Motor Sailing the Great Loop

Started the loop with zero knowledge. First boat, first boat trip. Chose to do the loop because I bought the boat at City Island Yacht Club in NY. I thought it would be a good idea. Some basic research into "The Great Loop" seemed like the exact kind of adventure I needed. Getting out of the forest for a bit was freeing.

Since June 28th I have learned many lessons. Some concrete and difficult, some philosophical in nature. Starting with the former owner we motored through Hell's Gate getting up to 8kts. We rounded Manhattan and Dave jumped off on a dock in the Bronx.

After taking off on my own, I first learned some anchoring techniques on the Hudson River. Nearly catching the boat on fire from a combination of poor electrical skills and lack of knowledge, I fried my first inverter. So I learned some shopping logistics and how to use an Amazon locker to receive a new inverter. It was a slow start in the Bronx. Three days later I was learning to raise/lower sails and some basic boat handling.

With help from a crew at Hop-O-Nose Marina in Catskill we unstepped (took down) the mast. I built some wooden crutches using their tools and resources and started back up the Hudson Albany. In Albany I happened to stop where there was a reggae concert starting. That was great except for the 6' tide. Ask for the full story. Then to Troy for my first lock. Then up the Erie Canal's first 5 locks, the elevator for a few lessons in boat handling. The Erie Canal was long. They let me stay there for a couple nights in Lockport in a small area adjacent to the lock. Ask me the story.

From the Erie Canal to the Mohawk and Seneca Rivers after an eventful ride on the Oneida River and Oneida Lake. Ask me the story. I continued on to Tonawanda where I docked for a couple nights. I took an uber from my dock to Niagara Falls, walked across into Canada and walked back and through the entire Niagara Falls Park. This was a great experience for me. It was a quick trip into the Niagara River and on to Buffalo. Then I failed trying to motor under the Peace Bridge for 5 hours. Finally a Seatow boat came up to me and said it was impossible with my little 6hp Tohatsu outboard. Ya don't know what you don't know. I recovered quickly the same day as the last boat through a lock to navigate past the Peace Bridge.

Arrived in Buffalo and was overwhelmed at how cool it was to dock downtown in a major city. From Buffalo to Cleveland and a great stop where I nearly got crushed by a barge after watching a great concert from the water. Now I know why no one was tied up in that area. A public dock was available less than a 1/4 mile away. Ask me the story.

Entering the lakes was a big deal to me. It was the first time I saw any lake that size. It was challenging underpowered and no mast. A few folks used the word crazy. Might have heard something something, "death wish" something something. Then some guy raced his little John Boat past me at some point and set a record doing so at 71 yrs old. Robert did me a huge favor. He showed bridge tenders, dock and harbor masters and the larger boating community that anything is possible. So rather than try and stop me, I was mostly prayed for, encouraged and given a ton of local knowledge along the way. Nothing replaces local knowledge. But encouragement and knowledge are never enough to do something big. Sometimes you have to confront everything inside as well as every condition imaginable. Most often hurdles become blessings. I got stuck in several places after narrowly avoiding disaster. Lake Erie was a long ride. Exciting but long. I used the time and my cameras to work inside the cabin for hours at a time on auto-pilot. It was Lake Erie where I learned how to find places to hide from wind and wavefronts. Oscodo on Lake Huron taught me this after a brutal night of holding on all night in bed. Waiting for weather windows was difficult. Stranded at marinas for days, as many as six days in a row in two places. Wanting to leave. But this was also where I met some lifelong friends. I spent my birthday in Alpena Marina with what are now lifelong friends. Ask me about the Road to Nowhere!

I took chances, did things I should not have done and survived a few situations that I just didn't know were so dangerous until much later. It was perfect. Finally rounding Mackinaw City after being stuck in thirty degree weather and hitting rocks the same day trying to take a short cut were indicative of the journey to that point. Rounding the Northern tip of Michigan was a thrill. For days I walked to a nearby point and looked across to the Mackinaw Bridge that I needed to pass. But that area was relentless with records winds before I got there over ninety miles per hour. I crossed Lake Michigan under the most perfect surreal conditions imaginable. From Ludington to Sheboygan. Cheboygan was a previous stop for a weather window that was really great. Great people and a great wall to dock. Farmer's markets are really great. Time your stops around them if you can so you can get fresh bread and vegetables. Or great distilleries as was the case in Troy New York where they had the largest city farmer's market I had seen. Ask me for more stories in Troy. Absolute pristine beauty (South Manitou Island) and shear terror was my experience in Lake Michigan as I slowly moved down to my exit point and a huge personal milestone.

Going through the lock and arriving in downtown Chicago was extremely emotional for many reasons. Going down the Cal-Sag, navigating the Illinois River and meeting a former neighbor and new friends in Peoria was epic. We partied pretty hard. Then I hired a local mechanic to do some routine maintenance on my Tohatsu and learned to never trust anyone else with anything on your boat. Be prepared if you can to do everything yourself whenever possible.

Three weeks later, $2,700 in a new 9.8 MFSC was my first indication that I would run out of money quickly. At this early point everything that could go wrong financially had happened and it was going to get worse. I had no idea how good I had it on the Erie Canal. As marina prices climbed the further I went South, navigating the Mississippi was a welcomed distraction. By the time I left Paducah an awesome and historic town, I reached Lake Barkley and Kentucky Lake. I had just navigated the Ohio and Cumberland Rivers and finally acquired warmer clothes. Some friends were far ahead after my Peoria weeks and I finally caught up, passed and as a result arrived in Carrabelle early due to another weather window closure.

I had just dodged a storm on the hook at Dog Island before entering the port. Some local legends gave me advice, a place to dock for free behind some shrimp boats (more stories) and I spent Thanksgiving happily eating stale Doritos and a sausage sandwich I made from something I found at Family Dollar store on the boat. Actually, I worked all day. It was super productive but my normal is going to at least two Thanksgiving feasts with untold family blessings. My Carrabelle stay was well protected and I got an extra fuel can. To this point I was very well protected in every situation. Carrabelle was cold for a few days, in the thirties. The Full Moon tides had my boat on the ground during the day. I could access town by climbing up a broken down dock, through a piles of old marine debris and into the shrimp boat yard. I was right in town though and there several really fun nights. This is where I started a new community on X where I finally started sharing what I've learned and some of my personal experience. It's called, "The Modern Looper" for folks who are working, sailing, motoring and want a place to ask questions, provide insights and learn together. Check it out. Before leaving Carabelle, Fl. I wrote, "I'm aware that it's likely fear driving me forward at this point. Financial fear, wave height/period and wind fear. Still not really knowing what I'm doing is on my mind as I plan to cross the Gulf. It's all doable and I'm assuming many have done it in this size boat. But uncertainty awaits 50 miles offshore. I'm here for it and I'll be sharing my stupidity, luck and what I've learned. Also, I'm already planning to sell Leandra, my 25' Masthead Sloop soulmate on the water. She's amazing and unstoppable.

Fear didn't really come until around 8pm. The wind picked up, the boat started moving fast. 6mph at first as the waves started to build. I remember making a video of a magical Sunset as the Full Moon rose exclaiming that I was likely in for a magical night. I was thinking of how wrong people were about my Lake Michigan crossing. They were right but wrong about my exact crossing. This time I had waited a week for the exact right conditions which changed in about an hour. The front that I waited to safely pass stalled ahead of me and the front that I left in Carrabelle picked up speed. I'll paste what Gemini explained to me when I later asked, "WTF just happened!"

The crossing felt like my Mom and the former boat Captain's Mom, Leandra were both with me. But instead of the usual protection I felt from my Mom, the two of them were hell bent on delivering all of the excitement and adventure I had hoped for in a neatly packaged 13 hour nocturnal jet. They were with me but they were having fun watching me hold on as the Gulf got big, waves got square and my only option became holding on. It was too rough to put gas in the tanks. So I kept the jib flying which provided a slice through the waves that I needed. But still all I could do was hold on. I had been up since 3am trying to get my boat off the ground. So the other thing I did was collapse on the floor, twice from exhaustion. When day broke I expected it to calm down but it wasn't until 9am that I could even think about turning east and losing my sailing ability from a due East wind. I had just travelled 100 miles in 13 hours veering offshore an additional 10-15 miles. So there I was trying to figure out how to get to land. I couldn't motor into the waves because the prop wouldn't stay in the water. I couldn't sail directly into the wind. I tried various tacks North and South but each tack only aimed me to Cuba or Steinhatchee in Florida's armpit. I'm laughing as I write this because I know it sounds like a great sea adventure but it was really just a novice that got handed a can of opened whop ass for the first time. I decided that I must do something as I was being blown further out to sea. I had left Carrabelle with one thing that I just took a chance on not having enough of, water. I didn't have enough water to spend a week out in the Gulf waiting for another window.

I decided the take my circumstances out on the motor. I would use the motor until the prop came out of the water so many times it would break. So I started motoring into the waves. That's when I learned a lesson that I didn't process until today in Clearwater. Sometimes you must take extreme chances to achieve extremely good results. Nearly as soon as I started motoring, the waves started getting smaller. The ladies had not only given me the adventure of a lifetime but also a lesson in letting go and going for it without fear. For the next 9 hours I motored safely towards shore. For 8 hours I still didn't see land. Then Land Ho! It felt like a movie. LOL

I motored past the crab traps at night, navigated the channel and arrived at Anclote Key, the first place I could anchor in my float plan. It was blissful. Of course a day later a freak lightening storm scared the absolute shit out of me. It was my first lightening storm and the boat rocked more than it did at Oscodo, Mi. At one point I called the USCG on the phone and gave them my coordinates. Shortly thereafter they issued a new weather bulletin about the storm. I heard multiple may days and large vessels turning back to harbor. I needed water and everything calmed down for my trip through the tight channel past wrecked and grounded sailboats into Tarpon Springs Marina. Oh and here's another lesson I learned. When you arrive in a new port, ask the folks at the marina where the best food and things to do are located. They will often tell you of a place with great food but you want to ask about bakeries. Go there, buy the harbor master the thing they mention that's great about the bakery. In fact, buy two. Take it to them humbly and tell them you appreciate their help and hospitality. The magic will find you.

Tarpon Springs was unique. A sponge dock town ruled by Greek mafia. Laughing I say this but that was the vibe. Four non-Greeks working downtown, two skaters at the dispensary and some boat crew. I had a gyro and cannoli. I also found a bar that would sell me Guinness out of their fridge. I took a short ride across the channel to get fuel and ice and met some guys who were working on a Christmas float. A pontoon boat with a Jeep on top. I packed the cooler and headed towards Dunedin for an easy night just South of the Causeway.

The next morning I woke to wind. I had left the cabin door open even though it was in the fifties. The wind was picking up but I was in a good position considering all things. But then I realized the boat was perpendicular to the wind. This is not a good sign. Only a really strong current could cause the boat to be sideways in 15kt winds. Or in my case, the boat was silently dragging through mud until it wasn't. I was up assessing the situation when, "thud" I was aground. I started the motor quickly and it easily powered me off the sandbar and I motored back into the narrow channel. My anchorage only provided a foot of water under the boat so the margin for error was already tight. So without coffee, I sailed to Dunedin Marina for safe harborage to make repairs to the front anchor line guide. A lady who I later learned was emboldened possibly by her sexual relations with a Sherriff, yelled at me to go away. I motored to some broken down docks that had been destroyed by hurricane Helene. She left me alone mostly because legally she had just put me into a very tough situation illegally. Read up on safe harbor laws.

Got the repairs done, inspected my anchor line and got back underway unsure where to go next as the tide was too low to go into Caladesi Island State Park as I had planned to do later that day. I used a heavy dose of common sense and found the place I am anchored now, Clearwater Beach Causeway Anchorage. Last night I visited my first real grocery store in months. It was surreal. I'll probably head back over there tonight. It's a 3 minute paddleboard ride to shore. This place is a blessing. Glassy water, easy shore access, friendly sailor neighbors, Christmas lights, tourist boat fishing and party tours passing by, it's Florida. I made it to Florida just a few hours from where I was born.