Bonnie and I toured South Florida off the Gulf of Mexico to pursue charter and teaching opportunities. We sent sailing in Charlotte Harbor and fell upon Let’s Go Sailing Englewood, which closely resembles my brand Let’s Go Sail Williamsburg. This excursion was the highlight of our ten-day trip.

Sailing in Charlotte Harbor, Williamsburg Charter SailsCapt. Levi provided us a low-key, superior sail along Lemon Bay in the upper reaches of the Peace River. His 1977 Hunter Cherubini was restored with the help of his late father to accommodate up to six comfortably. He typically takes couples out for private tours without having to mix them together. The result is a quiet cruise to view dolphin, pelicans and other birds. We saw a bald eagle swoop down and fly away.

When he had the sails up and turned off the engine, Levi asked, “Hear that?” We listened closely and heard nothing. “It’s silence.” There wasn’t much wind, and what little there was blew in the wrong direction. But it didn’t matter in the slightest. When asked, Levi explained the local waters and vegetation in detail, having spent nearly his entire life here and on the water. 

Levi retrofitted the bow with a jury-rigged pulpit. “It looks like Frankenstein’s bow because it’s made from two bow pulpits from different boats that were welded together. My plan is to make a bigger version that extends out in a half circle over the bow for people to sit and enjoy the view.”

He runs on auto-pilot with a remote control that looks like a small TV clicker. “My favorite seat on the boat is to extend a hammock from the forestay at the bow to the mast and lie there. People do a double take and wonder who’s running the helm, but I’m doing it myself with the remote.” He grinned.

Levi once took a 23-footer from Englewood to Key West for a week-long trip “with the future mother of my children.” It took 27 days to reach their destination, and she was pregnant with twin boys. “This boat can make it overnight to Key West. It has sailed within sight of Cuba. I’d love to see Cuba now that travel restrictions have eased.”

Unlike my charter, he fishes off the stern with matching outriggers. “I just let the line troll and see what happens. One time, a big pontoon boat raced behind me too close and caught both lines. I let the lines run all the way out so as not to lose the rods and reels. I hope they fouled his prop.”


My father had a parrot that he loved, and he would let him out of the cage on the back of the boat to stand on the rail. One day we heard a loud noise like a rifle shot and didn’t know what it was. An osprey had dived and caught the parrot and swept it away. All that was left was a few feathers blowing in the wind.”

Here is a guy who simply loves the water and everything that entails, including boat restoration and maintenance. “Have you ever seen the movie ‘Capt. Ron’? He made me the man I am today.”

Let’s go sail. To see the rates and reserve a date this spring for a sailboat charter, click here. To check out reviews from sailors,  click here. To become a crew member on a charter sail or to tell us your sailing story,  click here.

More from the Captain...

Basilone Returns

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.

Full Story >
Learn About Best Winds to Sail

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

Full Story >
Spinn Sailing

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

Full Story >