Charleston’s waters are a natural magnet for sailing enthusiasts and curious visitors alike. Known for its historic harbor, scenic bridges, and abundant wildlife, Charleston offers a variety of sailing adventures that cater to both relaxation and active participation. Whether you want to unwind with a private sunset cruise, spot dolphins during a morning sail, or help hoist the sails on a classic schooner, Charleston’s sailing scene delivers authentic experiences with stunning views.
Unlike many other coastal cities, Charleston’s navigation-friendly harbor and rich maritime heritage make it an ideal place to explore by boat. The city’s landmarks—like the Arthur Ravenel Jr. Bridge, the USS Yorktown, and Fort Sumter—are all visible from the water, making each trip a scenic history lesson combined with fresh air and sea spray. Plus, the chance to see bottlenose dolphins and other wildlife adds a lively dimension to any sailing day.
In this guide, we’ve rounded up the ten best sailing experiences around Charleston. From luxurious private yachts to active sailing excursions, each offers a unique way to enjoy the city’s maritime charm. Whether you’re celebrating a special occasion or just want to see Charleston from a new perspective, there’s a perfect sail waiting for you.
1. Private Sailing, Dolphin and History Tour on Mystique
At number one, the Private Sailing, Dolphin and History Tour on Mystique stands out for its personalized approach. For around $499, your group of up to six people gets exclusive access aboard a well-maintained 43ft sailing yacht. This 2-hour cruise departs from Harbor City Marina, offering a peaceful escape from the city’s buzz.
What makes this tour special? The boat is yours alone, allowing for a tailored experience—whether you want to relax, take photos of the Arthur Ravenel Jr. Bridge, or actively watch for dolphins frolicking nearby. The crew provides shade, drinks, and restroom facilities, making it a comfortable ride. Hosts like Rob and Maddie gather rave reviews, with guests emphasizing the peaceful atmosphere, good company, and prime wildlife sightings. The itinerary typically includes passing by the Charleston Battery and sometimes getting close to Fort Sumter, adding a dash of history.
Bottom line: This tour is perfect if you’re after a private, relaxed cruise with excellent chances of dolphin sightings and personalized attention.
2. Private Sailing Charter with Captain, BYOB
Next on our list, the Private Sailing Charter with Captain, BYOB offers a slightly longer experience—about 2.5 hours for $500, accommodating up to six guests. This cruise is about kicking back with your own drinks and snacks, taking in Charleston’s sights from the water without lifting a finger.
What makes this trip stand out is the flexibility—you can choose to sail at sunset or during the day. It’s particularly popular for romantic evenings or special celebrations. The captain takes you past landmarks like Fort Sumter, the USS Yorktown, and the Ravenel Bridge while sharing insights into Charleston’s history. Guests consistently rave about the friendly, engaging captain Will and the opportunity to enjoy a private, relaxed atmosphere with personalized service.
Bottom line: Ideal for those wanting a flexible, BYOB experience with the option to customize timing for sunset or afternoon.
3. Charleston: Schooner Sailing Harbor Tour & Dolphin Watch
The Charleston Schooner Sailing Harbor Tour & Dolphin Watch is a classic for its active sailing vibe. For just $25 per person, you help hoist the sails on a three-masted schooner and enjoy a 1.5-hour cruise through historic Charleston Harbor.
This tour is notable for its participatory nature—it’s not just sitting back but actively raising the sails and experiencing what sailing was like a century ago. The crew shares stories of local history as you pass landmarks like Fort Sumter and Castle Pinckney, with plenty of opportunities to spot dolphins playing nearby. The boat’s design emphasizes tradition and charm, making it a hit with those interested in maritime heritage and hands-on experiences.
Guests mention the peaceful ride and the friendly crew that made the trip enjoyable for families and solo travelers alike. The low price makes it an easy add-on for those wanting a taste of sailing without a big commitment.
Bottom line: A fun, affordable option for active travelers eager to participate in sailing and wildlife watching.
4. Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
If a romantic evening is on your mind, the Private Luxury Sunset Sail on the sailing yacht Fate is hard to beat. For $760, your group of up to six can enjoy 2 to 4 hours on a luxurious 50ft yacht. The tour begins in the late afternoon and often extends into the sunset, providing spectacular views of the Charleston skyline and landmarks like the USS Yorktown and Fort Sumter.
This tour includes the chance to see playful dolphins and learn about Charleston from an experienced skipper. You can bring your own drinks and snacks, or opt for onboard catering, making it ideal for celebrating a special occasion. The boat’s elegant design and attentive crew make it a top pick for couples or families seeking a romantic, high-end experience.
Guests rave about Captains Scott and Will, who deliver top-notch hospitality. Many mention the breathtaking sunsets and how well the trip was tailored to their desires, including the option to play music and relax in style.
Bottom line: This cruise provides a high-end, private setting perfect for romantic dates or special celebrations, with a focus on comfort and scenic beauty.
5. Charleston: Private BYOB Luxury Yacht Cruise
The Charleston Private BYOB Luxury Yacht Cruise offers a 2.5-hour private tour on a sleek yacht for $500. It’s designed for small groups wanting a luxurious yet relaxed experience. The focus here is on personalized sightseeing—from the water, you’ll see The Battery, Ravenel Bridge, and even Fort Sumter if conditions allow.
It’s especially suited for romantic evenings or special anniversaries. Guests appreciate the professional crew who make the trip seamless. The option to bring your own drinks makes it easy to customize the experience, and the boat’s high-end amenities ensure comfort. Many reviews mention how attentive the staff is and how memorable the views are.
It’s a flexible option, with multiple departure times, making it suitable for various schedules. The combination of luxury, privacy, and scenic views makes it an excellent upgrade for travelers looking to splurge a little.
Bottom line: Perfect for those seeking a high-end, private sailing experience with customizable timing and onboard amenities.
6. Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
For a laid-back, afternoon escape, the Private BYOB Afternoon Harbor Sail on Fate is a top pick. Priced at $599 for up to six guests, it offers 2 to 4 hours of private sailing. The cruise takes in highlights like The Battery, Ravenel Bridge, and USS Yorktown, with the chance to get close to Fort Sumter.
Guests love the personalized service and the ability to bring their own drinks or opt for catering. The boat is described as beautiful and comfortable, with reviewers pointing out the crew’s professionalism and friendliness. It’s well-suited for relaxing afternoons with friends or family, especially if you prefer a private setting to enjoy scenic views at your own pace.
During the trip, you can expect dolphin sightings and plenty of photo opportunities. The flexible departure times are a plus for fitting into busy schedules.
Bottom line: A luxurious, customizable afternoon sail that’s ideal for unwinding and enjoying Charleston’s waterfront in style.
7. Private Sunset Sail BYOB Dolphin/History Tours on Mystique
Number seven, the Private Sunset Sail on Mystique, is a top-rated choice for romance or special evenings. For $599, your group up to six can enjoy a 2 to 4-hour private cruise aboard an elegant 43ft yacht. Departing from Harbor City Marina, this tour combines dolphin watching with scenic sunset views.
The vessel is operated by professional crew, ensuring comfort and safety. Reviewers often mention the attentiveness of the crew, with some highlighting how the captain shared local secrets and sailing stories. The itinerary includes passing by Fort Sumter, The Battery, and the Ravenel Bridge, with opportunities for wildlife sightings.
A key feature is the private setting, making it perfect for romantic dates, celebrating milestones, or just indulging in quiet luxury. The reviews emphasize the personalized experience and the beauty of Charleston’s skyline at sunset.
Bottom line: This flexible, private sunset sail is ideal for those seeking a romantic, peaceful evening with dolphin encounters and scenic views.
8. Private Afternoon Sailing/Dolphin & History Tour on Mystique
The Private Afternoon Sailing/Dolphin & History Tour on Mystique offers another chance to enjoy Charleston’s water in a private setting. For $525, the 2-4 hour cruise departs from Harbor City Marina, focusing on dolphin sightings, history, and scenic views.
Guests mention the peaceful boat ride, with Captain Scott and Sam providing informative commentary about Charleston’s landmarks, such as Fort Sumter and the Yorktown aircraft carrier. The tour is praised for its relaxing atmosphere and the visibility of wildlife. The itinerary usually includes the Battery, White Point Gardens, and sometimes the Patriot’s Point Naval & Maritime Museum.
This experience suits travelers wanting a combination of wildlife and historic sights in a private, comfortable environment. The reviews highlight how the crew’s attention to detail and knowledge enhance the trip.
Bottom line: An excellent choice for those who want a private, educational, yet relaxing cruise with dolphin sightings.
9. Charleston: Private Daytime or Sunset BYOB Sailing Charter
The Private Daytime or Sunset BYOB Sailing Charter is a flexible 2.5-hour option priced at $500 for groups up to six. It offers an intimate experience with the option of day or sunset sailing, making it adaptable to your schedule.
You’ll see The Battery, Ravenel Bridge, Fort Sumter, and Castle Pinckney from the water, with plenty of time for wildlife watching and photo ops. The USCG-licensed captain ensures safety and local knowledge, sharing insights about Charleston’s landmarks along the way. Guests rave about the personalized experience and the hands-on feel of helping with the sails if desired.
Bringing your own drinks adds to the relaxed, celebratory atmosphere, perfect for families, couples, or small groups wanting a flexible, private cruise.
Bottom line: This is a versatile and budget-friendly option for a personalized, scenic sail at your preferred time.
10. Private Morning Excursions on Yacht Kismet
Finally, the Private Morning Excursions on Yacht Kismet caters to larger groups, offering up to 18 passengers for $1,549. This upscale vessel combines style and comfort with water activities like swimming and lounge floats.
The cruise can include visits to Fort Sumter and the USS Yorktown, with ample time for photo opportunities. The boat’s spacious design makes it great for families or groups celebrating special occasions. The crew provides bottled water and coolers, and the boat is ideal for lasting memories in a relaxed, elegant environment.
This tour is particularly suited to larger groups or families seeking an exclusive experience with plenty of space and activities onboard.
Bottom line: If traveling with a sizable party, this luxurious yacht offers a memorable, comfortable way to enjoy Charleston’s waters.
How to Choose Your Perfect Charleston Sailing Experience
When selecting the right sailing adventure, consider your budget, time available, and what kind of experience you’re after. If you want a private, romantic sunset, the Luxury Sunset Sail on Fate is a top option. For those interested in participating actively in sailing, the Schooner Harbor Tour offers hands-on fun. If privacy and personalized service matter most, the Mystique private tours and BYOB options are excellent choices.
Budget-conscious travelers might prefer the Dolphin Watch Schooner, which offers a relaxed yet scenic experience at a low price. Larger groups or families should look into the Yacht Kismet for spacious comfort and water activities.
Booking early is advisable, especially during peak season (spring through fall), to secure your preferred date and time. Some tours, like the Mystique private sunset, are popular for special occasions and fill up quickly.
Final Thoughts
Charleston’s sailing options run the gamut from intimate private cruises to active participatory sailing. For a romantic sunset, the Fate yacht delivers luxury and stunning views. If you want to combine wildlife viewing with a history lesson, the Mystique tours and Dolphin Watch Schooner are hard to beat. Large groups and families will appreciate the spacious Yacht Kismet, offering comfort and fun for everyone.
Whichever experience you choose, Charleston’s waters promise memorable sights, wildlife encounters, and a taste of maritime history. Be sure to book ahead, especially for peak seasons, to ensure your perfect day on the water.
This overview aims to guide you in finding a sailing experience tailored to your preferences, so you can enjoy Charleston from the best possible vantage point—on the water, with the wind in your hair and plenty of stories to tell.