New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Charleston Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Historic Charleston Exploration

Morning

Start your day with a visit to the iconic Charleston City Market. This bustling market is a great place to experience the local culture and pick up some unique souvenirs. After exploring the market, head over to Callie's Hot Little Biscuit for a delicious Southern breakfast. Their biscuits are legendary and will give you the energy you need for a day of sightseeing.

Afternoon

In the afternoon, take part in The Best History Walking Tour in Charleston!. This guided tour will take you through some of Charleston's most historic sites and provide fascinating insights into the city's past. After the tour, visit St. Michael's Church, one of the oldest churches in Charleston with stunning architecture. For lunch, stop by Husk, known for its innovative Southern cuisine.

Evening

End your day with a relaxing stroll along Charleston Waterfront Park. The park offers beautiful views of the harbor and is a perfect spot to unwind after a busy day. For dinner, dine at Fleet Landing Restaurant & Bar, which offers fresh seafood and waterfront views. If you're up for it, join Charleston Boo-Hag and Brews Haunted Bar Hop for an evening of spooky stories and local brews.

Bedtime

Find amazing hotels in Charleston, SC.

4.67
Charleston City Market
Book Now

5.00
The Best History Walking Tour in Charleston!
Book Now

Architectural Wonders and Maritime History

Morning

Begin your second day with a visit to Rainbow Row, a series of colorful historic houses that are one of Charleston's most photographed spots. Afterward, enjoy breakfast at Miller's All Day, where you can savor classic Southern dishes with a modern twist.

Afternoon

In the afternoon, explore maritime history at Patriots Point Naval & Maritime Museum. This museum features historic ships like the USS Yorktown and provides an immersive experience into naval history. For lunch, head over to Poogan's Porch, known for its charming atmosphere and delicious Southern fare.

Evening

Spend your evening visiting The Battery and White Point Garden, where you can enjoy scenic views of historic mansions and cannons along the waterfront. For dinner, try Hall's Chophouse, renowned for its steaks and elegant setting. Cap off your night with an adventure on the water by joining Charleston Private BYOB Luxury Sailing Cruise.

Bedtime

Find amazing hotels in Charleston, SC.

4.81
Rainbow Row
Book Now

4.80
Patriots Point Naval & Maritime Museum
Book Now

Plantations and Gardens Galore

Morning

Start your third day with a trip to Magnolia Plantation and Gardens. These beautiful gardens are among America's oldest public gardens and offer stunning landscapes to explore. Enjoy breakfast at their on-site cafe before wandering through the lush grounds.

Afternoon

In the afternoon, continue your exploration of Charleston's plantation history with a visit to Boone Hall Plantation & Gardens. Known for its moss-draped oak trees lining the entrance drive, this plantation offers tours that delve into its rich history. Have lunch at nearby restaurant Coleman Public House which offers hearty American fare.

Evening

Conclude your day by visiting another historical gem: Drayton Hall. This well-preserved plantation house provides insight into pre-Revolutionary life in South Carolina. For dinner head back into downtown Charleston to dine at FIG – famed for its farm-to-table cuisine featuring local ingredients.

Bedtime

Find amazing hotels in Charleston, SC.

4.49
Magnolia Plantation and Gardens
Book Now

4.26
Boone Hall Plantation & Gardens
Book Now

Historic Homes and Cultural Tours

Morning

Begin your fourth day with a visit to Heyward-Washington House. This historic house museum offers a glimpse into Charleston's colonial past and is filled with period furnishings. For breakfast, stop by Another Broken Egg Cafe for a hearty meal to start your day.

Afternoon

In the afternoon, take part in Charleston Women and Wine Tour. This unique tour combines Charleston's rich history with wine tastings at some of the city's best spots. After the tour, visit Joseph Manigault House, another beautifully preserved historic home. For lunch, enjoy a meal at Magnolias, known for its upscale Southern cuisine.

Evening

Spend your evening exploring the spooky side of Charleston with Charleston Supernatural 90-Minute Ghost Tour. This guided tour will take you through some of the city's most haunted locations. For dinner, dine at Peninsula Grill, famous for its elegant setting and delicious Lowcountry cuisine.

Bedtime

Find amazing hotels in Charleston, SC.

4.84
Heyward-Washington House
Book Now

5.00
Charleston Women and Wine Tour
Book Now

Bridges and Beach Adventures

Morning

Start your final day in Charleston with a visit to Arthur Ravenel Jr. Bridge (Cooper River Bridge). This iconic bridge offers stunning views of the city and is perfect for a morning walk or bike ride. Afterward, have breakfast at The Daily, known for its fresh pastries and coffee.

Afternoon

In the afternoon, head to Folly Beach for some fun in the sun. Take part in Charleston Folly Beach Stand Up Paddleboard Dolphin Safari for an exciting adventure on the water where you might spot dolphins! For lunch, enjoy beachside dining at Lost Dog Cafe, a local favorite.

Evening

Conclude your trip with a relaxing evening back in downtown Charleston. Visit Circular Congregational Church, one of the oldest continuously worshipping congregations in the South. For dinner, savor your last meal in Charleston at SNOB (Slightly North of Broad), known for its creative Southern dishes.

Bedtime

Find amazing hotels in Charleston, SC.