Escape the Chill: Best Winter Getaways for Couples in 2026

Not just warm water, clear skies, but a chance to reconnect, recharge, and share experiences together under the glow of sunshine throughout the day. A winter getaway designed for two. Whether you’re after a quick thaw or a bucket-list beach, winter is a great time to not only escape the cold, but explore the world, see other countries in their prime seasons, and bring a little sunshine back home with you.  

At Kensington, we craft personalized winter getaways to the world’s sunniest destinations, designed by experts who handle every detail so the two of you can focus on making memories. If you’re ready to trade in the snow for the sand on a romantic couple's trip, winter is a perfect time to travel to some of the world’s best beaches and warm weather locales. We’ve rounded up a few of our best places to visit for winter vacation, sunny relaxation, and escape with the person you want to spend time with most. 

Your Guide to the Best Places for Couples to Visit in Winter: Andrew Drummond 

Andrew Drummond, Kensington’s Director of Product, has spent more than a decade shaping how travelers experience the world, and as a Toronto, Canada local, he understands what the best places to visit for winter vacation can do for you.  
 
“I enjoy the four seasons. I do love winter, but I get to a certain point in the year where I crave a bit of warm weather and a break from having to shovel snow.” Drummond leads the product team that designs Kensington’s most unforgettable itineraries. His personal passion for travel, and experience putting the boots away, and packing the sandals, means he knows how to deliver the very best of winter travel.  

Drummond and his team work tirelessly to ensure that every trip is designed with our Destination Experts to perfectly fit your needs, without you having to worry about anything other than remembering to pack sunscreen when it’s near freezing outside. Here are six of his favorite itineraries to inspire your winter getaway.  

Thailand Signature: Elephants & Islands 

“Thailand is probably one of the best places to visit for winter break. And December to March really is the right time to go,” says Drummond “It’s the cool and dry season, so it is the most comfortable month to travel.” 

This itinerary balances culture, wildlife, and beachside luxury. Start with a few days exploring Bangkok, its markets, and historical center, including the majestic Grand Palace, before heading north to immerse yourself in the rainforest, including an incredible visit to an elephant sanctuary. You’ll wake up in a luxury tent to the sounds of birds and gibbons and explore inland waters. Finish your trip by stretching out on the coast, soaking up the sun and turquoise water at polished resorts. 

The cuisine cannot be missed, and our Destination Experts work with you to match your style, including night-market stalls one night, a Michelin-starred reservation the next, and spice levels tuned to you.  

This itinerary makes for an unforgettable winter escape for couples and honeymooners, but it’s also easy to customize for different styles. As Drummond notes, “We can rev up the activities if you want to be a bit more adventurous. Rainforest hikes, canoeing, culinary tours, it's really a destination where we can meet whatever activity level you want.” 

Big Five Safari & Zanzibar Escape 

If you’ve always dreamed of seeing the big five—African elephants, Cape buffalo, rhinoceros, leopards, and lions—a safari is one of the best winter escapes for couples. “It's calving season. Thousands of animals are being born, and it draws a lot of wildlife into the area,” says Drummond.  

This itinerary invites couples to explore Kenya and Tanzania with expert rangers, combining visits to Ngorongoro Crater, the Serengeti, and the Masai Mara in 4x4s that put you in prime locations for spotting wildlife. Your Destination Expert will help you combine these breathtaking adventures with luxury touches like golden-hour sundowners and sunrise hot-air balloon rides over the plains. 

The trip ends in Zanzibar, with time for some rejuvenation before you and partner’s trip back home. “There's really no better way to unwind from that adventure than to spend a few days along the Indian Ocean on a pristine, sandy beach,” says Drummond. 

While this trip is perfect for a first safari, it's also great for those looking for wildlife in new landscapes. Either way, don’t be surprised if you and your partner find yourselves coming back, “Most people think they want to go on a safari one time, but when they get back they call us saying ‘I've got to go and do that again.’” 

Seychelles Island Getaway 

For couples who want warm Indian Ocean waters and room to breathe, the Seychelles deliver one of the best places to visit in winter—serene beaches, sculpted granite boulders, and reefs formed as if specifically for snorkeling and scuba. It requires longer flights than heading to the Caribbean or Costa Rica, but that’s why it stays less busy in peak winter sun.  

As Drummond puts it, “If the Seychelles were as close as the Caribbean, it would be one of the most visited destinations for North Americans.” Since it isn’t, couples can enjoy paradise without the crowds. 

Pair restorative resort days with explorations: a sunrise hike to panoramic viewpoints, a market stop to experience the island rhythm, exploring other beaches, and visiting historic plantations. Many travelers extend their safari with a stop in the Seychelles, finishing the safari adventure with ocean serenity as a couple. 

Expect crystal-clear water, soft sand, gentle lagoons, and vibrant coral just offshore. “If you envisioned paradise, and then opened your eyes in the Seychelles, you'd realize you were very close.” 

Cornerstones of Costa Rica 

“Costa Rica is one of my favorite destinations. I try to find a way to get there every winter,” says Drummond. Not only do winter months deliver a warm winter getaway, but it’s also dry season, meaning ideal weather for exploring rainforests and smooth travel between the inland, coast, and volcanoes. 

This itinerary links Arenal’s hanging bridges and hot springs with Monteverde wildlife and beach days around Manuel Antonio, where the golden sand meets the jungles. Your trip can be as energetic or as leisurely as you like. Couples can tailor their trip for shared adventure or relaxation. Whether you want active mornings, unhurried afternoons, lodges with pools and spa time, or hikes to waterfalls.  

Wherever you go, you’ll find astounding wildlife. “Our guides know the trees that a sloth might want to be in, or where you would find a particular bird species. They can bring you to the right locations quickly.” That expertise means you’re likely to sight monkeys, toucans, macaws, and more while creating memories together. 

“Costa Rica has a little bit of everything for everyone,” says Drummond, and you can relax knowing that your winter getaway supports protecting these special places, “It's hugely impactful for conservation, providing sustainable income for communities, and keeping this wilderness intact.” 

Jamaica Ultraluxe Villa 

Life inside this Jamaican villa is seamless. Unpack once, settle in, and let the private chef tailor menus to your tastes—you and your partner’s favorites, island classics, celebratory dinners. We’ll translate what matters from home life into villa life, including sleep schedules, fitness, and dietary needs, so your winter getaway actually restores you.  

Work with your Destination Expert and Villa Specialist to choreograph your days: beach mornings, a guided Blue Mountains outing for coffee and waterfalls, snorkeling over vibrant reefs, and then get on the water with your partner—catamaran, kayaks, or a gentle river raft, sharing time afloat.  

With a private, ocean-view home as your base, this escape is ideal for couples traveling together who want sun, space, and togetherness, and who might want to extend the invite to their friends. On-island, connect with place and people, “You can enjoy the villa, experience the destination, immerse yourself in the island, and meet locals to get a perspective of why it is such a beautiful island. This winter getaway is about just making perfect memories.”  

Insider tip: book this trip early. Winter is a busy time for North Americans to book this popular location. 

Magical Maui in Style 

“The whales alone are a huge reason to go on this itinerary,” says Drummond. That's because on this romantic winter getaway for couples, humpback whales migrate past Hawaii, “It's a really great opportunity to see them get really close to shore.”

If you’re looking for a more adventurous view, Drummond recommends seeing them from a helicopter, "It's just unbelievable. One of those awe-inspiring moments where you think, wow, I cannot believe I can see this enormous humpback whale all the way down in the water below.” 

And don’t just look at the water, get on it. Enjoy a luxurious trip on a catamaran to relax side by side and spot wildlife. On land, couples can explore jungles, waterfalls, and coves, or ride along the famous Road to Hana to witness the beauty across the island. 

This winter getaway features The Ritz-Carlton, Kapalua—a frequent home to PGA Toureents—placing you near world-class fairways, snorkel bays, and cliffside trails. It’s an ideal winter getaway for couples, babymoons, and honeymoons: a blend of activities and lazing by the water, “It's always important to have the opportunity to dip your toes in the sand, hop in the water, and enjoy the fantastic beaches.” 

Book Your Winter Escape Today 

If you’re a couple ready to trade gray skies for warm seas and slow, sunlit days, winter is the ideal time to travel. Grab your loved one and wake to clear horizons, linger over long lunches, and walk hand-in-hand along rainforest trails and around bright, vibrant coves. 

At Kensington, we make sure that you’re getting just what you and your partner need out of your winter reprieve, whether that's humpbacks breaching off Maui, big five game drives, Zanzibar’s white sand, or lounging in a Jamaican villa, waiting for a private chef to service an intimate anniversary dinner. We craft travel for your style, your pace, and your perfect day. Private guides, insider access, and our attention to detail ensure that couples only need to focus on enjoying themselves. Contact us today, and get ready for the couples winter getaway that you’ve always dreamt of.