Pailolo Channel Tandem 2022

The story for this swim goes back to last year when I came to Maui to swim the three channels making up the Maui triangle: Kalohi (Molokai-Lanai), Auau (Maui-Lanai), and Pailolo (Maui-Molokai). Even before we arrived on Maui, the weather indicated that swimming Pailolo (the most finicky of the channels wind-wise) would not be possible on that trip. I still had a blast joining Steven Minaglia and some of his friends to swim Kalohi and Auau (read that recap here), but I felt like I had some unfinished business in Pailolo. So when I found out that I would be returning to Maui for a vacation with some swim friends, I reached back out to Steven to see if he could help me plan an attempt at Pailolo. Steven connected me to Captain Keith Baxter and I convinced my swim buddy Kerianne to join me for a tandem crossing. We also made a backup plan to do another swim in case the winds proved too strong again.

When we arrived in Maui last Sunday, I called Captain Keith and he said the best looking weather days were Friday and Saturday September 16th and 17th and that he was piloting a Kaiwi Channel attempt on Thursday so the best day for our attempt would be Saturday. We agreed that if the winds stayed low, we would swim Maui to Molokai and if the winds were too high we would follow our backup plan. It’s been a while since I have attempted a swim with a weather go/no go and it was nerve wracking to wait for the captain’s call that the swim was on. He did call on Friday and we prepared for a splash Saturday at sunrise.

Before the start.

On Saturday morning, Kerianne, her wife Deedee, and I met up with Captain Keith at the Mala Boat ramp in Lahaina and loaded his gorgeous boat the Kanaloa. We discussed two potential starting locations and decided on a rocky outcropping under the Kapalua cliff house, which would mean a rocky start but would not be too difficult to climb. When we reached the spot, Deedee helped me and Kerianne put on sunscreen, SafeSea, and grease and get ready to splash. Captain Keith had a raft attached to the back of the boat and Kerianne ran and dove gracefully into the water. My entry was more sedate and I walked down the raft and jumped feet first into the blue water. Even though I had been swimming in the water all week, I was still surprised how warm it felt. We swam over to the rocky spot that Captain Keith had indicated and climbed carefully up to a dry spot. We fist bumped, waved back at Deedee on the boat to show that we were starting, posed for a picture, and slid carefully into the water.

On dry land.

Captain Keith’s plan was to drag a parachute and a large tire in the water behind the boat to create drag and slow him down to our speed and prevent him from needing to shift in and out of gear constantly, but it was immediately clear that the speed wasn’t quite right. We stopped for a moment while he fiddled with the drag, and I got hit with my first jellyfish. Captain Keith told us we could continue on ahead, but we were too nervous about large wildlife to swim away from the boat and the water was warm enough to just wait for him. We swam over reef for a while and started to get into a rhythm with Kerianne keeping the boat on her left and me keeping Kerianne on my left. It was so nice to be able to see Kerianne in the water, as the water we are used to in San Francisco is much less clear. At this point, the water was still fairly flat and the wind was around 3-5mph (Captain Keith told me afterward), and I was still finding my rhythm and we were still hitting lots of jellyfish. We stopped for our first feed and Kerianne seemed to be in a very good mood, while I was working to stretch out my stroke and get used to all the stingers in the water.

Maui in the rearview.

We were aiming for a point on the left-hand side of Molokai, because the current was flowing left to right across the channel, and we did not want to get pushed too far to the right. It always takes me a while to start enjoying a long swim, but I always forget this fact, so at 90 minutes into the swim, I was still pretty grouchy and had counted 21 jellyfish stings. Kerianne still seemed to be in a pretty good mood, and we were clearly making progress away from Maui. The water was so incredibly blue and around 2 hours I finally started having fun in the increasingly swelly seas. Whenever we stopped for a feed, Deedee and Captain Keith told us how great we were doing. I never knew whether to believe them, but it was still nice to hear.

As we got into the middle of the channel and the seas picked up a little bit, I could still see some jellies floating beneath us but I stopped getting stung. That made swimming much more enjoyable and I marveled at the gorgeous clear warm water.

Mid channel.

While the swell felt like it was coming over my right shoulder, it seemed like the current was increasing in strength from our left. Captain Keith seemed to be turning the boat to the left and angling us directly into the current so that we did not get pushed too far right, but we were not making much progress. He called to us and told us that we were fighting a current but that he was trying to find a way across it for us. The strong current made it harder for Kerianne and me to stay together but it did seem like we were getting past it. Captain Keith told us that we should turn back toward the island and that he had found us a small channel through the current. It was somewhat reminiscent of swimming the English Channel watching the island slide past us but we were making progress toward it again.

Molokai getting closer

Kerianne and I had discussed before the swim how we were both really nervous to run into large sharks, so we stayed close to each other and close to the boat. After we were about halfway across, we were just swimming along when suddenly I heard an unmistakable dolphin squeak. I swam head up for a few seconds but didn’t see anything and the folks on the boat weren’t reacting so I figured that the dolphin must be far away and the sound just travelling. We stopped for a feed, and I didn’t say anything to Kerianne about hearing a dolphin in case it scared her. A second later, Kerianne said “DOLPHIN!” and sure enough, there was a dolphin swimming right at us head on. It swam up to each of us, getting as close as maybe 1 foot away, before checking out the boat in the same way and then zoomed off again. This brief encounter felt like we were being greeted by a guardian of Molokai.

I never let myself ask where we are early in a swim, but by 4 hours in, I knew that we had to be at least halfway and probably over halfway, because Molokai looked closer than Maui. My armpit started to chafe, and I asked Deedee if she could pass me some grease on the next feed. She had a hard time hearing me and repeated back to me “you want grease” (or so I thought). We swam for another half an hour and when we stopped to feed, there was a waffle attached to my bottle. When I asked why I was getting a waffle (usually reserved for the last feed or when the boat crew thinks I am struggling), Deedee responded “you asked for treats!” We laughed about how treats and grease sound similar, and she promised me grease on the next stop.

Getting closer.

The seas had started to pick up, but I could tell that we were getting close now and I was looking closely to see if I could see the bottom through the water. As I was getting tired, I kept going on autopilot and had to keep reminding myself to stick close to Kerianne. Eventually, I started to be able to see sand beneath me maybe 15-25 feet down, but it looked like we were still at least a mile or more from shore, so I didn’t let myself get too excited yet. We continued swimming in the choppy water, and I saw a turtle hanging out on the bottom, as if it was welcoming us to Molokai. Deedee called us over for a feed and told us that this was going to be our last feed. Captain Keith told us we needed to swim over the reef, but that he needed to take the boat around it and meet us on the other side. We headed over the reef, and I enjoyed looking at the brightly colored fish, even though I did not like being so far from the boat. Captain Keith had promised us that he would escort us into the beach as far as possible, so we met up with him on the other side of the reef. I saw another turtle and a bat ray. There was another even more shallow reef on the other side, so Captain Keith directed us to make a 90 degree turn to the left and cut around the reef and then turn back to the right and swim parallel to shore for about 5 minutes.


This was frustrating because it did not feel like we were making any progress toward the finish. I asked why we couldn’t just head to shore but Captain Keith told us that we had to find a public beach and could not land on private property. Suddenly, Captain Keith shouted that we should turn and head into a small sandy beach bookended by 2 jetties. As we turned and swam towards shore, the water got increasingly murky and warm. We saw a few people on shore and waited for them to pass by before climbing onto dry sand. We posed for a few pictures and then headed back to the boat.

All done!

This was my first tandem swim and it was a total blast. I am so proud of Kerianne for completing her first channel swim and so grateful to Deedee for supporting us and for Captain Keith for his expert navigating! We finished Pailolo in approximately 6 hours and 10 minutes and I can finally say that I have completed all 3 Maui triangle channels!

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