Private Sailing Charters for Special Occasions in Charleston, SC
Everything Zen Sailing
Special Occasions
Your most memorable moments, set to sail.
Every reason to celebrate
What Are You Celebrating?
The perfect moment
Proposals & Engagements
A private harbor stage set for the question of a lifetime.
Send her off in style
Bachelorette Parties
Toast the bride-to-be with the Charleston skyline as your backdrop.
Your day, your way
Birthdays
Sail into another trip around the sun, fully private and fully yours.
A milestone on the water
Anniversaries
Rediscover Charleston Harbor together, unhurried and uninterrupted.
Team outings & client events
Corporate Events
An unforgettable off-site that will actually be talked about.
Any reason to celebrate
Custom Celebrations
Graduation, reunion, or just because. We make it special.
Why a private charter
Exclusively Yours from the First Moment
Intimate by design
The Leopard 42 carries a maximum of 6 guests per Coast Guard regulations. No strangers, no shared tours. Every charter is booked exclusively for your group.
Charleston Harbor as your backdrop
Sail past the Battery, Fort Sumter, and the Arthur Ravenel Jr. Bridge, landmarks that are simply more powerful when seen from the water.
Fully customizable
Let the captain know you're celebrating something. From sunset timing to catering arrangements, the details are shaped around you.
Captain Todd at the helm
An experienced Charleston Harbor captain who has hosted dozens of proposals, birthdays, anniversaries, and corporate events. He knows how to make it happen.
Send her off in style
Bachelorette Parties
Toast the bride-to-be with the Charleston skyline as your backdrop. A private sunset sail is the kind of send-off stories are built around: champagne, open water, and the whole harbor to yourselves.
Book the Sail
Your crew
Captain Todd and First Mate Kathy have hosted proposals, milestone birthdays, bachelorette parties, and anniversary sails across Charleston Harbor. Together, they know what makes a moment unforgettable.
When you book a special occasion charter, a note in your reservation is all it takes. Todd will handle the sail and positioning while Kathy makes sure every detail on deck is exactly right.
Add something special
Onboard Catering
Nothing says celebration like champagne on the water. Through our partnership with private Chef Mari Jo Ramie of Marjoram Cuisine, you can arrange a full catered menu for your charter.
Prefer something simpler? The captain can arrange a charcuterie board waiting for you when you step aboard: cured meats, cheeses, crackers, and seasonal fruit. Starting at $85.
View Catering OptionsFrequently Asked Questions
Can you help with a surprise proposal?+
Absolutely. After booking, message Captain Todd directly to share your plan. He's helped coordinate dozens of proposals, from having champagne ready at the right moment to positioning the boat for the best sunset light at the Battery. The deck is yours.
How many guests can join a special occasion charter?+
Up to 6 guests per charter, per Coast Guard regulations. Every booking is fully private: no other groups, no shared sails. The Leopard 42 and Captain Todd are dedicated entirely to your group.
Can we bring our own alcohol and food?+
Yes. Every charter is BYOB-friendly. Feel free to bring wine, champagne, beer, or spirits. Just no glass bottles near the water. You're also welcome to bring your own food. If you'd like something handled for you, we can arrange a charcuterie board or connect you with our catering partner Marjoram Cuisine.
What is included in a special occasion charter?+
Your charter includes fuel, a licensed captain, and full use of the vessel: the rooftop sun deck, saloon, and bow. Bluetooth audio is available aboard. Catering is an add-on arranged separately. Let the captain know what you're celebrating and he'll make sure the experience reflects it.
How far in advance should I book?+
As early as possible, especially for weekend dates and sunset slots. Summer and fall dates can book out weeks in advance. If you have a specific date in mind for a proposal or birthday, don't wait. Check availability now and lock it in.
Ready to Plan Your Celebration?
Weekend dates and sunset slots fill up fast. Reserve your private charter now and let us know what you’re celebrating.
Book Your Charter