Why Winter is the Perfect Time to Visit Hawai’i (and How to Get There Easily)

Hawai’i is my favorite place in the entire world. There’s a magic to the islands that’s hard to put into words—something that captures your heart and never lets go. For some, it’s a yearly tradition; for others, it feels like a far-off dream. But here’s the truth: visiting Hawai’i has never been easier, and there’s no better time than this winter.

Getting to Hawai’i: Start Your Vacation in the Sky

When my family travels to Hawai’i, we usually fly into LAX before catching a Hawaiian Airlines flight straight to the islands. Over the years, this has become more than just our go-to—it’s part of the vacation itself.

Why Hawaiian Airlines? It feels like you’re stepping into island life the second you board. From the aloha spirit of the crew to the Hawai’i-inspired cabin design, you’re welcomed with warmth and authenticity. My kids especially love it—the excitement starts before we even leave the runway.

On board, you’ll find complimentary beverages, Hawai’i-made products, and thoughtful touches like warm sandwiches, island-inspired drinks, and even Starlink Wi-Fi. It’s comfort and culture wrapped into one experience. And with their wide range of flight times and competitive prices, traveling to Hawai’i in style has never been more accessible.

This winter, Hawaiian Airlines is offering excellent fares, which makes it the perfect time to book your trip. Trust me—winter is hands-down the best season to visit the islands.

Why Winter in Hawai’i is So Special

Every season in Hawai’i has its beauty, but winter has our hearts. Part of the reason? Both of my kids were born in late fall, so winter trips to Hawai’i have become a family tradition. But even beyond personal ties, winter offers experiences that are truly unforgettable.

Perfect Weather

While summer months can feel hot and sticky (with highs around 87°F and humidity that pushes the “feels-like” temps even higher), winter brings a more comfortable balance. Days are warm enough for the beach, while evenings are cool and breezy—ideal for watching the sunset on the lanai with a drink in hand.

Whale-Watching Season 🐋

But the weather isn’t the biggest reason we return every February. That honor goes to the humpback whales. Each year, mother whales migrate to Hawai’i’s shallow waters to give birth and raise their calves. From January through March, you can sit on the beach and witness them breaching, slapping their tails, or swimming alongside their babies.

It’s one of the most breathtaking natural sights you’ll ever experience, and it never gets old. If seeing whales in the wild is on your bucket list, winter in Hawai’i is the time to make it happen.

Which Island Should You Visit?

With your flights booked, the next question is: where should you stay? Hawaiian Airlines makes island-hopping easy if you want to see more than one, but here’s a breakdown to help you choose based on my personal experiences.

Maui

Maui holds a special place in my heart—I’ve spent about seven weeks of my life here. We usually rent a car, stay near the beach, and shop locally for breakfast and lunch. Dinner is always an adventure, with endless food options and some of the best shopping in Hawai’i.

The Hana Highway is a must-do (though it can get crowded), and the island’s beaches are spectacular. If you’re looking for a mix of beautiful scenery, dining, and shopping, Maui is an easy choice.

Bonus: Moana 2 is releasing this November, and visiting Maui will feel extra magical if your kids are fans of Polynesian legends.

Kauai

Our most recent trip took us to Kauai, and it might just be my new favorite. Hanalei, a laid-back surfer town, feels like stepping into paradise with its lush mountains and cascading waterfalls. Waimea Canyon (often called the “Grand Canyon of the Pacific”) is breathtaking, and the snorkeling and hiking opportunities are endless.

If you’re drawn to nature, adventure, and a slower pace, Kauai is where you’ll want to land.

Hawai’i (The Big Island)

The Big Island is full of unforgettable experiences. We’ve flown over lava fields in a helicopter, swum with manta rays, lounged on a green sand beach, and marveled at the Waipi’o Valley. Kona, with its volcanic landscapes and vibrant food scene, is especially worth visiting (don’t miss Kona Brewing Company if you’re a beer fan).

Oahu

Oahu is the most populated island and offers a completely different vibe. While it’s busy, the energy is contagious—great nightlife, incredible food, and world-class surfing. You’ll also find historic sites like Pearl Harbor and cultural experiences like touring pineapple plantations.

For travelers who love vibrant cities with a tropical backdrop, Oahu is the place to be.

Time to Book Your Trip

If Hawai’i has been sitting on your dream list, this is your sign to make it a reality. Between Hawaiian Airlines’ winter specials and the unforgettable experiences the islands offer, there’s truly no better time to go.

A word of warning: don’t be surprised if you find yourself scrolling Zillow while you’re there. I can’t count how many times I’ve been tempted to buy a home in paradise—it’s just that special.

So, what are you waiting for? Pack your bags, book your flight, and get ready to experience the magic of Hawai’i this winter. Aloha! 🌺