Crewed Sailing Adventures

Our crewed sailing charters include sunset cruises, daysails, and weekend and extended sailing cruises.

Two Hour Bay Tour and Sail We depart from the historic Naples City Dock in Crayton Cove. We will motor down Naples Bay enjoying the breathtaking scenery and elegant mansions that line this beautiful waterway. Wildlife abounds as we are escorted by a myriad of birds including Pelicans, Herons, Egrets, Osprey, and Bald Eagles. Hopefully, a dolphin or two will pop up and greet us and maybe even a manatee. As we near Gordon's Pass, we will raise our mainsail and enter the Gulf of Mexico. With our jib unfurled, we enjoy a short sail along one of Naples' beautiful beaches while you enjoy complimentary beverages. Your captain will point out interesting sights as well as introduce you to the sheer joy of sailing.

Three and Four Hour Bay Tour and Sail With our half-day sail charter, you will enjoy everything the Two Hour Sail offers and more. These longer sails give you more time to explore the Gulf of Mexico along with Naples' fantastic beaches. Cruise along Port Royal's famous beachfront homes on the way to the Historic Naples Pier. Sailing off the Pier, we often see Naples' most famous and friendliest residents, the dolphins. We have pods of bottlenose dolphins that often swim and frolic alongside the boat. North of the Pier, we sail along pretty homes and beautiful hotels. We often see frigate birds and pelicans diving after schools of fish and sea turtles paddling by. Want to work on your sailing skills? Your captain will be happy to turn over the wheel so you can experience the thrill of sailing first hand. Your captain will explain how the boat sails and guide you through maneuvering a performance sailing yacht. Sounds like too much work??? Then sit back and relax and soak up some of the Florida sunshine while enjoying cold complimentary drinks.

Full Day Sailing Odyssey Enjoy all the fun of the other trips at a more leisurely pace. Spend your day sailing or make a stop at Marco Island's Snook Inn Restaurant for some great local seafood and ambiance. To reach Marco, we sail along unspoiled Keewaydin Island. The undeveloped white sandy beach is truly stunning contrast to the emerald waters of the Gulf. As an alternative to Marco, you may want to anchor (weather permitting) along Keewaydin's beach and dinghy ashore for some of Florida's Best Shelling. Or spend the day working on your sailing skills; all of our Captains are happy to provide you with instruction. Bring your own lunch or we can arrange catering. As always, we have lots of cold complimentary drinks aboard.

Sunset Sails Nothing is more spectacular or romantic than gliding along Naples' magnificent beaches as the Sun dips towards the West. As you sip your favorite wine, the sky becomes an explosion of color gradually changing from yellow to magenta as it reflects off the clouds and the beach. As you enjoy your leisurely sail, the sun eventually drops from sight; sometimes emitting a bright "green flash." You cruise back to the dock as twilight fades and the pretty Naples City lights brighten your horizon. Sunset sails are truly a fantastic event not to be missed.

Engagements Have you ever dreamed of a romantic sail in paradise as the backdrop to your wedding proposal??? Then sail off into the sunset as you sip champagne as the newly engaged!! We specialize in helping you with that wonderful moment. We can even cater the event and arrange chilled champagne; we have even had an aircraft streaming a "Will You Marry Me?" banner. We can play any special music you like. Let us customize a truly once in a lifetime engagement for you.

Weekend Getaways Want to get out of town???? We offer two and three day weekend getaways. Sail to Marco Island or Fort Myers Beach and spend the night aboard your private yacht. Put your feet up and enjoy an evening drink in the cockpit before wandering off to a local restaurant or anchor out and enjoy grilling off the back of the boat at sunset. Spend the rest of the evening enjoying the local nightlife dockside or stargazing at anchor. These week-end sailing jaunts are a great way to relax for visitors and locals alike. Your Captain can do all the work or you can join in and learn some basic cruising skills.

Week Long Cruises or Longer Spend a week cruising Florida's wonderful West Coast or the Beautiful Florida Keys. Sail to Fort Myers Beach, Sanibel or Captiva Islands, Cabbage Key, Venice, St. Petersberg, Key West..... Charter a sailboat for a week, pick where you want to go, and one of our Captains will accompany you on a vacation of a lifetime...