When most people picture the holidays, they imagine snow-dusted pines and crackling fireplaces. But what if your winter escape traded snowflakes for orchids, hot cocoa for mai tais, and sleigh bells for slack key guitar? At Four Seasons Resort Maui at Wailea, the festive season gets a serious tropical upgrade—and honestly, it’s everything your Instagram feed has been missing.
A Wreath You Can Actually Walk Through
Forget the wreath on your front door. This year, Four Seasons Maui is going big—like, walk-through-it big. Starting December 2, renowned local floral artist Noah Harder is transforming the resort entrance with a show-stopping installation that’s equal parts art gallery and holiday magic.
Picture this: a giant wreath draped in sumptuous velvet, dripping with orchids, and glowing from within. We’re talking clusters of velvet bows, ornaments, dried flowers, and natural elements in rich jewel tones and deep emerald greens—all woven together with tropical and seasonal greenery. It’s the kind of entrance that makes you pause, pull out your phone, and think, “Yeah, this is definitely going on the grid.”
“The team has been hard at work weaving together experiences that honor the spirit of the season and the rich culture that makes this place so extraordinary,” says Konrad Gstrein, Regional Vice President and General Manager. Translation? They’re not just decorating—they’re creating moments you’ll actually remember.
Sunset, Hula, and Bubbly: The Ultimate Golden Hour
New this year is Sunset Mele on the Pā, and it’s exactly as dreamy as it sounds. Every evening from December 21 through January 3, guests gather on the traditional pā in The Queen’s Garden—a space honoring Hawaiʻi’s last reigning monarch, Queen Liliʻuokalani.
As the sun dips below Maui’s pristine coastline, live hula dancers or slack key guitarists take the stage while servers pass around bubbly. It’s cultural immersion meets happy hour, and it’s completely complimentary. Pro tip: Arrive early to snag a prime spot for those golden hour photos.
Mahjong Meets Mai Tais (Yes, Really)
If you’ve been scrolling TikTok or Instagram lately, you’ve probably noticed mahjong having a major moment. The centuries-old tile game is trending hard, and Four Seasons Maui is bringing it straight to paradise with their new Mahjong and Mai Tais experience.
Partnering with Mahjong Country Club—founded by women who learned from their moms and grandmothers—the resort is hosting sessions that blend ancient strategy with serious tropical vibes. Whether you’re a mahjong newbie or a seasoned player, expert instructors will get you up to speed before live play begins. And yes, mai tais are absolutely included.
Sessions run December 21-24, 26-30, and January 1-2 from 1 p.m. to 3 p.m. at KOMO. It’s the perfect fusion of trending culture and island relaxation.
Honoring Traditions, Hawaiian Style
Four Seasons Maui knows the holidays mean different things to different people, and they’re celebrating it all. Nightly Hanukkah services run December 14-21, complete with a latke-making demonstration led by Executive Chef Ryan Schelling on December 21.
Christmas Eve brings Santa’s dramatic arrival—not by sleigh, but by outrigger canoe at Wailea Beach. Because when you’re in Hawaii, even Santa knows how to make an entrance. Families can also join the pastry team for holiday cookie decorating, creating edible memories with an island twist.
For the competitive families, the three-day Wailea Challenge tournament (December 21-23 and December 28-30) features canoe racing, spear throwing, and obstacle courses. Or keep it casual with the Tropical Pickleball Mixer round-robin tournament on December 27 and January 3.
Wellness With an Ocean View
Between the festivities, the resort offers plenty of ways to recharge. Daily beach yoga, oceanside massages in traditional Hawaiian hale (thatched structures), and vitamin IV therapy through the resort’s collaboration with Next|Health keep wellness at the forefront.
But the real showstopper? Floating Sound Baths at the Adult Pool on December 22, 29, and January 5. Imagine floating under Maui’s star-studded sky while sound waves wash over you. It’s meditation meets vacation, and it’s exactly the kind of unique experience that makes Four Seasons Maui stand out.
Ring in 2026, Island Style
New Year’s Eve at Four Seasons Maui is a multi-venue celebration. Start with dinner at DUO Steak and Seafood’s buffet, Chef Russell Rummer’s holiday menu at Ferraro’s Restaurant & Bar, or Wolfgang Puck’s seven-course tasting at Spago Maui.
The night culminates with the Electric Aloha New Year’s Eve Party on the Oceanfront Lawn at 10 p.m., featuring live music from the band Halfmoons and midnight fireworks over Wailea Beach. And if you’re feeling ambitious, kick off 2026 with General Manager Konrad Gstrein’s New Year’s Day morning run along the stunning Wailea coastline.
Why This Matters
In a world where holiday experiences can feel cookie-cutter, Four Seasons Resort Maui at Wailea is proving that tradition and innovation can coexist beautifully. They’re honoring Hawaiian culture while embracing trending experiences like mahjong. They’re creating Instagram-worthy moments while maintaining authentic connections to place and community.
Whether you’re returning to familiar shores or discovering Maui for the first time, this festive season offers something genuinely special: a chance to celebrate the holidays in a way that feels both fresh and timeless.
Ready to trade your winter coat for a lei? The complete schedule of festive programming is available at fourseasons.com/maui or by calling (808) 874-8000.
About Four Seasons Resort Maui at Wailea
This Forbes Five-Star oceanfront resort sits on 15 breathtaking acres along the Wailea Coast, featuring 383 rooms, world-class dining at four celebrated restaurants (Ferraro’s, Spago Maui, DUO Steak and Seafood, and KOMO), three pools overlooking the Pacific, and one of the nation’s top-rated spas. It’s luxury that lives in harmony with its environment and community—exactly what the holidays should feel like.
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Set Boundaries Stress often arises when family dynamics, expectations or traditions clash. You can reduce this by setting boundaries and communicating them early. Speak openly with the relatives and friends you’ll see about what’s comfortable for your family and what isn’t (e.g., physical space, travel, topics to avoid). Let your children know what to expect, as the lack of routine during this time can be particularly challenging. Modeling clear boundaries helps your children learn to express their own needs, too. Prioritize Your Physical and Emotional Health Amid the hustle, your own basic care often slips, but your well-being is key to being present for others. Consider establishing routines, such as:
