people in a boat

Cruising Hilton Head’s Waters and Beyond

It was cold as we cruised out of the lock at Windmill Harbor. Colder than expected. But, exceeding expectations would become the theme of our trip on our 60-foot schooner Leopard from Hilton Head Island offshore to St. Augustine and then along the Intracoastal Waterway to Cumberland IslandJekyll IslandSapelo IslandSt. Catherines IslandSavannah and then back home.

If you are a boater, or have even crossed over one of our bridges, you know the Lowcountry abounds with old oaks wearing Spanish moss like knitted shawls, palm fronds sprouting from trunks like a fireworks finale, egrets and herons gingerly walking along the shorelines and kamikaze pelicans diving for dinner. These are the sights and sounds that moved writers like the late Pat Convoy to literary genius, visual artists like Jonathan Green to paint brilliant works and lyricists like Johnny Mercer to compose “Moon River.”

Cruising the Lowcountry, I realized these awe-inspiring elements also attracted some of our nation’s greatest leaders and entrepreneurs. Henry Flagler was drawn to St. Augustine. Nathanael Greene, the Carnegies and countless statesmen and military figures to Cumberland. The Morgans, Rockefellers, and Vanderbilts to Jekyll. Howard E. Coffin and R.J. Reynolds to Sapelo. Button Gwinnett to St. Catherines. James Oglethorpe to Savannah. And Charles Fraser to Hilton Head. As we anchored or docked along the way and toured each island, I found myself thinking more and more about these famous figures.

women waling on beach

Highlights From The Route

(Aside from miles upon miles of protected coastline)

St. Augustine
The Lightner Museum
Flagler College
The Castillo de San Marcos
The Spanish Quarter
St. Augustine Lighthouse
The Bridge of Lions

Cumberland Island
The Dungeness ruins
50 miles of hiking trails
Plum Orchard
Greyfield Inn

Jekyll Island
Jekyll Island Club
Jekyll Island Historic District
Jekyll Island Museum
Georgia Sea Turtle Center

Sapelo Island
Hog Hammock
The Reynold’s mansion
The Sapelo Island lighthouse

St. Catherine’s Island
The beach

The Riverfront and Savannah Historic District
Forsyth Park
Cathedral of St. John the Baptist
Bonaventure Cemetery

people in a boat

Returning to Hilton Head—with Americana rock already pumping from the always down-with-a-party Daufuskie on our right, and Buck Island and Calibogue Sound ahead like old friends—I had a greater understanding of the Lowcountry and I basked in the warmth of pride of place. I felt thankful my husband, three daughters and best friends Brucie Holler and Greg Schenkel had  joined me on the journey. And I vowed to continue cruising Hilton Head’s waters and beyond with the excitement of knowing there’s much more to be explored.

Becca Edwards a blogger for the Hilton Head Chamber and owner of b.e.WELL+b.e.CREATIVE.


Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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