TropicBird out of Goodland, Florida 10 minutes from most locations on Marco and about ˝ hour from Naples offers full day private sailing adventures for groups up to 6 deep into the 10,000 Islands aboard their 34 ft Gemini catamaran. You can help crew the boat as much or as little as you like, guided by a round the world sailor, who is also a Florida master naturalist and serves an excellent lunch. It’s a good opportunity to sample the cruising life. Coolbeans out of nearby Capri Isles offers shorter trips on an individual place basis and Sweet Liberty (a large cat out of Naples City dock) offers a similar service. There are also a number of day charter sailing vessels offering their services too from Naples City dock which you can check out on a nice stroll. See TripAadvisor and also check out Florida's Paradise Coast - Family Vacations Florida | Florida Beach Vacations | Naples, Marco Island & Everglades
for lots of other on the water and sailing options in the area.