Have you ever returned from a vacation feeling like you only skimmed the surface — as if you missed the true heartbeat beneath the beaches and sunsets?
If your dream Maui getaway in early 2026 involves more than lounging seaside — if you crave experiences that connect you to the island’s spirit, creativity, and people — this guide is your key to an unforgettable journey.
The first half of 2026 is shaping up to be a celebration of music, art, nature, and community. Whether you’re traveling as a couple, a family, or a solo explorer, these events go beyond entertainment — they invite you to feel Maui.
From slack key guitars to whale festivals and art studio tours, each experience offers the chance to enrich your stay and return home with stories that linger.
Slack Key Festival
January 18, 2026 | Maui Arts & Cultural Center
What if one evening could connect you to the very soul of the islands?
The Slack Key Festival celebrates the beloved Hawaiian ki ho‘alu (slack key guitar) — a fingerstyle technique as gentle as a Maui breeze and as soulful as its sunsets.
Each note tells a story — one of heritage, harmony, and home.
Why you’ll love it:
- Feel the rhythm of Hawaiian culture through live music and graceful hula.
- Share an evening of serenity and storytelling that stirs the heart.
- Perfect for couples and families seeking an authentic cultural highlight.
Plan ahead: If your travel window includes mid-January, lock in your lodging now so you can add this enriching experience to your schedule.
Maui Open Studios
February 14 – March 1, 2026 | Island-wide
Looking for souvenirs with real meaning?
During Maui Open Studios, local artists open their doors and welcome you into their creative world.
Wander through Upcountry workshops, seaside galleries, and home studios where inspiration flows as freely as the ocean breeze.
Why it’s special:
- Meet the artists behind Maui’s vibrant creative scene and take home one-of-a-kind pieces.
- Enjoy a calm, self-paced day away from the crowds — perfect for reflective travelers.
- Experience Maui through the eyes of those who call it home.
Travel tip: Rent a car and plan a “gallery crawl by car.” Each weekend highlights a different region, so map your route and make a full day of it.
World Whale Day Festival
February 9–15, 2026 | Kihei
February marks peak whale season on Maui, and the World Whale Day Festival turns that wonder into a weeklong celebration.
Hosted by the Pacific Whale Foundation, 2026 marks the 45th anniversary of this beloved event — blending fun with purpose as the community honors Maui’s marine life and ocean heritage.
Why you’ll love it:
- Watch whales breach offshore as you enjoy live music, food, and educational exhibits.
- A family-friendly way to connect with nature and ocean conservation.
- Opportunities to join whale-watching tours that directly support marine research.
Make it easy: Stay in Kihei for quick access to the festivities, and plan at least one whale-watch cruise during the week. It’s an experience you’ll remember long after you’ve unpacked.
Valley to the Sea Half Marathon & 5K/10K
March 14, 2026 | Iao Valley to Kihei
Craving a vacation that makes you feel alive? The Valley to the Sea Run does just that — starting amid the emerald peaks of Iao Valley and finishing beside the shimmering Pacific.
Whether you jog, walk, or cheer from the sidelines, it’s an unforgettable way to see Maui from a new perspective.
Why it’s worth it:
- Soak in breathtaking scenery — from lush valley trails to oceanfront views.
- Celebrate wellness and connection with family or friends.
- Earn bragging rights for running (or walking) across paradise.
Plan smart: Book a vacation rental in South Maui for easy race-day logistics and a peaceful recovery afterward.
Maui Marathon & Half Marathon
April 26, 2026 | Kaanapali
Imagine watching the sunrise paint the ocean gold as you run along one of the world’s most scenic coastlines.
The Maui Marathon, one of the oldest in the United States, draws runners from across the globe for its spectacular route along the island’s west coast.
Why it’s unforgettable:
- Experience sweeping ocean views with every mile.
- Choose your challenge — full marathon, half marathon, or 5K.
- Feel the island’s spirit of endurance, joy, and aloha.
Make it happen: Whether you run or cheer from the sidelines, secure your accommodations early. Late April is a busy travel period, and staying near the start or finish line makes all the difference.
Kihei Fourth Friday
Every Fourth Friday | Azeka Mauka Center, Kihei
If you’re craving a night that feels spontaneous yet perfectly Maui, head to Kihei Fourth Friday — the island’s beloved monthly town party.
The atmosphere is friendly, festive, and filled with live music, food trucks, and family fun.
Why it’s a must:
- Sample local eats from some of Maui’s best food vendors.
- Shop handcrafted art, jewelry, and gifts directly from local makers.
- Experience real community — laughter, music, and genuine island pride.
Plan it in: Stay nearby in South Maui so you can stroll home under the stars after the festivities.
East Maui Taro Festival
Exact Date TBA (Typically in Spring) | Hana
If you’re drawn to authentic cultural experiences, the East Maui Taro Festival is one to watch for.
This annual celebration honors taro (kalo), the sacred root of Hawaiian food and life, through traditional dishes, live music, and storytelling.
Why it’s meaningful:
- Connect with the roots of Hawaiian culture through taste, craft, and community.
- Enjoy a rare chance to explore Hana’s lush, spiritual beauty.
- Perfect for travelers seeking experiences that feed the soul.
Travel note: When dates are announced, plan an overnight or full-day trip. The scenic drive to Hana is part of the adventure — take it slow and savor every turn.
Smart Rental Strategy for Maximum Benefit
- Book early – February through April draws many visitors, so secure your rental early for the best locations and rates.
- Choose location wisely – Pick an area that offers access to at least two of your chosen events — for example, South Maui for Whale Day and Fourth Friday.
- Balance your pace – After a high-energy event, plan slower days. Stroll the beach, unwind by the pool, or relax on your lanai at sunset.
- Pack intentionally – Bring a light jacket for evening events, layers and water shoes for Hana, and running gear if you’re joining a race.
- Reserve extras – Private chef dinners, stroller rentals, or a beach photographer? Book them in advance to elevate your stay.
Make Every Moment on Maui Matter
When you look back on your Maui getaway, it won’t be the photos you remember — it’ll be the sound of slack-key strings under a starlit sky, the thrill of spotting whales offshore, the pride of crossing a finish line, and the warmth of locals welcoming you in.
Choose your key events. Book your stay with AAOceanfront — where comfort, convenience, and island charm come together effortlessly. Then let Maui do the rest.
Don’t just visit Maui in 2026 — live it, feel it, and be part of it.
Your adventure begins the moment you choose your event, plan your stay, and let Maui’s rhythm carry you away.
