I'll be there, too, also in May. Hope to see some good responses.

Aside from cycling, if anyone has some good running spots/routes to recommend, those would be appreciated, too.

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Attacking this day with enthusiasm unknown to mankind.

I would recommend that you work on your bike.

Either way, call Bike Works, (808) 326-2453. They're located over in the industrial area about a mile or so from the pier.

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Team Kiwami
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BikeWorks has a shop in Kona just off the Queen K and another shop in Waikoloa in the shopping center. I've used the Kona store twice to purchase nutrition while at a training camp there. Several others participating in the camp shipped their bikes to Bike Works who reassembled for them. A few others rented road bikes from them. I'm not sure if they rent tri bikes though. They are very nice and I have not heard anyone at camp have a problem with them or their work in the past 2 years that we've been going there.

+1 to this. I've used both the Kona and the Waikoloa stores. Both have friendly staff and are quite helpful, prompt, and useful. The Kona store has a larger selection if you need to purchase stuff that you've forgotten. I've rented tri bikes (and a road bike) from them at both locations and had zero problems. I also have shipped my bike with me on the plane and had them reassemble. For a small fee too they are willing to store your bike case for you (at least Waikoloa was). I'd recommend making a reservation for rentals though - you can reserve online. I also made a reservation for reassembly and I dropped it off, checked into the hotel, and went back and it was ready and checked out (and they even upgraded the firmware on my Vector's for me at no charge (my request)).

There are two bike shops in Kona, Bike Works and Cycle Station. Both are very familiar with tri bikes and both rent bikes.

I've rented from each, both were fine. Bike Works is closer to town, has a better selection and were easier to deal with in general.

One update: Cycle Station recently shut down. So your Kona and Kohala Coast option is now Bikeworks. Fortunately they are a great shop and always up to date with the latest equipment and accesssories.

Not sure what will happen for Trek owners as Cycle Station was the local dealer. Perhaps something will be worked out with Bikeworks?

Bike Works has a great selection of everything you'll need, and mechanics who really know their way around tri and road bikes. The Kona Store is bigger than the Waikoloa shop.
They do have tri, road, and mtb rentals. http://www.bikeworkskona.com/bike-rentals-kona/ Grant is the owner, and, I think, Verne is the manager.
The public pool, just a couple blocks away from the shop, is free, and there's also a Masters Swim group, also a group who swims every morning at the pier.

If you want to ride to Kawaihae and up to Hawi, then starting from Waikoloa is the way to go. Plus, there is in incredible public beach in Wailkoloa.
You can grab ready made food and groceries at the Island Gourmet market too. http://islandgourmethawaii.com/waikoloa/
No, this isn't a public service announcement for Waikoloa, but it's a nice place to spend a couple of days.

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Karen ST Concierge

BikeWorks.

Their shop is 2 blocks west of where Palani meets with QK. The parking lot backs onto QK. But can't get to it from QK. (I circled for 15 minutes looking for their driveway first time I was there.) Entrance is off Luhia st. They share the same driveway with Enterprise rent-a-car. Drive to the end of the driveway and park.

They rent tri bikes and know how to work on them.

While you are there, pick up food at Island Naturals. It is next door.

 
I just returned from 9 days in Waikoloa - wish I was still there.