Charleston’s waterfront is one of its biggest draws, and nothing beats exploring it from the water. With its historic harbor, the sweeping views of the Ravenel Bridge, and the chance to spot playful dolphins, Charleston lends itself beautifully to sailing. Whether you’re after a romantic sunset, a lively day with friends, or an educational sail with active participation, this city has a lot to offer. We’re especially fans of private charters like the Private Luxury Yacht Charters, BYOB & Dolphins, which offer tailored, luxurious experiences with the freedom to bring your own drinks and capture the moment with a photographer. It’s a perfect way to unwind and see Charleston from a unique perspective.
One thing that sets Charleston apart is the diversity of its sailing options—everything from intimate private yachts and elegant sunset cruises to lively schooner tours and even family-friendly daytime sails. Many tours include wildlife sightings, like dolphins, and highlight iconic landmarks such as Fort Sumter and the USS Yorktown. Whether you prefer a relaxing afternoon or a spirited active sail, there’s a tour designed to match your style. Let’s explore the top options available.
1. Private Luxury Yacht Charters, BYOB & Dolphins
At number 1, this private luxury yacht experience combines flexibility with class. For around $499 per group, up to six people can enjoy a 2.5-hour cruise tailored to your preferences. You can choose your departure time—perfect for sunset or daytime—and bring your own drinks and snacks, or upgrade to gourmet catering. The yacht’s crew will set sail from Charleston harbor, giving you stunning views of downtown, Fort Sumter, and the Ravenel Bridge. One highlight is the chance to spot dolphins frolicking nearby, making this a memorable trip for families or couples alike.
Guests love the personalized touch, with reviews calling it “incredible,” “relaxing,” and “worth every penny.” The captain and crew are praised for their friendliness and knowledge, making the experience both luxurious and educational. It’s ideal if you value privacy, flexibility, and an intimate connection with the water.
Bottom Line: This private yacht is perfect for celebrating special occasions or just indulging in a luxurious, customized experience. If comfort and privacy top your list, this one’s a winner.
2. Charleston: Schooner Sailing Harbor Tour & Dolphin Watch
For those who want an active, hands-on sailing adventure, number 2 offers a classic three-masted schooner experience. Priced at $48 per person for a 1.5-hour tour, it’s an accessible way to enjoy the harbor and participate in hoisting the sails. The crew will teach you how to work the sails yourself, adding an interactive element to your day. Along the way, you’ll enjoy views of Fort Sumter, Castle Pinckney, and the city skyline while keeping an eye out for dolphins.
This tour is especially well-suited for families or anyone interested in learning about traditional sailing techniques. Guests comment on the lively breezes and the crew’s engaging storytelling, which makes the experience feel authentic and fun. The short duration makes it ideal if you’re on a tight schedule or traveling with kids.
Bottom Line: With its active participation and scenic setting, this schooner ride offers a taste of Charleston’s sailing heritage without breaking the bank.
3. Private Sailing, Dolphin and History Tour on Mystique
Number 3 on our list is a private, 2-hour sailboat tour that combines sightseeing with dolphin spotting. For $499, up to six guests can enjoy a personalized trip from Charleston’s Harbor City Marina. The yacht’s itinerary includes passing the Arthur Ravenel Jr. Bridge, Fort Sumter, and the USS Yorktown, all in a relaxed, intimate setting.
What makes this tour stand out is the balance of history and wildlife—your skipper will share insights about Charleston’s landmarks while keeping a lookout for dolphins. The reviews rave about the “beautiful” boat and the “friendly, knowledgeable crew,” emphasizing the personalized attention and the chance to enjoy a peaceful, crowd-free experience.
Bottom Line: If you want a private, well-rounded trip with the possibility of dolphin sightings and scenic views, this tour fits the bill.
4. Private Sailing Charter with Captain, BYOB
Number 4 features another private option, priced at $500 for up to six people for approximately 2.5 hours. This experience emphasizes the ease of relaxing on the water with your own crew and the freedom to bring your own beverages and snacks. The captain will take you past major landmarks like the Ravenel Bridge, Fort Sumter, and the USS Yorktown, with flexibility to set your schedule—perfect for sunset or afternoon cruises.
Reviews highlight the “beautiful boat,” “friendly captain,” and “easy setup,” making it a favorite for celebrating milestones or simply enjoying a quiet day. The focus on comfort and customization makes it a top choice for those seeking privacy and control over their sailing experience.
Bottom Line: This private charter offers a laid-back, customizable outing suited for romantic evenings or small groups seeking exclusivity.
5. Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB
For a romantic, upscale experience, number 5 is hard to beat. The 2-hour sunset cruise on the Fate costs around $760 but offers an intimate setting for couples or small groups of six. You’ll enjoy panoramic views of Charleston’s skyline, with sightings of The Battery, Ravenel Bridge, and the USS Yorktown as the sun dips below the horizon.
Guests rave about the “fantastic voyage,” “wonderful crew,” and “beautiful yacht,” emphasizing the romantic atmosphere. The experience allows you to learn about Charleston’s landmarks or play your own music for a personalized evening.
Bottom Line: If you’re after a romantic, high-end experience with spectacular sunset views, this yacht cruise is a top contender.
6. Charleston: Private BYOB Luxury Yacht Cruise
Number 6 offers a 2.5-hour private cruise on a luxury yacht, costing $500 for up to six people. This experience emphasizes relaxed sightseeing with the freedom to bring your own drinks and snacks. It’s perfect for celebrating special occasions or simply enjoying a tranquil day on Charleston Harbor.
The reviews note the “beautiful scenery,” “friendly crew,” and “dolphins swimming nearby,” making it an enjoyable, personalized outing. The focus on luxury and flexibility makes this ideal for travelers who want comfort and privacy.
Bottom Line: For a quiet, private day or sunset cruise with personalized touches, this luxury yacht is a top option.
7. Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate
Number 7 is a 2-hour private sailing cruise costing $599 for up to six guests. It’s the perfect way to experience Charleston’s harbor from the water, with highlights like The Battery, Ravenel Bridge, and the USS Yorktown. The boat’s size and amenities make for a comfortable, relaxed sail, with the flexibility to bring your own drinks or opt for on-board catering.
Reviews mention the “beautiful boat,” “knowledgeable crew,” and “dolphins swimming alongside,” emphasizing the value of privacy combined with active wildlife viewing. It’s well-suited for families or small groups wanting a flexible yet luxurious outing.
Bottom Line: This cruise balances comfort, flexibility, and wildlife encounters, ideal for afternoon explorations.
8. Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique
Number 8 offers a private 2-4 hour sail for $525, operated by Charleston’s longest-standing private charter company. It’s a favorite for its blend of sightseeing, dolphin watching, and historical narration. The yacht departs from Harbor City Marina, and reviews praise the “informative,” “relaxing,” and “beautiful” experience, especially for families and friends.
What makes this tour special is the focus on delivering a high-quality, personalized trip with amenities like shade, restrooms, and plenty of space for up to six people. The crew’s deep knowledge adds an educational touch to this leisurely sail.
Bottom Line: If you prefer a well-reviewed, flexible private charter with a mix of wildlife, landmarks, and comfort, this is a go-to choice.
9. Charleston: Sunset Sail on Luxury 55ft Catamaran with Bar
Number 9 is a 2-hour sunset cruise aboard the Palmetto Breeze, costing $65 per person. The bar onboard complements panoramic views of Charleston’s skyline, Fort Sumter, and the Ravenel Bridge. It’s a popular choice for those seeking a relaxed, social experience with stunning scenery and wildlife such as dolphins.
The reviews highlight the “beautiful boat,” “fun atmosphere,” and “spectacular sunset,” making it a great option for couples or groups wanting a lively yet scenic outing. The spacious, cushioned deck ensures comfort during the cruise.
Bottom Line: Perfect for a social, scenic sunset with drinks and wildlife viewing, this cruise offers great value and scenic indulgence.
10. Charleston: Private Daytime or Sunset BYOB Sailing Charter
Number 10 offers a customizable 2.5-hour private sail on a 35-foot boat, costing $500 for up to six people. You can choose a daytime or sunset cruise, giving flexibility for sightseeing or romantic evenings. Sightings include the Ravenel Bridge and other Charleston landmarks, all from a comfortable, private vessel.
Reviews commend the personalized experience and the chance to bring your own drinks, making it ideal for celebrations or relaxed exploration. The professional, USCG-licensed captain guarantees a safe and enjoyable outing.
Bottom Line: For a flexible, private cruise that can be tailored to your schedule, this experience is hard to beat.
11. Private Morning Excursions on Yacht Kismet
Number 11 is an exclusive, large-group option for up to 15-18 people, with prices starting at $1,549. This yacht offers a spacious, stylish setting for morning or daytime cruises, including swimming off the boat, lounging, and enjoying the views. It’s perfect for family reunions, corporate outings, or big group celebrations.
The reviews note the comfortable, luxurious design and the crew’s ability to make large parties feel personal. The vessel’s size allows for plenty of activities, including floating on rafts or water hammocks.
Bottom Line: If you’re planning a large group gathering or special event, this yacht provides a high-end, versatile platform.
12. Charleston Afternoon Sail – Lux Catamaran w/Seating & Shade
Number 12 is a relaxing 2-hour afternoon cruise on a spacious 50-foot catamaran. For $59 per person, you’ll enjoy shaded, cushioned seating and the chance to spot dolphins and coastal birds. The panoramic views include Fort Sumter and the Ravenel Bridge, making it a great way to unwind after sightseeing or before dinner.
Guests appreciate the comfortable deck and the low-key atmosphere, perfect for families or couples who want a gentle sail with wildlife viewing.
Bottom Line: A laid-back, comfortable afternoon sail that combines wildlife, scenic views, and relaxation.
13. Private Sunset Harbor Tour 18 passenger party Yacht Kismet
Number 13 offers a highly customizable sunset cruise for up to 15 people, with prices at $1,549. The vessel provides an elegant setting for celebrations, complete with the option to bring your own drinks and even have catering. It’s perfect for birthdays, anniversaries, or just a memorable night on the water.
The reviews highlight its “luxurious,” “private,” and “spectacular” nature, along with the ability to incorporate swimming, sightseeing, or relaxing. The crew ensures a tailored experience, making your event truly special.
Bottom Line: For a large-group celebration with privacy and customization, this yacht delivers a top-tier experience.
14. Charleston: Sunday Mimosa Catamaran Sail w/Mini Brunch Bites
Number 14 is a cheerful 2-hour Sunday cruise aboard the Palmetto Breeze, costing $65 per person. It combines mimosas, light brunch bites, and scenic views of Charleston’s harbor. The spacious catamaran features cushioned seating and a partly shaded deck, making it a comfortable choice for a relaxed weekend morning or afternoon.
Reviews mention the beautiful scenery, good drinks, and fun atmosphere. It’s especially suitable for friends or couples looking to enjoy a laid-back, social outing.
Bottom Line: A perfect weekend activity to combine light bites, drinks, and scenic harbor views in a relaxed setting.
15. Charleston: Private Yacht Charter
Finally, the Private Yacht Charter offers a bespoke experience for up to 15 people, starting at $1,000. It focuses on day and sunset cruises, with plenty of time to relax, swim, and enjoy wildlife like dolphins. This is a top choice for those seeking total privacy and a tailored schedule.
The emphasis on comfort, flexibility, and the chance to reconnect with loved ones makes this ideal for special occasions or those wanting to indulge in a luxurious, private outing. Booking early is recommended as it’s popular for celebrations.
Bottom Line: This option is for travelers wanting full control over their day on the water, with luxury and privacy at the forefront.
$1,000 per group up to 1
How to Choose Your Perfect Charleston Sailing Experience
Choosing the right sailing adventure depends on your interests, budget, and the kind of experience you want. If privacy and customization are your priorities, consider private options like the Luxury Yacht Charters or the Fate sunset sail. For active travelers or families interested in participating, the Schooner Sailing Harbor Tour & Dolphin Watch offers a hands-on experience.
On a budget or looking for a quick taste, the Harbor Tour & Dolphin Watch delivers charming scenery and wildlife with a modest price. If you’re celebrating a special occasion, the Sunset Yacht or Kismet sunset cruise can turn an ordinary evening into a memorable event.
Timing is key—scheduling a sunset cruise adds romance, while a daytime sail suits families and active groups. Booking early is advised, especially for private yachts and peak summer weekends.
Final Thoughts
Charleston offers a wide array of sailing options, from private luxury escapes to lively schooner adventures and relaxing daytime sails. If you’re after a personalized, luxurious experience, the Private Luxury Yacht Charters or the Fate sunset cruise should top your list. For active travelers or families wanting to get involved in sailing, the Schooner Harbor Tour makes a perfect choice.
No matter what you pick, booking ahead ensures a spot in these popular adventures. Charleston’s waters are calling—time to set sail and make some memories on the Lowcountry’s beautiful harbor.