There’s something undeniably transformative about watching the city skyline drift by or the sun sink low from the water. For the last five years, Charleston visitors and locals alike have had the unique privilege of experiencing this shift in perspective firsthand aboard Everything Zen.

Whether celebrating a milestone or simply seeking an escape, the experience is defined not by the gentle harbor breezes or spotting local dolphins, but by the personal touch of owners Captain Todd and "Best Mate" Kathy.

We recently had the pleasure of sitting down with the duo to learn more about their life aboard, their favorite hidden spots in the harbor, and why they believe Charleston is best experienced with the sails up.

Everything Zen

Everything Zen Sailing Charters is a locally owned, owner-operated luxury sailing experience aboard a beautiful 42-foot Leopard catamaran in the heart of Charleston Harbor. Every charter is personally hosted by owners Capt. Todd and Kathy, who live aboard their yacht part of the year and love sharing Charleston from the water. Whether you’re celebrating an anniversary, girls’ getaway, birthday, engagement, or simply looking for a relaxing afternoon on the harbor, each sail is private, unhurried, and tailored to your group.

Most charters are 2½ hours, taking guests past Charleston’s historic waterfront, Fort Sumter, Castle Pinckney, the Ravenel Bridge, and some of the harbor’s favorite dolphin spots. Sunset sails conclude with the traditional sounding of the ship’s conch shell as the sun disappears over the city skyline.

As a special benefit for guests of Planters Inn, every charter includes a complimentary handcrafted charcuterie board—the perfect pairing with your favorite bottle of wine or champagne (they are BYOB friendly).

Meet the Team

Capt. Todd

Todd's been sailing for 50 years — ever since his parents said no to a Jon boat and an 11-year-old set his sights on a dinghy sailboat instead. After a 32-year career leading hospitals as a healthcare executive, Todd traded boardrooms for blue water and now holds a USCG Captain’s License. Some 15,000 miles later, he's sailed the Atlantic, the Gulf, the Caribbean, and the Med, and he and Kathy still live aboard when they cruise south for the winter.

His passion is helping guests experience Charleston from a perspective few visitors ever see while sharing local history, sailing stories, and life aboard a cruising catamaran. Todd’s a retired healthcare CEO, Florida State fanatic, and a certified rum connoisseur who alongside 3 friends, once caught 83 sailfish in Guatemala (ask him for the details on that one).

Kathy

Known affectionately as “Best Mate Kathy,” she helps create the relaxed, welcoming atmosphere guests consistently rave about. Toronto-born and a Lowcountry local since 1998, she's happiest snorkeling turquoise water in the Exumas or hunting down the perfect ceviche with a waterfront view. (Oh, and Kathy spent her career as an ICU nurse — so yes, you are in very good hands out here.)

From greeting guests dockside to helping with photos, local recommendations and making everyone feel at home, Kathy is an essential part of every charter. She's the reason every experience feels personal and truly tailored to each group.

Together, Todd and Kathy have welcomed hundreds of guests aboard Everything Zen and love introducing visitors to the beauty of Charleston Harbor.

Local’s Insight Q&A

Favorite time of year in Charleston?

We love our summer sails with those sea breezes keeping it less hot than anywhere else in Charleston but early fall (September/October) is hard to beat. Comfortable temperatures, lower humidity, beautiful sunsets, and steady sailing breezes make for ideal days on the water.

Best waterfront drink?

After a sail, it’s hard to top cocktails overlooking Shem Creek at Saltwater Cowboys or a rooftop drink while watching the harbor at The Rooftop.

Favorite casual lunch?

For fresh seafood, 167 Raw is always worth the wait but Chubby Fish and the coconut cake at Peninsula Grill has our heart. For a relaxed waterfront atmosphere after your sail, Tavern & Table is another favorite.

Favorite Charleston experience visitors often miss?

Seeing Charleston from the water. Most visitors walk the historic district, but the city’s skyline, church steeples, dolphins, forts, and harbor are even more spectacular under sail. It’s one of the most peaceful ways to experience Charleston. We love sharing stories about the Holy City as well as our live-aboard sailing adventures (would you sail to the Bahamas straight through without seeing land for 3 days?!).

What’s your favorite part of every charter?

Watching guests completely unwind. Phones get put away, conversation slows down, dolphins often appear unexpectedly, and Charleston seems to move at a different pace from the water. Sailing into the sunset from Fort Sumter to the Battery is the absolute bomb part of the sail.

One Charleston “must-do”?

Spend one evening watching the sunset on the harbor. Whether from the deck of Everything Zen or along the waterfront, it’s an experience that stays with visitors long after they leave. Oh and don’t sleep on one of the carriage tours or a walking tour of downtown - so many great stories about our fine city.

Arrange time on the water with Everything Zen during your next stay at Planters Inn through our Concierge. Sails up!