Nennella Sailing offers year-round sunset and daytime charters on a classic 1964 Pearson Vanguard 32-foot sloop. Only about 400 of these yachts were built. Nennella is No. 109. When these boats were made, sailors navigated the seas using paper charts, sextants and the stars above.

Step onto the boat—with her high bow and raised transom, full keel, original spruce boom and teak-lined cockpit—and get unstuck in time: you will be transported, literally and metaphorically, across the waters of Charleston Harbor and through the history of one of the most fascinating cities in the U.S.

First settled in 1670, Charleston became the epicenter of rice production during the antebellum period, and the most significant port of entry in North America of the transatlantic slave trade.

Here, determined American Patriots defeated the mighty British Navy in the Battle of Sullivan's Island. Here, the first shots of the Civil War rang out. In this harbor Robert Smalls commandeered the Confederate transport ship CSS Planter and piloted it and its enslaved passengers to freedom. Here, the courageous 54th Massachusetts Volunteers fought the Second Battle of Fort Wagner.

The history is rich, troubling, fascinating. Learn about it, as well as the details of contemporary life in Charleston, aboard the classic sailing yacht Nennella!