Four Phases of Sailboat Shopping

Sailors May Buy Boats in Four (or Five?) Phases

Autumn is here and so is the return of my annual pilgrimage: the Annapolis Sailboat Show. For more than 30 years, I have rarely missed the event that excites me more than Christmas. Just ask my youngest son, who used to lament that he was born on October 12 and forced to celebrate his birthday at the boat show rather than Chuck E. Cheese. Yes, I too was one of those moms pushing strollers on the weekend and dreaming that someday I’d own a sailing vessel longer than our 11-foot Snark. Eventually, I learned it was wiser to take a day off from work and pay the extra money to attend preview day on Thursday since it was less crowded and focused on the “serious buyer.” After all, wasn’t I serious?

author sailboat show
The author at her favorite place to dream of sailboat buying: the Annapolis Sailboat Show.

Recently it occurred to me that sailboat shopping has phases that correspond to life phases. It wasn’t that obvious to me 30 years ago, but as I’m entering perhaps the fourth phase, as defined below, I think I’m onto something. Let me know if you agree.

Phase 1: Dreaming

For some, the dreaming phase of boat ownership begins in childhood when introduced to the feeling of freedom that comes with being on the open water. This is especially true for young sailors, who often learn on small sailing dinghies like Optis and Lasers powered only by the wind and stabilized with a daggerboard. For me, I learned on a Snark that my dad purchased from Sears & Roebuck, and the occasional Sunfish we’d rent by the hour at a seaside resort. The ability to steer something on my own, many years before I’d be old enough to drive a car, was an absolute thrill. I still say that sailing small boats is “real sailing” because every tiny adjustment matters, especially when learning how to keep the sail, wind, and boat position in balance with a tiller.

While I loved sailing as a kid and teen, I experienced a serious gap of 10 years before the dreaming phase resumed in earnest. College, career goals, early marriage, and parenthood interrupted my sailing plans. When life settled down, I began to take occasional sailing lessons on keelboats and pocket cruisers. I also subscribed to several sailing magazines for inspiration and to regularly remind myself that I needed to prioritize my sailing goals. I began attending the fall sailboat show in Annapolis. Indeed, it was at the sailboat show that the dreaming phase took hold.

At first, I toured mostly boats similarly designed and sized to those I was used to sailing, which included J/22s and daysailers. I’d occasionally slip off my shoes at the stern of a 30-plus foot production cruiser and wander below to pipedream, not just about the boat itself but the skill set needed to confidently handle such a large vessel.

As the years passed and my experience grew, I toured the show with other sailors and took free seminars, both of which expanded my knowledge base. I ventured into the tents to visit various vendors, often wondering why I would possibly need that gadget they were hawking. Without having a boat of my own, it was rare that I purchased anything other than a consumer product like sunglasses and tees. But still, I dreamed, observed, and became more educated.


The couple ended up buying a Gozzard cruising sailboat based on relationships forged at the sailboat show.

Phase 2: Early Boat Ownership

Eventually, I met and married another sailor who also dreamed of Bay cruising. Suddenly, the dream got real. The boat shopping began in earnest. Two years after we met, we bought our first boat together and named her Blind Date. While she was a used boat, not purchased at the show, we were positively influenced by several years of touring her newer sister boats.

Now that we owned a boat, our priorities shifted, and boat show attendance became booth-centric. In fact, my husband refused to tour any boats at the show. He was solely focused on improving the boat we had and viewed the boat show as a unique opportunity to become educated about a wide range of products and services. On the other hand, I still enjoyed touring a few boats, just because it was still Christmas for me.

Three years after purchasing Blind Date, my husband was ready to step onto other boats again. By then, we had sailed to many points of the Chesapeake Bay and had upgraded our boat according to our budget and the boat’s value. He had started to research more seaworthy vessels and suggested we explore the boat show docks that house the pricier yachts. Gulp. Okay, I guess we can still dream.

Phase 3: Upsizing/Upgrading

And dream we did. We attended the early years of Cruisers University and met coastal and ocean cruisers. We became members of the Seven Seas Cruising Association (SSCA) and attended their Annapolis GAMs, intentionally scheduled just before the fall boat show. And because we continued to go on sailboats at the October show, we discovered a different yacht brand that met our updated sailing goals. We decided to upsize, bought another used vessel, and had her refitted at the original manufacturer with whom we had met and chatted at the show.

For the last 10 years, we have sailed more than 3800 coastal miles from Maine to Florida on Belle Bateau, our Gozzard 44. Additionally, we have averaged more than 600 miles per year exploring dozens of beautiful Chesapeake Bay coves, and yet there are many gunkholes we have yet to visit. During those years, the fall boat show offered us the opportunity to research and learn about innovations in yacht designs and boating systems as well as chartering opportunities abroad. For me, it is still my Christmas in October.


The Annapolis sign has become a signature selfie station at the Jeanneau area at the Annapoils Sailboat show

Phase 4: Downsizing/Simplifying

Now, we are entering a new boat shopping phase. My husband is ready to curb his boating appetite, but I am not. So, I spent a full day at last year’s boat show looking at smaller and simpler boats that I can singlehand. It was interesting to watch the faces of various brokers last October as they asked, “Do you have a boat now?” and I responded, “I have a Gozzard 44, but am looking to downsize.”

It’s a whole new research project than what I began 30 years ago. I’m far more educated about boat systems and features and which are priorities for me at this stage in life. Instead of marveling at galley designs, I find myself far more interested in engine access and how easy that next oil change might be. Or whether the boat comes with a windlass and wash-down pump, which surprisingly are not guaranteed features on boats that could cruise the muddy Chesapeake.

As I giddily prepare to make my annual pilgrimage this month on preview day, I’m grateful for the fall sailboat show where I can shortlist yacht manufacturers, become educated at vendor booths, and just hang with like-minded passionate sailors.

Is there a fifth phase?

It has been suggested to me that there’s another phase for sailors as life progresses on the water. Although my mind refuses to wrap itself around this thought, I do know several sailors who have crossed to the “dark side” and have purchased a powerboat after many years of harnessing the wind. Some have moved onto trawlers, while others have embraced small runabouts or large power yachts. In any case, one should never say never. So, I won’t.

But I will say if sailors go that route, it technically isn’t a fifth phase for SpinSheet readers. Because once we cross over, I believe we begin the first phase of an article for PropTalk. Just sayin’…

About the Author: Captain Cheryl Duvall is a USCG Licensed Master, Inland 100 GRT. She resides in Annapolis and still happily sails her Gozzard 44, at least for the near term. She can be reached by email [email protected] or via sailingbelle.net.