I decided not to sail with my friend Tony on his Alaska to Mexico journey. I’ll explain why not in a future post. The next day, the anxiety hit.
Going on a long sailing journey has been a dream of mine since I moved to Seattle. I have made some terrible decisions for love in the past. Had a chosen poorly?
Also, in preparation for the sailing trip, I had already rented my house out from May through August. May was just around the corner. I now had three weeks to either rent an apartment (disappointing - and probably expensive) or buy my own sailboat and take my own trip (expensive).
I waded into the sailboats section of Craigslist. There were dozens of sailboats being sold in the $10-20,000 range. It is currently a buyers market for sailboats. Many boats had been on the market for more than three months. To facilitate my decision, I made a spreadsheet of every sailboat on Seattle area Craigslist that met my specifications: 29-33 feet, working diesel engine, $20,000 or less. I also noted the features that I wanted: lifesling, anchor windlass, swim step, working head and galley. Then I plugged the whole spreadsheet into DeepSeek and asked it to find the best deal and the one that would have the best resale value.
The thing was, I didn’t really want to own a sailboat again. I wanted to enjoy a sailboat for the summer and then not have to deal with the continued maintenance (isn’t that what everyone wants?) Owning a 100 year old home keeps me busy enough with maintenance. I thought perhaps my best plan was to buy a boat, sail it, and sell it in August.
According to AI, the best Craigslist deal for this plan was a rickety looking 33 foot Newport selling for $8,000. However, after calculating in 10% sales tax, plus the repairs and upgrades it would certainly need, even if I could resell it it would still be several thousand dollars net loss. I realized with a sinking feeling that buying a boat was probably not the wisest choice for an unemployed person.
Then I had a creative idea: I could rent a boat!
As I always do in times of crisis, I pulled a few tarot cards.
Buy a boat: 3 of Swords
Rent a boat: Queen of Wands
Something else?: Wheel of Fortune
It seemed like the Tarot was trying to tell me that buying a boat wasn’t a good option. Three of Swords is the card of heartbreak. The Queen of Wands is a positive card, especially for new ventures, so renting a boat looked better. I don’t have any ASA certifications, so I couldn’t charter a boat, but maybe someone who had been trying to sell their boat for months would be amenable to renting their boat to me. I made an ad advertising myself as an experienced and responsible sailor. I printed it out and biked over to the Bremerton Marina office to ask them to hang it on their tenant’s bulletin board.
I waited a day for replies to my ad. Nothing. What was I doing? I felt unmoored.
In defiance of the tarot, I returned to my Craigslist search. And there it was: The Free Boat. Someone in Ballard was offering their Newport 33 for free. The catch was that it hadn’t been sailed (or washed) in almost 20 years. The engine hadn’t been started in as long, but according to the ad, it turned over.
Well, this was something else. The Wheel of Fortune.
I sent an email.