Use PROMO Code 3FOR2 on any 3-Hour Cruise for an hour on us!
105 Free Court Southeast, Port Charlotte, Florida 33952
Sailing Cruises in Charlotte Harbor & Beyond
Sunset Sailboat Charters on Charlotte Harbor from Port Charlotte | Punta Gorda
Experience the beauty of Charlotte Harbor on a private Sunset Sail. Our captained yacht charters depart from Punta Gorda and Port Charlotte, offering an unforgettable evening cruise with golden skies, calm waters, and unmatched tranquility. Perfect for couples, families, or small groups looking for a peaceful Florida getaway. Starting at $319 + tax "The most peaceful evening we’ve ever had on the water — Capt. Curtis made it perfect!" — Sarah M., Punta Gorda
Day Sailing Charters on Charlotte Harbor from Port Charlotte | Punta Gorda
Set sail for a relaxing daytime adventure on Charlotte Harbor aboard a private captained yacht. Our day sailing charters depart from Punta Gorda and Port Charlotte, offering a peaceful, customizable cruise for families, small groups, or couples. Enjoy sunshine, coastal breezes, and panoramic views from the comfort of a spacious sailboat. Whether you're celebrating a birthday, sightseeing with family, or just unwinding on the water — this experience is designed to reconnect you with nature and leave you refreshed.
“Our daytime sail was the highlight of our vacation — so peaceful and personal.” — James L., Fort Myers
2 and 3-Day Private Yacht Getaways from Punta Gorda and Port Charlotte
Escape for a 2 or 3-day private yacht getaway from Charlotte Harbor to the Barrier Islands on the Gulf Coast. Our captained sailing adventures depart from the top of Charlotte Harbor to the areas around Cayo Costa and Cabbage Key, offering overnight stays, customizable routes, and total relaxation aboard a fully equipped yacht. Enjoy quiet anchorages, coastal sunrises, and the freedom to explore the beauty of Southwest Florida at your own pace. Whether you're celebrating an anniversary, honeymoon, or just want to unplug for a few days — this extended charter delivers adventure, privacy, and unforgettable memories.
“Three days aboard felt like a week of pure calm. We’ll be back next season.” — Adam & Kelly, Tampa
Learn to Sail with a USCG Captain on any of our Charters
"We're not licensed instructors, and no certifications will be awarded, but we're happy to think out loud and teach you stuff. " --Capt Curtis
Get hands-on sailing experience with a certified captain aboard a private yacht. Learn to read the wind, trim the sails, and take the helm in a calm, safe environment on Charlotte Harbor. Whether you want to sail your own boat someday or simply understand the fundamentals, this immersive experience offers more than just a ride — it’s real learning on the water.
“Captain Curtis made sailing approachable and fun. I learned more in one afternoon than from any online course.” — Brian T., Cape Coral