Misadventures in Key West

I am not making this up. The following account actually happened last night here in Key Weird.

We woke to winds out of the north at 15 to 20 knots. We decided it was not too rough to take the dinghy into Key West Bight and spend the day on the town. By the time the sun began to set we found ourselves looking out over the harbor at huge waves. The wind was now a stready 30 with gusts to 35. The trip back to our boat looked impossible.

We spoke with some locals liveaboards who were all standing around the dinghy dock either waiting or preparing to attempt it. Some said, “No way I’m going out there.” We watched one single guy attempt it, only to turn around and come back in. I was willing to give it a try, but Kim said, “No way I’ going out there.”

As we walked the docks we decided to try to find someone with a bigger boat who might be willing to give us a ride and tow our dinghy behind. We found one taker only, Crazy Bruce. Bruce has an old barge type junker about 20 feet long. It sports 3 outboards on the transom. All are way too small for his boat. Turns out the starboard side engine didn’t run. The port side engine was “having problems”. Only the center engine actually ran properly. It was a 4 horse-power Mercury.

So…. we set out with our dinghy in tow, along with another dinghy that Captain Bruce had rescued from certain destruction after it broke free of its mothership. I wish I had pictures of this sorry sight, but all of this took place in the dark. As we cleared the sea wall at the Coast Guard station, the wind and waves hit us full force directly on the bow. We stopped! The engine was running and in gear, but we weren’t moving. Bruce gunned the little motor and we started making way at about 1/2 knot.

It was slow and laborious, but it looked like we’d make it eventually. We managed to get 3/4 of the way to our vessel when it all went wrong. A sailboat had drug anchor and was drifting into the channel. “That’s my buddy’s boat,” yelled Captain Bruce. “I gotta save it.” So we gave up all our forward progress and plowed over to the runaway boat. Bruce drove his barge right into the transom and rammed it hard. “What the hell are you doing?” I screamed. Bruce said he was going to push it up on the anchor and give it a chance to set. We rammed the boat several more times. Bruce asked if I was salty enough to jump aboard it. I was wearing flip-flops, I was cold and wet, and I’d had a few drinks. (recipe for disaster). I told Bruce I wasn’t about to try to board it.

Then his outboard came to an abrupt halt. It just locked up and quit running. Problem? We wrapped a lobster trap in the prop. We drifted away from the sailboat a bit but caught fast as the pot held us.Now we are stern-to and taking waves over the transom. Bruce yells he has a knife somewhere on board, Help! It’s pitch-black dark, blowing like stink, and we crawl on our hands and knees digging through assorted junk looking for a knife. Kim finds it. Bruce cuts the pot loose but some line is still wrapped. Now we are drifting free with no running engine. We are headed for the sea wall at an alarming pace.

Bruce switches gas tanks to the port side engine. He pulls and yanks and it doesn’t want to start. We are rapidly approaching a concrete wall in large seas, in the dark. We turn sideways and our dinghy comes alongside us. Kim and I grab it and prepare to abandon ship. the motor starts. Kim thanks Jesus. Bruce gives the motor all it can handle and we very slowly start putting distance between us and the wall. It looks like he’s heading back towards his buddies boat. I say “No effing way dude. Just get us to our boat.” He say okay, he understands. He alternately laughs maniacally and cusses the Gods. He threatens to kill a lobsterman. I thought he’d howl at the moon at any minute. We pass the sailboat that appears to have stopped drifting and the motor starts to cough. Kim prays to Jesus again. It revs up, it dies down. Bruce screams to the heavens.
He steers towards the closest boat with a plan to tie off, switch back to the good engine, and attempt to clear the line from the prop. We almost make it.

The little engine dies about 15 feet short of our goal and we are adrift again. Back we go towards the seawall. It was probably my imagination but it seemed like the wind picked up even more. Bruce is screaming at his motors like a madman. He is slashing and cutting at lines. Dinghy lines get in the way and he threatens to cut them loose. The wall looms large in the darkness. Once again we prepared to abandon ship, but the good motor fires and we veer away with 20 feet to spare. Back into the fray we go, pounding and bouncing and splashing once again towards our vessel.

As we finally approach, I ask how we are going to go about this. Bruce has me take a line up on his bow as he nears our transom. My weight up front causes waves to break over. Kim is in the floor on her hands and knees. He gets me close and I jump onto our swim platform with a bow line in my hand. I tie him off and now we have to get Kim aboard. She is terrified. Bruce times the waves. Kim tries to move and he screams at her. Wait. Not yet. Now! Go!! Jump!!! I’m there to grab her and we stumble together through the transom door and into our cockpit.

Bruce declares he needs to leave the other dinghy he’s towing with us, so he can rescue his buddies boat. I didn’t want it, but I agreed. No time to think or argue. We tie it off and untie Bruce and he wheels off into the maelstrom to do another good dead. We can’t see him for long. He’s obscured by the waves and the darkness. He had promised to return to pick up the extra dinghy, but he did not. I still have it.

I went for the rum locker but Kim had beat me to it. She was shaking and trembling in the salon. We were both drenched and beaten, but now safe aboard our own vessel. Once she settled down, I went to our bow and let out an additional 50 feet of chain to our anchor. It was a long sleepless night after that. The wind is still howling here. We are holding well though. Some of our neighbors were not so lucky.

When the wind dies we’re getting out of here. It really is not a good place for cruisers.

If something like this ever happens to you, don’t let Captain Bruce give you a ride. Lock up the dink and get a hotel room, sleep in the bushes, whatever.

wind in the anchorage of key west

35 thoughts on “Misadventures in Key West

  1. Diane

    I believe you! That’s the type of story you just can’t make up!!! We were in Key West for about a month last December and experienced similar circumstances with the weather. We bounced around different anchorages until we found one that was fairly protected and we finally got a good nights sleep. We anchored for one night in the spot you are currently in, according to your map. Our anchor dragged {{shudder}} and my Captain was up all night keeping watch. Try moving to the outer end of Flemming Island (saying that you are on in inside end of Flemming Island) it has a little bit more protection from the wind. You would be a little farther from the dinghy dock but… I also agree with your statement about Key West not being friendly to cruisers… if you are hanging off the hook which we always do. I think it might be a little bit different if you rented a mooring ball but we couldn’t afford that. Our best experience in the Keys was at Key Largo. Love, love, loved Key Largo!! PS I’m enjoying following your travels! Fair Winds and Following Seas to you and Kim.

      1. Diane

        We were on a mooring ball at Camp Pennekamp for one night and went snorkeling at the reefs. Then we moved over to the Gulf side and anchored in Dolphin Cove. They have a very nice dinghy dock at the City Hall, Sheriff’s Dept, etc. Fresh water available there and a grocery store within walking distance. The Captain likes to lobster dive and the gulf side was very generous with the “bugs”.

    1. Tina

      Wow what a night and we just brought home a old houseboat two days ago which is rafted to us. We spent the better part of last night trying to make sure everything was secure at one point our dinghy was shoved under our dive platform we could have lost our engine had I not been a light sleeper and heard something wrong. We fixed it by pulling our precious little dinghy alongside our sailboat
      I know Capt Bruce he has a good heart he is a true Salty Dog as true as I have ever known.
      He loves giving a advice on how to live out here
      I’m glad you made it back safely. You have to be hard core to live out here. We will be looking for calmer waters very soon.
      Dave and Tina S\V Oremae

      1. Ed Robinson Post author

        Hi Dave and Tina! btw, we didn’t drag any, we just let out more chain. I saw you up and about as well as the sailboat behind us in the wee hours. tough to sleep for sure.

  2. Bill

    Sounds like a true Keys misadventure, and Bruce a regular Keys critter! If you have any questions about cruising around key Largo, get in touch.

  3. leonrenaud

    Glad to hear it ended as “An Adventure” because it sounds like it came real close to being another Mystery of the Devils Triangle!

  4. Matthew Connolly

    Beware of Crazy Bruce. Some friends of mine hired him as crew for a crossing to Puerto Rico. It did not go well.

  5. Bert

    A warning to my fellow sailors: Do not go out on the water with Crazy Bruce, in any sort of weather. Do not trust anything he says. We have friends who had very disturbing and dangerous experiences with him.

  6. karen butler

    Capt. RL & I on the s/v Last Call are anchored behind, beside or how ever the wind is blowing, to Leap of Faith. We witnessed much of your misadventure from our cockpit. We made it back to our boat just before sunset and it wasn’t pretty. We were soaked and our dinghy was filled with water. We were hitting wave after wave head on the entire way. We watched the sailboat dragging anchor first, then saw as you were being towed out. What a night is all I can say! Glad you made it back to your boat,

  7. Jamie Sorenson

    As a couple of future live-aboards, these stories are the grit on the sandpaper for us. It’s the real stuff. This is the type of thing you can’t get living in our suburb. No matter how hard we try, the best we can get is a couple snitty moms arguing at soccer practice. What I admire most is the apparent camaraderie between cruisers. It’s similar to what I’ve experienced, working with the RV community. Give a hand when you can. Don’t know Crazy Bruce, but sounds like his heart was in the right place. Sure, part of his brain may have been left elsewhere over the years and he’s yet to claim it, but whatever. You guys are safe, he made it, you’re getting a bazillion views, and it’s one more rum-soaked tale to tell.

    You two are truly an inspiration to Danielle and I, and if you’re still out there cruising when we hit our retirement date, we’ll look you up. Thanks!

  8. Jean Baillargeon

    Glad you made it safely back. One note «drug» is not past tense for drag. «dragged» is past tense, «Dead» is not deed. I guess the dinghy ride shook up your spelling too !! 😉

  9. S/V Namaste

    Just read this account of a normal cold front passage in Key West. As a long time live aboard sailor I’ve got to say, you guys are total neophytes to the reality of respecting mother ocean.

    First off “Crazy Bruce” did you a huge favor even offering you a ride. Had it been me I would said “get a room”. The fact that he had redundancy in outboards tells me at least he thought and planned ahead. Obviously you guys did not.

    Second, did you even think to check out wind reports and consult with the locals before you left your boat? Us locals would have told you stay with the boat, put out an extra anchor, and stream Netflix.

    Though you enthusiasm for this lifestyle is admirable your preparation and planning is in two words “piss poor”. Do yourselves a big favor: get smarter or give it up!

    1. Ed Robinson Post author

      Such an unpleasant response to a fellow liveaboard! We’ve spent roughly two thousand nights at anchor. That hardly qualifies us as neophytes. Yes, we made a mistake that one day, two years ago. Hopefully others can learn from our experience. I’d also add that one bad dinghy trip in six years isn’t a bad ratio. I’d wager that anyone living at anchor in Key West fulltime has had many bad trips to and from shore. We try to “get smarter” every day. We have no plans to “give it up.”

  10. Capt. Seth

    Good ol’ “Bad news Bruce” I would trust him to help a fellow sailor in need evertime but I’m sure that his methods would be extremely questionable!

  11. marie

    HAHAHA We call him Bad News Bruce. What a trainwreck. I met him shortly after his last prison stay, in Summer 2015. He’s the reason I left the boatyard. I wonder if he’s still alive?…


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