Maui (Part 1) – How to Fly With Your Bike and Arriving in Maui

Maui (Part 1) – How to Fly With Your Bike and Arriving in Maui


Maui (Part 1) – How to Fly With Your Bike and Arriving in Maui

My wife tried for weeks to sell me on the idea of going to Hawaii. I’m simply did not want to go. I’d gone many times in the past prior to having a family of my own. She wanted to go to Maui, which, from the last time I went, I recalled being kind of boring and uneventful. Basically, remembering the feeling that there simply wasn’t much to do there. She tried for weeks. There she did something that totally reminded me of why I love this woman and why she is so awesome…. This is a story about what she found and how a regular ol’ family trip turned into one of the most amazing challenges and accomplishments ever…


The island of Maui is shaped like a number 8 that tripped and fell and wasn’t able to get back up. And the reason for this is that it sits between two mountains and is sometimes referred to as the “Valley Island.” It was here that my crafty significant other found something that would entice to be interested in taking a trip to Maui (since I was too blind to see how awesome going there would be). She found me a bike ride in the month of June called Cycle to the Sun.

Now, I wouldn’t even have considered this had I not just done another ride called Breathless Agony a few months before. “What’s the difference?” you ask? In terms of climbing, Breathless Agony is like an elevation gain buffet while Cycle to the Sun is more like a fine steak restaurant where everything is sold ala carte. 12,000 feet over 112 miles versus 10,000 feet in 36 miles. I figured, I was as ready as I would every be…

And so the adventure began.

Getting There (With My Bike)

I needed a way to get my bike there. Cost was no object in this regard. I ended paying $150 each way to get my bike there an bike. There’s something to be said about traveling with your bike and having all your stuff with you. The Thule Round Trip is excessively large and you’ll still want to use foam rollers to pack the frame carefully. The handle bars will need to be removed but it comes with two wheel bags and an integrated bike stand. Money.

Another alternative, if you can do without your bike for a week or so is to have it boxed and shipped from your LBS to the bike store to Maui Cyclery in Paia town. This is also the same bike shop that hosts and organizes this annual ride (or race).

That’s it. You can pack light since it’s all beach wear and sun block. You’ll want something warm for elevation. The island is in between two mountains after all.

Arriving and Getting To the Hotel

Consider taking the red eye from the west coast to Maui. Why? Because you’ll end up getting in your rental car and driving in the dark all the way to the hotel. For us it was the Westin in Kaanapali. The entire drive from the airport to the hotel was pitch black. Virtually no street lights and just the sound of crashing waves with the windows down. Pitch black.

We rolled into the hotel very late or relay – deepening on how you see it, and literally crashed. We couldn’t even appreciate the amazing  indoor/outdoor lobby of the Westin. Straight. To. Bed.

Here is the scene that greeted us the very next morning from the hotel room balcony:

It was like we went to sleep and woke up in this magical new land the very next day. Actually, that is exactly what happened.

If you take the red eye, you’ll save some scratch and have this great experience waking up (late) the next morning.

The Plan

Cycle to the Sun was 2 days away. Not going to lie – there was a bit of anxiety and anticipation around the ride – especially as we went around the island enjoying good food and fun. The plan was to go around the island checking out new places. This would include a scouting run with a drive up to the top of Haleakala the day before the ride.

The anticipation was growing and I kind of wished that we had planned the trip so that the ride took place at the very beginning.

Stay Tuned for Maui Day 2…


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