The trip up the rest of the ICW from North Carolina was mostly uneventful. Lots and lots of motoring and many anchorages in small backwater places. The waterway is mostly swampy, muddy water, but it was still an enjoyable experience. Once I got into the Chesapeake, the game changed. The water in the Chesapeake was deceptively calm my first day. There was no wind to speak of, and I had a glassy motor over from Norfolk to Cape Charles on the tip of MD. My goal was to work my way quickly up the Chesapeake and see what I could while still making progress toward Rhode Island. I had a little stopover in Cape Charles to let some weather pass through and to get a little rest. I planned on moving on an early Monday morning, so I moved out of a nice slip into an anchorage overnight, which proved to be a good plan. I was prepped and ready to depart easily from anchor into the lower Chesapeake. The winds were forecasted to be 15 to 18 with some higher gusts. However, I didn’t recognize the significance of a small craft advisory. I had not been paying attention to these details in the weather coming up the ICW as it was never an issue. However, in the lower Chesapeake, it was definitely an issue. I got out into the water, and it was a fairly comfortable ride at first. I turned my bow north, and as the sun started to come up, the wind started to pick up with it. I was seeing gusts upwards of 25 knots and higher. At one point, I saw 32 knots. That’s a lot. The real problem was the waves and chop. What was predicted to be 1 to 2 feet suddenly was climbing up to more like 4 and 5 feet, and the direction of the waves could only be described as “Every direction”. I was having trouble keeping the boat pointed where I wanted to go, which was due north. The winds and waves had a different plan for me. I was being pushed out further and further into the middle of the Chesapeake where I really didn’t want to be and had no business being.

The boat was slamming up and down with so much force that the inside items that were put away with care and thought were flung about the cabin and spilling all over the floor. At one point, something flew across from the port side to the starboard side with such force that it smashed in the wooden louvers on the door under my cooktop. My gas-filled cans strapped to the bow of the boat were popping up and down like ping pong balls, and I felt like I was riding a very large bucking bronco that I could not get off. At one point, I realized that I had crossed into the path of some oncoming fishing vessels. These are not little boats out fishing. These are huge net fishing ships on the Chesapeake that don’t care what the weather is doing and don’t care that it’s pushing a small sailboat into their way. I called out to the boat about to run me down on the radio. “RappaHancock, RappaHancock, RappaHancock, Integrity. I’m the small sailboat in your path!! Channel 16, Over.” There was a crackling on the radio, but no voice. Then the fishing boat behind me belched out some black smoke and turned quickly to their port side. I was probably never in any real danger… but better safe than sorry, right? It was closer than I would have liked. I did get a picture of the same fishing ship, but on a day when the wind and waves were not throwing me around like a ragdoll.

I managed to make it to a safe spot after about 4 hours of taking a beating. I learned my lesson on the Chesapeake. Don’t ignore a small craft advisory. The 27’ Island Packet is capable, but it bucks like an angry bull.

The following days were much gentler, and I spent my time sailing further north. I stopped in Solomons Island for a night. Waiting out another small craft advisory. Now very hesitant and being cautious, I kept pushing further north to the C&D Canal. This cuts over the top of the Chesapeake and connects it to the Delaware. I planned my move here very carefully and stayed in a marina that is about halfway up the C&D Canal called Schaffer’s Marina. They had a wonderful bar and good food. My plan was to leave at 3 a.m. and follow the outward-flowing current as far and as fast as I could. This worked excellently, and I followed the current all the way out the canal and down the Delaware all the way to Cape May in one shot. I pulled into the Cape May Marina, where I was able to stop and rest up and wait for the next leg. This leg was the big one. The outside of New Jersey leg that is open ocean with no really good or easy places to stop, so I needed to be rested and the boat needed to be ready.

As I began my preparation for the long leg, I was working on the basic maintenance for the diesel engine and realized that the raw water pump had finally had enough. I was nervous about trying to keep running the pump with it leaking so much water. This was going to be 25 to 27 hours straight, and I needed to be able to trust the engine. So I scrambled and came up with a plan. Amy, my lovely wife, wanted to help and bring me a spare pump that I had purchased before the trip and had delivered to the house. I was hoping that I would not need it until I got the boat to Rhode Island, but it was time. I originally was going to have her overnight it to me along the route, but the original pump was holding up, so I neglected to have her send it. Since I was only 6 hours away, she was willing to get in the car and drive it to me! I’m so grateful to have a wife and partner that is willing to go to those lengths to help me on my adventures. Thank you so much, Amy! I had not seen Amy since April 30th, so the reunion was a much-welcomed break in the boat life I had grown accustomed to living. It made me want to be home all the more and increased the desire to keep moving north.

After installing the new raw water pump and leaving the cute marina behind in Cape May, I set out from the very southernmost end of NJ to Sandy Hook just south of NYC. This leg of the trip as a solo sailor was the hardest for me. The first 15 hours went by uneventfully, but as the night started to set in, of course, something had to happen. The autopilot was making an awful noise. These wheel autopilots always make an awful noise, so it wasn’t obvious that something was wrong until it would just not hold a course. It kept losing its ability to stay on track. I ended up hand-steering for about 13 hours. That really put a damper on my ability to take naps while doing this part of the leg. At one point, I was so tired that I just locked the wheel straight and hoped for the best for a quick 10 minutes of shut-eye. That went okay when there were no following waves to push me off course, so over the next few hours, I managed to get a couple of 10-minute “rests” in between putting the boat back on course.

As the sun came up, I was just turning into the sandy hook area where the Coast Guard station is set up on the back side of the peninsula. I motored to an anchorage, dropped the hook, and passed out.

When I woke up a few hours later to a hot cabin and rolly conditions, I looked at the clock and it was 10 a.m. I had planned to make my way into NYC harbor starting at 10AM and I didn’t want to miss my window for timing the incoming tides and currents as that area looked particularly challenging. I quickly weighed anchor and headed toward NYC. The sail into the main harbor was uneventful and enjoyable! The huge ships and all the ferries zipping around like ants made the lack of sleep melt away. With all the boat traffic, you have to really pay attention. I made my way over to the Statue of Liberty. Such a cool experience to be able to sail my own boat right up to such an iconic landmark. I took a few selfies and then anchored right between the statue and Ellis Island. There is a designated anchorage there, but I think the sightseeing boats deliberately try to make it more uncomfortable so that you move. It was easily a terrible spot to anchor for very long. Fortunately, I was exhausted and fell asleep riding the waves to slumber. I was anchored for a few hours here to time the currents again around NYC. There is a channel called Hells Gate, and it has a current that is close to 4 knots. If I got that wrong, it would be a disaster for my slow-moving, underpowered sailboat motor to even attempt. So I had about 4 to 5 hours to wait until the current shifted.

Once the time was right, I weighed anchor again and started making my way across the most choppy and confused water I have seen. It was giving my bad Chesapeake day a run for its money in challenging waves. I crossed over the 1-mile-across from the anchorage to the East River and hit the outgoing current just right. I was able to calmly and quickly sail my way out of NYC and right into the Long Island Sound. I was rewarded with some amazing views of the city and with an amazing experience.

Now I’m sitting at another Safe Harbor Marina where I am a member and taking full advantage of the free transient slips. I have used that bonus about 8 or 10 times now on the trip from Key West to home. It’s been a lifesaver and I thank them for having that amenity in their offering. I have about 120 miles to go and the weather today has me pinned down again with a small craft advisory. I have learned from past experience. I’m going to wait and get the weather right and zip home as quickly as I can.

My final 3 days of the trip ended up being different than the days before. The weather was being uncooperative, and my normal pattern for the trip was to get up early and make miles, then settle in for the night. However, the weather was a bit too strong for me on the first of the last 3 days. It settled down in the evening, so I left the dock around 6 p.m. and made a run for as far as I could before anchoring. I was able to make almost 25 miles before I settled in for the night. That was the difference between getting in late on Sunday vs. getting in early afternoon. Sometimes you just have to go when the weather cooperates and not pay attention to the time. Be safe and go.

Another fun thing to happen was that my friend Dave was actually only a few miles from a marina that I was staying at while sailing home. I was able to get to spend some time with Dave and his wife, Farrah. We had a nice dinner, and the next day they came back down to hang out, which was a great break in the monotony. It was a wonderful way to spend the last few days of the trip.

I then rounded Point Jude, which I was worried would be heavy seas and weather, but it turned out to be very calm, which was a great surprise for the sail home. It took me no time at all to get to the Jamestown Bridge and feel like I was in home waters. I turned the motor off, and I was able to sail into the harbor under full sail under some of the most beautiful clouds and sky I had seen on the trip so far.

It took me about 2 months to make the entire trip once I started going. I had set out to buy a boat in Florida, sail through the Keys, and then bring the boat home up the ICW. That is exactly what I accomplished and so much more. I enjoyed having my sister on the boat on the trip south to Miami, and I enjoyed having my friend Joe on the boat for a couple of legs. Out to the Dry Tortugas and then back to Key West. He then joined me for the ocean jump across from Ponce Inlet to Charleston. We experienced some crazy squalls and some intense boring parts of the ICW. He then kept me sane with updates on weather and waves for the remainder of the trip. It was a big help to have support. My wife, Amy, who put up with my being gone for such a long time to follow this dream of sailing this little boat home. She supported me every step of the way and even saved the day with bringing me a pump that had failed. I couldn’t have done it without her support.

There were many moments being by myself that I wished that it was going faster, but there was never a moment where I felt like I wasn’t enjoying myself. The entire trip with all the amazing, scary, and boring moments was incredible, and I’m so happy that I took the time to do it. I really enjoy being on the water and being on a sailboat and completing a task that I set out to do.

Now to start planning the next sailing adventure!