As the winter months loom in the distance, many are already envisioning the impending cold weather and gray skies. Even when not residing in a cold-weather destination, the winter months can feel long without something to look forward to on the horizon. Whether you’re hoping to escape the snow for a while or are simply dreaming of summer days that slipped away too fast, a vacation to the Hawaiian Islands may be just what you need to add a bright spot to this winter’s calendar. Give yourself something to look forward to and slip away on a winter getaway to Oahu, Hawaii!

Best Winter Activities on Oahu, Hawaii

Because the Hawaiian Islands are blessed with year-round warm weather, the outdoor activities during winter are nearly endless. And with temperatures that drop slightly after sunset, the evenings are cool and comfortable. From wildlife watching to surfing epic waves, winter on Oahu promises endless fun! Be sure to add some of these top winter Oahu activities to your itinerary and enjoy the Oahu winter weather!

Whale Watching

It’s not just human travelers who make their way to Hawaii for the winter. This is also migrating season for humpback whales, who spend the winter months enjoying the warm waters surrounding the Hawaiian Islands. This makes winter a spectacular time for visitors to experience Hawaii’s exciting marine life. Whale spouts can often be seen from the shoreline for those who have a keen eye, but to truly appreciate the vastness of these mammals, travelers should consider a whale watching tour on Oahu. When it comes to whale watching outings, boat excursions can range from the fast, wild ride of a Zodiac to the leisurely cruising pace of a Catamaran. Both options will get you up close and personal with these stunning creatures, and you’re likely to spot dolphins and sea turtles along the way as well. Bring along your camera and capture amazing photos of Hawaii’s whales as well as scenic island views!

Beach Hopping

Of course, one of the best things about visiting Oahu in winter is that nearly every day is perfect for hitting the beach. The west side of Oahu tends to be the sunniest, and this coastline is graced with countless white sand beaches perfect for hitting the beach. The Ko Olina Lagoons are known for their picture-perfect calm waters framed by white sand crescent beaches. Enjoy a leisurely stroll along the beachfront path, lounge in the sand, or enjoy a refreshing swim, snorkel, or stand up paddle boarding excursion in the water. There are also nearby beaches perfect for surfing, whether you’re a complete beginner or you have some experience under your belt. Further up the western coast, the sands of Makaha Beach and seclusion of Yokohama Bay beckon, offering unforgettable beauty and spectacular Hawaiian sunsets. And of course, the famed beaches of Waikiki also await, with their bustling waterfront and abundant activities!

Celebrating the Winter Holidays in Hawaii

A getaway to Oahu over the winter holidays will mean even more potential activity options to add to the itinerary. Whether this is your first time away from home over the holidays or you’re used to a white Christmas, you’ll quickly realize that even on a tropical isle, a festive spirit is in the air. From palm trees strung with lights to shopping for gifts with a peppermint mocha in hand, you’re sure to enjoy the holiday season on Oahu. Be sure to add some of these Oahu holiday activities to your itinerary


Of all the Hawaiian Islands, Oahu tops the charts when it comes to the best shopping experience. From local pop-up markets that feature locally made goods to lavish shopping malls, the Oahu shopping experience will not disappoint. Ala Moana Shopping Center is the largest outdoor mall in the world, and it is located right here on Oahu. Even for reluctant shoppers, Ala Moana provides a pleasant experience with its open-air vibe and beautiful center stage that features entertainment such as Hawaiian music and hula. You’ll find everything from big-name brands to unique local finds at Ala Moana Center, with plenty of options for gift-giving.

Holiday Festivities

Christmas activities on Oahu include everything from watching Santa paddle his outrigger canoe onto the beach to catching a traditional rendition of The Nutcracker on stage. The Polynesian Cultural Center is also known for their Christmas activities, from a live nativity to a special snow day featuring real snow for the kids!

Winter Accommodations on Oahu

Whether you’re getting away for a week or planning to hide away for the entire winter, our Oahu in winter accommodations provide a great place to base your winter retreat. At Ola Properties, we offer upscale accommodations perfect for couples, families, and groups to enjoy an unforgettable winter in Hawaii. Contact our team with any questions you may have!