🏛️ CulturalLong weekend · from Jacksonville, FL
Sea Islands: St. Simons, Fort Frederica & St. Augustine
The Sea Islands stretching from the Georgia coast to northeast Florida hold the deepest layers of southern American history — a colonial-era fort that decided the future of the continent, a Gullah-Geechee island accessible only by boat, and the oldest continuously inhabited European city in the United States.
Day 1 — St. Simons Island & Fort FredericaDay 2 — Cumberland IslandDay 3 — St. Augustine
Day 1 — St. Simons Island
Day 1 — St. Simons Island
🚗 1 hr 30 min driving📍 7 stops
🌅
Morning
🚗
Drive
Jacksonville, FL → St. Simons Island
1 hr 30 min8:00 AM → 9:30 AM
Fort Frederica National Monument
★ 4.7The most significant colonial military site in American history — a 1736 British fort built by James Oglethorpe that blocked Spain's northward expansion from Florida in 1742 at the Battle of Bloody Marsh, ending Spain's claim to what would become the United States. The archeological remains of the original fort and town are preserved on the Frederica River; the interpretive museum documents the pivotal battle.
9:30 AM📍 See location
🍽️
Lunch
St. Simons Lighthouse
★ 4.7The second lighthouse to stand on St. Simons Point — the 1872 brick tower is 104 feet tall and still operational. The Museum of Coastal History in the lighthouse keeper's cottage is a well-curated introduction to the Sea Islands' history, particularly the antebellum plantation era and the Civil War's impact on the freed Black population of the islands.
10:30 AM📍 See location
Halyards Restaurant
★ 4.6A St. Simons waterfront restaurant with views across St. Simons Sound — Georgia shrimp, local crab, and fresh fish prepared with the simplicity the Sea Islands' ingredient quality demands. One of the best kitchens on the Golden Isles.
11:30 AM📍 See location
☀️
Afternoon
Village of St. Simons — Neptune Park
The compact village at the southern end of St. Simons has a charm unusual for a beach resort town — independent bookstores, galleries, and the kind of wraparound-porch restaurants that preceded the chain hotel era. Neptune Park's pier extends into St. Simons Sound with views of the Jekyll Island Bridge.
12:30 PM📍 See location
Hamilton Plantation — African American Historic Site
★ 4.4The ruins of the Hamilton Plantation tabby slave quarters on St. Simons are among the most intact antebellum slave settlement remains in the South — tabby concrete walls of the original cabins stand to roof height in some cases. The associated Gullah-Geechee Heritage site documents the survival of West African cultural traditions in the Sea Island population.
1:30 PM📍 See location
🌙
Evening
Southern Soul Barbeque
★ 4.6A low-country BBQ shack with a cult following on St. Simons — smoked ribs, pulled pork, Brunswick stew, and Georgia sides served under a pecan-tree canopy on Demere Road. Consistently rated among the best BBQ in the state; cash-friendly and no-frills. Arrive before 8 pm when popular items run out.
5:00 PM📍 See location
🛏️
The King and Prince Beach & Golf Resort
A 1935 Atlantic beachfront resort in the original Sea Island tradition — oceanfront rooms, a pool complex on the beach, and dining that has served St. Simons visitors for nearly a century. The original dining room still operates.
Day 2 — Cumberland Island National Seashore
Day 2 — Cumberland Island National Seashore
🚗 2 hr driving📍 6 stops
🌅
Morning
🚗
Drive
St. Simons Island → St. Marys, GA — Cumberland Island Ferry
30 min8:00 AM → 8:30 AM
Cumberland Island National Seashore — Dungeness Trail
★ 4.8Cumberland Island is the largest undeveloped barrier island on the East Coast, accessible only by ferry from St. Marys. The island's 17.5-mile length is occupied by a maritime forest of live oak, wild horses that have run free since the 1800s, and the ruins of the Carnegie family compound — Dungeness Mansion, the hunting lodge, and the slave cabins that predate the Carnegie ownership. The Dungeness Trail to the beach passes through all of it.
8:30 AM📍 See location
🍽️
Lunch
Cumberland Island — Atlantic Beach & Dunes
★ 4.7Nine miles of undeveloped Atlantic beachfront on the eastern shore, backed by dunes high enough to block the island's interior from view. The loggerhead sea turtles nest here in summer; the beach glass and shell middens from centuries of island occupation wash up constantly. No vehicles, no concessions, no noise beyond the surf.
9:30 AM📍 See location
Sea Camp Beach Picnic — Provisions from St. Marys
★ 4.9Pack lunch from the excellent provisioners in St. Marys' historic waterfront district before boarding the ferry — the island has no food service beyond the inn. The Sea Camp beach picnic area near the ferry dock has shaded tables.
10:30 AM📍 See location
☀️
Afternoon
Plum Orchard Mansion
★ 4.7A 1898 Carnegie-era shingle-style mansion on the island's western shore, accessible by the free NPS van tour from Dungeness. The mansion has been under restoration and is open for guided tours — the interior detailing of the Carnegie family's second Cumberland property is extraordinary, and the setting above the Brickhill River is peaceful.
12:00 PM📍 See location
🚗
Drive
St. Marys, GA → St. Augustine, FL
1 hr 30 min1:00 PM → 2:30 PM
🌙
Evening
Meehan's Irish Pub & Seafood
★ 4.5A St. Augustine institution on the waterfront — local shrimp, fish and chips, and Guinness in a convivial pub that draws both visitors and locals. The outdoor patio on the Matanzas River is the best outdoor table in St. Augustine.
5:00 PM📍 See location
🛏️
Casa Monica Resort & Spa
A Moorish Revival hotel on King Street built in 1888 by Franklin Smith and expanded by Henry Flagler — one of the most dramatic hotel lobby interiors in the South, with hand-painted Spanish tile, turret towers, and the long King Street portico where St. Augustine's history walks past.
Day 3 — St. Augustine
Day 3 — St. Augustine
🚗 45 min driving📍 5 stops
🌅
Morning
Castillo de San Marcos National Monument
★ 4.7The oldest masonry fort in the continental United States, built by Spain between 1672 and 1695 from coquina shell limestone quarried on Anastasia Island. The fort repelled every British attack during its 145 years of Spanish occupancy — the coquina walls absorbed cannonballs rather than shattering, an accident of geology that saved St. Augustine repeatedly. The NPS demonstrations and the harbor view from the ramparts are exceptional.
8:00 AM📍 See location
St. Augustine Historic District — Colonial Quarter
The Oldest City's 144-block historic district includes the oldest wooden schoolhouse in America (1716), the original Spanish government buildings, the 1887 Flagler-era hotels, and the Minorcan quarter where the descendants of Minorca's 18th-century indentured servants still live. A morning walk through the narrow colonial streets and the Flagler-era commercial district covers 300 years in a few blocks.
9:00 AM📍 See location
🍽️
Lunch
Flagler College — Ponce de León Hotel
★ 4.7Henry Flagler's 1888 resort hotel for the very wealthy is now Flagler College — the building is one of the greatest examples of Spanish Renaissance architecture in America, with a dining hall Tiffany glass ceiling that took 79 craftsmen three years to install. Free tours of the public areas on the hour during the school year.
10:00 AM📍 See location
Preserved — A Southern Kitchen
★ 4.9A St. Augustine restaurant focused on Southern preservation techniques — pickled shrimp, house-cured charcuterie, and a Florida produce-driven menu in an intimate downtown space. The best kitchen in the oldest city.
11:00 AM📍 See location
☀️
Afternoon
Lightner Museum
★ 4.7Henry Flagler's other St. Augustine masterpiece — the 1888 Hotel Alcazar, now housing a three-story museum of Gilded Age decorative arts. The swimming pool (once the largest in the world) is now the café; the ballroom, the Moorish arcade, and the casino are intact. The collections of Tiffany glass, mechanical musical instruments, and late 19th-century American decorative arts are substantial.
12:00 PM📍 See location
🚗
Drive
St. Augustine, FL → Jacksonville, FL
45 min1:00 PM → 1:45 PM
Plan your own escapeExplore more trips →