SAIL & BOAT THE CHARLESTON HARBOR

VIEW ALL AVAILABLE SAILING TOURS

VIEW ALL AVAILABLE BOATING TOURS

HAVE UNFORGETTABLE MOMENTS ABOARD SV SHENANIGAN!

MOST POPULAR 3-HOUR CHARTER

Most Popular!

$550

6 p.m.
3 hours

SUNSET SAIL

Our 3 hour sunset sail from the cockpit of Shenanigan, a stunning 50-foot classic yacht! Relax and look over the City of Charleston skyline from the water for a different perspective and a sunset you will never forget!

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MOST POPULAR 6-HOUR CHARTER

$1050

9 a.m.
Most Popular - 6 Hour Sail

ISLAND CHARTER

We offer sailing trips to barrier and sea islands in the Charleston Harbor and along the coast. Ask about longer day sailing trips to Kiawah Island, Seabrook, Beaufort, Georgetown, Cumberland Island, and more!

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ABOARD SV SHENANIGAN

$550

9 a.m.
3 hours

MORNING SAIL

Start your day enjoying all the sights Charleston has to offer from the water! Set sail, relax on deck, and cruise by the Charleston Waterfront. Spend quality time with friends and family for a great day out on the water!

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$550

1 p.m.
3 hours

AFTERNOON SAIL

Enjoy your afternoon and all the sights Charleston has to offer from the water! Set sail, relax on deck, and cruise by the Charleston Waterfront. Spend quality time with friends and family for a great day out on the water!

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$1050

9 a.m.
6 hours

CUSTOM DAY SAIL

For a more personalized day on the water, sail out to a barrier island, drop the hook, and take a swim!

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WHAT WE OFFER

Try something out of the ordinary to reset, relax, and change the way you do your time off!

See Historic Charleston from the water as the sun slowly sets over the city. Our private crewed sails show you the historic sights of the Charleston Harbor such as the Charleston Battery, Rainbow Row, Fort Sumter, the Sullivan’s Island Lighthouse, or you can even sail right under the Ravenel Bridge! Our customized chartered sails cater to your requests as best the tides and winds allow as they vary from day to day. Spend time on the water on our most popular sail with friends and family for a memory of a lifetime!

SV SHENANIGAN

Our stunning 50-foot classic yacht has plenty of deck and cabin space plus a full galley and fridge to stock for your trip.

DOS CAPITANAS

Our two awesome female captains are very knowledgeable about their vessel and sailing.

CHARLESTON

Sail the beautiful Charleston Harbor and see historic Charleston landmarks from the water.

⚓ HEAR FROM OUR HAPPY SAILORS! ⚓

Sundog Sailing experience

AMAZING EXPERIENCE !!! I loved every second of the sailing adventure from start to finish. Had so much fun bonding with friends on the boat while the very professional crew sailed us around and made sure we had a fun and relaxing time. Jen and Janet did a great job at making sure we got to see all the beauty of Charleston and helped us watch one of the best sunsets I’ve seen.

– Matthew W. ☀ TripAdvisor

Incredible sunset cruise in the harbor!

To say that our experience was perfect is an understatement! Front the awesome views to the dolphins swimming right beside us, it was a trip I will definitely be taking again! Captains Jen and Janet were amazing...professional and laid back, they made us all feel at home and totally relaxed. A must-do in Charleston!

– Lisa D. ☀ TripAdvisor

Loved it!

History, dolphins, the harbor of Charleston.... and a little wine. We really couldn’t have had a more perfect trip! The ladies Captaining the Shenanigan were very knowledgeable and made us feel safe the whole time. We plan on going again soon!

– Matt R. ☀ TripAdvisor

OMG!!!

So much fun! It was amazing! Can’t wait to go again! We saw dolphins and the most amazing views! They like to knew everything about the harbor!

– Emily W. ☀ TripAdvisor