Category Sailing

Charleston · SAILING

Top 8 Sailing Trips in Charleston

8 reviewed

Private Luxury Yacht Charters, BYOB & Dolphins

Private Luxury Yacht Charters, BYOB & Dolphins - Getting to the marina (and why that matters for a 2.5-hour trip)

1.Private Luxury Yacht Charters, BYOB & Dolphins

★★★★★★★★★★5.0 · 395 reviews · 2 hours 30 minutes (approx.) · from $499Our pick

Private BYOB yacht charter in Charleston Harbor for up to 6, with Fort Sumter, Ravenel Bridge sunset views, and dolphin chances.

“Friendly Captain (Holly) and Crew (Jules). Good communication before and during the sail. Holly took safety seriously including watching a potential storm in the distance and adjusting course for it. Jules took care of us by serving us and checking to see if we needed anything which allowed us to sit, relax and enjoy the cruise. We enjoyed being on the water, seeing all the other ships, the smooth sailing and seeing dolphins. I would definitely recommend this as a special thing to do while in Charleston.”

Check availability →Read our full review

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch - Charleston Harbor Views: Fort Sumter, Castle Pinckney, Fort Johnson, Yorktown Point

Private Sailing Charter with Captain, BYOB

Private Sailing Charter with Captain, BYOB - Timing matters: booking for sunset and planning what to wear

3.Private Sailing Charter with Captain, BYOB

★★★★★★★★★★5.0 · 64 reviews · 2 hours 30 minutes (approx.) · from $500

BYOB private 2.5-hour sunset sail in Charleston. Cruise past Fort Sumter and Ravenel Bridge with Captain Will and photo-ready views.

“WONDERFUL evening spent with Captain Will on the sunset cruise with my husband and two young children. Will really engaged with my 5 year old daughter and taught her how to drive the boat, which she was thrilled with, and created some really special family memories. We loved the flexibility of bringing wine and snacks onboard. It was overall just the most wonderful, memorable evening on our vacation and we are so thankful we did this!”

Check availability →Read our full review

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB - The 50ft Yacht Fate Experience: BYOB, Comfort, and Real-World Service

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate - Your Crew on Fate: Captains Who Make the Ride Feel Easy

5.Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.) · from $599

Private BYOB sail on a 50ft yacht in Charleston Harbor. See the Battery, Ravenel Bridge, USS Yorktown, and sometimes Fort Sumter.

“The Sailboat is absolutely beautiful and perfect for a sail around the harbor. Captain Will & First mate Sam were great hosts and super knowledgeable! They made the trip that much more enjoyable... Highly recommend...”

Check availability →Read our full review

Charleston: Private BYOB Luxury Yacht Cruise

Charleston: Private BYOB Luxury Yacht Cruise - Your Boat and Your Group: Up to 6 People, No Sharing

6.Private BYOB Luxury Yacht Cruise

★★★★★★★★★★5.0 · 39 reviews · 2h 30m · from $500

A private Charleston yacht cruise with BYOB options, Holy City harbor views, and chances to spot dolphins nearby. Up to 6 people.

“We had a wonderful experience on our boat tour! From the moment we stepped on board, Erin, our hostess, made us feel incredibly welcome. She was warm, friendly, and attentive throughout the entire trip. The captain was just as kind and accommodating, ensuring we felt safe and relaxed while enjoying the beautiful views. Both Erin and the captain went above and beyond to create a fun and memorable outing. Highly recommend this tour to anyone looking for a great time on the water with an exceptional crew!”

Check availability →Read our full review

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique - Patriots Point and the Yorktown aircraft carrier from the water

Charleston: Private Daytime or Sunset BYOB Sailing Charter

Charleston: Private Daytime or Sunset BYOB Sailing Charter - Ashley Marina logistics and meeting the captain on time