Learning to Sail

Learning to Sail

After they sailedWhile visiting Williamsburg in their RV, Kayla O’Driscoll booked a Lessons Cruise for her husband Brent. They drove all the way from Utah, where they live and work. Two other couples joined us on a cloudy day, and they preferred to socialize and drink instead of drive.

That gave Brent carte blanche to learn all three points of sail, in which he excelled under a brisk breeze that occasionally altered direction. He indicated a desire to buy a boat, but I steered him to getmyboat.com first to experience different boats Judging by his enthusiastic response under sail, he’s hooked.

Test Sail

A test sail is a great way to weed out the painted vixens before spending your hard-earned cash on a marine survey. Sure, you could ride around with a Mimosa in one hand while the broker regales you with tales of far away, exotic lands, but a smarter move would be to approach your test sail with planning and a critical eye. Here’s how to glean as much info as possible about your potential purchase during a test sail. – Practical Sailor, April 2024

Test SailLet’s Go Sail offers a 3-hour Boat-Buying Tour that largely attempts to talk him out of it while his wife quietly cheers my advice. A boat is a big commitment of time, not to mention money. Other hobbies and sports get subordinated if you take the sailboat seriously. Golf and tennis? Forget about it.

That said, the first thing to do is to stand back and take in the view. Are the lines clean and free of mildew and mold? Is the gelcoat brightly waxed? Is the engine clean? All of these suggest sufficient care has been expended on the boat. Then go out under motor and put up the sails. See if they meet your previous experience. Is your wife happy? Do you move through the water smartly?

I highly recommend as an alternative to buying that sailors simply rent a boat for half a day to get the feel of a given model in given waters. Wherever you travel in America, the website getmyboat.com can find a worthy sailboat to test drive. It usually includes the owner, which is great because he/she will regale you with the pros and cons.

Family Sail

Family Sail

Later that day, a family of six largely from Williamsburg went out us the wind picked up. Karin Bilderback said once the sails were up, “This is heaven. I just retired after 44 years as an RN, and I have looked forward to such serenity. But where are the buoys? We sail in Maine on the Penobscot, where there are buoys and lobster pots everywhere.” I explained that we have only two buoys nearby in the river, and we are between seasons for crab pots.

Family Sail

Sure enough, we encountered a rogue pot a half-mile off the head of Sarah Creek. I used the Boat US app to capture the Lat/Long and radioed it into the US Coast Guard for Hampton Roads. Crab pots are a menace to boaters, but they’re usually in 10 feet of water where we don’t go. This one was well out in the river. Later, we heard the hazard-to-navigation alert by the USCG on Channel 22.

Family SailUp on the bow, a mother and daughter hugged as the breeze sped by. I got to talking to Matt Scalia, who just retired as a full colonel in the US Army. He served as commander or XO of a battalion in Iraq and brigade in Afghanistan during their wars. (Brigades are made up of 2,000-5,000 soldiers, normally split among three to five battalions.)

I asked about the difficulty of making the rank of general if one has to retire within two years. “Well, the retirement number is 30 years in the Army, but if you make general you can keep going indefinitely. Try to make four stars.”

Family SailI facetiously asked his brother-in-law Craig Bilderback what he did that was important, compared to Matt. Without hesitation, he replied, “I invented and sell the inflated batting cage for baseball. We also make inflatable backstops, bounce houses, soccer nets and more. They’re less expensive that steel cages and they’re highly portable. Since most new fields today are [artificial] turf, you don’t have to tear up the ground to build a permanent structure. Plus, you can move these around.

“I was watching TV once when Cal Ripken appeared with our cage in the background. Social media blew up, and I could see it in real time.”

Family Sail

From his website: “Our revolutionary AIRCELL™ products feature patent-pending air-sealed technology that makes your perfect game finally within reach. We have models that support many sports, including baseball, softball, soccer, golf, and lacrosse.”


Why would anyone go to the trouble of jacking up a dilapidated shack for a new foundation instead of just razing it and rebuilding? “Because,” a contractor told me, “This house is grandfathered in a commercial zone—provided we don’t tear it down. We intend to gut it and rebuild it entirely.” It’s on Route 143 in York County, just east of Penniman Elementary School.


Kansas SailorsKansas Sailors

A couple visiting Williamsburg from Kansas were on their way to Columbia, SC, where their son in based in the US Army. I explained the aftermath of the 1781 Siege of Yorktown to include Gen. Washington awarding the very first Purple Heart, though it was called something else at the time.

Kansas SailorsPaul White responded, “Our son is an Army chaplain who is one of the few chaplains to have earned the Purple Heart. He got it in Afghanistan while running toward a bunker during a rocket attack. He suffered a traumatic brain injury as a result, and went from being very, very smart to just normal smart. Today he’s assistant dean of the Chaplain School at Ft. Jackson.

Kansas Sailors

For the first time in six weeks, we got to see a US Navy warship transit Yorktown. The USS Delbert D. Black was coming in from Norfolk to the Naval Weapons Station. The previous day, the Whites took a Navy tour out of Waterside. “We spent two hours cruising up and down the Elizabeth River,” Paul said. “We saw two or three submarines and the USS Ford aircraft carrier while a Navy patrol boat stayed with us the entire time.”

Close SailClose Sail

In the afternoon, brisk westerlies maintained course and strength as three people sailed the York. One of them bore a resemblance to actor Glenn Close, perhaps William & Mary’s most famous living alumnus. “People tell me all the time I look like her,” said Mary Lou Stufano. “I went to the dedication last Fall of her fine arts building on campus, but I didn’t get to meet her. Five people thought I was her sister.”

Close SailMary Lou is a costumed interpreter at Colonial Williamsburg, where she interacts from time to time with the 14 Nation Builder actors who roam the Historic Area and give lectures. “My daughter goes to William & Mary, and she says that only in Williamsburg can you stand in line for coffee at WaWa with Jefferson and Washington behind you.”Bridge Canard

Bridge Canard

Len and Deb Baxter joined Mary Lou sailing. They live in Michigan and told a harrowing tale. “Small cars have been known to get blown off the Macinack Island bridge that connects the Upper Peninsula. They cross the deck and when they get to the steel grate, the wind just comes right under them. Officials close the bridge in high winds, but still.” Wow, what a way to go. Wait. It’s not quite true. See here.

Women enjoy sailing today more than ever, and particularly a romantic cruise. Couples get to enjoy a romantic getaway as they sit up on the bow for privacy, and Let’s Go Sail provides professional photos for free. First-time or skilled mariners are welcome to sail a modern-32-foot sailboat in a unique setting of wildlife and Fall foliage or Spring bloom. It makes for an extraordinary anniversary idea.

Let’s Go Sail

Check rates and pick a day for a sailboat charter. Scroll down reviews on Trip Advisor. Go back to the home page of Williamsburg Charter Sails.   

The best Williamsburg boat tour offers safe “social distance sailing” daily for up to 6 people. It’s an extraordinary experience for couples. Leave your worries behind. Enjoy the thrill of moving with the wind without a care in the world. Put life back on an even keel with a romantic experience for a birthday or anniversary. 3-hour sailboat cruise as a semi-private yachting charter lets you exhale and relax as you enjoy comfort, stability and speed.

learning to sail learning to sail learning to sail learning to sail learning to sail

More from the Captain...