Best Winter Vacation Ideas for 2020: 24 Trip Ideas from Anguilla to Egypt

As temperatures drop, we’re turning our attention to the places to be this winter. To help you plan your winter vacation, we’ve tapped Indagare’s well-informed staff for intel on the most coveted lodges, resorts and tours. Whether you’re looking for an Alpine chalet where you can sip après ski cocktails by a roaring fire, a tropical island where you can relax with a beach read or a far-flung destination with adventures to satisfy every member of your family, these are the winter vacations that should be on your radar. From a new property in the Cotswolds to behind-the-ropes access at the Pyramids of Egypt, here are 24 reasons to start planning your winter trip.

Contact Indagare to start planning your winter travel today. Popular destinations like the ones below are booking up quickly between Thanksgiving and New Year’s. Our dedicated trip designers can secure reservations at the best hotels, restaurants and more.

Winter Vacations for Sun Seekers: The Caribbean

Following the destruction of Hurricanes Irma and Dorian, resorts in the Caribbean have been making a Herculean effort to reopen its top hotels and beaches. One of our favorite islands that has made particularly successful progress is Anguilla. Travelers are once again able to stay at resorts such as the Four Seasons, the Belmond Cap Juluca and Malliouhana, where they can enjoy miles of private, white-sand beaches, golfing and sailing. Another perennial favorite: Turks & Caicos. This archipelago is one of our go-tos for sun-seekers, with a clutch of ultra-luxurious properties, like Amanyara, COMO Parrot Cay and Grace Bay Club.

In the words of Indagare member Corie Tappin: “We absolutely loved Anguilla and the Four Seasons. The beach in August was spectacular. The snorkeling was great there as well, and we did a private snorkel boat trip.”

Winter Vacations for Skiing in Europe: The Alps

This winter, skiers and snow bunnies should escape to the Alps (French, Swiss, Austrian or Italian) with a private villa rental or a stay at one of our favorite hotels. Of particular note in this area is Chalet Pelerin, a stunning property from the ultimate adventure brand Eleven Experience that is nestled above a farming village, Le Miroir, on the French and Italian border. The Chalet offers unparalleled access to seven world-class ski resorts—including Val d’Isѐre, Sainte Foy, Tignes, Les Arcs and La Rosiѐre—which can be reached in less than an hour by car or by helicopter. For larger groups traveling with family and friends, Indagare can arrange private villa and chalet rentals throughout the Alps, including such locales as Les Trois Vallées and Gstaad.

In the words of Indagare member and ski aficionado Christopher Leach: “France has the most charming ski scene in the Alps. I  recommend visiting the lowest altitude village in Tignes, Tignes les Brevieres, which is quaint and has wonderful restaurants.”

Winter Vacations for History Buffs: Egypt

As one of the most exciting destinations in the world, Egypt offers an epic desert escape that’s a considerable value. The country 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), as well as soon-to-open Grand Egyptian Museum—making it a bucket list vacation for history buffs, culture lovers and trailblazers. Indagare can arrange exclusive, behind-the-ropes access to such iconic sites as the Sphinx and charter yachts for an unforgettable cruise down the Nile River.

In the words of Indagare member Jason Storm: “Egypt was the trip of a lifetime! My guide was full of energy, knowledge, spirit and passion for Egypt‘s history and even took me off the beaten path to places like little-seen Nubian villages on the Nile. What an adventure!”

Winter Vacations for Outdoor Adventurers: Swedish Lapland

There are few destinations that deliver on the notion of a “Winter Wonderland” better than Swedish Lapland. Its 42,000 square miles of snowy forests, icy lakes and glittering tundra are ideal for such Arctic activities as dog sledding, ice fishing, cross-country and heli-skiing and Northern Lights viewing. For hearty meals, cozy, fur-lined beds and invigorating saunas after a day in the wilderness, Lapland offers a variety of hotel options, from the family-friendly Fjellborg Arctic Lodge to the whimsical Treehotel.

In the words of Indagare member Stephanie Roberts: “At Fjellborg Arctic Lodge, we loved dog sledding and snowmobiling on a special Christmas-themed treasure hunt that the staff arranged for our children. “

Related: The Top 10: Fun Ideas for a Multigenerational Vacation

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

In London, a host of hot new restaurant openings are sure to entertain in between shopping for presents at Harrods and cozy afternoon teas at such locales as Claridge’s, whose Christmas decorations are absolutely over-the-top (in the best way). To offset the festive bustle of the city, unwind with a few days in the countryside at a relaxing property such as Heckfield Place, an idyllic estate just a 30-minute drive from London.

In the words of Indagare’s Emma Pierce: “One of the most picturesque countryside hotels I’ve ever been to, Heckfield Place is a true labor of love for its owner, who has been fine-tuning the property for the past seven years prior to opening. With a culinary program by the chef of London’s acclaimed Spring restaurant, plush amenities like a movie theater, spa, fitness center and more, Heckfield is much more than a relaxing weekend getaway.”

Winter Vacations for Scene Seekers: St. Barth’s and St. Moritz

Many of St. Barth‘s best hotels used the destruction wreaked by Hurricane Irma as an opportunity to renovate. Le Toiny built a new pool and eight villas, and Cheval Blanc St-Barth Îsle de France recently acquired neighboring hotel Taiwana and is renovating its 20 rooms to join Îsle de France. Meanwhile, there are two new competitors on the scene: the nautical-chic Le Barthélemy, a retreat with a restaurant overseen by the chef of Paris’s Grand Véfour.

For a scene set in colder climates, the Swiss resort town of St. Moritz—with its upscale hotels, slope-side restaurants and state-of-the-art spas—combines challenging athletic pursuits for both couples and families with leisurely pampering. One of its most glamorous ski areas is Corviglia, accessible from ski-in/ski-out Suvretta House, and gorgeous views, not to mention 15 mountain restaurants.

Related: Indagare’s Caribbean Island Matchmaker

Winter Vacations for Wine Lovers: Lisbon & the Douro Valley

Lisbon has everything a traveler could want: great food, fabulous art, robust history, sensational wine and a bustling contemporary scene. During the winter months, mild weather (sunny, in the 50’s and 60’s) makes Lisbon a top choice for travelers who want to spend time exploring outdoors, and many pleasant afternoons can be spent wandering the city’s hilly, cobblestoned streets. In addition to day (or overnight) trips to the cities of Sintra, Cascais and Porto, the perfect winter itinerary must include a few nights’ stay at the Six Senses resort in the Douro Valley.

In the words of Indagare member Julie Enderson: “The Six Senses was our favorite hotel. It was just beyond…We could have stayed there the entire time. The activities, restaurants, service, spa, wine—everything was fantastic.”

Related: The Shopping Guide: Lisbon

Winter Vacations for Foodies, Design Lovers & Trendsetters: Mexico City, Lima and Singapore

This year, Mexico City is a must-visit destination for foodies and design lovers. Spend a few days in the capital taking in the murals of Diego Rivera and the architecture of Luis Barragán and eating at top restaurants, including Pujol; then, explore the towns of San Miguel de Allende and Oaxaca, romantic hotspots with dreamy hotels, impressive craftsmanship and hip dining scenes. Indagare can arrange workshops with artisans, private studio visits and guided street food tours.

In the words of an Indagare member: “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. “

Meanwhile, further south, in Peru, Lima has become a mecca for travelers who plan their itineraries around a destination’s gastronomic delights. Such a schedule here might include a food tour of a local market to sample exotic produce, a cooking class with an expert chef and meals at the city’s top restaurants—don’t miss El MercadoIsolina Taberna Peruana and Osaka—whose chefs give their own innovative twists to the country’s indigenous cuisine.

For the especially adventurous foodie, Singapore is the place to go this season. “Mod-Sin” (modern Singaporean) cuisine is having a moment, and there are more than two dozen Michelin-starred establishments in the tiny nation, including a street food vendor at one of the city’s famed hawker centers (open-air food complexes). While there, try Singapore’s national dish, Hainanese chicken rice, at the lauded Hong Kong Soya Sauce Chicken Rice & Noodle. The dish costs just $1.85, making it the cheapest Michelin-starred meal in the world.

Winter Vacations for Classic Europe: Vienna, Prague and Budapest

For a European escape filled with chic hotels, Christmas cheer and holiday soirées, Vienna, Prague and Budapest combine urban style and tradition in perfect measure. Spend your days touring decadent imperial palaces, shopping the Christmas markets for festive trinkets, sipping beer and mulled wine in the Ruin Bars and reading by the fire in your hotel’s lounge. For an unforgettable winter celebration, Indagare can arrange a Champagne cruise down the Danube on a heated boat or book a private table at one of Vienna’s world-famous winter balls.

In the words of Indagare’s Emma Pierce: “Viennese balls are, of course, legendary. The Austrian city hosts over 450 a year, ranging from small, community-oriented gatherings to exclusive events with calligraphy invitations.”

Winter Vacations for Multigenerational Families: American West

For a trip that’s closer to home, but still offers an exciting array of activities, a buzzy hotel and restaurant scene and a host of comfortable amenities, 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 lodges and slopes.

In the words of Indagare’s Trip Designer Kelly Brennan: “Aside from an excursion to Discovery Ski Area, there is little other reason to leave The Ranch at Rock Creek‘s vast premises during a winter holiday. Whether bowling at the on-property alley, watching a movie in the private theater, playing darts at the Saloon, ice-skating on the pond or enjoying freshly baked chocolate chip cookies by the fire, guests at the all-inclusive resort can indulge in nearly anything their hearts desire.”

Related: Indagare Matchmaker: Dude Ranches

Winter Vacations for Top Shoppers: Tokyo and Marrakech

With its numerous subcultures and trendy cult fashion, the Japanese capital offers shoppers everything from antique tea sets to the latest J-pop fashion, as well as clothing and accessories from every European and American designer of note. Among the best Japanese finds are paper goods, kitchen knives, matcha tea, sake, handmade fans, kimonos, pottery and snacks like matcha tea Kit Kats.

For flea market lovers, Marrakech’s legendary souk—an atmospheric and labyrinthine marketplace—is a shopaholic’s dream, where you can pick up everything from latticed lanterns and Berber kilim rugs to argan oil and leather bags. Marrakech also has plenty of upscale boutiques, in Gueliz and near the Majorelle Garden. Locally made treasures include embellished kaftans, glassware, ceramics, slippers and one-of-a-kind furniture. Contact us to book a shopping tour.

Winter Vacations for Nature Explorers: Iguazú National Park, Chilean Patagonia and Hawaii

For a winter getaway that offers tropical temperatures, bright colors and otherworldly wildlife, look no further than the banks of the Iguazú river in Argentina, home to Awasi Iguazú. The secluded resort sits in the heart of the rainforest, 20 minutes from the legendary waterfalls, and contains 14 eco-friendly private villas with plunge pools that cater to couples and families. Although Awasi Iguazú is a destination in its own right, Indagare can also arrange trips that include stops at the Awasi sister properties in Chilean Patagonia and the Atacama Desert (subject to availability, which may be very limited) for a more dynamic South American adventure, where outdoor enthusiasts can trek, bike or horseback ride through mountains ranges and glacial valleys that are home to wildlife such as condors, guanacos and pumas.

For nature-lovers who also want to lounge on the beach, Hawaii offers the perfect balance between adventure and relaxation. The 50th state abounds in breathtaking natural beauty as well as spectacular ways for active travelers to experience it, from surfing on Oahu and snorkeling on the Big Island to hiking through Kauai’s jungle and climbing Mauna Kea volcano on the island of Hawaii.

Indagare Tip: Protect your skin and the Hawaiian ecosystem with reef-safe sunscreen, made without the ingredients oxybenzone and octinoxate, which have been shown to stunt the growth of juvenile coral and cause bleaching.

Related: The Ultimate Exotic Beach Vacations

Winter Vacations for Health Nuts: Himalayas, California and Spain

Wellness involves both body and mind, and those looking to focus on the latter should visit a holistic spa. Located in northern IndiaVana offers meditation, yoga and Ayurvedic treatments, and Ananda wellness resort has treatments like aromatherapy for emotional balance. Those looking to revamp their diets should visit a spa that makes eating healthy easy. California’s The Ranch at Live Oak Malibu has an intensive exercise program and gourmet vegan food. Spain’s SHA Wellness Clinic touts a macrobiotic menu and services like genetic testing and massages.

How to Prep: To get in the right mindset for your trip, look for books by Deepak Chopra or Thich Nhat Hanh, and eliminate toxins pre-trip: cut down on caffeine, artificial sweeteners and alcohol. Plus, reach out to us for advice on the best hotel for you.

Contact Indagare to start planning your winter travel today. Popular destinations like the ones below are booking up quickly between Thanksgiving and New Year’s. Our dedicated trip designers can secure reservations at the best hotels, restaurants and more.

– Elizabeth Harvey on October 16, 2019

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