South Carolina & Georgia: Charleston to Savannah

Travel to Charleston and gather at the Ansonborough, the first hotel on our itinerary. If you’re flying in, you may arrange to meet VBT’s complimentary shuttle upon arrival at Charleston International Airport. The shuttle departs at 2:00 p.m.

We recommend flying into Charleston and out of Savannah. For guests driving to the tour, parking is available at the Ansonborough and at Charleston International Airport. At the end of the tour, you may join the VBT van returning from Savannah to Charleston airport. If you’ve left your car at the Ansonborough, a taxi from the airport to the hotel is available.

Your safety briefing and bike-fitting session is scheduled for 3:00 p.m. Enjoy a warm-up ride through historic “South of Broad,” taking in panoramic views of the harbor and Fort Sumter. Continue past the historic market and St. Philip’s Church—one of Charleston’s oldest—on charming Church Street.

This evening, get to know your fellow travelers during a tour orientation, welcome reception, and dinner at a local restaurant.

Today's Ride Choices

Afternoon: Charleston Warm-Up Ride — 4 miles

What to Expect:

Cycling south, you’ll pass the large fountain at the entrance to Waterfront Park—a lovely spot for an evening stroll, with sailboats drifting across the harbor and sunsets over the Ravenel Bridge. On East Bay Street, take in “Rainbow Row,” a historic stretch of pastel-colored homes. As you ride along the Battery, enjoy views of Fort Sumter, guarding the harbor where the first shots of the Civil War were fired in 1861. In a city defined by its steeples, St. Philip’s Church stands out with one of the oldest; you’ll ride past it on your warm-up loop. Then, continue to the historic City Market, where artisans still handcraft sweetgrass baskets with local pride. Watch for horse-drawn carriages as you pass the stables on Anson Street, returning to the Ansonborough Inn.

Cumulative Distance Range: 4 miles

Included Meals: Dinner

After breakfast, cycle along a dedicated bike and pedestrian lane on the dramatic Arthur Ravenel Bridge, soaring over the Cooper River. Traverse Sullivan’s Island, then cross another bridge to reach the Isle of Palms. Your route follows the scenic shores of the Intracoastal Waterway, passing some of the area’s most sought-after homes and offering soothing beach vistas. During your lunch stop, you’ll have the opportunity to change into swimwear and enjoy a dip in the ocean.

After lunch at a local restaurant on the Isle of Palms, continue cycling to historic Fort Moultrie. Edgar Allan Poe was stationed here from 1827 to 1828 while serving in the U.S. Army. The fortress played a significant role in both the Revolutionary War and the Civil War. After your visit, return to Charleston via the Arthur Ravenel Bridge.

Once back at the Ansonborough, take time to explore Charleston on your own—perhaps with a stroll along the Battery, the promenade flanking the city’s scenic harbor.

Dinner is on your own this evening.

Today's Ride Choices

Morning: Charleston to Sullivan’s Island and Lunch — 14 miles

Afternoon: Sullivan's Island to Charleston — 17 miles

What to Expect:

Cycle from the Ansonborough Inn over the Arthur Ravenel Bridge, enjoying expansive views of downtown Charleston, the harbor, and the Atlantic. Continue to the Isle of Palms for lunch, with the option to swim at the beach. Afterward, ride back through Sullivan’s Island to visit Fort Moultrie, a National Monument rich in Revolutionary and Civil War history. Then retrace your route to the Ansonborough Inn by bike or shuttle. This evening, enjoy free time to explore Charleston and dine at one of its many Southern-style restaurants.

Cumulative Distance Range: 14 – 31 miles

Included Meals: Breakfast, Lunch

Today, you shuttle about 70 minutes south to Beaufort, where you’ll cycle the scenic Spanish Moss Trail. Once the route of the Port Royal Railroad, this 12-foot-wide, multi-use paved trail offers sweeping marsh and water views, coastal wildlife sightings, and historical points of interest as it winds through neighborhoods shaded by moss-draped oaks. The invigorating ride brings you to Port Royal, a quaint Lowcountry town nestled in a biologically rich estuarine ecosystem. After time to admire its homes listed on the National Historic Register, continue along another section of the trail to Beaufort. Upon arrival, enjoy lunch on your own at one of the town’s many inviting restaurants.

End your rewarding day in Beaufort, named “The South’s Best Small Town” by Southern Living magazine in 2017. This charming haven is known for its Sea Islands, historic downtown, and signature Lowcountry cuisine. Settle in at the Beaufort Inn, ideally located for exploring the city’s downtown and waterfront.

This evening, enjoy a traditional Lowcountry boil before taking part in a beloved Southern tradition: a Beaufort social hosted by a local historian. Try your hand at the Virginia Reel—a spirited Colonial-era folk dance—and gain fascinating insights into Beaufort’s rich culture and history.

Today's Ride Choices

Morning: Spanish Moss Trail — 15 miles

What to Expect:

Cycle along the tranquil Spanish Moss Trail to Port Royal, home to several buildings and homes listed on the National Register of Historic Places. Stop at the Sands boardwalk and observation tower for sweeping views of the Beaufort River and a chance to spot dolphins. As you ride through Port Royal, take time to visit the Cypress Wetlands, a unique local ecosystem. Your ride concludes at your inn in the heart of Beaufort.

Cumulative Distance Range: 15 miles

Included Meals: Breakfast, Dinner

Enjoy breakfast in town, then cycle through scenic farmland to St. Helena Island, passing the historic Chapel of Ease along the way. During the Colonial period, planters who lived too far from the churches of Beaufort built informal “chapels of ease” on their plantations. Constructed in the mid-18th century, St. Helena’s Chapel of Ease was largely destroyed by fire more than 100 years later. Its four original tabby walls remain, making it an evocative and haunting historic landmark.

Your visit to Fripp Plantation begins as you ride down its white fence-lined driveway, where you’ll be welcomed by your VBT trip leaders and a local guide. While your leaders prepare a picnic lunch, your guide shares the rich history of the plantation during a walking tour of the property. After the tour, enjoy your lunch under the shade of pecan trees overlooking the water.

This afternoon, ride to the Penn Center for an included visit. A designated National Monument, the Penn Center was the first institution in the South to recognize the Reconstruction Era. Founded in 1862 to educate newly freed slaves, it now serves as a cultural hub for the Gullah community. Dr. Martin Luther King Jr. once held annual retreats here for the Southern Christian Leadership Conference. After this enlightening stop, return to Beaufort by shuttle or bicycle.

Later, join a guided walking tour of Beaufort. As you stroll past antebellum mansions, moss-draped live oaks, and 1950s-era storefronts, your local guide will highlight why this town has become a favorite of Hollywood filmmakers. Beaufort has served as the setting for several acclaimed movies, including Forrest Gump, The Prince of Tides, and The Great Santini.

Tonight, enjoy dinner on your own in Beaufort, with a variety of excellent restaurants to choose from.

Today's Ride Choices

Morning: St. Helena Island Loop — 22 miles OR Beaufort to St. Helena Island — 36 miles

What to Expect:

If you wish, you may shuttle to St. Helena Island to begin this morning’s ride. Enjoy a pleasant route along coastal roads, pausing at Land’s End Point to explore the beach. Continue along Seaside Road through beautiful farmland before returning to the Penn Center. Guests seeking a longer ride may begin from the inn, cycling across Lady’s Island to St. Helena Island. After your visit to the Penn Center, you may shuttle or cycle back to Beaufort in the afternoon.

Cumulative Distance Range: 22 – 36 miles

Included Meals: Breakfast, Lunch

This morning, shuttle to Savannah (approximately 90 minutes). Upon arrival, your Savannah bike tour begins with a ride through the moss-draped gardens of Bonaventure Cemetery, an 18th-century burial ground featured in John Berendt’s acclaimed novel Midnight in the Garden of Good and Evil. Naturalist John Muir also spent six nights here during his “Thousand-Mile Walk” to the Gulf of Florida.

Continue cycling toward the Isle of Hope, passing attractive historic homes dating from the early 19th century and enjoying views of the Intracoastal Waterway. Your destination is the site informally known as Wormsloe Plantation, a Georgia State Historic Site. One of the most photographed places in the South, it features a 1.5-mile-long avenue of live oaks framed by a graceful stone arch. The estate’s tabby ruins—constructed from lime, ash, and crushed oyster shells—are the oldest standing structure in Savannah.

Enjoy a picnic lunch hosted by your trip leaders before continuing the ride back into Savannah. This evening, celebrate with your fellow travelers during a festive farewell dinner.

Today's Ride Choices

Morning: Isle of Hope — 22 miles

What to Expect:

Ride through Bonaventure Cemetery, then continue to the Isle of Hope, passing stately homes and scenic marshlands. Visit Wormsloe Historic Site before cycling through Savannah’s neighborhoods, showcasing a variety of architectural styles.

Cumulative Distance Range: 22 miles

Included Meals: Breakfast, Lunch, Dinner

After breakfast this morning, join a local guide for a walking tour of Savannah. VBT’s complimentary shuttle will take departing guests to the Savannah/Hilton Head International Airport (SAV), departing the hotel at 11:15 a.m. and arriving at the airport around 12:00 p.m. for your departing flight. We recommend scheduling a flight that departs no earlier than 2:00 p.m. Guests who need to arrive at the airport earlier or later must make their own arrangements.

The VBT van is also available to transport guests to Charleston International Airport (CHS), arriving at approximately 1:45 p.m. If you’ve left your car at the Ansonborough, you may take a taxi there from the Charleston airport.

Included Meals: Breakfast

Travel to Charleston and gather at the Ansonborough, the first hotel on our itinerary. If you’re flying in, you can arrange to meet VBT’s complimentary shuttle after your arrival at Charleston International Airport.

For guests who are driving to the tour, parking will be available at the Ansonborough for the week at a daily charge or at the Charleston airport. At tour’s end, you may join the VBT van to return from Savannah to the Charleston airport.

After your safety briefing and bike-fitting session this afternoon, enjoy a winding warm-up ride through historic “South of Broad,” where you’ll take in wide views of the harbor and Fort Sumter. Then continue riding through the historic market. You also ride past St. Philip’s Church, one of Charleston’s oldest, located on appropriately named Church Street.

Tonight, get to know your fellow travelers during a tour orientation, welcome reception, and dinner at a local restaurant.

Today's Ride Choices

Afternoon: Charleston Warm-up — 4 miles

What to Expect:

Cycling south, you pass the large fountain at the Waterfront Park entrance. It’s a wonderful place to stroll in the evening and watch the sailboats on the harbor or the sunset at Ravenel Bridge. On East Bay Street, pass “Rainbow Row,” the historic neighborhood of pastel-colored houses. Biking along the Battery, you see Fort Sumter, which guards the harbor entrance where the first shots of the Civil War were fired in 1861. In a city defined by its steeples, St. Philip’s Church boasts one of the oldest. You ride past it during your warm-up ride, then head to the historic City Market, where sweetgrass baskets are still handcrafted with local pride. Mind the horse carriages as you pass the stables on Anson Street back to the Ansonborough Inn.

Cumulative Distance Range: 4 miles

Included Meals: Dinner

After breakfast, you cycle along a dedicated bike/pedestrian lane on the dramatic Arthur Ravenel Bridge over the Cooper River. Traverse Sullivan’s Island, then cross another bridge to the Isle of Palms. Your route follows the scenic shores of the Intracoastal Waterway, passing by some of the area’s most sought-after homes. As you ride, enjoy soothing vistas the beach. During your lunch stop, you have the opportunity to change into swim clothes and go for a swim.

After lunch at a local restaurant on the Isle of Palms, continue cycling to Fort Moultrie. Edgar Allan Poe was stationed here from 1827 to 1828 while serving in the U.S. Army. The fortress played a key role in both the Revolutionary and Civil Wars. After your visit, you return to Charleston via the Arthur Ravenel Bridge.

Once at the Ansonborough, you have time to explore Charleston on your own. Perhaps enjoy a stroll along the Battery, the promenade flanking the city’s scenic harbor.

Dinner is on your own tonight.

Today's Ride Choices

Morning: Charleston to Sullivan’s Island and Lunch — 14 miles

Afternoon: Sullivan's Island to Charleston — 17 miles

What to Expect:

Cycle from the Ansonborough Inn over the Arthur Ravenel Bridge, enjoying expansive views of downtown, Charleston Harbor, and the Atlantic. Arrive at the Isle of Palms for lunch, where you can go for a swim at the beach.

After lunch, ride back through Sullivan’s Island to Fort Moultrie. Explore this National Monument and then retrace your way back to the Ansonborough Inn by bike or shuttle. Upon your return, you may enjoy Charleston on your own and choose from a range of Southern-style restaurants.

Cumulative Distance Range: 14 – 31 miles

Included Meals: Breakfast, Lunch

Today, you shuttle about 70 minutes south to Beaufort, where you cycle the stunning Spanish Moss Trail. Formerly the path of the Port Royal Railroad, this 12-foot wide, multi-purpose paved trail offers beautiful water and marsh views, coastal wildlife viewing, and historic points of interest as it meanders through neighborhoods draped in Spanish moss. The invigorating trail delivers you to Port Royal, a quaint Lowcountry town in the heart of a biologically rich estuarine ecosystem. After time to admire its houses listed on the National Historic Register, follow another segment of the Spanish Moss Trail to Beaufort. Once in Beaufort, lunch will be on your own; the town offers many restaurants to select from.

End your rewarding cycling day in Beaufort. Named “The South’s Best Small Town” by Southern Living magazine in 2017, it is a charming haven renowned for its Sea Islands, historic downtown, and savory Lowcountry food. Check into your hotel here and make yourself at home. The Beaufort Inn is conveniently located to give you easy access to the city’s downtown and waterfront.

Enjoy a Lowcountry boil before experiencing firsthand a famous Southern tradition at your inn: a Beaufort social hosted by a local historian. Enjoy this fun opportunity to dance the exuberant yet dignified Virginia Reel, a Colonial-era folk dance, while learning about the culture and history of Beaufort and its people.

Today's Ride Choices

Morning: Spanish Moss Trail — 15 miles

What to Expect:

Cycle along the tranquil Spanish Moss Trail to Port Royal, where several buildings and homes are listed on the National Register of Historic Places. Stop at the Sands boardwalk and observation tower for views of the Beaufort River and possible dolphin sightings. As you pass through Port Royal, take time to visit the Cypress Wetlands to see an ecosystem unique to the area. Your ride will conclude at your inn in the center of Beaufort.

Cumulative Distance Range: 15 miles

Included Meals: Breakfast, Dinner

Enjoy breakfast in town, then ride through beautiful farmland to St. Helena Island, passing the historic Chapel of Ease along your way. During the Colonial period, rice and cotton planters who found themselves too far from the churches of Beaufort constructed informal “chapels of ease” on their plantations. Built in the mid-18th century, St. Helena’s Chapel of Ease was largely destroyed by a fire more than 100 years later. Its four original walls remain, making it an evocative historic landmark.

Your visit to the Fripp Plantation starts with a cycle down its white fence-lined driveway. You will be greeted by your VBT trip leaders and a local tour guide. As your VBT trip leaders prepare your picnic lunch, the local tour guide will share the history of the Fripp Plantation, including a walking tour of the home. After this tour, enjoy your picnic lunch in the shade of the pecan trees on the plantation grounds overlooking the water.

After lunch, ride to the Penn Center for an included visit. The Penn Center is a National Monument and the first institution to recognize the Reconstruction Era of the South. Founded in 1862 to educate freed slaves, it’s now a cultural center for African American residents of the Sea Islands, a community also known as the Gullah. Dr. Martin Luther King Jr. held the annual retreat for his Southern Christian Leadership Conference at the center. After an enriching visit, return to Beaufort via shuttle or bike.

Later, embark on a walking tour of Beaufort. Stroll past the city’s mix of antebellum mansions, live oaks, and charming 1950s storefronts with a resident guide, who explains why the town has lured so many moviemakers to its lovely streets. A number of critically acclaimed films have used Beaufort as their backdrops, including Forrest Gump with Tom Hanks, The Prince of Tides with Barbra Streisand, and The Great Santini with Robert Duvall.

Make your own dinner plans in Beaufort this evening; there are many excellent restaurants from which to choose.

Today's Ride Choices

Morning: St. Helena Island Loop — 22 miles OR Beaufort to St. Helena Island — 36 miles

What to Expect:

If you wish, you may shuttle to St. Helena Island to begin this morning’s ride. During this pleasant ride on coastal routes, pause at Land’s End Point to explore the beach. Continue on Seaside Road through beautiful farmland, then return to the Penn Center. Those who want a longer ride can start from the inn and cycle across Lady’s Island to St. Helena Island. After your visit at the Penn Center, you can shuttle or cycle back to Beaufort in the afternoon.

Cumulative Distance Range: 22 – 36 miles

Included Meals: Breakfast, Lunch

This morning, shuttle to Savannah (approximately 90 minutes). Once you have arrived, your Savannah bike tour starts with a ride through the moss-hung gardens of Bonaventure Cemetery, an 18th-century cemetery featured in John Berendt’s critically acclaimed novel Midnight in the Garden of Good and Evil. John Muir also sojourned here for six nights during his “Thousand-Mile Walk” to the Gulf of Florida.

Continue cycling toward the Isle of Hope. Here, ride past attractive old homes dating from the early 19th century, enjoying views of the Intracoastal Waterway as you ride.

Our destination is informally known as Wormsloe Plantation, a State Historic Site. One of the most photographed locations in the entire South, it features a 1.5-mile-long live oak avenue framed by a graceful stone entry arch. The remains of the estate—which was constructed using “tabby,” a building material similar to cement and made from lime, ash, and crushed oyster shells—are renowned as the oldest standing structure in Savannah.

Enjoy a picnic lunch hosted by your leaders before continuing the ride back to Savannah. Tonight, celebrate with the group during a farewell dinner.

Today's Ride Choices

Morning: Isle of Hope — 22 miles

What to Expect:

Ride through Bonaventure Cemetery before continuing to the Isle of Hope, riding past stately homes and enjoying marsh views. Visit Wormsloe Historic Site and ride through Savannah neighborhoods of different architectural styles.

Cumulative Distance Range: 22 miles

Included Meals: Breakfast, Lunch, Dinner

After breakfast this morning, join a local guide for a walking tour of Savannah. VBT’s complimentary shuttle is available to take departing guests to the Savannah/Hilton Head International Airport (SAV), leaving the hotel at 11:15 a.m. and arriving at the airport around 12:00 p.m. for your departing flight. We suggest a flight departing after 2:00 p.m. Guests who need to get to the airport earlier or later must make their own arrangements.

Included Meals: Breakfast