Autobiography - More Sailing Stories


I have endless sailing stories so I will try to be selective. Having children helped me find sailing opportunities closer to home. Priscilla pointed out I was spending every Saturday and sometimes entire weekends sailing in Chicago when Lake Bluff had a perfectly good yacht club five minutes from our house.

The Lake Bluff Yacht Club was a Sunfish sailing/racing club located at the east end of East Scranton Ave on the beach of Lake Michigan. We lived at 206 East Scranton Ave so this was quite convenient. I went to the beach and saw a posting with a post office box for the LBYC. I sent two letters requesting someone contact me regarding membership. Crickets. I went to the beach on the Sunday race day and approached one of the racers as they came ashore. I asked how I could become a member. This was Jack Sheppard. He finally got someone to call me. I raced with the LBYC for over 20 years. I was the commodore and then became the membership chairman for 15 years. It became so easy to become a member of the LBYC that we had to increase the membership limits. Priscilla and I are still members 35 years later.

The Sunfish is a one person, one design sailboat with a lateen rig. The boat is 13’ long and weighs 135 pounds. I bought a used boat from a local club member for $750. I started at the bottom of the fleet as most new comers do. I read the book Successful Sunfish Sailing by Derrick Fries. I read the book 10 times and took notes. I created a set of laminated notecards based on the wind and waves conditions. I started setting up my boat to maximize the speed in each condition. I creeped up the fleet and became fleet champion two years in a row in 1986 and 1987 and won the Commodores Cup in 1987. It was a very blowy day and everything came down to the last race in the series. I capsized on the first leg but got the boat back up quickly and won the race and the Cup. The tradition was to mix beer and champagne in the trophy and pass it around to all the racers to have a swallow. That is one tradition that will not repeat. Years later the LBYC invited Derrick Fries to make a presentation to our fleet and I met him and thanked him.

Becoming fleet champion required showing up. This was a challenge when I was taking the family camping on weekends. We would depart on Friday and get up at the crack of dawn on Sunday, pack up and head home so I could be on the starting line by 1:30 pm. Sometimes we would take two cars so I could leave earlier. After two years as fleet champion Priscilla said it was time to move on. As always, I took her advice.

The LBYC is also a social club with many activities such as cocktail parties, brunches and a lobster boil. All of our Lake Bluff friends continue to be social members.

In September 2002, the year after 911, we bought a keelboat. Priscilla’s advice was buy the biggest sailboat you will ever want so you don’t put money into it and keep selling it to get a bigger boat. Great advice. We bought a 1989 Pearson 39-2. In 18 years of racing and cruising on the Great Lakes we never felt we needed a bigger boat. We wanted to focus on racing our new blue sailboat Blue Heaven. We sold our pop-up camper and Sunfish. We joined the Waukegan Yacht Club and started racing on Wednesday nights. Finding crew to race on a 39’ sailboat is challenging. We joined the spinnaker fleet which requires eight crew. In hindsight it might have sense to start in the jib and main fleet. For the first few years we accepted anyone that could fog a mirror and our results reflected it. We had old sails and an untrained crew. Priscilla and I would walk off the dock shaking our heads saying why do we do this to ourselves. It was against the sailors code of conduct to poach crew from other boats. All the good crew were taken.

Priscilla and I decided up front to get involved with volunteering and joining committees at the Waukegan Yacht Club. It is the best way to meet club members and make new friends. I joined the Race Committee and Priscilla joined the House Committee. One of my jobs on the race committee was to maintain the website. We had a link to sign up to race on a sailboat. Each year on January 1 we would delete all the prior year sign ups and start over with a blank list. I deleted everything. A few hours later I logged on to make sure everything was deleted. It was blank except there was a new listing. Someone had signed up on January 1. I desperately needed crew so I called Stacy Simpson. She had been crewing for Bob Don for several years and just found out Bob had just sold his boat without telling his crew. Bob Don had a highly successful national janitorial supply business. One of his top selling items was the breath mints used in urinals. On a sad note, Bob’s son moved to California to run the west coast business and died in an off road biking accident a few years later.

I decided to put Stacy to the test. I told her if she would host my annual crew party at her house she would be on my crew. She agreed and was a gracious host and ha been a good friend ever since. Even though my boat’s name is Blue Heaven (named for the bar and restaurant in Key West) she was more popularly known as Blue Harem. The majority of my crew were woman. I had Priscilla, Holly, Molly, Holly, Andrea and Donna. They were an outstanding crew, very reliable and eager to learn. This was a turning point in our racing program. I bought new racing sails and we practiced. The more we practiced the luckier we were in our races. I launched Blue Heaven early in May each year and we would have five or six practices before the first race. Some of our competitors came to the starting line while putting up their sails for the first time. One time we heard yelling and screaming nearby. We saw a Tarten Ten raising their mainsail and clumps of something falling into the water and into the boat. It turns out one of the owners had stored the sails in his garage for the winter. Mice had made a home by chewing up the sail to make nests. As the crew hoisted the sail, the mice fell into the boat and ran around.

Several years later Stacy met her future husband Jeff Logan through an introduction from one of my crew. It is nice when good things happen. Jeff and Stacy owned several large fishing boats over the years and always invited me and my family and friends to fish with them. Jeff was an accomplished fisherman and we always put fish in the boat. Stacy drove the boat and always put us on top of the fish.

Racing at the Waukegan Yacht Club was our main program. This included weekend races and port to port races. The port to port races were fun because the fleet would spend the night at an away harbor and party like sailors. Our other major race was the Chicago to Mackinac Race. This is a 333 mile race that we raced on Blue Heaven thirteen times. There was lots of preparation and expense involved in the race including having eight crew committed fir a week. I did have an advantage when my family raced the Mac because we were half of the crew. Often our shore crew that met us on Mac Island was twice the size or more than our boat crew. I would make dinner reservations for 22.

The first year we owned Blue Heaven we raced in the Hook Race. It is a 220 mile race that stays on the west side of Lake Michigan. The course follows the Wisconsin shoreline and turns into Green Bay at the north end of Door County and turns south to Sturgeon Bay. The course is the shape of a hook. The entrance to Green Bay is called Death’s Door because so many ships have wrecked there. I asked some old sailors what strategy would win the race. They sail sail the rhumb line which is the shortest distance. We sailed the rhumb line while most of the fleet went east or west. With light breeze and lots of dead calm areas we crept north and took fourth place in section one. We had been the last boat to start. This was our practice Mac because we had our first overnight race and all that entails with safety equipment, watches and provisioning.

Each of our 13 Mac Races had their own personality. Some were slow and hot while the crew was eaten alive by black flies. Some races had rain. Most races had storms. Often the winds unfavorable from the north but once in a while we would south winds, pop the chute and blast north. In one of our first Mac races we had winds from the south that kept building. We had a 1.5 ounce storm spinnaker that we called the bumble bee because it was black and yellow. We had a reefed mainsail and the bee up as we approached the Manitou Islands. We had the sheet and guy strapped down and we were sailing the boat under the chute because the winds were so strong. We made the good decision to drop the chute, jibe the boat and put the chute back up. That decision probably saved us from breaking the mask or killing some of the crew. Our foredeck crew started wearing helmets in case the after-guard dropped the spinnaker pole on them. They also learned to stand on the opposite side of the forestay from the pole.

During one Mac race we were blasting through the Manitous with the full spinnaker. I was off watch below but could hear the crew cheering as the boat speed reached numbers that defied physics. Blue Heavens too speed was 7 knots based on the length of her waterline. I heard the crew say 10 knots and cheer and then 11 knots and cheer. I knew I better get up on deck. As the crew called out 12 knots the boat was making a humming noise and then we broached. The helmsman could no longer steer the boat so she went sideways. Everything becomes silent after a broach because the boat is dead in the water on her side. It is important to get some crew on the high side to keep the leeward rail out of the water which could sunk the boat by filling the cockpit and then the cabin. We cleared away the spinnaker, got the boat on her feet and put up a jib.

During one of our final Mac races a severe storm had been forecasted to hit around midnight when we were in the Manitous. We could see the massive storm on our GPS and we could see the west sky light up like daylight with lightening. We cleared the decks and reefed the mainsail. Priscilla, Alison and JP went below. We didn’t need nine crew in the cockpit. Our plan was to run downwind with the storm until the winds abated. When the storm hit there was a massive wind gust that laid us on our ear. As I turned the boat to follow the breeze, Blue Heaven sat up and away we went in forty knots of breeze. One good thing about 1,000’s of lightening strikes is it improves the visibility so we can see the boats around us. After about 10 minutes the winds started to lighten. Yes the waves had turned the minutes to hours but it very exciting. We tacked over and put up our jib. As we were doing this we heard a May Day call from another racer. A few miles north of us a non traditional race boat had capsized and the owner and his girlfriend were killed. We could hear over the radio that there were already several boats attending to them. Soon a Coast Guard helicopter passed overhead. As with most storms the aftermath is they suck all wind out of the after they pass. For several hours we had barely enough breeze to move the boat. A Coast Guard ship approached us (the bouy tender Mackinac) and put their giant spot light on us. They asked if we were in distress and needed help. We told them we were fine and moved on the next boat. We could see bent and broken spars and shredded sails on boats near us.

The boat that capsized was a New Zealand designed mono hull called Wing Nuts that had large fiberglass wings extending out from the cockpit. The boat was very light and the crew were the ballast. The crew would crawl our six feet onto the wings to keep the boat flat. When the storm approached the captain ordered the crew to get into the cockpit. With no weight on the wings the wind gust lifted the boat and flipped it upside down. Since the boat did not have a weighted keel she could right herself. The owner and his girlfriend were knocked unconscious and drowned. The rest of the crew, including the owners son, were able to release their tethers and climb up onto the bottom of the boat.

We also participated in several other offshore events including the Queen’s Cup that raced across Lake Michigan from Milwaukee to Grand Haven and the Tri State that raced from Chicago to Michigan and Indiana. These races always had great parties. One year we were returning to Waukegan after finishing the Tri-State race in Chicago. There was a Jimmy Buffett concert at Wrigley Field. I had one of the first Sirius Satellite radios on my boat. We could listen to the live music as we sailed past the concert venue. Jimmy!

We also cruised three times in the North Channel of Lake Huron. This is one of the most beautiful cruising grounds in the world. The North Channel is the south coast of Canada and includes Manitoulin Island. Aside from from no salt, no sharks and no worries there are numerous uninhabited islands and beautiful beaches. We would convert Blue Heaven from a racer to a cruiser after the Mac races. We would remove six bags of racing sails and attach a full camper inclosure. It was a full days sail to Harbor Island and another full day to Meldrum Bay in Canada. I will provides the details in another chapter.

One of the good things that came out of the pandemic is we took Blue Heaven out of racing retirement and started racing with the Anchorage Yacht Club. We raced in the jib and main section with our family crew of JP, Alison and Priscilla. We finished second overall in section. We still got it!

Blue Heaven had fallen into a bit of cosmetic disrepair over the years. When Priscilla and I would return from Florida to Lake Bluff in May it was usually bad weather until the boat launched in mid-May. I had not kept up on waxing the hull or varnishing the teak toe rail. In addition the bottom paint exploded off the bottom after she was hauled this year in 2020. I spent four weeks straight working on her almost everyday. I had to strip the hull with heavy duty floor stripper three times. This required scrubbing every square inch with a Scotch Brite pad to remove the Poli-Glo polymer that has faded and streaked. Then I applied two coats of wax. I wonder how many times I moved my ladder around the boat. Then I started over by removing years of peeling varnish off the teak toe rail with a heat gun. The next step was to tape and caulk the toe rail on both sides. I had Larsen Marine soda blast and sand the bottom and apply a copper racing bottom paint. Larsen’s invited the Pettit paint rep Tony Palabrica to look at Blue Heaven’s bottom. It was a catastrophic failure of two Pettit products Eco and Hydrocoat. Huge sections peeled off. Tony offered to provide free paint to repaint the bottom. I asked him to get the Pettit laboratory involved and try to show me some love by paying the $4,000 in labor. I have not heard back from Tony. The irony of the situation is Tony and his predecessor Bob Harris have been giving me my Pettit bottom paint for free forever. Pettit is a sister company of Rust-Oleum. They are both owned by RPM. Here I am asking for payment for labor to replace the free paint. We shall see.


When Blue Heaven launches in the spring she will be looking better than she has in many years. I also upgraded to inside storage so all my work will still look good in the spring. I am looking foreword to turning my three grandchildren into racing sailors. Future crew!

Blue Heaven at the start of a Mac Race

Blue Heaven at the start of a Mac Race

Blue Heaven at the finish of the Mac Race.

Blue Heaven at the finish of the Mac Race.

Blue Heaven flying her chute.

Blue Heaven flying her chute.

Blue Heaven crew on Mackinac Island after the big storm that flipped Wing Nuts.Carol (Cut It) Caldwell, Dale Arnold, Cap’n John, Priscilla AlisonMark Boruta, Rich Chapman, JP

Blue Heaven crew on Mackinac Island after the big storm that flipped Wing Nuts.

Carol (Cut It) Caldwell, Dale Arnold, Cap’n John, Priscilla Alison

Mark Boruta, Rich Chapman, JP

Blue Heaven’s bottom paint disaster in 2020

Blue Heaven’s bottom paint disaster in 2020

Blue Heaven’s new copper racing bottom paint with future crew Eleanor (age 5) and Parker (age 2.5)

Blue Heaven’s new copper racing bottom paint with future crew Eleanor (age 5) and Parker (age 2.5)

John Simons