Round Trip Angel Island is a notoriously difficult 10-mile swim in the San Francisco Bay. The swim begins and ends in Aquatic Park and the loop around Angel Island can be completed either clockwise or counterclockwise. The San Francisco Bay has three busy shipping channels, and a swimmer must cross them all twice during this swim. Strong currents and cold water also contribute to the challenge. It is featured on the Toughest Thirteen list hosted by the Marathon Swimmers Federation.

I had been interested in Round Trip Angel Island for a few years, but for one reason or another, the timing just hadn’t worked out. I was excited to finally have the opportunity to attempt this swim, especially after my DNF in the English Channel. I woke up at the obscene hour of 0100 for a 0215 meet at Horseshoe Cove in Sausalito. While driving through San Francisco, my wife and I were amused by the groups of people in the streets who were still awake and partying.
I was in the absolute best hands for this swim. There were four incredible crew on the boat to support my journey – Kelly piloted, Deedee and Sylvia crewed, and Christina observed. Sylvia, Kelly, and Christina all have their own story with the English Channel and know mine well. My wife, Deedee, often knows me better than I know myself and is a pillar of strength for me in all aspects of life. Beyond them, only four other women who are all very dear to me were aware I would be doing this swim. I wanted to surround myself with a small but powerful cloud of support that I could lean on if things ever got dark.

My approach to Round Trip Angel Island was intentionally very different from that of other recent swims. I kept this attempt quiet so I could focus inward and reconnect with my love for this sport. Instead of creating a rigid feeding plan, I decided to keep things flexible. It is inordinately difficult for me to ask for help, and a feeding plan with minimal structure would force me to communicate my needs to my crew in order to be successful. Deedee knew to feed me after 45 minutes and then every 30 minutes for the duration of the swim, but if I wanted anything beyond liquids, I would need to ask. I told myself this was just a training swim and not a marathon attempt. My hope for this swim was to cultivate an experience free of pressure to perform where the focus would be solely on swimming.
It was windier than I anticipated and the strong gusts during the safety briefing made it hard at times to hear Kelly. The plan was to motor over to Aquatic Park Cove and if the water was too chaotic, I wouldn’t swim. The conditions seemed good enough by the time we reached the cove, so I put on my suit and prepared to swim. Because of the early start time, I decided to just apply Vaseline for chafing protection and avoid the thick layer of zinc I typically use to prevent sunburn. Kelly reminded me that this experience was for me, and to take as much time as I needed on shore before raising my arms to signal that I was ready to officially start the swim. Once on the sand, I looked around at these familiar surroundings and reflected on my intentions and hopes for this experience before reentering the water.
Around 0320, I began the familiar swim to the opening of Aquatic Park Cove. The water felt calm, but I know not to judge the conditions outside the cove by the conditions inside. As I approached the opening buoy, I felt the familiar surge of energy that signals the water is a bit rough out there. It was dark, but my surroundings were well illuminated by the Ghirardelli sign. I was happily humming to myself and enjoying the bioluminescence dancing from my fingertips. At 45 minutes, I took my first feed. I struggled to find the bottle in the water and said something like “that wasn’t so smooth” before continuing to swim along. I was feeling a bit nauseous and had a few minor vomits, but nothing that I needed to stop swimming to manage.
In the early part of the swim, I thought a lot about my stroke and focused on staying long and relaxed. During the English Channel, I was dissociated to the point that when I review videos from that swim, I don’t even recognize my stroke. I was determined to stay present and in my body for Round Trip Angel Island. I was swimming with the boat to my left, which is typically my preference during long swims. Occasionally, I have the tendency to veer to the left, but felt I was being very mindful of my stroke and keeping my power even bilaterally. To my dismay, I kept finding myself right up against the boat every few minutes! I couldn’t maintain an appropriate distance and though I was feeling strong and steady, I got a bit discouraged that I might not be swimming as well as I thought. As I was doubting myself, Deedee sent out an unprompted caffeinated gel in addition to my usual liquid feed. I was thankful for the boost of energy, but wondered if this extra nutrition was confirmation that I was swimming poorly. Instead of wallowing in self-doubt, I imagined what my support crew would tell me if I shared these concerns. Their imagined responses encouraged me to trust the strength I was feeling in my body and not the lies my mind was trying to tell me.
For the portion of the swim before daylight, the crew illuminated a red and green flashing light when it was time to feed. I was also told before the swim they would use this light if they ever needed me to stop so they could relay information. Soon after I began to see Point Blunt peeking over the boat, the red and green light was illuminated so Kelly could tell me I needed to pick up the pace by 10% for the next 10 minutes. The only anticipated traffic during my swim was an inbound tanker around 0530 and this instruction from Kelly was part of her effort to ensure a safe passage. I settled into a slightly faster stroke cadence and brought in some kick to support the increased effort. All of a sudden, I was surprised to see the ship that my crew had been diligently watching for some time. It was moving so quickly!
After the ship passed, Kelly asked if I was having fun. I let my crew know about the dark moment and reassured them that it was very brief and I was already back to having a great time. I continued swimming up the eastern part of Angel Island and the water was a bit warmer and calmer than it was in the shipping lanes. The sun was beginning to come out and I started to see the facial expressions of my crew. I entered Raccoon Strait with the lights of Tiburon and Belvedere to my right. Flocks of pelicans flew overhead. It was all quite magical!
As I rounded Point Stuart, I started swimming into a headwind and the conditions got gnarly. The water had a lot of energy here and was surging rather aggressively. I enjoyed the challenge and wondered for how long the water would remain this chaotic (spoiler alert: the rest of the swim!). When I reached Point Knox, I noticed people on a nearby fishing boat watching me swim as they motored by. I yelled “hi” at them and waved, and they waved back! That made me laugh and I wondered what they must think about me swimming in the wild water.
The conditions continued to challenge me, and I felt like I was utilizing a massive amount of energy to keep myself moving forward. I intermittently requested gels in addition to my liquid feeds. As my energy levels stayed high and I continued to feel amazing in the water, I wondered if inadequate nutrition may have contributed to my difficulty in the English Channel. The feeding plan I have been using was developed a few years ago when I was ~10 pounds lighter, and I never reevaluated as my body composition changed. Oops! I have heard many endurance athletes talk about needing to augment their feeding plans with time but failed to realize when my nutrition stopped working the way I expected. This insight was so illuminating and I look forward to creating an updated feeding plan to ensure I am giving my body what it needs to be successful for future marathon swim attempts.
There was a stretch of time for about an hour after seeing the fishing boat where I was charging ahead and feeling so strong and capable. Deedee lovingly watched over me from the railing of the boat, smiling and blowing me kisses when we made eye contact. Every so often, I would breathe when Kelly was looking towards me. She had an expression of profound joy to see me in my element swimming like myself again, and it made me so happy to see her happy.
Angel Island faded into the background and I started being able to see Alcatraz to my left. I could tell that Alcatraz was far away, but I had never seen it from this perspective so wasn’t sure exactly how far. Sylvia warned me that this stretch of the swim can feel like forever, so I tried not to pay much attention to Alcatraz. I could see the Golden Gate Bridge to my right, but it looked exactly the same for close to two hours. Conditions stayed choppy for the duration of my trek back to Aquatic Park, but I felt strong and connected to the water. I was in the zone and absolutely loved feeling the power of the bay. I worked together with the waves to move forward, changing the timing of my stroke to accommodate the surges.
I usually like to swim very close to the boat, but during this stretch, I noticed that at times, I was swimming a lot further away than usual. I wondered why I kept swimming into the boat at the beginning of the swim and was now unable to stay next to it. Kelly would reposition closer to me intermittently and I felt safe the entire time, but it was a bit unnerving to not be as close as I am used to. At a feed, Kelly told me that the strong westerly wind was pushing the boat away from me, but I was swimming in a good spot and all was well. This feedback put my mind at rest and I was able to stay calm and focused with full trust in my crew. I also now had context for why it felt so challenging to regulate my body position along the boat in the beginning of the swim… the wind was being windy!

Soon, the silhouette of Alcatraz was towering over us and Kelly told me, “It’s just an Alcatraz swim now!” I knew I likely had 45 to 60 minutes left swimming, so I pushed the pace until the next feed. As suspected, Deedee told me it was the last one. Kelly instructed me to continue sighting off the bow and suddenly I was at the opening to Aquatic Park. There were a number of sailboats moored in the cove, and Kelly directed me to keep them all to my right. She would stay out of Aquatic Park Cove and my crew would watch me finish via binoculars.

I don’t usually pick up my pace at the end of marathon swims, but this time, I sprinted. I pushed as hard as I could to the beach and as I stood on the sand with my arms in the air, I looked around at everyone enjoying the sunshine on a very normal Saturday morning. Nobody had any idea what I had just accomplished, or that I had been standing on this very spot at 0320 this morning feeling very differently about myself. There were no hugs. There was no celebration. It was just me on the sand with the quiet knowledge of what had just happened. This moment was just for me.
I am so thankful to Deedee, Sylvia, Kelly, and Christina for showing up for me and creating this incredible experience that reconnected me to my strength and love of the water. I also have immense gratitude for the four women on land who held this secret with me in quiet support. There was such incredible energy surrounding this swim and all of the love was deeply felt. This was one of the hardest swims I have completed, and I could not have done it without their support. Thank you!

WOW! Your my hero! I loved reading this and vicariously swimming This Round Trip Angel swim through your story (It’s a bucket list swim for me).
I love reading your beautiful, authentic and vulnerable telling of this journey you had, especially in context of having read your English channel postband having shared some of the similar mental health challenges and carrying that into some of my swims (Also a beautifully vulnerable and important Article)
I cried ta few tears of joy while reading your recounting of Deedee being there for you and blowing you kisses♥️
You have inspired me to imagine and potentially pursue some future long swims and hopefully one on this route in the future, even though I had all but written off wanted to do anymore marathon swims.
Thank you so much for sharing these stories and for being vulnerable. I hope to see you around AQuatic Park and hopefully swim with or behind you (I am slow)
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