Sailing Serenely

People wonder out loud, “Is sailing a serene experience?” Entirely! A couple from the Shenandoah Valley went to Richmond to visit old friends in May 2018. Then they included a trip to Williamsburg where we wound up sailing serenely on the York River. Right off the bat, we saw dolphins as we exited Sara Creek […]
She Said Yes While Sailing

Sometimes I get asked, “Do men propose to women on the boat?” Yes indeed. Brent Russell surprised his girlfriend Andrea Lefont with a sailing cruise on the York River, where he proposed marriage on the bow. She was stunned. He and I had arranged it so that we would sail downriver in brisk seas […]
Hurricane Coming

People ask, “What do you do in a hurricane?” The latest thing to do near Williamsburg is to batten down the hatches for the hurricane coming. Not since Isabel 19 years ago has a Cat 4 threatened the Virginia coast. At York River Yacht Haven, the yard crew pulled 33 boats of all sizes in […]
Shades of Improved 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 […]
Learning to Sail Big

Two fellows from Hampton Roads set out on a brilliant Saturday morning to advance their sailing skills by learning to sail big. Dan Fisher and Jim Brock took the ASA 101 basic keelboat course separately. Now they assembled for the next step, ASA 103 intermediate coastal cruising. They had never met before. Dan has a […]
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

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

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

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 […]
7 Menu Ideas for a Sailboat

People frequently ask, “Can we eat on the boat?” Yes! Everything is better on a sailboat, especially food. Here are 7 menu ideas for a sailboat to make the voyage a culinary adventure. Subway Consider Subway a metaphor for any take-out food from chains, supermarkets and restaurants. Subway just happens to be the most popular […]
Marry Me? Yes!

People often ask, “Can I get married on a boat?” You bet. Ziquine Hopkins and Crystal Dorsy went on an evening cruise along the York where he proposed to her on the bow of the sailboat. She was totally surprised and slightly astonished that Zi had already told her family. The couple enjoyed a catered […]
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

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 […]
First-Time Sailors

Some people ask, “Can you take me sailing even if I’ve never been on a boat before?” Hop aboard! Ian Whitfield and Makini Clay brought another couple with them from Richmond. They celebrated Ian’s birthday with a unique outdoor adventure near Williamsburg. I asked if he had sailed before? “No, I’ve never been on a […]
Celebrate 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 Summer’s End

People ask, “Is Labor Day Weekend busy on the river?” Too busy for me, as a professional mariner. Labor Day weekend brought us to sailing summer’s end. It came complete with all kinds of amateur motorboaters who consistently drove across my bow, sometimes too close. While I lament that so few boats are on the […]
Sailing with Family

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

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 All Over America

People ask, “Where do your clients come from?” All over the East Coast and occasionally out West. A family from Sacramento CA went sailing on the York River while touring Williamsburg. “We’ve never been on the East Coast,” said Kristin Marco, “and tomorrow we’re seeing Washington.” They became the first of multiple families this week […]
Sailing Off Brazil

I get asked, “Does it take imagination to sail?” Oh sure. Two adult siblings and their spouses arrived from southwest Louisiana to check out the bayou known as the York River, otherwise sailing off Brazil. They were on adventure while vacationing at Williamsburg. Brothers-in-law Timmy Brunet and Darrell Scott have known each other for years […]