How to Sail Like a Pro

How to Sail Like a Pro

People ask, “What’s the best way to sail like a pro?” Don’t forget to wear an ascot. WATCH VIDEOS—This is a good first step because you can choose from myriad short videos on You Tube to see how things work. Focus at first on the Close Reach, Beam Reach and docking. The rest is details. […]

Shades of Improved Ego

50 Shades of Improved Sailing Ego

People wonder, “Is sailing an ego trip?” When you start out to sail, you set yourself apart from the rest of mankind who lack your ambition. You have chosen an adventure that takes time to learn, time to hone, time to perfect. Not everyone can do it. Already you feel better. You think, This beats […]

Sailing with Heroes

Sailing with Heroes

People ask, “Who has inspired you the most?” Among 900 essays in the Captain’s Blog over the past seven years, Sailing with Heroes from 2016 is the most poignant. On a dark and dreary afternoon, a couple from Portsmouth drove up to the Peninsula to go sailing on the York River. Then they found the […]

Sailing Wisdom, Life’s Metaphors

Sailing Wisdom. Life's Metaphors

People often ask, “Why is sailing so special?” Unlike any other sport, sailing lends itself to inspiration, as these three illustrations show. No other mode of transportation is so inspiring, except maybe trains (“City of New Orleans”), or the bus ride with Kathy in Simon and Garfunkel’s “America.” Sailing memories are a pleasant reminder of […]

Destroyers Compared

Destroyers Compared

Sometimes people ask, “Can you compare Navy ships?” Yes, but preferably in profile. On a whim, Daniel Katekovich took his bride Connie sailing along the York River on their 30th anniversary. She had never been on a sailboat before, “if you don’t count a small catamaran.” She did great as we zoomed across the river […]

8 Little-Known Ways to Sail

8 Little-Known Ways to Sail

I get asked, “Are there different ways to sail?” Yes, here are eight ways. 1. Caribbean Day Sail—The common expectation for a trip on a yacht rental in St. Thomas or St. John is to fly in and take a bareboat out for a week with another couple or two. That’s fine, but pricey and […]

Sailing Back to Virginia

Sailing Back to Virginia

People ask, “What if it rains?” Two weeks of rain led to a third week, but we were away in Florida. Finally, the skies cleared and charter returned as we went Sailing Virginia again. On this day we got to fly the spinnaker not once, but twice, and gybing as well. Check out the video […]

Sailing on Memories

Sailing on Memories

People ask, “Why do people go sailing on vacation?” Visitors to Williamsburg go sailing on memories. They are surprised to discover so much water surrounding them. Indeed, when the second capital was formed in the city in 1699, it had ports on both sides of town along creeks extending to two rivers. Today as they […]

Sailing the High Seas

Sailing the High Seas

People ask, “What’s it like to sail the high seas?” Two independent couples from New York and Virginia went sailing on the high seas of the York River as fresh easterly breezes provided a speedy route down river. In recent days the winds have been strong after a front blew through. By now they have […]

Celebrate Summer by Sailing

Celebrating Summer by Sailing

I’m often asked, “Can you sail in light winds?” Yes, but it’s more challenging. Light winds on the York were enhanced by lively conversation among two groups one bright summer day. A New York City family joined a Richmond couple on a beautiful afternoon that left us celebrating summer by sailing. Daniel Rodriquez brought his […]

Sailing with Family

Sailing with Family on the York River

The question arises from time to time: “Can you take more than 6 people sailing?” Alas, no, for it’s a USCG license limitation. Karen Gillingham of Yorktown booked a sailing cruise with family, but she didn’t get to go because the USCG limit on six-pac license is six people. Her husband Ron turned out to […]

Sailing from Rural America

Sailing from Rural America

I get asked, “Do you do birthday sails?” Yes, here’s a 50th birthday sail. The week began with a continued warm front offering flat seas in the morning and rising seas in the afternoon. A couple from rural South Boston VA were celebrating her 50th, and a family from rural North Carolina were in Williamsburg […]

Sailing at 85

Sailing at 85

  People sometimes wonder, “Who’s the oldest sailor?” Here he is. A Maryland family rescheduled a rain date and wound up sailing the York in a rising afternoon breeze that they found a magnificent adventure. Weeks earlier, Kathy Self had hoped to bring her uncle along with her father Jack Green as a birthday surprise […]

Captain’s Choice

Captain's Choice

People often ask: “Is it hard learning how to sail?” No, not at all. Two couples from Richmond and Lynchburg had never met until they went out on the York River to learn how to sail. What they got was a primer on the water and a rare view of a passing Navy submarine. En […]

Name that Boat

People are always asking, “What are the best and worst boat names?” Most boat names like these at right reflect bad puns, good women or bad situations.  While traveling through North Carolina and South Carolina, I found a curious set of names at a marina in Wilmington. The US Coast Guard has strict naming rules […]

Sailing Through a Storm

Sailing Through a Storm

People often ask, “What’s it like to sail through a storm?” It’s challenging, for sure. A young couple from Charlottesville drove all the way to Williamsburg to take three children sailing on the York. They wound up learning quickly about sailing through a storm. Actually, when a storm approaches is the best time to roll […]

Sail Alaska

Sail Alaska

People sometimes ask, “Can you sail in Alaska?” Certainly. Tripp Wood lives in Charlotte NC and Alaska. It’s rare to find anyone who can sail Alaska. “My sons help as deck hands and first mates on our fishing charter out of Whittier, Alaska. I used to sail, and I’ve always wanted them to experience the […]

Sailing Teamwork

Sailing Teamwork

A Portsmouth couple bought a 27 Seward to dock near their house. Then they set out to learn how to sail as a team by mastering a Capri 22 through ASA SailTime Virginia Beach. So began four outings in three days of sailing teamwork. Days 1 and 2 were compounded by considerable Navy activity around […]

Who Goes Sailing

Who goes sailing

“It’s remarkable how quickly a good and favorable wind can sweep away the maddening frustrations of shore living.” – Ernest K. Gann Those who cruise with Let’s Go Sail on the York River cross all demographics, but they tend to skew more affluent. They are slightly overweight but never obese, and they have some college […]

Mega-Yachts at Sea

Mega-Yachts at Sea

Can super-yachts handle very rough seas? By Ron Larson, Encinitas CA I’ve never been on a super yacht in rough seas. However, I would say no. I would not want to risk my life on one in a major storm. I suspect that they would be fine, to a tipping point, then all hell would […]