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 […]

7 Menu Ideas for a Sailboat

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!

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

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 […]

First-Time Sailors

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

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 […]