Third Date and Engaged in Key West… and Dragging Random Shit Through the Ocean
What a week.
I got together with my buddy and two friends who have been a couple since after high-school and who I have known since elementary school! Which means these are people who knew me before I had money, a boat, or any common sense. So naturally I put them all on my boat in the middle of the ocean.
We sailed and fished down to the Dry Tortugas and Marquesa Island. Or as I like to call it, “How many different ways can Dave embarrass himself offshore.”
The week started classy though. Engagement dinner at Blue Heaven. The proposal happening upstairs overlooking the street. Romantic, beautiful, birds chirping, roosters crowing.
Oh, and I have now officially decided I have three favorite restaurants in life. Sailor Oyster Bar. Blue Heaven in Key West. And Spondivits. If I ever disappear, check those three places first.
Now let’s get to the sailing part where things went exactly according to plan…if the plan was written by an idiot.
PredictWind absolutely nailed the forecast. Wind, waves, direction, everything perfect. We had 20 plus knot winds on the beam and broad reach. We should have been flying.
We were doing 8 knots.
Eight. On a boat that should be moving like it is late for happy hour.
I am standing there pretending I understand physics. Talking about sail trim like I am in the America's Cup. Meanwhile the boat feels like it is dragging a Walmart behind it.
Turns out…we were.
We look back and see a buoy the size of a mooring ball. We are dragging it like it is part of the boat. No problem, I say, trying to sound like a captain and not a guy who just hooked the ocean.
We stop, cut it loose without getting in the water. I am feeling pretty proud of myself.
We start moving again.
Still slow.
Because now…we are dragging a trap.
At this point the ocean is basically repossessing my dignity one object at a time.
So now I have to anchor in shallow water and go in. Waves about three feet, current ripping, and my friends tie me to the boat like I am a toddler at Disney.
I jump in, swim down to the props, look around…nothing.
From the boat I hear, “Hey Dave…we think it floated away.”
So, I just got tied to a boat, jumped into moving water, risked becoming a YouTube video, for absolutely nothing.
We were back underway in minutes, which is impressive considering my ego needed a little longer to recover.
Trip down was a little sporty. Two-to-three-foot waves hitting us on the beam. We did have quite a few big hits on the rods and manage to catch a 22-inch mackerel which we later cooked and ate like we had just conquered the sea instead of being mugged by it.
We made it to Fort Jefferson right on time and set a perfect anchor, which I took full credit for, giving out high-fives for a successful voyage, obviously ignoring everything that happened earlier.
Next day we toured Fort Jefferson. Amazing place. History, views, seaplanes landing in front of us like it is some kind of tropical Uber.
We walked the beach and made friends with a hermit crab who chose a cashew over a Dorito. Even the wildlife down there eats better than I do.
That night we are playing Farkle, which is basically gambling for people who are afraid of casinos, when we get entertained by a group of massive groupers swimming in the underwater boat lights.
My buddy Jim has his mask on, face in the water, talking to fish like he has known them his whole life.
And these groupers are swimming up, letting us pet them. Rolling over, showing their bellies.
At one point I thought, this is either magical…or we are about to be on the menu.
Next day we head to Marquesa Island. Beautiful, remote, one of those places where you look back at the boat and have a moment.
After everything the past few years…standing on that beach, looking at Ohana, I just said, “I did it. I set a goal and I achieved it.”
Of course, five minutes later we are back on the boat catching catfish and my buddy Jim is complaining like we just insulted his entire family. Apparently catfish are beneath him and disgusting, useless fish.
Food the entire trip was ridiculous. My buddy cooked everything. She had homemade breakfast bread, homemade dinner bread, fresh meals, things with names I cannot pronounce but happily ate anyway. At this point I am basically a kept man on my own boat.
We make it back to Key West, clean up, and I dink everyone into town and show them a hidden gem, the Chart Room Bar. A literal hotel room turned bar where Jimmy Buffett used to play for free drinks.
And yes…perfect ending to the week.
My elementary school friends were there.
My buddy, or better yet my fiancé, was there.
Yes, fiancé.
Yes, it was me who proposed at Blue Heaven.
And yes…it was only our third date.
Look, when you find someone who checks everything on your list, does not yell at you for not putting your seatbelt on fast enough, and has you adding things to that list you did not even realize you wanted in a woman…you don’t wait around.
