Spanish moss, Southern grace & seaside history.
Historic

Spanish moss, Southern grace & seaside history.

Spanish moss, Southern grace & seaside history.

Charleston, SC 29401St. Augustine, FL 32084

3 days11 stops
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3
Days
11
Stops
4
Highlights
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Region

Charleston, SC 29401St. Augustine, FL 32084

Journey through the heart of the Lowcountry, where ancient oaks draped in Spanish moss line cobblestone streets and Gullah-Geechee traditions echo through time. From the refined elegance of Charleston to the haunting beauty of Savannah's squares, this trip is a feast for the senses, steeped in history, art, and classic Southern cuisine.

Trip highlights

Boone Hall Plantation & Gardens
Boone Hall Plantation & Gardens
Forsyth Park
Forsyth Park
Bonaventure Cemetery
Bonaventure Cemetery
Castillo de San Marcos National Monument
Castillo de San Marcos National Monument

The route

  1. 1Charleston, SC 29401Start · 32.7813, -79.9295
  2. 2The Historic Charleston City MarketStop · 32.7807, -79.9326
  3. 3HuskStop · 32.7780, -79.9321
  4. 4Boone Hall Plantation & GardensStop · 32.8583, -79.8231
  5. 5Angel Oak TreeStop · 32.7171, -80.0804
  6. 6The Olde Pink HouseStop · 32.0796, -81.0898
  7. 7Forsyth ParkStop · 32.0692, -81.0956
  8. 8Perry Lane Hotel, a Luxury Collection HotelStop · 32.0752, -81.0917
  9. 9Bonaventure CemeteryStop · 32.0451, -81.0510
  10. 10Castillo de San Marcos National MonumentStop · 29.8980, -81.3115
  11. 11St. George StreetStop · 29.8928, -81.3127
  12. 12The Floridian RestaurantStop · 29.8921, -81.3130
  13. 13St. Augustine, FL 32084End · 29.8929, -81.3138

Day 2

The Historic Charleston City Market
Shopping

The Historic Charleston City Market

Begin your journey in one of the nation's oldest public markets. Browse the stalls for local crafts, including the famous sweetgrass baskets woven by Gullah artisans, a direct link to West African heritage.

Photo by Bonnie Turner

Husk
Dining

Husk

Enjoy an iconic Southern lunch at this celebrated restaurant, which reinterprets heirloom regional ingredients. The menu changes daily, but classics like shrimp and grits are elevated to an art form.

Boone Hall Plantation & GardensHighlight
Historical Site

Boone Hall Plantation & Gardens

Drive down the breathtaking, three-quarter-mile Avenue of Oaks. Explore the historic brick slave cabins and learn about Gullah culture through powerful live presentations, offering a vital and multifaceted view of plantation life.

Day 3

Angel Oak Tree
Scenic Viewpoint

Angel Oak Tree

Before leaving the Charleston area, stand in awe beneath the sprawling branches of this Southern live oak, estimated to be 400-500 years old. Its massive, twisting limbs create a magical and humbling experience.

The Olde Pink House
Dining

The Olde Pink House

Arrive in Savannah and head straight for a quintessential Southern dining experience in an elegant 18th-century mansion. Known for its sophisticated Lowcountry cuisine and romantic, candlelit atmosphere.

Photo by Marie McCarron

Forsyth ParkHighlight
Outdoor Adventure

Forsyth Park

Stroll through Savannah's most famous park, instantly recognizable by its iconic cast-iron fountain. It's the perfect place to admire the Spanish moss-draped oaks and soak in the city's enchanting atmosphere.

Perry Lane Hotel, a Luxury Collection Hotel
Lodging

Perry Lane Hotel, a Luxury Collection Hotel

Settle into this chic, art-filled hotel in the heart of Savannah's Historic District. Don't miss the panoramic city views from the Peregrin rooftop bar, a perfect spot for a sunset cocktail.

Day 4

Bonaventure CemeteryHighlight
Historical Site

Bonaventure Cemetery

Explore one of the world's most beautiful cemeteries, made famous by 'Midnight in the Garden of Good and Evil.' Its Victorian monuments, ancient oaks, and riverside setting create a hauntingly beautiful landscape.

Photo by addi

Castillo de San Marcos National MonumentHighlight
Historical Site

Castillo de San Marcos National Monument

Travel south to America's oldest city and witness the power of the oldest masonry fort in the continental US. Explore its ramparts, learn about its strategic importance, and enjoy stunning views of Matanzas Bay.

St. George Street
Local Experience

St. George Street

Wander down the pedestrian-only heart of St. Augustine's historic colonial district. This bustling thoroughfare is lined with unique shops, centuries-old buildings, hidden courtyards, and local eateries.

Photo by Justin C

The Floridian Restaurant
Dining

The Floridian Restaurant

Conclude your trip with a meal celebrating updated Southern comfort food with a focus on fresh, local ingredients. Their 'country-cured' fried green tomatoes are a must-try finale to your coastal journey.

Photo by Ja ck

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The Historic Charleston City Market

The Historic Charleston City Market

Begin your journey in one of the nation's oldest public markets. Browse the stalls for local crafts, including the famous sweetgrass baskets woven by Gullah artisans, a direct link to West African heritage.

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Coastal Lowcountry