2025 Charleston Sailing Tours Guide

Life in the Lowcountry is all about slowing down and taking a moment or two to relax, and locals and visitors both agree that Charleston's Waterfront Park is the perfect venue to stretch out and soak up the scene. With a prime location overlooking Charleston Harbor and the Cooper River, and more than 10 acres of room to roam, (most of which is waterfront), Waterfront Pak is essentially a romantic, engaging, serene, and perfectly picturesque destination that will make any newcomer fall in love with this unique southern city.

Art lovers will want to reserve an afternoon or two to explore the acclaimed Gibbes Museum of Art, a stunning addition to Charleston's historic district that is simply impressive both inside and out. Home to an ever-rotating and permanent collection of 10,000 priceless works of art, the historic building exudes prestige, and invites visitors of all ages and interests to peruse at their leisure, and discover something beautiful, historic, and inspiring at this distinguished and massive Charleston County collection.

The Charleston City Marina is often deemed the "Mega Marina," as it is easily one of the largest marinas in the southeastern United States. Conveniently located at mile marker 469.5 along the Intracoastal Waterway (ICW), and just a stone's throw away from the historic downtown, the marina is one of the most visited spots and temporary homes for mariners from all across the country. Accommodating for both travelers by land and by sea, with a host of amenities and incredible views of the harbor and the Ashley River, the expansively grand marina is sure to make any visitor yearn for an evening or afternoon on the water, and an adventure on the high seas.

The Nathaniel Russell House Museum has a reputation that has garnered it both regional and national familiarity and significance, and which has earned it a place of honor as one of the most distinctive buildings in Charleston. Serving as the home base for the Historic Charleston Foundation, this notable collection of small hidden offices and gloriously restored 1800s grandeur is a worthy stop on any historical home tour through the streets of Downtown Charleston.

Spend a full day by the seashore at scenic, sprawling Folly Beach County Park. This expansive park which takes up the entire portion of the southwestern end of Folly Beach features plenty of room for multiple towels and umbrellas, with well over 3,500' feet of ocean frontage, and 200' feet on the opposite side of the island along adjacent Folly River.An easy-to-access and easy-to-enjoy stretch of sand that features anything a beach lover could possibly need on a long, lazy outdoor vacation day, a visit to this Charleston County Park is, quite literally, a day at the beach.

The Miles Brewton House may seem, at first glance, one of many impressively grand and antique southern mansions that line the downtown streets of Charleston, but this home is a favorite among any guided or self-led walking tour for both its story and its local prestige. Considered one of the finest national examples of a "double house" or "town home" of the Colonial Era, the massive brick house with dual levels of white pillars has been the temporary home for some of Charleston's most famous, but undesired residents.

Charleston, South Carolina is well-known as a city of "firsts," but one of the most remarkable first sites in this town is the toweringly impressive Dock Street Theatre. Located in the French Quarter of the Historic District, this well-renowned landmark, still operational and freshly back in business after a $19 million dollar restoration, has the distinction of being the oldest theater in the country - a title which it proudly honors by hosting a seasonal arsenal of plays to seasoned theater goers and Charleston newcomers alike.

Washington Square and Meeting Street visitors are encouraged to take a minute's stroll over to Elizabeth Street to admire the Governor William Aiken House, also known as the Aiken-Rhett House. The sprawling home is a treasure in Charleston, and holds a lot of distinction in an already diverse town that is positively steeped in history.

The expansive James Island County Park has a unique distinction as being one of the most entertaining and diverse destination in the Lowcountry. Able to accommodate a world of interests, from camping and fishing to splashing around in a seasonal spray play fountain, outdoors fans of all tastes will find something to love about this exquisitely fun outdoor oasis.

Located at the edge of the Ashley River, next to the Joseph P. Riley, Jr. minor league baseball stadium, Brittlebank Park is a refreshing breath of fresh air that serves up some of the best water views in the region, while serving as an occasional venue for some of Charleston's most beloved events.

Washington Square Park, with its seasonally blooming azaleas, trickles of Spanish moss hanging off of ancient live oaks, and quiet setting in the heart of the city, is a romantic, serene destination that brings the inherent laid-back charm of Charleston, South Carolina to vivid life.

Enchanting gardens, interactive history, and breathtaking views abound at Middleton Place, one of the top-ranked attractions by Charleston newcomers and seasoned vacationers alike.

Fort Sumter, a historic site which can be viewed from virtually any point along the Charleston Harbor, is one of the most recognizable landmarks in this history-rich southern city. Easily one of the most famous forts of the Civil War, the Fort Sumter National Monument is internationally known as one of America's most important coastal landmarks, and cements Charleston's long and legendary role in American History.

History is embedded in Charleston's culture, and the Circular Congregational Church is a prime example of how this sometimes stormy and always fascinating history can be beautifully brought to life, and easily enjoyed by any strolling passerby. One of the most distinguished chapels in the area, and anchored by the oldest cemetery in Charleston, the church ranks high on the list of top attractions for architectural aficionados, ghost story fans, and anyone who appreciates a quiet sanctuary with an impressive veneer.

Many of Charleston's most notable public buildings once served as a launching point for some of the biggest events in our country's history, and the stately Hibernian Hall is certainly no exception. The modest Greek-style columned structure holds a distinctive role in both Charleston and American's legacy as the meetingplace for a faction of the 1860's National Democratic Convention, and ever since, this once marginally notable structure has risen to fame as one of the most important meeting venues in the South.

The towering Cathedral of St. John the Baptist is one of Charleston's premier religious structures, and arguably one of its busiest. With daily mass, multiple Sunday masses, and a heavy schedule of calendar of events, this gothic chapel is likely to be occupied during any quiet tour or visit. Distinguished as the mother church of the Roman Catholic Diocese of Charleston, the unique and impressive structure belies a stormy history that involves not one, but two such magnificent chapels, that is sure to fascinate visitors or all denominations.

New Charleston visitors are often advised to start their regional tour with a visit to the historic City Market, a massive four block meeting place that sells homegrown goods and exquisitely crafted arts and crafts from all over the low country. A Mecca for commerce for well over 200 years, and anchored by the historic Market Hall which gives the ensuing indoor / outdoor shops a worldly entrance, City Market is sure to wow visitors with endless stations of vendors, and keep avid shoppers busy for hours, if not for days.

Freshfields Village, located at the crossroads of Seabrook Island, Kiawah Island and Johns Island, is more than just a shopping Mecca for visitors who want to give their wallets a little exercise. It's also one of the hottest spots along the South Carolina coast for great cuisine, great brews, and a gorgeous setting that takes advantage of the Lowcountry's scenic outdoors. With a relaxing "Americana" feel, and tons of boutiques, restaurants, services, and accompanying little local attractions, Freshfields Village has just about everything a visitor could possibly need for a perfectly accommodating seaside vacation, and then some.

On a sunny Fall Saturday afternoon, the Johnson Hagood Stadium may very be one of the most popular and exciting spots in the city of Charleston. Home to the Citadel Bulldogs, the official football team of the world-renowned Citadel, the stadium can squeeze in 21,000 football fans to cheer on their favorite cadets and players, enjoy the action, and celebrate one of Charleston's favorite local sports teams.

If it weren't for the telltale palmetto trees and notable landmark neighbors, like the historic Dock Street Theater, a visitor might mistake this church for an authentic French house of worship, tucked away in a European countryside of decades ago.

It's almost ironic that The Charleston Museum, which paints a complete portrait of Charleston's centuries of history, has a unique history all its own. Well known as "America's First Museum" and recently named one of the top five museums in Charleston by The Travel Channel, the museum is certainly worthy of exploration for patrons of all ages, tastes and interests.

Fishing, incredible views, and romantic strolls overlooking the "Edge of America" are all on the agenda at the Folly Beach Fishing Pier, officially known as the more long-winded moniker the "Edwin S. Taylor Folly Beach Fishing Pier." A whopping 1,045' long, and 25' feet wide, the pier is the second longest on the East Coast and is easily one of Folly Island's most esteemed, and most visited, local attractions.

Visitors do not necessarily have to be a horticulturalist or garden lover to appreciate the toweringly impressive Angel Oak Tree, one of the most significant and oldest trees in Johns Island, if not the entire East Coast. With far-reaching branches that produce an estimated 17,200 square feet of shade, the almost mythic-looking Johns Island landmark is easily one of the most photographed sites in the Lowcountry.

The South Carolina Aquarium may be one of Charleston's newest local attractions, but it is certainly making waves as one of its most exciting and entertaining venues in an already packed southern destination.

The Sullivan's Island Lighthouse, also commonly known as "Charleston Light" holds a unique title in Carolina Lighthouse lore as one of the most modern lighthouses in the country. The unique triangular and slim structure, which is broken up into two black and white color blocks, is hard to miss, and is a distinctive local landmark that hovers over the beach scene.

A treasure of a home that is managed by The Charleston Museum, the Joseph Manigault House is a prime example of Charleston's hardworking efforts to protect the relics of its lush, although often somber, past. The grand three story home is considered one of the best representations of Adam style architecture, (a typically 18th-century neoclassical design), and despite its central location on Meeting Street, is well known for its quiet and unpopulated tours. A true delight for interior designers, with ornate touches and authentic furnishings, this sprawling Charleston showpiece paints a complete portrait of typical pre-Civil War Charleston life, from the decadent rooms and finishings owned by the city's wealthiest residents, to the hardworking but enslaved hands that crafted them.

High-spirited visitors will adore a tour of Firefly Distillery, a 48 acre vineyard and winery that is located on Charleston's "back porch," also known as neighboring Wadmalaw Island. As the only domestic winery in the Charleston County Lowcountry region, the locale has a little something for everyone, regardless of legal drinking age, including walking trails, a petting zoo, a spectacular seasonal garden, a scenic large pond, and of course the winery itself.

The White Point Garden public park certainly provides a scenic slice of Charleston life, with incredible views that span across the intersections of the Ashley and Cooper Rivers. Fort Sumter, Castle Pinckney, and the Sullivan Island Lighthouse can all be spotted in the distance from this downtown region, however, like most public parks and gathering spaces in Charleston, this wide open patch of green space is equally known for its centuries of historical events as it is for its sheer beauty.

The Old Exchange is one of the most visited historic sites in Charleston, both for its grand stature as one of the colonies' earliest statuesque public buildings, and its unique array of interior assets - including the famous Provost Dungeon in the basement of the building.

Even cadets at the Citadel need to relax every once and a while, and there's no better place to escape the everyday drills than at neighboring Hampton Park. This historic park – one of the oldest in the city – boasts 60 acres of natural beauty on the western edges of Charleston's downtown, with plenty of features and amenities to keep any outdoor lover perfectly entertained. An ideal locale for a pick-up game of baseball, an afternoon picnic, or just a quiet stroll amidst the shaded gazebo and southern gardens, Hampton Park is sure to entice anyone into a stress-free, Lowcountry state of mind.

The Kahal Kadosh Beth Elohim Synagogue, a famous icon just off of Market Street, has a fitting place among Charleston's long list of historical churches and buildings as the county's second oldest Synagogue, and the oldest Synagogue that remains in continuous use. The Grecian structure, one of the many hallmarks of Charleston's blossoming 19th century architectural era, is more than enough to grab a passer-by's attention, but the astounding details within, including an ornate domed ceiling and walls of tastefully appointed windows, will surely take anyone's breath away.

The Magnolia Plantation and Gardens is easily one of the most spellbinding sites in the city of Charleston, with acres of wildly growing gardens that have captivated visitors for generations. A romantic and altogether enchanting destination located far away from the downtown distractions, the distinctive plantation house, rich in history, and the famed acres of free-flowing gardens are sure to be a favorite local attraction for any visiting naturalist.

The Charleston Tea Plantation is a unique attraction along secluded Wadmalaw Island, with an equally unique claim to fame. As the proclaimed "only tea garden" in the United States, and the country's only tea plantation, the site has a long history of churning out America's only locally grown brew, a legacy that modern visitors can still enjoy on any sunny Charleston County afternoon visit.

Rainbow Row is a famous historical Charleston neighborhood that certainly lives up to its name. The collection of brightly-colored homes, which are stacked side by side, is arguably one of the most photographed sections of the city, and attracts dozens of artists who regularly set up easels around the East Bay Street neighborhood, and break out the watercolors or acrylics to capture the colorful scene.

Like many of Charleston's institutions, The Citadel is an impressive nationally recognized landmark that both serves an instrumental community function, while boasting a long and fascinating history. This South Carolina military college, one of the six Senior Military Colleges in America, churns out hundreds of military leaders every year, a tradition that has been faithfully adhered to since the college was founded in 1842.

Fort Moultrie, one of the oldest still-standing forts along the Eastern Seaboard, is a "must see" destination for history buffs. The low-laying coastal structure, which encompasses a large parcel of Atlantic Ocean bordering beaches on the southern tip of Sullivan's Island, began as a Revolutionary War defense before being transformed into a secondary Confederate stronghold during the Civil War.