Your boat. Your people. Charleston from the water.
Step aboard SV John Galt, our private sailing catamaran, for an afternoon or sunset on Charleston Harbor. Up to six guests. No crowds. No canned tour. Just sailing, good company, and Charleston from the water.
Private Charleston Sailing Charters
THE EXPERIENCE:
This Isn’t a Harbor Tour. It’s Your Sailboat for the Afternoon.
Hollyday Sailing is private by design. No crowds, no loudspeaker, no rigid route.
You’ll have the SV John Galt, our 34-foot sailing catamaran, to yourselves with up to six guests. Stretch out on the bow, settle into the cockpit, put on some music, bring your favorite drinks, and let Charleston unfold around you from the water.
We’ll sail when the wind allows, explore the harbor, watch for dolphins, take in the skyline, and shape the trip around the day rather than race through a checklist of landmarks.
Some guests want to learn a little about sailing. Some want a quiet sunset with someone they love. Others want music, friends, cold drinks, and nowhere particular to be.
That’s the point.
Your people. Your pace. Your Charleston.
Choose Your Sail
Sunset Sail
2–2.5 Hours - Up to 6 guests
The signature Hollyday experience.
Leave the dock in the late afternoon, sail Charleston Harbor as the heat fades, and settle in for sunset on the water. Perfect for couples, small groups, birthdays, anniversaries, or anyone who understands that Charleston looks considerably better with a drink in hand and the sun dropping behind it.
Charleston Harbor Sail
3 Hours - Up to 6 guests
More time to sail, explore, and see where the wind takes us.
Cruise past the Charleston skyline, the Battery, Fort Sumter, Castle Pinckney, and the Ravenel Bridge while keeping an eye out for dolphins along the way. Take the helm, learn a little sailing, or simply claim a spot on the bow and enjoy the ride.
Half-Day Adventure
4 Hours - Up to 6 guests
For those who want more than a lap around the harbor.
With four hours aboard John Galt, we have time to stretch our legs, chase better wind, explore farther, drop anchor when conditions are right, and build the day around your group.
Ideal for families, visiting friends, celebrations, or anyone who would rather spend half a day on the water than almost anywhere else.
Meet the SV (Sailing Vessel) John Galt:
John Galt is a 34-foot Gemini sailing catamaran built for exactly the kind of day Hollyday Sailing is about: comfortable, social, relaxed, and close to the water.
With a wide beam, spacious cockpit, open bow, and plenty of room to spread out, she gives six guests space to actually enjoy the sail instead of spending three hours politely negotiating elbow room.
She’s equally happy ghosting across Charleston Harbor under sail, reaching in a fresh breeze, or dropping anchor somewhere beautiful when the day calls for it.
On board you’ll find comfortable seating, shade, music, cold drinks, a private head, and plenty of places to stretch out and watch Charleston slide by.
She feels like your boat for the afternoon.
34 feet • Sailing catamaran • Up to 6 guests • Private head • Bluetooth audio • Comfortable cockpit and bow seating
Charleston From the Water
Charleston is beautiful from the street; from the water, it feels different.
The steeples rise above the peninsula. The Battery stretches along the harbor. The Ravenel Bridge towers to the North. Fort Sumter sits low on the horizon. Dolphins surface beside the boat. Container ships move through the channel like big box buildings with engines.
And then there’s the light.
Late afternoon on Charleston Harbor has a way of turning everything softer: the city, the marsh, the bridges, even the pace of the day.
From John Galt, you’re not looking at Charleston through a windshield or following a tour group down a sidewalk.
You’re seeing it the way people first encountered this city: from the water.
For centuries, sailors, merchants, privateers, pirates, and newcomers arrived through this harbor with Charleston rising ahead of them.
Out here, that old perspective comes back.
Wind in the sails. Salt in the air. Skyline ahead.
This is Charleston with room to breathe.
Your Captain
Hollyday Sailing is personal because John Galt is personal.
Your captain, David (“Doc”) Hollyday, has called Charleston home for more than 25 years and has spent years sailing, boating, and exploring the Lowcountry from the water.
He knows the harbor, but just as importantly, he knows the rhythm of a good day on it: when to chase the wind, when to slow down, when to tell you what you’re looking at, and when to simply turn up the music and let the boat do the talking.
If you want to learn a little about sailing, take the helm. If you want local history, ask. If you’d rather stretch out on the bow with a drink and watch the city drift past, that works beautifully too.
His goal isn’t to perform a tour; it’s to make you feel comfortable, safe, and completely at home aboard John Galt.
Local knowledge. Real sailing. No captain’s license required. (except for the Captain!)
Frequently Asked Questions
Is the boat private?
Yes. Every Hollyday Sailing charter is private. John Galt is yours for the trip, with your group of up to six guests and your captain. No strangers added to fill seats.
What should we bring?
Sunglasses, sunscreen, a light layer if you're sailing near sunset, and whatever you'd like to drink. Soft-sided coolers are welcome. We provide cold water, ice, and plenty of room to settle in.
Can we bring alcohol?
Yes. Guests 21 and older are welcome to bring their own beer, wine, or cocktails. We want you to relax and enjoy yourselves, while keeping things safe enough that everyone returns to the dock with the same number of limbs with which they left.
Is there a bathroom aboard?
Yes. John Galt has a private marine head below deck. We'll show you how it works before departure. Marine plumbing has opinions.
Do we actually sail?
Absolutely, when the wind cooperates. John Galt is a sailboat, not a sightseeing boat wearing a mast as decoration. Conditions determine the exact route, and some days involve more sailing than others.
Where will we go?
There is no rigid tour route. Depending on the wind, weather, tides, and length of your charter, we may sail past the Charleston peninsula, the Battery, Fort Sumter, Castle Pinckney, the Ravenel Bridge, or farther into the harbor.
The weather gets a vote.
Can I help sail the boat?
Please do. If you're curious, you're welcome to take the helm, learn a few basics, and get involved. If your preferred contribution is reclining on the bow with a cold drink, that is also considered acceptable seamanship aboard John Galt.
Will we see dolphins?
Very often, but dolphins have declined to sign a performance contract. Charleston Harbor has a healthy population of Atlantic bottlenose dolphins, and spotting them is one of the pleasures of being out there.
Can we swim?
On longer charters, swimming may be possible when conditions and location make it safe. It isn't guaranteed, and the captain makes the final call.
Are children welcome?
Yes. Families are welcome aboard. Let us know the ages of any children when booking so we can have the appropriate safety equipment ready.
What should we wear?
Comfortable clothes and soft-soled shoes are perfect. Bare feet are usually welcome aboard once we're underway. Avoid high heels or hard-soled shoes that make moving around a boat unnecessarily adventurous.
What happens if the weather is bad?
Your captain watches the forecast closely. A little cloud cover doesn't ruin a sail, but thunderstorms and lightening, unsafe winds, or other poor conditions may require us to delay, reschedule, or cancel.
If the captain cancels because conditions aren't safe, you'll have the option to reschedule or receive a refund.
What if I'm worried about seasickness?
Charleston Harbor is generally more protected than the open ocean, and John Galt's wide catamaran design provides a stable platform. If you're particularly sensitive to motion, taking your preferred motion-sickness remedy before departure is usually smarter than discovering your susceptibility halfway across the harbor.
Where do we meet?
Our Charleston departure location and parking instructions will be included with your reservation. Please plan to arrive about 15 minutes before departure so we can get everyone aboard and underway without sacrificing perfectly good sailing time.
Can we bring food?
Yes. Simple snacks, picnic food, and charcuterie-style fare work especially well aboard. We recommend avoiding anything requiring elaborate preparation or a white tablecloth in a 15-knot breeze.
Is gratuity expected?
Never required, always appreciated. If your captain or crew helped make your time aboard exceptional, gratuities are welcome.
What if we have something special in mind?
Tell us. Proposals, anniversaries, birthdays, visiting friends, family outings, and spontaneous reasons to celebrate are all excellent excuses to go sailing.
Your sail doesn't have to fit neatly into a package. That's one of the advantages of having the boat to yourselves.
Come Sail With Us!
Hollyday Sailing is getting ready to launch.
We’re putting the finishing touches on John Galt, dialing in the experience, and preparing to welcome our first guests aboard.
If a private afternoon or sunset sailing Charleston Harbor sounds like your kind of day, join our launch list.
You’ll be among the first to hear when reservations open, along with early charter dates and occasional invitations to special sails.
No crowds. No canned tour. Just your people, a sailboat, and Charleston from the water.
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Already planning something special?
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