Positano, Italy.

February always feels like the perfect time to plan a vacation. Whether you’re dreaming of escaping wintry weather, want to get your family together for a memorable occasion, or simply long for a change of scenery, it’s the ideal time to begin thinking about a getaway. To help us get inspired, we reached out to four travel experts to find out which destinations they’re excited about for 2020. From ideas for adventure-seekers to picturesque villages to pristine beaches, here are their recommendations.


“Italy is always a good idea,” Drenda Roberts of Bentley Travel Design in Edmond, Oklahoma, reports. “It never goes out of style, and with 20 regions that each have their own history, food, and culture, you can return time and time again and always discover something new.” Though travelers should keep in mind that many hotels in smaller towns close from Christmas to April, this is not an issue in larger cities. Roberts recommends Rome as a year-round destination, and suggests that visitors find respite when not out on the town either at Hotel Eden, a 130-year old property, or Hotel de la Ville, a modern hotel situated atop the Spanish Steps. No matter where you rest your head, amazing discoveries abound at every turn (Roberts shares that a fun way to see the city is to book a golf cart tour, during which you’ll see many of the sights—and cover a lot of ground). If you venture to popular Positano on the Amalfi Coast (a favorite for its beautiful pebble beaches and colorful buildings), Roberts says that the Il San Pietro hotel is a must-stay.

Grand Cayman, Cayman Islands

Grand Cayman is the largest island in the British West Indies, and is well known for its beautiful pristine beaches and crystal blue waters. Marianne Cook Windham of Huntsville, Alabama’s Windham Travel & Leisure reports that sun-seekers are drawn from all over to 7 Mile Beach for snorkeling and swimming, as well as various sanctuaries and natural habitats for exotic wildlife. On the upper end of Seven Mile Beach lies the gorgeous new property The Kimpton Seafire Resort & Spa. The five-star diamond resort is a design masterpiece, both inside and out, with each room offering an ocean view. Cook advises traveling between January to early-March, and recommends mixing a little adventure into your R&R. “Take a luxury boat tour, which allows you the freedom to customize your experience based on your interests,” she says. “Favored stops include Stingray Sandbar, Stingray City, Reef Snorkeling, Starfish Point, and Booby Cay.” If you enjoy shopping, Cayman is the ideal location to indulge this pursuit. Luxury goods such as jewelry, watches, clothing, and alcohol are both duty and tax-free, and can be purchased at much lower prices than in the United States.

The Maldives

Image courtesy of Joali Maldives.

This area offers relative exclusion due to a Maldivian law that allows only one resort per island in the Indian Ocean, so no area is overrun with tourists, maintaining the pristine tropical locale. Now is the time to visit, ideally from December to March, as climate change is predicted to drastically change the landscape of the Indian Ocean and surrounding islands of The Maldives. Emily Lockard-Furry of Traveluxe Official in Houston, Texas, notes that one of The Maldives’ best kept secrets is that it is family-friendly heaven, with great kids’ clubs and tons of activities to keep little ones entertained. Her favorite resorts, all offering a little something unique but with the utmost luxury, include Joali Maldives, Waldorf Astoria Maldives Ithaafushi, and Gili Lankanfushi. One of Lockard-Furry’s favorite experiences is dining at the Terra Restaurant at Waldorf Astoria Maldives Ithaafushi in one of the seven intimate dining pods perched high above the beach.

Cancun, Mexico

If your perception of Cancun is a place overrun with spring break revelers, it’s time to rethink this south-of-the-border destination. With weather that’s lovely any time of year and a close proximity to the U.S., it’s ideal for quick weekend getaways. You’ll have no shortage of luxe options when visiting Cancun, says Lockard-Furry of Traveluxe Official, who recommends the Nizuc Resort, which is a quick eight-minute drive from the Cancun airport. With well-appointed suites and private villas featuring private pools, plus endless activities, from kayaking to spa treatments, this is the perfect locale to take in the Mexican Caribbean. If you’re more interested in an adult-only, all-inclusive option, Lockard-Furry recommends the all-adult Unico 2087 Hotel Rivera Maya or the Atelier Playa Mujeres. If you want to venture out of the resorts, one of Lockard-Furry’s favorite dining options is Tseen Ja within the hotel Azulik in Tulum, which offers elevated reserved seating areas for groups or even a private dinner. For an incredible al fresco dining experience, she suggests spending an evening at Banyan Tree Mayakoba dining at their signature restaurant, Saffron, on the deck over the water.

New Zealand

Hooker Lake, New Zealand.

With gorgeous scenery, friendly people, great wine, luxurious accommodations, and the well-earned moniker of “adventure capital of the world,” New Zealand is not to be missed. “The beauty in New Zealand is truly like nowhere else,” says Kimberly Georgi of For Travelers Only in Memphis, Tennessee. “Many parts outside of the cities still feel very untouched. While December to March is summer in New Zealand, Georgi prefers to travel in the shoulder season when the crowds are smaller and the price is slightly better, opting for their late spring (November) and end of summer (March). She opts to stay at The Luxury Lodges of New Zealand properties with multiple outstanding locations throughout the country, each offering exceptional hospitality and fantastic itineraries and add-ons to maximize your time in country. In order to take advantage of all New Zealand has to offer, Georgi recommends visitors plan on lots of adventure activities in Queensland, from paragliding, Shotover Canyon boating, zip lining, and a not-to-be-missed helicopter flight over Milford Sound that includes landing on a glacier.

South Africa

Many consider South Africa a once-in-a-lifetime destination, but according to Georgi of For Travelers Only, once you go, you’ll want to return again and again. From culture and opportunities to learn about the history of Apartheid to world-class winelands, beaches with penguins, shark diving, whale-watching, gorgeous gardens, and of course, safaris with incredible game viewing, luxury lodges, and truly life-changing experiences, the country has much to offer. Georgi reports that Cape Town has recovered from the water shortage of the past two years, and now there’s a favorable exchange rate with the American dollar, a booming art scene, and no visa or shots are required for travel from the United States. Since there are variable climates throughout the country, you can travel to South Africa any time of year depending on the activities and destinations you have planned. The Cape is warmest from November to February, but this can be the rainy season in the north; dry season in the game reserves is the best time for game viewing. Georgi favors stays at Singita properties because their conservation model supports wildlife and communities. “The lodges are incredibly luxurious, but even more important is their mission to protect the land, the wildlife, and the people of the communities,” she shares. “They are truly making a difference while giving their guests the most incredible experience of fantastic game viewing and luxurious lodges and service.”


Santorini, Greece.

“Greece has something special to offer everyone, from families to honeymooners,” Roberts of Bentley Travel Design shares. The dynamic destination offers up rich history, beautiful whitewashed towns, and sun-drenched islands, and the prime times to visit are April to July and in September. Roberts reports that the Canaves Oia Suites in Santorini is a must-stay, with suites featuring individual plunge and infinity pools. Whether you choose to stay on the mainland, island-hop, or take a Greek Isles cruise, you’ll be immersed in rich culture and encounter plenty of friendly locals. For a truly luxe experience, Roberts recommends looking into chartering a private yacht with your very own skipper and chef.

Galapagos Islands

A nature lover’s dream vacation, the Galapagos Islands are home to many marine and land animals that can’t be found anywhere else on earth. Windham of Windham Travel & Leisure finds that the most unique and exciting way to experience this pristine habitat is on the yacht formerly owned by Princess Grace Kelly of Monaco. The princess and Prince Rainier spent their honeymoon getaway aboard the yacht, which was a wedding gift to the couple from Aristotle Onassis. Built in 1928 and remodeled in 2017 (with a very rich history between), M/Y Grace can carry 16 passengers and 12 crew members. While aboard, guests circumnavigate the Daphne Major Islet, which is home to a variety of birds, including Galapagos martins and blue footed boobies. They will also visit Santa Fe Island—home to some of the best snorkeling with its crystal-clear waters, and one of the best locations to see sea turtles, swim with sea lions, and get a glimpse of the Galapagos White-tipped Shark.


Image courtesy of Ashford Castle. Photography by Aervisions.

The Emerald Isle always charms with its astounding beauty and warm people. There’s truly never a bad time to visit, but Roberts of Bentley Travel Design says that summer is the most crowded, with longer daylight hours and more time for exploring. She prefers the shoulder seasons, April to June and September to November, when the weather is still pleasant, but the crowds have dissipated. Roberts recommends booking accommodations at Adare Manor, situated in the lovely village of Adare, County Limerick, with 840 picturesque acres and home to a Michelin star restaurant. Another option is Ashford Castle, in Cong, County Mayo, an 800-year-old castle that’s the former home of the Guinness family that offers gorgeous interiors, a variety of estate activities, and a state-of-the-art spa. If you’re looking to immerse yourself in Irish city life, Roberts suggests The Westbury in Dublin, a hotel that exudes understated elegance. Meanwhile, Windham of Windham Travel & Leisure recommends The Great Southern Killarney, a beautiful boutique hotel known for its traditional afternoon tea located in Killarney, County Kerry, in the Southwestern part of Ireland.

In terms of sightseeing, Windham says train enthusiasts will enjoy the Belmond Hibernian Train, which offers a unique way to take in the countryside and two, four, and six-might itineraries (beer and whiskey fans will find itineraries devoted to the beverages that include private meetings with the owners of some of the most famous establishments in the country), and both Roberts and Windham suggest trying your hand at falconry. Windham recommends booking a private guided “walk with hawks” excursion with Killarney Falconry, which she describes as an intimate leisurely stroll through the beautiful settings of Killarney with a falconer and a hawk. “You witness the amazing abilities of trained birds, and their relationship with their human partners,” she says, adding that under instruction from the falconer, participants are able to handle and fly the hawk themselves, as well as enjoy a close encounter with an owl. “It is truly an amazing experience,” Windham says.


While it might seem counterintuitive given the bushfires, Lockard-Furry of Traveluxe Official thinks that now is the best time to head down under to Australia for a vacation, as the country has been devastated and needs tourism to help it thrive again. The Aussie wildlife is like none other—koalas, platypus, and kangaroos abound, as well as an abundance of bird and sea life species—making visiting the country a bucket list experience not to be missed. For a Great Barrier Reef adventure, Lockard-Furry recommends booking your stay at qualia, where you’ll enjoy complete immersion in the reef, as well as sailing, boating, diving, and snorkeling options. Or, you can opt to spend time in the Greater Blue Mountains and enjoy a different kind of Australian splendor when you book your stay at the One & Only Wolgan Valley, where you can take in true Australian adventures, from glow-worm tours to horseback explorations and conservation activities. For a more boutique experience, Lockard-Furry says to head to Saffire Freycinet, a small luxury lodge nestled in the magnificent Freycinet National Park and Wineglass Bay in Tasmania.