• 2, 3, or 4-hour sunset sails​

  • 2, 3, or 4-hour day sails

  • 1/2 and full day sailing adventures

  • Overnight trips

  • Weekend getaways

  • Extended cruises

Special occasion? Let us know!

  • Birthday
  • Anniversary
  • Proposal/Engagement
  • Couples night
  • Ashes scattered at sea

Pricing for Island Time, 47' Beneteau:

  • 2-hour sunset or day sail​:   $375
  • 3-hour sunset or day sail:   $450​

  • 1/2 day (4-hour) sail:           $550

  • Full day (8-hour) sail:          $800

  • Overnight trip:                       $850​

We also sell gift certificates!

Go sailing with Naples' premier sailing charter company ... Island Sailing.  We offer many different captained private sailing adventures, including 2, 3, or 4-hour sunset sails and day sails, overnight/weekend trips, and week-long adventures along Florida's southwest coast, Florida Keys, or to the Bahamas.  Enjoy a bay tour, set sail in the gulf, and enjoy what nature has to offer aboard Island Time (47' Beneteau) or Island Dreams (31' Catalina). Be on the lookout for dolphins and various FL birds! 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.   Each private charter permits up to 6 guests.

We depart from the historic Naples City Dock in Crayton Cove. We 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 sail along one of Naples' beautiful beaches while you enjoy complimentary beverages (water and soda provided). Your captain will point out interesting sights as well as introduce you to the sheer joys of sailing.  Bring your own food and/or alcohol and there's a few local options near the dock. 

What is a captained charter?

Pricing for Island Dreams, 31' Catalina:

  • 2-hour sunset or day sail​:   $325
  • 3-hour sunset or day sail:   $400

  • 1/2 day (4-hour) sail:           $475

  • Full day (8-hour) sail:          $700

  • Overnight trip:                       $750​

Price is per private charter - includes up to 6 guests.

Prices subject to change and do not include tax or captain's gratuity.

Naples' Premier Sailing Charter Company

Island Sailing - Naples, FL​​

Island Sailing Naples | 800 12th Avenue South, Naples, FL | islandsailingnaples@gmail.com | 239.398.1483