We chose to take our New England trip this year, because we had to cancel our plans to do the trip last year due to work-related reasons. So many stars had to align on land and we constantly had to manage schedules and commitments to keep the 2+ weeks open and clear. In the end, we still missed out on a couple of personal activities and calendar items, but that was part of the sacrifice. This post walks you through a number of important items related to the planning and preparing for the trip.

This would be the first time we have spent more than a few days aboard the boat. I want to tell the story about someone that is still working a full-time job, is maintaining their boat, but has dreamed of taking a long vacation on their boat. In reality, we have worked really hard on Skyward to get it ready, and we are tired of looking out these portholes and wishing we were somewhere else!
Destinations, timing, reservations and Dockwa
Based on feedback from friends, we knew we wanted to go to Cuttyhunk and Martha’s Vineyard. We’d already been to Block Island, and so we crossed that off our list for this trip. Also, we really wanted to go to Provincetown to experience sailing in Cape Cod and going to the tip of Massachussetts. The biggest attraction was going back to NYC and participating in the Sail250 event. I put it all in a spreadsheet showing each leg, trip length, and target destination.

With so many stops, I couldn’t imagine doing this trip in under 16 days. Leaving on 6/20 just after high school ended and coming back on 7/6 seemed like a tight timeline. Dockwa made it all possible, but we started reserving mooring balls between early March through April which meant we had to be committed or otherwise cancel because mooring fields book up quickly once Dockwa opens them up for reservation. I’ll revisit an interesting timing issue that we came across while on the trip in a future blog.
Setting up the boat for offshore
The work on Skyward really intensified in the days and weeks leading up to departure. I installed jacklines (yellow) that run from the bow to the aft deck. I also installed dedicated control lines (red) on both port and starboard for my adjustable backstays which made deploying them more straightforward. This took some engineering and trial, but it did work well when we were out in the ocean.

A funny not-so-funny story is that I went through my inventory of flares and decided it would be wise to have at least 1 rocket parachute flare. Of course, this was last minute thinking. I found one online, purchased it, and had it shipped to me priority/overnight via FedEx. I’m telling you, it was a real trip, and it involved me driving to a FedEx distribution center because they would not deliver it without a signature as it was labeled “Explosive”. Word to the wise, if you chose to buy one online, beware of the issues in shipping and think ahead. About a week after returning from the trip, I happened to browse the Annapolis West Marine and found that they carried about 15 of them in the store!
After tying up the anchor to ensure it stays in place if we got heavy seas, I spent some time trying to tighten up our bowsprit. The bowsprit is a very nice, fixed, stainless steel tube which sets on our port side anchor roller. We had Kato Marine modify it a few years ago to avoid interference with our then-new UltraMarine anchor. Unfortunatley, there was a different in diameter between the anchor roller holes, the bowsprit mounting holes, and the bolt which fastened them together.

Those few millimeters of gap created a bit of rattle whenever we hoisted the spinnaker. I found some custom washers on McMaster which made the apparatus solid. NOTE: Whenever I type “M” on my search engine browser, the autofill word is “Mcmaster.com”.
We set up the removable inner forestay with our hank on staysail. It was all rigged up for a just-in-case situation. I don’t want to be caught offshore with a situation having to rig this up on the deck. Some day we will convert this to a removable furled staysail.
We most of the remaining spare parts we had been storing at home on the boat. We pulled them off during the deck replacement, and I thought it was a good time to bring them back. After the diesel was filled up, we also filled the water tanks – more on that later.
Fixing and improving things
For fun, I picked up a couple of Ruuvi Pro sensors to monitor our freezer and refrigerator temperatures. Those things came in real handy on this trip, and we could see when we had a blip or a trend in the wrong direction. We caught the freezer temperature rising over night, and we troubleshooted it quickly the next morning.

Then we got some professional help to fix the aft window which started leaking in June. We pulled it out and had it completely re-built with new acrylic and gaskets. Prior to re-install, I also had to repair some gelcoat from around the window frame. We replaced an original closet light fixture that finally died and hung up some fruit baskets which worked very well on the trip.
The freezer stopped working, the generator overheated and our Sprayhood Extension frame cracked all just before the trip. Even better, our water tanks sprung a leak while filling them for the trip. There were boat demons working against me as I spent several days and nights upside down, drilling, cutting, and prying on things. We actually got everything working enough to take off. We took off with one water tank (110 gallons) working and 4x 7 gallon plastic jugs on deck. Running the numbers that seemed plenty to get us going.

I almost forgot to mention that within a month of leaving, the hydraulic Navtec backstay adjuster failed again. We had oil dripping on the deck, and we were both disappointed to see that but also struggling to find answers. Back again it went to our friends at The Rigging Co. – I even dropped it off at their office during the night; they were very accommodating to us. A long time ago, Jimmie advised that they should build us a backup stay just in case the Navtec were to have an issue in the future, and that came in handy. After doing some careful research and analysis on the backstay adjuster, they rebuilt the unit with a kit from the factory, and they turned it around for us. Thankfully, it is now re-installed and working great and reliable.
Weather, and weather service and routing
We had been checking the weather days in advance for our departure date. We knew the trip up to Cuttyhunk would be a good couple of days, maybe 3 days and we wanted the best possible weather window. With work and home life being so busy, we felt that we just couldn’t spend enough time studying gribs and all of the various apps plus we felt that a lot of the models contradicted each other and we didn’t have time to find the truth. I called upon Chris Parker at MWXC to give us a boost of knowledge and confidence about our departure. I had used Chris on previous Antigua trips, but never directly as a boat captain.

Working with MWXC was simple, and I just bought 5 credits and East coast weather reporting. I plugged in my boat and destination information, and they reached out like clockwork. The people I interacted with were competent, clear about their advice, and they responded in a timely manner and often. I highly recommend anyone in a similar situation to give a professional weather service a try. I would do it all over again if I was in the same situation.
Insurance, provisioning, and testing
About a month before the trip, I thought about our insurance and how we were restricted from sailing with the boat outside certain boundaries. To my delight and surprise, the insurance company lifted all of the restrictions and notified me that I was free to move the boat anywhere that I want along the US East Coast and coastal waters.
Days before departure, we stocked up on drinks, food and all sorts of other provisions. We left the refigerator and freezer running during the week prior just to keep them cold and operating and to monitor their performance. That turned out to be a good move.
Engine: Smoke on the Water?
Our Volvo Penta TMD31L-A is a 4-cylinder 100hp diesel that has started and run very well the past couple of seasons thanks to some great maintenance work we’ve done. I’ve become more concerned lately as I continue to see an increased level of smoke coming out of the exhaust.
We started to study this more deeply before the trip and during the trip. Our theory is that the engine is having incomplete combustion issues due to the fact that the exhaust side is occluded with build-up both on the elbow but also the turbo. The plant for the Winter is to rebuild the turbo and replace the elbow.



Is the World Against This Trip?
There are so many events and issues that culminated prior to our departure – too many to list. It felt like the world was against this trip. We pressed on nevertheless as you will (hopefully) read about in future posts.
The final event that tested our resilience involved water. During all of the chaos and activities leading up to the departure date, going to and from the boat often, we accidentally left the saloon hatch partially open one evening. Yes, it poured rain that night and soaked the entire saloon area. Luckily, we came again to the boat the next day only to discover the aftermath, and then we cleaned everything up. I am amazed that there was no damage anywhere.

This might not seem like an upbeat post, but I wanted to share the realities of our preparation and planning. I am quite proud that we were able to get off the dock successfully and navigate so many issues. We pressed forward despite the forces working against this trip, and once you see the things we accomplished, you too will agree that it was all worth it.






