It was late in the summer of 2014 as we wrapped up a beautiful day of sailing on the lake when we pondered that it had been 5 years since we first raised a sail. We never had an engine on our first boat, the Coronado 15 aptly named Bosco, after our beloved friend who passed just a few years before. With the wind at about 15 knots our sails were full and we were racing at near max-hull-speed within 20 yards of the dock and we smoothly rounded up into the wind. Jake was at the helm while I very efficiently and without much though unwound the ropes (sheets) that were holding up the main and jib sails. Without missing a beat, I grabbed a paddle and tossed it to Jake as we easily glided our way towards the dock. With just a few small paddle strokes we pulled up alongside the deck cleats perfectly. A small group of people were watching us from the shore and came up to catch our lines. We were quickly met with the comment, “wow you guys look like you’ve been sailing your whole lives.” We both looked at each other and laughed out loud because they couldn’t have been more wrong about us. The truth is that we really have only been sailing for about 4 years up to that point.

Jake was always very active in all things outdoors. He grew up so far inland and rarely travelled outside his home state that the first time he actually saw the ocean was in the USMC training Depot in San Diego. He had occasionally seen sailing yacht races on TV, but sailing was so far removed from his existence that he really had no concept of that world.

I, Jill, grew up extremely outdoorsy and athletic. As a tomboy I would spend hours playing outside getting my hands dirty. I’ve always been drawn to nature and even though my mother owned a small sunfish sailboat, i never had any inkling or desire to play on it.

Since neither of us grew up sailing, we very deliberately decidied to make ourselves into sailors.

Whether we knew it at the time or not, the dream was ultimaily born on a holiday family vacation. It was Christmas ’09, we were at the famous Walt Disney World Resort celebrating the holiday with family. It was a cool December evening at Epcot and as we were about an hour early before a dinner reservation, Jake and I visited a classic (at the time) the Norway experience. It was a short jaunt into the magical diorama-infused land of Norway, on a boat. Afterwards is a short video about the culture of Norway, and very specifically how celebrated sailing and viking craftsmanship are and infused in adventures all the way up to this modern day. The spirit of Norway ie- sailing. At this, both Jake and I look at each other with the same thought…

We simultaneously blurt out, “we should sail to Norway” followed by, “we should sail everywhere.”

The smallest seed of an idea was planted that night and it quickly took root in our minds that sailing everywhere would really be the ultimate adventure that could show us the world in a completely different light. It also made us think that we could pull it off on a “relatively” small budget because the sailboat is the home that follows you where you go, and sailing is more-or-less free transportation after you own the boat and all materials needed to run it!

The First Taste of Sailing

The following summer, a fellow adventurous couple that we befriended came into a small O’Day 15′ sailboat and invited us to their local reservoir for a weekend of camping and sailing. As soon as Jake set foot in the boat, he was HOOKED. I took a bit longer to catch the fever, but from that point on it was full speed ahead. Jake read every sailing book he could find and the more he learned (and myself by association) the more we felt like this is IT.

So we did a little searching and found various sailing schools. We chose ASA because it seemed like that organization had more worldwide recognition. Soon thereafter we had our dates selected for Jan. (so it wouldn’t interfere with climbing), and we picked Florida because it was a fairly affordable destination. Jake found a school that actually highlighted they worked with couples specifically, so we thought it was perfect! The trip was booked with Captain Jennifer Maclean and her company, Sunshine Sailing Adventures. She has been voted Best ASA Instructor for several years and one of the top 50 women in sailing. Most of all she had an adventurous spirit which is just what we wanted!

That trip was probably one of the most significant of our lives, because not only did we have an amazing time and worked our asses off, but we felt completely at peace with the world and LOVED being on and living in a sailboat for a week. It felt like time stood still (or really flew by) because before we knew it the trip was over. We came back home to a wintery world but took the next step and immediately got on craigslist to shop for our very own sailboat. The boat in question was definitely going to be small, one that we could mess up, break and learn to fix, one that was forgiving enough to learn but fast enough to keep us interested. That’s when we found our first baby, the Coronado 15 dubbed Bosco (the first), for only $700! And although it was in perfect sailing condition, we decided to strip it apart and refinish it with a new skin, then put it back together again; learning about a million skills along the way!

Up until then, we had only a handful of pretty cheap tools and generally called a Mr. Fixit (professional) to come and do any handiwork around the house. But in that rebuild, both Jake and I broke all of the cheap tools and vowed to replace them with only high-quality tools from here on out. We also learned how to fix ANYTHING around the house because really it forced us to be more handy and less lazy. We also realized that its not that hard to fix stuff if you have a little patience. Plus we had the notion that once we do this epic adventure (if it ever actually comes!), that we’d have to be our own electrician, plumber, diesel mechanic and carpenter. That winter was the first time Jake said that he felt a sense of pride from building something with his own hands…sort of.

Once she was all pretty and new, we put Bosco ‘young’ on the water and we learned very quickly that we still had LOADS to learn. The entire summer on SV Bosco were some of the best times and also some of the scariest. Our first few months out, we ran aground (i.e. – sailed too shallow and the keel scraped the bottom of the lake), we almost lost our mast because it wasn’t rigged right, almost sank the boat because we forgot to plug the boat plug, trapped in the middle of the lake because we didn’t have a motor (or paddles yet), almost capsized on a regular basis and learned that its difficult to climb back into the boat once you jump (or fall) out. We had virtually no clue how to set up the rigging, or sails or really anything but we didn’t let that stop us! Because our love for sailing was so strong (and perhaps because our drinking went up a great deal due to increased stress) we were always excited and ready for more.

Practice Practice Practice

We knew we needed more experience and after another year of sailing, saving money, and studying, we decided to sign up for the next ASA Course..the 104. We wanted to do this trip in a different location, one that is more high-traffic and someplace that we’d never been. So the choice came down to Annapolis, MD which would commence with Captain Dave Renoll and his school R & R Sailing.

After this trip we chartered a few boats all by our lonesome. The first was in Chicago, on Lake Michigan and another on Lake Dillon in Colorado. When I say adventure, I mean one that is not all fun and games, but hard, somewhat stressful and scary. This trip was a bit more scary because just a few days before we recovered from our very first capsize experience which felt completely epic. But what is life without a little bit of the negative?…because I tell you the positive that comes from it overshadows all.

Looking back at these 5 years we want to point out that while it seems like fun and games, it is also a ton of hard work and dedication. And yes its not completely free, but it was also very important to take the time and do these trips to help with the learning curve and build our confidence and experience more quickly. Plus we really did love the process. Each step has brought us closer to our dream (which is literally just around the bend) of becoming full-time cruisers. Many sacrifices were made and the end goal is nearly at our fingertips.