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Sailing Vacation Destinations from Jacksonville FL

Island Hopping Destinations from Jacksonville

Ft George and Talbot Islands

Woman and child exploring the sandbars at Ft George and Little Talbot Islands Florida

Explore Kingsley Plantation or enjoy the beach, sandbars, and ocean swimming at Talbot Islands State Park. This is a great overnight destination from Jacksonville. The Fort George River provides a protected anchorage nestled among the salt marshes and sand flats. This remote area of the park is only accessible by boat. Here you can bird-watch or play and swim off the extensive sandbars that appear and disappear with the tide. It is a captivating dinghy ride winding your way through the back waters and dunes of the Fort George River arriving at a beautiful flat sandy almost private ocean beach of Little Talbot Island. Here you can swim in the ocean waves as they roll over the sandbars off the island.

A possible destination on a 24 hour overnight charter.

Amelia Island

Guests relaxing in colorful Adirondack chairs on the streets of Fernandina Beach Amelia Island Florida

You will want to spend some time exploring this quaint seaside village of Fernandina. Founded in 1562, the town we see today was largely built after the civil war. The tree lined streets are dotted with Victorian homes, interesting shops and many excellent restaurants. It's easy to spend an afternoon (or 2) exploring the town and dining out. Fernandina Harbor Marina makes a great overnight stopover if you are on a 2 or 3 (or more) day vacation from Jacksonville.

Great overnight stopover on a 2 or 3+ day vacation.

Cumberland Island

Dungeness mansion ruins on Cumberland Island National Seashore Georgia

Cumberland Island is a National Park and Georgia's largest barrier island. Enjoy vistas of pristine maritime forests, undeveloped beaches, wild horses, and wide marshes. Walk in the footsteps of early natives, explorers, and wealthy industrialists. Go ashore and explore the remains of the Carnegies' mansion, Dungeness, or take the tour of the preserved Plum Orchard mansion. You can sail out the St Marys inlet for an ocean trip to Jekyll Island and come back on the ICW that allows you to circumnavigate Cumberland Island.

Requires a 3 day charter from Jacksonville.

Jekyll Island

Group biking on the beach at Jekyll Island Georgia

Another 4–5 hours north of Cumberland is Jekyll Island, GA. In 1886, a group of millionaires purchased the island and converted it into the country's most exclusive club. You can visit the Millionaires' Village and see the beautiful restored homes formerly belonging to the Rockefellers, Macys, Goodyears, J.P. Morgan & more. The Jekyll Harbor Marina has a waterfront cafe, pool and hot tub for a wonderful overnight stay. Borrow one of their bikes to ride the island or take our dinghy up to Jekyll Wharf for a stroll through the Millionaires' Village.

Requires a 4 or 5 day charter.

Green Cove Springs

Happy couple relaxing on the deck of Now and Zen catamaran on the St Johns River at Green Cove Springs

Green Cove Springs is a charming historic town nestled along the St Johns River, just a short sail south of Jacksonville. Known for its natural spring-fed pool — one of the largest in Florida — the town offers a relaxing stop with a beautiful waterfront park, unique shops, and excellent dining. The spring pumps out millions of gallons of crystal-clear 72°F water daily into a public swimming pool right on the river. Tie up at the city dock and explore the quaint downtown, or simply enjoy the peaceful anchorage as the sun sets over the river.

A great overnight destination on the St Johns River.

St. Augustine

Bridge of Lions lit up at night with full moon reflecting on the water in St Augustine Florida

Just 40 miles south of Jacksonville, St. Augustine is the oldest continuously occupied European settlement in the United States — and one of the most magical places to arrive by sailboat. Sail down the Intracoastal Waterway and anchor in the shadow of the iconic Castillo de San Marcos, a 17th-century Spanish fort that has stood watch over the harbor for over 350 years. Explore the cobblestone streets of the historic district, browse the unique shops and galleries on St. George Street, and dine at one of the many outstanding waterfront restaurants. The Bridge of Lions, the old city gates, and the Lightner Museum are just a short walk from the marina. Whether you spend one night or two, St. Augustine is a destination that will leave you wanting to come back.

A perfect 3-day charter destination from Jacksonville.

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