Maui: Whale watching private air tour with guide & drinks

Summary

Flying above Maui’s whales with a local pilot, laughter in my headset, and that wild blue below us

You’ll fly over Maui’s coast with a local guide during whale season, spotting humpbacks from panoramic windows while listening to live commentary and sipping cold drinks. From takeoff near Kihei to circling Molokini Crater, you’ll get rare views and moments you’ll remember long after landing.

What’s the experience like?

“Did you see that splash?” our pilot, Kaleo, called out through the headset just as I was squinting at the water off Molokini Crater. I’d never been in such a small plane before — just four of us and Kaleo up front — and honestly, I was a little nervous at takeoff. But once we lifted off from the little airport near Kihei, Maui just opened up under us. The sugarcane fields looked like someone had ironed green sheets all the way to the sea. There was this salty tang in the air even inside the cabin, or maybe it was just my hands still sticky from sunscreen.

Kaleo kept chatting about whale season (December to April — I didn’t realize it was so specific), pointing out where he’d seen humpbacks breaching last week. He grew up here and you could tell; he knew every curve of coastline and even waved at another pilot passing by like they were neighbors. We circled above Molokini, that weird crescent of volcanic rock, and then — there! A tail slap, clear as day from above. It’s wild how small boats look next to those whales. My friend tried to snap a photo but mostly got her own reflection in the window. Still makes me laugh thinking about it.

The whole flight was maybe an hour? Hard to say because time felt strange up there — everything slowed down except my heart when we banked over Sugar Beach Resort and saw three whales moving together below us. The light kept shifting on the water; sometimes silver, sometimes almost turquoise near Kihei’s beaches. At one point I forgot about taking pictures and just watched them move through that endless blue. It’s not something you really expect to feel so much from inside a metal airplane, but yeah… I still think about that view.

Step-by-step itinerary

Day 1 — Maui Whale Watching Air Tour

• The starting and ending point of your aerial Whale Watching adventure!
• Fly over central valley of Maui
• Soar over Sugar Beach Resort
• Birds-eye view of Kihei and Kamaole Beach parks
• View Molokini crater and Humpback whales
• Observe Humpback whales splashing and breaching
• Enjoy a bird's eye view
• Soar above Maui
• Perspective redefined
• A bird's eye view
• Truly uplifting experience

Top questions

How many people can join the Maui whale watching private air tour?

The private air tour seats up to five people per booking.

When is humpback whale season in Maui for this tour?

The tour operates during whale season: December 15 to April 15.

Where does the Maui whale watching air tour start?

The flight starts and ends near Kihei in central Maui.

Is there live commentary or a guide on board?

Yes, your local pilot provides live commentary via headsets during the flight.

Are drinks included on this private air tour?

Beverages are included during your flight experience.

Do I need full mobility for this activity?

Yes, full mobility is required for boarding and safety reasons.

Can we skip lines or crowds on this experience?

This is a private flight so you skip long lines entirely.

Will we definitely see whales on this Maui air tour?

Sightings are likely during season but not guaranteed since whales are wild animals.

What’s included

Your day includes a private cabin airplane with panoramic non-tinted windows for clear views, live commentary from your local guide via headset, all landing fees covered, beverages served onboard, plus you’ll skip any lines since it’s just your group flying together.