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CharlestonSailing trips & boat tours

Our most recommended Charleston Sailing trips & boat tours

Charleston: Fort Sumter Entry Ticket and Ferry Ride

1. Charleston: Fort Sumter Entry Ticket and Ferry Ride

Enjoy a ferry ride to the grounds of Fort Sumter and explore the grounds at your own pace. Pass by the Arthur Ravenel Jr. Bridge and take in the sights of Charleston’s stately Rainbow Row and Battery homes. As you approach Fort Sumter, graceful sailboats and playful dolphins add to the photogenic scene. If you depart from Mt. Pleasant you will enjoy views of the USS Yorktown Aircraft Carrier from up-close, while tours embarking from downtown will see Aquarium Wharf as they depart and return. Arrive at The Fort Sumter and Fort Moultrie National Historical Park, which sits prominently at the mouth of the Charleston Harbor, a strategic location that was crucial to its defense.  While here, explore the grounds of Fort Sumter. Stand on the grounds where America’s deadliest war began at Fort Sumter and Fort Moultrie National Historical Park. The first shots were fired here, igniting a conflict that saw more than 700,000 casualties. Experience the opening battle of the American Civil War and explore its origins with a National Park Ranger. Your approximate 1-hour visit to Fort Sumter allows ample time to explore well-preserved fort ruins and browse Museum Store souvenirs. A visit to Fort Sumter and Fort Moultrie National Historical Park provides a window into the life and trials of America’s heroes, from the Civil War to today’s modern conflicts. Learn about the events leading to the war from knowledgeable National Park Rangers who will relay stories of courageous heroes in action from the Civil War’s first battle. Walk in the steps of those who shaped this nation alongside a National Park Ranger. Then enjoy the beautiful views of the city as you ride the ferry back to Charleston.

Charleston: Luxury Harbor Dinner Cruise

2. Charleston: Luxury Harbor Dinner Cruise

Embark on a true Charleston Harbor dining experience aboard the Spirit of Carolina. Enjoy a three-course dinner, made to order from local seasonal ingredients. As you dine on a delicious multi-course plated dinner, cruise through the beautiful Charleston Harbor, past Fort Sumter, along the Battery and beneath the Ravenel Bridge. Take in the views from the large enclosed air-conditioned dining decks or the open-air observation deck. Enjoy music throughout the cruise, as well as a full-service bar. Dinner menu: Soup: Charleston she-crab soup Salad: Edisto green salad with a blend of baby lettuce, dried cranberries, crumbled feta cheese, and toasted almonds with herb vinaigrette (gluten-free) Entrées: (All entrees include freshly baked bread and butter) • Braised short rib of beef (gluten-free, dairy-free) with cabernet reduction, roasted garlic whipped potatoes (gluten-free), and seasonal vegetables (gluten-free)• Seared wing tip chicken breast (gluten-free) with white wine lemon sauce, sautéed spinach and feta cheese fillings, roasted garlic whipped potatoes (gluten-free), and seasonal vegetables (gluten-free)• Low country shrimp and grits (gluten-free) with sautéed shrimp, tasso ham, and andouille sausage. Served on creamy stone-ground grits and topped with aged cheddar cheese and bacon jam garnish• Roasted sliced cauliflower (dairy-free, vegetarian) with roasted red pepper drizzle, wilted spinach, lemon and olive oil mixed ancient grains of quinoa, farro, toasted barley (dairy-free, vegetarian), and grilled asparagus (gluten-free, dairy-free, vegetarian) Desserts: • New York-style cheesecake with strawberries and whipped cream • Chocolate pot de crème (gluten-free) with whipped cream and chocolate shavings ($6.00 each) Food is not prepared in a nut-free, shellfish-free, or gluten-free facility.

Charleston: Daytime or Sunset Historic Harbor Cruise

3. Charleston: Daytime or Sunset Historic Harbor Cruise

Cruise through the Charleston Harbor on an old-fashioned 1920s-Bay-Steamer-replica yacht. Enjoy live narration from the captain and purchase treats from a fully-stocked drink and snack bar. See the Civil and Revolutionary war sights and keep an eye out for dolphins. Relax in the enclosed observatory or on the partially-covered upper deck. Listen carefully as your captain guides you on a journey through more than 300 years of American history. You’ll pass by 75 landmarks and points-of-interest on this 20-mile trip. Get close-up views of the “Holy City,” including Fort Sumter - where the first shots of the Civil War were fired. Glide past Confederate and Union army forts and see the famous “Fighting Lady” of World War II. Pass by remnants of the Civil and Revolutionary wars and look for local wildlife like dolphins and pelicans splashing nearby. Choose between indoor or outdoor seating.

Charleston: Historical Downtown Tour by Horse-drawn Carriage

4. Charleston: Historical Downtown Tour by Horse-drawn Carriage

Ride in a traditional horse-drawn carriage through historic downtown Charleston on a guided tour. Listen to live commentary about the city as you pass by the Charleston Harbor, Rainbow Row, King Street, White Point Gardens, and Charleston Battery. Begin the tour at the activity provider's stables. Board a beautiful custom-built carriage and depart from the barn. Ride toward the city gate, located in the Old City Market. Learn about the city's rich history from a professional guide while traveling aboard a unique vehicle. Gaze at vibrant neighborhoods and elegant buildings from your seat. Experience the highlights of the historic downtown area, such as Charleston Harbor, Rainbow Row, 4 Corners of Law, King Street, White Point Gardens, and the Charleston Battery. Take in informative and entertaining commentary from your guide, before arriving back at the stables.

Charleston: Magnolia Plantation Tour and Transport

5. Charleston: Magnolia Plantation Tour and Transport

Witness a slice of living history at Magnolia Plantation and its world-famous gardens, owned by the Drayton family for 12 generations. Visit the Historic Gardens, Petting Zoo, and The Conservatory. Begin your half-day tour by boarding a climate-controlled coach in Charleston. Meet your professional guide and ride to Magnolia Plantation, dating from 1676 and the time of the British colony. Step into one of America's first tourist attractions and first public gardens, which have been open to the public since 1870. Take a guided walk through America's last large-scale romantic garden. Experience history on a 45-minute narrated tram ride through the Audobon Swamp Gardens and visit important locations like Drayton Home (not Drayton Hall), Orientation Theater, and the Old African American Cabin.

Charleston: Historic City Highlights Guided Bus Tour

6. Charleston: Historic City Highlights Guided Bus Tour

The bus tour departs from Charleston Visitor’s Center where you’ll hop on board a deluxe, climate-controlled shuttle for a 90-minute tour of the city’s historical highlights. Accompanied by a knowledgeable, local guide, pass by 100 of Charleston’s most iconic sights of the past and present whilst listening to amazing tales and anecdotes about the city. On your tour, travel through some of the city’s most historic parts. Visit Charleston’s Historic Homes, The Battery Sea Wall, the Four Corners of Law, and Rainbow Row to name but a few. Other highlights of the tour include several historic churches, old markets, and picturesque neighborhoods.

Charleston: Haunted Carriage Evening Tour

7. Charleston: Haunted Carriage Evening Tour

Listen to spine-tingling tales of prisoners, rogues, and pirates that make up the history of Charleston. Cover over 300 years of history from the comfort of your carriage. Mysterious alleys and cobblestones await as your expert guide leads you through Historic Charleston on a 40-minute Haunted Carriage Tour. Start the tour at Old South Carriage Company's stables where the tour explores the 15 block core that comprises Historic Charleston. Along the way you will see Old Exchange & Provost Dungeon, Circular Congregational Church and Graveyard, Charleston City Market, and St. Michael's Episcopal Church. All tour guides of this activity are members of the Palmetto Guild, which indicates that they have successfully passed a comprehensive examination of the history of Charleston.

Charleston: 90-Minute Ghost and Dungeon Walking Tour

8. Charleston: 90-Minute Ghost and Dungeon Walking Tour

Test your nerve and explore the dark edges of Charleston's haunted historic district, deeply steeped in South Carolina's low country superstition on a guided walking tour. Venture through Charleston's haunted historic district, one of the oldest places in America, and learn about its terrifying history. Continue along the eerie back alleys and churches to find out why Charleston is known as "The Holy City." Visit the Old Exchange and Provost Dungeon to learn about its harrowing past, confining enslaved people, American revolutionaries, and British soldiers.

Charleston: Experience Charleston's History on a Guided Walk

9. Charleston: Experience Charleston's History on a Guided Walk

Experience the chapters of Charleston's history on a guided walking tour and explore the cobblestone streets of the only English, walled city in North America. Glimpse into the city's complicated past, from its colonial roots to many natural disasters. Meet your guide, Al Ray, and set off on a sightseeing walk in the beautiful walled city of Charleston. Stroll along the cobblestone streets, lined with colorful pre- and post-colonial homes, storefronts, churches, and public buildings. Get swept up in Charleston's fascinating and turbulent history as Ray gives meaning to each stop with insider tales and legends. Read the ancient symbols on the tombstones and relive the phases of the city's history, from rapid growth and the age of piracy to the rise of the rice planters. Learn about the numerous disasters that have made their mark on Charleston, including seven major fires, hurricanes, epidemics, sieges, and bombardments, plus a devastating earthquake. Come away with a new understanding of Charleston and the people and events that shaped it.

Charleston: 1-Hour Carriage Tour of the Historic District

10. Charleston: 1-Hour Carriage Tour of the Historic District

Explore Charleston's historic district on a horse or mule-drawn carriage tour. Listen to your guide tell you local stories and anecdotes as you go past iconic landmarks, buildings, churches, and more. Begin your tour at the Big Red Barn in downtown Charleston and meet your local driver/guide. Then, settle into a carriage drawn by either horses or mules for your guided tour. Follow a route that takes in some of the historic downtown district’s most elegant mansions and gardens, learning about the architecture of each place as you drive along. Catch the scent of jasmine flowers from deep, shady porches, and pass by rows of bristling palmetto trees. Get an overview of Charleston’s dramatic history, from long-ago pirate raids to plantations, Revolutionary battles, the Civil War, and Reconstruction. The city was founded in 1670, and Charleston's historic buildings have been meticulously preserved and restored. Conclude your tour with drop-off at the Big Red Barn.

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Frequently asked questions about Charleston Sailing trips & boat tours

What are other things to do than Sailing trips & boat tours that are worth visiting in Charleston?

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Which Charleston Sailing trips & boat tours are taking additional COVID-19 precautions?

These Charleston Sailing trips & boat tours are taking additional COVID-19 precautions:

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What people are saying about Charleston

Overall rating

4.8 / 5

based on 208 reviews

Having visited Charleston many times, we had a good basic knowledge of the city’s history and geography. But these two tours were very informative and we learned many new interesting things. Although different in scope, the bus tour and the harbor cruise complemented each other and made for a relaxing and pleasant experience. The bus tour was especially exceptional - the driver narrated the entire trip with both factual and anecdotal information.

Great way to spend a rainy day ! Alan was our bus tour guide and was awesome. Afterwards we toured Charleston Harbor and Stephen was our guide. He was awesome also !

Tour Guides were very knowledgeable and entertaining as well. I highly recommend taking the gray line bus tour and harbor cruise.

the guide , driver and doing a good job for charter and for boat, nice , quiet and lady guide too.

Wonderful! Ask for Steve the tour guide for the boat he is awesome!