Every summer I take Nanci Bond and Ellen Janoncyzk out on a commemorative sail on the mutual day of their late husbands’ birthday. They were both named Bob.

Commemorative SailOn a virtually still day with the York River like glass, we motored over to the other side of the river and all the way out to Tue Marsh. We covered myriad subjects: art, history, politics, family, children, grandchildren, weather, Colonial Williamsburg, sports, South Dakota, California, birds, movies, comedy, gardening, football, women, high school reunions, philosophy, clouds and more.

It was like a scene out of “My Dinner with Andre,” only better because it was on a sailboat. Curiously and fortunately, we did not discuss drugs, crime, war, work or Donald Trump. The waters remained placid.

Let’s Go Sail

Check rates and pick a day for a sailboat charter. See reviews on Trip Advisor from sailors like you. 

More from the Captain...

Beginners Guide

Scariest Sailing Moments

South Boston sailboat struck by lightning Let’s go sail the York River, where couples enjoy a serene three hours. Take one of 6 sailing adventures near the Chesapeake Bay for your best vacation excursion: Adventure, Event, Appreciation, History, Lessons, Boat Buying. Sit in the catbird seat or up on the

Full Story >

Robby Naish Became an Icon

By Danielle Rossingh and Shirley Robertson, for CNN, April 23, 2018 CNN —Robby Naish was a shy, 11-year-old kid growing up in Hawaii when he took his first ride on a windsurfing board. The son of a competitive surfer from California, it would alter the course of his life. From that

Full Story >
Make-A-Wish Sailing

Make-A-Wish Sailing

Take one of 6 sailing adventures near the Chesapeake Bay for your best vacation excursion: Adventure, Event, Appreciation, History, Lessons, Boat Buying. 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

Full Story >