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

contact us at islandsailingnaples@gmail.com  or  239.398.1483

What do we do if it is raining or there isn’t any wind?
We do not cancel charters for lack of wind; however, if the weather is too poor, the captain will make the final decision on canceling the charter.  

Where can/should we park?
Parking can get a bit crowded so we suggest you park in the City Dock Parking at the corner of 8th Street South and Broad Avenue South.  From there, you will walk south past The Cove Inn towards the Dock Restaurant.  The Naples City Dock is next to the restaurant.   

Do you accept credit cards?  
Yes, we do.  Unfortunately, we must also add on the 2.7% service fee from the point of sale provider.

Can we bring food and drinks on board?  Alcohol?
Yes and yes.  Please feel free to bring whatever food and drinks you would like to bring on board our vessels.  We have a corkscrew, glasses, plates/bowls and silverware for our guests to use and a refrigerator is available on each vessel as well.  We offer complimentary water and soda on both vessels.

Are there restrooms on the boats?
Yes, we have two heads on Island Time, one electric head and one manual pump.  We have one manual head on Island Dreams.

Will we see dolphins, manatees, or other sea life?
While we do not guarantee seeing sea life, we have not had a sail yet where our guests did not see dolphins.  Manatees are much shyer, so they are a rarity.  You will see sea eagles and osprey as well.  You may also see eagle rays and sea turtles on your trip.  

How much do we tip the captain?
Tips are more personal and depend on how satisfied you are not only with the sailing experience that the captain has provided but by how knowledgeable they are about the area.  If you feel that they have provided you with a good experience and shared local knowledge then a 15 - 20% tip is the normal range.  

Can we swim from the boat?
We normally do not get close enough to the beaches; however, our guests may swim from the boat while out in the Gulf.  Swimming from the boat may be done at your own risk.

Frequently Asked Questions