We had a bachelorette party with 8 girls and our sailing charter was the highlight of the trip. The…read moreboat was more perfect than we could've imagined - it was gorgeous and well kept. There was lots of space for everyone to lay out at the front of the boat and hang for the day. Plus lots of space at the back of the boat to eat and relax in the shade. Matt was easy going and a pleasure to work with. We were able to bring our own food/drink and play music from the speakers. Highly highly recommend!

We recently rented a catamaran from OM for a bachelorette party and it was the highlight of our…read moretrip! Matt and team are incredibly flexible with weather and we're so accommodating to our group. We had the best time and will definitely sail again with OM!

Looking for a relaxing, leisurely cruise around the harbor or the backwaters of the Lowcountry?…read more Lady Sadie is your charter. With an experienced, skillful captain and an attentive, personable first mate, you will have a most enjoyable day on a beautiful boat as you ply the waters surrounding Charleston. Captain Lee personally oversees the entire experience, while First Mate Ashton serves a delicious culinary feast comprised of a broad array of thirst quenching libations. The boat itself is gorgeous, ....beautiful inlaid wood, luxuriously upholstered lounges, an unlimited selection of music to appeal to all tastes, everything impeccably clean and well maintained. I encourage you to contact Captain Lee and make your reservation today.

Unforgettable experience on a GORGEOUS yacht!! Captain Mike…read morewas so well-versed in Charleston history. It was a truly amazing experience. Will definitely book again!

Booked a 6 hour inshore trip with Ronnie for our family. Our sons, 12 and 16yrs old had an amazing…read moretime. We will definitely save your contact and fish again with you. Appreciate the easy booking, very clean beautiful boat, and memorable day. Great skills on how to catch for specific fish & areas. Highly recommend for anyone looking for a day out in Charleston.

Ronnie was an absolute bro. Family friendly and very knowledgeable. Learned a lot from him in just…read morea short amount of time. Had an absolute blast and truly enjoyed his company. Will definitely be coming back to his company again, thanks bro!

We sailed with Charleston Harbor Sailing in October 2025. It was an amazing and magical…read moreexperience. The sailing captain is very friendly, knowledgeable, and great at his craft. The boat is very comfortable. The views of downtown Charleston and the historic homes are fabulous. The captain helped point out the many dolphins swimming near the sailboat . Highly recommend if you want to see Charleston from new perspectives. Great opportunity for photographers or just if you want enjoy beautiful scenes. Worth every penny and we will do this again next time we visit Charleston.

What an amazing sunset cruise with friends! Highly recommend this experience. The sailboat "Esprit…read morede Joy" is beautiful! Thank you Charleston Harbor Sailing!

I wonderful way to see Charleston from the water and have a good meal. The food was ok. They serve…read morea three course meal. It included a cup of crab soup, a salad, and a choice of three entrees. Short rib, salmon, or chicken with a side of green beans and mashed potatoes. I opted for the short ribs. They were ok, just needed a little more gravy because they were a tab bit dry. The best park was the view from the boat as the sun set. There was also some live music. Very entertaining. There was also a full service bar. Staff was super friendly and very accommodating.

If there were a 3.5 that's where we'd land. The service was great…read more The food was mediocre. She crab soup might've been the highlight, and that was pretty thick and salty. The salad was not great. Salmon overcooked - but we assumed it would be. Chicken dry and although it said Parmesan crusted, it really wasn't. Short ribs were also dry but probably the best entrée out of the three. Crème brûlée cheesecake was for dessert and that was mediocre as well. The cruise started at seven and sunset was shortly thereafter, so the majority of our time was spent in the dark on the water. It really should've started about an hour or so earlier so everyone could enjoy the scenery. Overall, a fine experience and we really didn't go thinking we'd have amazing food so weren't disappointed.

We wanted to experience a harbor cruise while in Charleston. I checked Yelp and found Charleston…read moreHarbor Tours which had good reviews. So I booked our tickets online. I was pleasantly surprised to find free street parking. We boarded the boat and headed out in the harbor. It was a beautiful night on the water and bonus, we got to see the sun set. They played a little music but mostly the captain gave us history of the harbor. We saw some old military ships and a couple of forts and went under the suspension bridge. They sell snacks, alcohol, soda and ice cream. I ordered a Pepsi and a chocolate chip ice cream cookie. And bonus, there is a bathroom on board. The staff was friendly. I would take another cruise with Charleston Harbor Tours.

The sunset cruise was beautiful and the staff were all very nice and helpful. I do feel like the…read morecruise was overbooked, and it was hard to move around or even find a bit of railing to lean against and not be in someone's way. This is a management problem, not a crew problem, unless the crew owns the boat. It was also hard to hear the narration once the crowd of people started talking. What I could hear was well-presented and interesting.

Booked this charter for my brother's birthday and we had the best time with Captain Campbell!! He…read morewas so friendly and is a hard worker! Such a great experience and will be booking again!

We booked this company to take 8 on a bachelor weekend activity. Sounded like a good idea but it…read morewasn't. One boat had no fishing action whatsoever. The captain brought the wrong bait and spent the whole trip unsuccessfully fishing for the correct bait. Not only was this a waste of money for nothing it was not fun in anyway. Made owner aware but no response. Super disappointed.

When deciding on what night to enjoy a boat rides opted for Weds as the extra ticket cost seemed…read morejustified to cover the cost of a few adult beverages. Sadly, they were unprepared and my friend and I could only enjoy 1 beverage because they ran out within 35 minutes of pulling away from the dock and 15 of this minutes were spent under cover due to heavy rain. Perhaps in the future you allocate 3 tickets per person and you bring in enough seltzer and beer to accommodate for that. Not like it cannot be used the next night

Last night's Margarita Monday sunset sail was so fun! Though tickets are usually $35, ladies get…read more$15 off for this sail, which is 2 hours and includes complimentary bottled water, sodas, snacks (chips&salsa, mini taco things, cookies), and margaritas! They also have a cash bar for beer and wine. The staff (only 2 of them) were fun and upbeat. Of course when you're on a catamaran with 20-100 people and only one person is serving margaritas from a beverage cooler, it's gonna be slow-going, but after the initial line weans down its easy to get a drink (until it runs out...which it did less than halfway through the trip)! Because of that, the captain took $2 of the price of Pinot Grigio...nice, but not the same as complimentary margaritas. The best part was climbing up top with my girl friends to sit near the sails! The different view and having to duck when they jived the sails made it more unique. Though it was raining in other parts of Charleston all day, we got lucky with nice, cool weather (though light cloud coverage did block the sunset a bit). We definitely want to come back in the future! The Palmetto Breeze takes off from Red's on Shem Creek at 6:30 (when the dolphins are OUT). It's probably best to buy your tickets online before the day of the event, but we were able to snag some spaces/pay the captain on the dock. Oh, and don't forget to take a picture behind the captains wheel and blow the conch shell.