Maui Air Tour: Private 5 Islands Flight for Small Groups

Summary

Private flight over Maui’s islands with panoramic views and local stories

You’ll feel your heart race as you lift off on a private Maui air tour, circling five islands with live stories from your pilot. Spot shipwrecks near Lanai, see volcanic craters and turquoise bays below, then glide past sugar cane fields before landing again—still buzzing from those sky-high views.

What’s the experience like?

I’ll be honest, I was nervous as we walked up to the little plane at Maui Plane Rides. The tarmac had that hot, baked smell, and my heart was thumping — not scared exactly, just… wide awake. Our pilot, Mike, greeted us with this easy “Aloha” and a grin like he’s done this a thousand times (he probably has). He handed us headsets and said we’d see five islands in one go — I thought he was joking at first. But no, that’s the whole thing: a private air tour from Maui over Lanai, Molokini Crater, even Kahoolawe. It felt weirdly personal — just us and the sky.

Once we lifted off, everything shrank so fast — beaches like tiny ribbons, lava fields looking almost soft from above. Mike pointed out Honolua Bay (I’ve snorkeled there before but never imagined it from this angle) and then the Nakalele Blowhole sent up a plume right on cue. The headset made it easy to hear his stories — he told us about the old sugar cane factory down below and how parts of Kahoolawe still have scars from WWII bombing practice. Sometimes he’d pause so we could just listen to the wind or spot turtles in the water. I tried to snap photos but honestly kept forgetting because I couldn’t stop staring.

There was a moment over Molokini Crater when the sun hit the water just right — all these blue shades I can’t name. My partner squeezed my hand and neither of us said anything for a bit. We flew over Wailea’s golf courses (so green they looked fake), then along Makena State Park where you could see both Little Beach and Big Beach curving away under us. At one point Mike laughed when I asked if people ever get tired of these views; he just shook his head and said “Not once.”

I didn’t expect to feel so calm up there — maybe it’s something about leaving everything on the ground behind for an hour or so. When we landed back at Maui Plane Rides, my hair smelled faintly like salt and engine oil (not unpleasant). If you’re thinking about a day trip from Maui that isn’t another beach or hike, this private air tour is different in all the right ways.

Step-by-step itinerary

Day 1 — Private Maui Air Tour Highlights

• Begin and end at Maui Plane Rides
• Fly over Nakalele Blowhole
• Pass by Honolua Bay
• Overfly Lanai and WWII shipwreck
• View Kahoolawe and Molokini Crater
• Fly over Wailea resorts and golf courses
• See Little Beach, Big Beach, and Makena lava fields
• Observe stunning lava fields from above
• Overfly Kamaole Beach Parks of Kihei
• Pass over historic sugar cane ghost factory

Top questions

How many people can join this private Maui air tour?

The plane seats two to five people comfortably in a private cabin.

Which islands do you see on the flight?

You’ll fly over Maui plus Lanai, Kahoolawe, Molokini Crater, and coastal spots like Makena State Park.

Where does the air tour start and end?

The flight begins and ends at Maui Plane Rides’ base on Maui.

Is live commentary included during the flight?

Yes, your pilot provides live commentary through headsets during the entire flight.

Are drinks provided on board?

Soda and bottled water are included for all guests during the tour.

Do you skip lines or wait times?

Your booking guarantees you skip long lines for boarding.

What are some highlights seen from above?

You’ll spot Honolua Bay, Nakalele Blowhole, Molokini Crater, Wailea resorts, Makena lava fields, WWII shipwrecks near Lanai, sugar cane factories—and more coastline than you’d expect.

Is there an age or fitness requirement?

The tour is suitable for all fitness levels but full mobility is required for boarding.

What’s included

Your day includes guaranteed skip-the-line boarding at Maui Plane Rides’ base, live commentary with clear headsets so you don’t miss any stories from your pilot, plus soda and bottled water on board. All landing fees and parking are covered too—just bring your sense of adventure (and maybe sunglasses).