I started writing about wanting to sail before I learned how to sail. The following is my love story with sailing.

COVID-19: Dreams of Sailing

The Ocean Plan Part 0

My relationship with water and the desire to learn to sail began amidst COVID-19.

During the quarantine of 2020, I was forced to reassess my life’s plan.  Prior to the global shutdown, I had concocted a plan to start a new chapter of my life and move to Berlin by the end of May.  However, due to COVID-19 and the closed borders, my Berlin plan was ixnayed by God.  I conceded to being stuck in Minneapolis for the Summer of 2020. I was depressed for months.

The feelings of helplessness and frustration ate at me for the rest of Spring.  I was bored, lonely, and aimless. I worked from home as a software engineer and was mostly uninspired. But then, one day I stumbled across this video that sparked some life into me.  It showcased a boat that these 30-something vloggers were living on. It seemed like The Life I was looking for!  I started watching videos documenting stories of ocean-crossings.  I was pregnant with a dream.

I then decided to pursue sailing as a lifelong adventure.

Sailing really resonated with me for a few reasons. Looking back, I had a fascination for pirates and privateers in my youth.  One of the first novels I read was The Old Man and The Sea. I played Puzzle Pirates for about a decade and still occasionally log in and play some pirate poker. Pirates of the Caribbean was one of my favorite movies.

I decided on adding “making a solo transatlantic voyage” to my bucket list.  This was obviously a lofty goal— but it seemed doable. 

Living in the Midwest is an obvious impediment to someone wishing to sail on the ocean.  Before packing my stuff and moving to San Diego or Florida,  I decided that sooner or later I would have to learn how to sail.  I figured that there wouldn’t be any classes during COVID-19, but I was wrong!  Classes were still happening, and they were filling up!  I hastily signed up for a fifteen-hour sailing course at the Minneapolis Sailing Center for about $300 dollars.  I later bought a discounted membership for $210. 

I wondered if maybe sailing was just a chapter of my life or if it was going to become the focal point of my whole life.  One thing was certain: I liked to sail.

Learning To Sail

The Ocean Plan Part 1

The only thing that I knew was that I liked water and that being on my paddleboard was my favorite thing to do. Is sailing really the life goal that I want to pursue?

I checked if there were any sailing classes in Minneapolis. Lo and behold the Minneapolis Sailing Center was offering classes as usual even during the COVID-19 pandemic. I hastily signed up for the Adult Beginner Keelboat 5-class course that would earn me a “Green Flag Certification” at the Minneapolis Sailing Center.

I showed up 45 minutes late to my first class, and earned myself a private lesson with the instructor. In fact, all but two classes I was on the tiller with a private instructor telling me her stories of sailing in regattas.

During the course, I learned the basics of how to sail: how to control speed, tack, jibe, dock, moor, and perform a man-overboard maneuver.

It wasn’t until about three weeks after my last lesson that I was back on the tiller. I wanted to refresh my sailing abilities with a close friend before trying to impress this girl.  I never got to go sailing with that girl, the weather was not ideal for that date, but I’m happy that I was able to go sailing with my friend on that beautiful Friday afternoon.

We walked up, asked for a boat, they brought a boat, we hoisted the sail and set off into Bde Maka Ska on a 90 degree day.  I wasn’t drinking at the time, but I had an edible and my friend was free to drink.  It was a mistake to try to teach him how to use the jib, and a good lesson for the next time I bring a friend.  I think of the jib as something that is nice to have if someone wants to help out and be a little more involved; but it’s by no means necessary to have a good time.

Racing Sailboats in Portland

The Ocean Plan Part 2

I moved to Portland in 2020 instead of moving to Berlin.

I quickly joined the Island Sailing Club and learned how to use an outboard engine. I didn’t use their boats more than ten times and the cost was astronomical compared to Minneapolis and it rained most of the year. But I still managed to learn some new skills and take some friends out on boats.

Myst, Meleges 24

I made a friend in Portland, OR who invited me to crew with her on the Columbia River.

I first raced on Myst, a Melges 24, skippered by Rod Buck in Portland.  I trimmed spinnaker and helped stuff it on the douses.  I would just let it out until it began to luff and then bring it back in just a little bit.  Over and over.  My head was tilted back like I was belaying a climber for most of the races.  Eyes entirely in the boat.  We would win.

I’ll never forget how chaotic the scene was at my first regatta start line.  There were a dozen or so boats and they were so close to each other. I didn’t know what to look at. I was humbled. I couldn’t conceptualize in my mind’s eye what was going on and why our skipper was making the decisions he was making. I started to try to see what he saw in the water and the boats around him.

BVI Trip

In March 2022, I was incredibly blessed to be able to join some people on a catamaran cruise through the BVIs. This was my first taste for cruising and I loved it. We went SCUBA diving twice a day and ate most of the meals on the deck. The sunsets were amazing and so was the weather. I loved sleeping on the boat and had some of the most amazing dreams of my life.

San Diego Sailing 2023-2025

Uplifted, B-29

In January 2023, I hastily decided to move to San Diego where it wouldn’t be raining two thirds of the year. For the first half year, I did no sailing. I focused instead on surfing — a hobby I picked up on the Oregon coast (Seaside + Short Sands Beach🤙). But then I took a trip to San Francisco to go to a frontend software conference and found myself romanticizing about all the sailboats in the bay. I decided to join a San Diego Facebook group I had heard about and post that I was looking for crew.

I quickly found myself on a boat called Uplifted training to fulfill the “bow” role. I was fortunate that Uplifted was skippered by an experienced sailor who was surrounded be veteran racers.

Uplifted regularly raced (and won) on Wednesday night races called Beer Cans and occasionally competed in weekend series regattas. As of December 2025, I am still regularly crewing on Uplifted.

Caravan, Farr-40

Thanks to one of the racers on Uplifted, I had the opportunity to sail in the Long Beach Race Week on a Farr 40. I wrote about it here

Fandango, J-92

Things were going well on Uplifted, but they were not competing in offshore races. I found my way onto a a J-92 called Fandango that competed on these longer offshore races. We would go on to win two Newport to Ensenada races in 2024 and then 2025.

I had a good few years sailing with these guys. Unfortunately sailing programs don’t last forever. Scott ended up retiring Fandango in November 2025.

Dinghy Sailing

Me and my buddy got memberships at the Mission Bay Aquatic Center and sailed a couple of ran-thru ILCA Lasers almost every weekend during the Summer of 2024. This was helpful for developing my helmsmanship.

In 2025 I took a trip to France/Spain and renting a Topaz in Valencia and a Laser Pico in Barcelona for a little daysail on the Mediterranean.

Owning a Sailboat

The Ocean Plan Part 3

In my early years of sailing, I dreamed of owning a cruising sailboat and taking all of my friends out on it for drinks and bbq. I never thought I’d be interested in buying a barebones fixer-upper without a head, cantina, or bunks.

Sometimes life isn’t so direct. In August of 2024 I was given an opportunity to buy a 25 foot racing boat designed by Leif Beiley called a B-25, named Prowler. The seller was a close crewmate and he promised to help me fix her up, put her in the water, and supply me with endless amounts hand-me-down equipment as he owned another, identical, B-25. So purchased my first vessel from one of my racing buddies, at a steal, and she came with a trailer.  Her name was Prowler and she was mine and she was a money sink.

It took a year of work and procrastination to finally get her in the water.

My Sailing Bucket List?

I wrote an early draft of this document and I completed almost every to do that I had listed out.

It’s kind of funny to think that 5 years ago I thought I was too late to the sport of sailing. I laugh at that notion now. I’m a competent crew member on a racing yacht and slowly becoming a better boat owner and skipper.

The following is a rough approximation of my future in sailing, in a way a bucket list.

• Learn to cruise and navigate (ASA classes?)
• Start a racing program on Prowler
• Train the crew
• Spend a lot of money on Prowler
• Win a race as a skipper
• Obtain a 6-pack captains license
• Bareboat charter trip in BVIs, Croatia, and Australia with friends as skipper
• Purchase a cruising monohaul in Mexico.
• Do coastal cruising up to to British Columbia and back to San Diego
• Refit boat and prepare for a Hawaii ocean crossing
• Sail to Hawaii with friends
• Repair any issues with boat in Hawaii
• Sail to South Pacific Islands with friends
• Sell sailboat in Indonesia, Japan, South Korea, or China
• Buy a new sailboat on East Coast
• Practice sailing sailboat and rig it for single-handed sailing
• Do a single handed sail up the Eastern US sea board
• Return to East Coast base with friends
• Plan voyage to France
• Sail across the Atlantic single handed before I die

Gratitude

None of this would have been possible without the support and tutilage of some great sailors.

• Minneapolis Sailing Center and all their donors for creating an affordable sailing program
• Mandy for getting me into the racing scene
• Rod for taking on an absolute beginner to sailing and teaching me to trim spinnaker
• Drew for his friendship and patience
• Scott for all the laughs and adventures
• Jeffrey for his comraderie, inspiration, and invites to crew for other boats
• Mission Bay Aquatic for making it easy and affordable to get into dinghy sailing
• Michael for his tireless help on Prowler and for teaching me advanced sailing techniques