state and destination’s government websites prior to making travel plans and take all necessary safety precautions, including mask-wearing, sanitizing and social-distancing, when traveling between states.

Related: 7 Up-and-Coming Wine Regions to Know Now

Winter Vacations for Classic Safari: Kenya, Tanzania and Zambia

In times of transition, travel can be a salve for the soul—and perhaps there is no better place to reflect on the end of another year, and the change of seasons, than the so-called Cradle of Humankind: East Africa. Kenya, Tanzania and Zambia are all open to U.S. travelers, and our favorite camps—including Segera, Angama Mara, Singita Grumeti Sabora, and Mwiba—are reporting some of the most vibrant wildlife activity that the reserves have seen in years, thanks to a decreased human presence. For a classic safari experience, with few other travelers (in an open-air, socially-distanced setting) and a renewed sense of meaning, Kenya, Tanzania and Zambia can be combined or enjoyed on their own for a romantic or family-friendly winter vacation.

In the words of Indagare Founder Melissa Biggs Bradley, who just returned from visiting Kenya for the first time since the outbreak of the pandemic: “As I went to bed on my first night, I started ticking off the regained joys of travel: The sound of foreign languages (Swahili greetings at the airport). Exotic nighttime smells (acacia fires). The novelty of an alien popular culture (local radio). Warm welcomes (hot soup on arrival). Remembered rituals (a hot-water bottle between the sheets). Missed sights (the Southern Cross) and beloved habits (falling asleep far from home, ready to awaken in discovery mode). And the lost pleasures kept returning as the days went on. We hiked along the ridge of the Great Rift Valley and the Laikipia plains, spotting elephants, giraffes and buffalo and relishing the return to Africa’s bush. Deep in Samburu country, we had sundowners around an impromptu fire. Kenya’s landscapes, with its forever views, made me feel miniscule and filled with humility, awe and wonder; they also emphasized the brevity of time. This year has seemed to drag on forever, but in the cradle of mankind, where our ancestors first walked upright, time stretched. Of course, at home I could have shifted my perspective, seen the current crisis as one in a long series, but distance itself provided a vantage point that had eluded me. Here, on a remote rock at sunset, I felt that urgency had been swallowed by eternity.”

In January 2021, Melissa will be returning to Kenya with a small group of Indagare travelers to host an exciting new Insider Journey. Email insiderjourneys@indagare.com for details and to reserve your spot!

Entry Requirements & Covid-19 Safety: As of October 28, Kenya, Tanzania and Zambia are open to U.S. citizens. To enter Kenya, travelers must present proof of a negative PCR-based Covid-19 test conducted within 96 hours of arrival, complete health forms and pass a health screening with a body temperature of 99.5°F or lower and no signs of a persistent cough, difficulty breathing or other flu-like symptoms (source: U.S. Embassy in Kenya). To enter Tanzania, travelers do not need to present a Covid-test; however, they must present a health surveillance form upon arrival and submit to enhanced health screening and testing upon arrival if deemed necessary by port health authorities (source: U.S. Embassy in Tanzania). To enter Zambia, travelers must present proof of negative results from a PCR Covid-19 test taken within 14 days prior to arrival in Zambia; travelers must also present a complete health questionnaire and submit to health screenings (and, if deemed necessary, additional testing) at the airport. Travelers must then self-quarantine for 14 days at the destination of their choice, and they must disclose to health officials upon arrival where they intend to reside and provide accurate contact information for regular follow-ups (source: U.S. Embassy in Zambia).

Related: Rediscovering the Meaning of Travel During Covid

Winter Vacations for Foodies and Design Lovers & Trendsetters: Mexico, Colombia and Peru

Central and South America is beginning to reopen—and for foodies and design lovers who are hungry for stimulation, now is the perfect time to start planning your next winter vacation, whenever it may be (but first—check out our new, virtual Indagare Clubs for Cooking and Design!). Together, Mexico City, Lima and Bogotá are home to five of 2019’s World’s 50 Best Restaurants—and all but one are open for reservations, which would normally be quite difficult to get; additionally, Indagare can arrange special-access tours of highlights like Mexico City’s Anthropology Museum, to ensure privacy and social distancing (in the words of an Indagare member, on a pre-Covid trip: “The night tour at the anthropology museum in Mexico City was absolutely incredible. We had the entire museum to ourselves—literally, no other visitors were there, just the security guards.”). For a quieter escape that is no less exceptional when it comes to cuisine, crafts and boutique hotels, smaller towns like San Miguel de Allende, Cartagena and Cusco are ideal. If you are not ready to travel to urban areas, Mexico‘s mountain and beach regions are home to indulgent, spacious resorts where you can hide away for a week, like Rosewood Mayakoba, Hacienda de San Antonio, Cuixmala and One&Only Palmilla—while Colombia‘s Andean coffee region provides a taste of adventure and culture, and Peru‘s Sacred Valley offers plenty of outdoor activities and supremely comfortable lodges like Belmond Sanctuary Lodge and Sol y Luna (both currently closed). Plus, Machu Picchu is scheduled to reopen in November, at a reduced capacity—which means you could have these awe-inspiring ruins (nearly) all to yourself.

Entry Requirements & Covid-19 Safety: As of October 28, Mexico is open to U.S. citizens who arrive by air. Covid-testing and quarantining are not required; however, you may be subject to health screenings including temperature checks and testing upon arrival. Please note there may be some restrictions on interstate travel (resource: U.S. Embassy & Consulates in Mexico). Peru’s borders are open to U.S. citizens who arrive via certain approved flight routes; direct international flights to Peru from Los Angeles, New York, Miami and Houston are expected to be approved starting November 1. To enter, travelers must sign a statement within 72 hours of arrival, agreeing to comply with a mandatory 14-day self-quarantine, and that they are free of Covid symptoms; additionally, travelers must present proof of a negative molecular Covid test and submit to health screenings upon arrival (resource: U.S. Embassy in Peru). Colombia is also open to U.S. citizens who present a complete immigration form and proof of negative results from a PCR Covid-test taken no more than 96 hours prior to departure for Colombia (resource: U.S. Embassy in Colombia).

Related: Join Our 2021 Insider Journey to Mexico City and San Miguel de Allende with Architectural Digest

Winter Vacations for History Buffs: Egypt

For lovers of history and ancient artifacts, the treasures of Egypt can now be enjoyed—without the crowds—for a far-flung winter vacation. Egypt is home to one third of the world’s antiquities and the only remaining monument of the Seven Wonders of the Ancient World (the Pyramids at Giza). Beyond the awe-inspiring temples of the Valley of the Kings, this destination also offers storied retreats (like the Old Cataract Hotel) and the chance to cruise along the Nile River. The next travelers to this ancient world will be the first to feel its magnitude with a post-Covid perspective—and hopefully become ardent stewards of its protection.

Entry Requirements & Covid-19 Safety: As of October 28, Egypt is open to U.S. citizens. To enter Egypt, travelers must present paper proof of a negative PCR Covid-test, taken at a maximum of 96 hours before their flight departure time; travelers must also present proof of health insurance upon arrival and submit to health screenings. Please note there may be some restrictions on interstate travel (source: U.S. Embassy in Egypt).

Related: Treasures of Egypt

Winter Vacations for Top Shoppers and Ultimate Indulgers: Morocco

Marrakech is a shopaholic’s dream, where you can pick up everything from latticed lanterns and Berber kilim rugs to argan oil, leather bags, kaftans, glassware, ceramics, slippers and one-of-a-kind furniture. For ultimate indulgers, palatial hotels and resorts like La Mamounia (which reopened after a renovation on October 16), Le Royal Mansour (which offers a 24-hour cancellation policy for arrivals up to December 19), Kasbah Tamadot and Dar Ahlam are worth the trip alone.

Entry Requirements & Covid-19 Safety: As of October 28, travelers arriving in Morocco via air from New York’s JFK international airport to Casablanca, with reservations with Moroccan hotels, are permitted to enter the country, provided they can present proof of a negative PCR Covid-test taken within 72 hours of departure and submit to health screenings. Please note that there are restrictions on interstate travel, and domestic travel between Casablanca, Fes, Marrakech, Tangier and other cities is prohibited unless you have a travel authorization letter from local authorities. Moroccan authorities have indicated that a hotel reservation in another city is sufficient reason to obtain a travel authorization(source: U.S. Embassy in Morocco).

Related: Discover Marrakech with the Institute of Classical Architecture & Art

Contact Indagare or email your Trip Designer to start planning winter vacations for this year and the future. Beloved destinations like the ones listed here are booking up quickly, due to increased re-booking policies. Our team can match you with the accommodations and activities that are right for you and provide information on coronavirus travel safety, destinations that are open to travel, Covid-19 hotel policies, transportation options, private villas and charters and more. 

– Elizabeth Harvey on October 28, 2020

Related Hotels

Become an Indagare Member Today!

Join Indagare sign in