Make the Most of the Sailboat Show… Tried and True Tips
My “Christmas in October” is almost here! After several decades of my annual pilgrimage, I never grow tired of all the hype and fuss leading up to the Annapolis Sailboat Show. As mid-October approaches, I’m like a kid on Christmas Eve, anticipating new toys and days of celebrations with family and friends. And I never leave disappointed.
Like most things in life, you reap what you sow. As you attend the show, October 9-12, keep the following in mind to enhance your experience.

Shopping
Whether you are window shopping or seriously in the market for a sailboat, there is no better place than Annapolis to step onto boats to shortlist must-have features and compare brands. If you already have your dream vessel, there are plenty of vendors ready to answer questions or provide upgrades, often with a boat-show discount. Booths are often staffed by senior personnel, including inventors of specialty items, who are willing to share their expertise and in-depth product knowledge.
Last year, I wrote about the four stages of boat shopping and mentioned that I was preparing for Stage 4, downsizing. And that stage has finally arrived. After 11 seasons with our Gozzard 44, my husband and I just put Belle Bateau on the market. While it’s a bittersweet occasion, I’m hopeful that her future owners will take her on new adventures just as I plan to find a smaller vessel that I can singlehand for continued Chesapeake cruising.
Although the Annapolis Sailboat Show is focused on new vessels, there are ample opportunities for potential buyers to tap into the used boat market or learn more about various brands and features to create their ideal wish list. By touring various brands at the boat show, I noticed that I tend to gravitate to boats with traditional details and medium-toned woods, and that rub rails and anchor wash downs are necessary options for my kind of sailing. Every sailor is different, as are their boats. What works for one may not be ideal for another. The boat show can help to hone your wish list.

Learning
One of the greatest benefits of the boat show is the abundance of educational opportunities. Free sessions are offered by Annapolis Sailboat Show and its sponsors, as well as other vendors. Additionally, for the week leading up to the show, Cruisers University offers individual or multi-day packages for those wanting more intensive or themed education. There are also First Sail Workshops for hands-on education for aspirational sailors.
For further education, I suggest perusing the vendor booths to learn about various boat systems and components, especially recent advances in marine electronics. These booths are staffed by experts who are eager to educate visitors and provide cost estimates. Last year, during an impromptu booth visit, I inquired about the cost to add dinghy davits, in case my future boat didn’t come with them. On the spot, I received a viable estimate and added that to my lengthening list of possible after-market purchases.
Before attending the show, I always review the exhibitor list on the website or in SpinSheet and highlight the ones I want to visit. I use the show map to circle prioritized vendors, which then creates an efficient path. This shortlist keeps me focused, ensuring I don’t miss the must-visit booths before continuing my random wanderings. Inevitably, I stumble across a new-to-me exhibitor who has just the product I want and might even need. It’s always grand fun to discover new boat toys.
Speaking
Are you a subject matter expert, or do you know someone who is? If so, make it a point to introduce yourself to those who routinely host educational sessions. Tara Flanagan, the boat show program coordinator, often seeks new topics and presenters for both the spring and fall Annapolis Boat Shows, for either free sessions or Cruisers University. Additionally, vendors and boat manufacturers often host educational events at hotels or venues near the docks. If you have an expertise you are willing to share, take advantage of these rare in-person opportunities to make yourself known.

Volunteering
Volunteers are always needed during the boat show. Many non-profits need to staff their booths or offer brief sails to interested would-be sailors. Mission-focused organizations, like Sail Beyond Cancer and Chesapeake Region Accessible Boating (CRAB), are eager to introduce their programs to attendees who may not know about their services. Additionally, the boat show is a great place to meet not-for-profit and trade associations that impart helpful safety and boating information. I enjoy volunteering in the booth of the Chesapeake Area Professional Captains Association (CAPCA), where I often greet boat owners who need to hire a captain to instruct them on their newly acquired vessel.
Working
For the experienced or passionate mariner, there are many opportunities to get paid to work the boat show. For several weeks prior, and a few weeks after, even a casual visitor to the Annapolis Harbor will observe the staging required to convert this historic city’s docks into two back-to-back boat shows. Last year, as I crewed on several Watermark vessels near the mouth of the Severn River, I heard VHF announcements on Channel 16 about boat show personnel moving floating docks from Back Creek to their staging areas.
Our passengers would ask, “What is that? A submarine?” I enjoyed telling them about our upcoming boat shows and how unrecognizable the city dock becomes, even to those of us who are fortunate to reside here.
Whether you work the show or not, watching the setup or breakdown is something to behold (especially the latter). Unfortunately, this year, we no longer have Pusser’s Restaurant from which to watch the “real show” with a Painkiller in hand. Alas. There are other vantage points, of course, but I’ll miss Pusser’s for lunch as well as happy hours. (Editor’s note: stay tuned for the next chapter in this waterfront space.)
I have several friends who enjoy getting paid to work the show, either before, during, or after. Some physically move boats or floating docks. Others work security or staff the entrance gates. Many enjoy the added perks of free entry and swag that comes with the job. What’s not to love about that?

Enjoying the show
Most of all, the sailboat show is to be enjoyed. I especially recommend Preview Day on Thursday, with fewer attendees and more serious buyers. Last year, due to speaking commitments and volunteering, I attended every single day of the sailboat show. I soaked in all of it. From listening to all the international languages to stepping onto beautiful boats, each moment was memorable.
But no moments were as serendipitous as being on the Pride of Baltimore during an after-hours party when the Northern Lights appeared. There are just some magical moments at the sailboat show that cannot be planned. Learn more
About the author: Captain Cheryl Duvall is a USCG Licensed Master, Inland 100 GRT. When she isn’t sailing Belle Bateau, you might find her at the helm of Watermark’s Miss Anne in Annapolis. Email her at [email protected].