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 […]