105 Free Ct SE, Port Charlotte, FL, USA
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 aboard Courageous, our classic 37ft cruising yacht. Departing from Punta Gorda and Port Charlotte—just minutes from Sunseeker Resort—this captained charter offers 2–4 hours of breezy daylight sailing, followed by a breathtaking Florida sunset. Whether you’re a couple seeking romance, a family looking for adventure, or friends wanting a peaceful getaway, a sunset sail on Charlotte Harbor is the perfect mix of relaxation, scenery, and pure Florida magic.
Starting at $319 + tax, includes up to 6 people
"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
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