​​​​​​island sailing 
Naples' premier sailing charter company

contact us at islandsailingnaples@gmail.com  or  239.398.1483



2 and 3-Hour Bay Tours and/or sunset sails

  • Island time:      2 hrs - $350  /  3 hrs - $425 *

  • Island dreams:  2 hrs - $300  /  3 hrs - $375 *

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 joys of sailing.

​Nothing is more spectacular or romantic than gliding along Naples' magnificent beaches as the sun dips towards the west. Bring your favorite wine and watch as 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.

1/2 day (4 hour) Bay Tour and Sail 

  • island time:      $525 *
  • island dreams:  $450 *    

With our half-day sail charters, you will enjoy everything the 2 and 3-hour sails offer 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 along. 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 (8 hour) Sailing adventure

  • island time:      $800 *

  • island dreams:  $700 *

Enjoy all the fun our other trips offer at a more leisurely pace. Spend your day sailing south towards Marco Island along Keewaydin Island or north towards Sanibel Island.  Full day sails may include the option to go ashore for some great local seafood, shelling, or just to enjoy the ambiance.   Not interested in leaving the boat?  Then spend the day relaxing or 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.

overnights and/or Weekend Getaways

  • island time:      $850 *

  • island dreams:  $750 * 

Want to get out of town? We offer weekend getaways! Sail to Marco Island, Fort Myers Beach, or Sanibel Island 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 weekend 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.  Bring your own food or we can arrange catering.  As always, we have lots of cold complimentary drinks aboard.

extended Cruises  

  • contact us for pricing 

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, or 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!​​​






2 hours $300$350
3 hours$375$425

4 hours

(1/2 day)


8 hours

(full day)



captained charters

Don't know what to get loved

ones for their birthday, anniversary, or the holidays?  Treat them to a gift certificate with Island Sailing!

what is a captained charter? 

Go sailing with Naples' premier sailing charter company ... Island Sailing.  We offer many different private sailing adventures with our captained crew, from a 2-hour romantic sunset cruise to a week-long adventure along Florida's southwest coast or to the Florida Keys.  We offer dolphin encounters and nature/bird watching.  We cater to our customers' every need and strive to provide our customers with the very best service possible.  Let your captain be your tour guide on your private charter. Contact us at 239.398.1483 or email us at islandsailingnaples@gmail.com to begin your sailing adventure.​​