Capt. Bill O'Donovan, Author at Williamsburg Charter Sails

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 bow. I get asked a […]

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 first trip, Naish went on […]

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 relax as you enjoy comfort, […]

Basilone Returns

USS John Basilone exited Yorktown Naval Weapons Station after reloading Tomahawk missiles for the Iran war. John Basilone stands as one of the most celebrated enlisted Marines in American history, a figure whose courage at Guadalcanal and Iwo Jima carved his legacy into the bedrock of the U.S. military story. His life is a study […]

Best Winds to Sail

Let’s go sail the York River, where couples enjoy a serene three hours. Find happiness and health outdoors near Williamsburg with exciting fun on an anniversary or birthday. Great memories! Learn navigation to become a sailor. See birds, dolphins, maybe a Navy submarine. Bring your dog. People always ask, “What are the best winds to […]

Spinn Sailing

Let’s go sail the York River, where couples enjoy a serene three hours. The best Williamsburg boat tour offers safe “social distance sailing” daily for up to 6 people. It’s an extraordinary experience for couples. Leave your worries behind. Enjoy the thrill of moving with the wind without a care in the world. Take one […]

Sailing Past a Navy Freighter

Myths About Sailing

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. People ask, “Are there are many myths about sailing?” Yes, many myths abound. Here are the big ones. HARD TO […]

Lessons Learned for Advanced Sailors

Let’s go sail the York River where couples enjoy a serene 3 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 bow. People ask, “Can you repair the boat yourself?” Out of […]

She Said Yes

While sailing the York River, Zedric Jose took Sopha Levy up to the bow and proposed marriage. She said yes, to great enthusiasm from a family also sailing. They are in the US Navy, she in Williamsburg and he in Mississippi. They hope to collocate when they get married. Stout Returns The guided missile cruiser […]

10 Things to Do

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 bow. First-timers or skilled mariners can learn to sail fast on a cruise Near Williamsburg VA. They get to sail a modern 32-foot sailboat […]

50th Surprise

A couple from Salisbury MD stayed at the Williamsburg Lodge 50 years after they honeymooned there. They took their grown children sailing on the York River and got the surprise of a lifetime. Submarine! Riverine sailors from Virginia Beach used two fast boats to clear the path for a US Navy sub coming up from […]

Orphans Sail

In perhaps the most significant sail of my life, I got to take out 12 orphans from the Milton Hershey School. Broken into two 2-hour sails with six boys each, they got to learn how to sail the York River off Yorktown and to enjoy the luxury of cruising on a beautiful June day. Their […]

Nautical Chaos

Dozens of deadrises and hundreds of observers on land and sea mingled during the annual Battle of the Boats off Riverwalk Landing. It was hard to determine who won after several heats. The next day offered a unique contest to see how fast a deadrise can go in reverse while docking. Tradition Revived The Yorktown […]

Big Winds & Big Noise by Navy

I’m sometimes asked, “What’s it like to sail in big winds?” Adventurous, but the winds come and go. On this day, big winds for days suddenly calmed by the time Debbie Kremer of Arizona brought her beau Bob Wickley of San Antonio to sail the York River. We quietly tacked back and forth near Yorktown […]

Furler Genius

In only six hours, Glenn Bates and Evan Harrell of Performance Rigging in Hampton replaced my 25-year-old jib furler by linking the topping lift atop the mast to the anchor chainplate to remove the old rig and install the new one. That saved $1,000 and a full day of labor normally required by dismasting the […]

Beginners Guide to Sailing in Virginia’s Tidewater Region

Virginia’s Tidewater region is one of the most welcoming places in America for new sailors.

History You Can See from the Water: Yorktown by Sail

Some places tell their stories in museums. Yorktown tells its story in the wind.

York River Sailing Guide: Winds, Tides and Seasons

Plan the perfect York River sail with this guide to local winds, tides, and seasonal conditions. Ideal for visitors, sailors, and charter guests.

Sailing with AARP

I get asked, “What’s the best publicity you ever got for sailing?” The best promotion I ever encountered was a page 1 piece in the AARP newspaper, supplemented by a terrific video. We had a blast sailing with AARP. Let’s go sail the York River, where couples enjoy a serene three hours. Take one of […]

Author: Capt. Bill O'Donovan