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About Island Sailing
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 aboard our two vessels, Island Time (47' Beneteau) and Island Dreams (31' Catalina). Let your captain be your tour guide on your private charter. Experienced sailors can bareboat Island Dreams for a half or full day sail. Enjoy cruising along Naples' sugar white sand beaches aboard a fun and easy-to-sail yacht. She is well equipped for your daysailing needs.
Opens in 19 min
Hours Today: 9:00 AM - 9:00 PM
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Ashley wrote a review May 2020
1 contribution
I came here today for my birthday & our captain Daniel honestly made my birthday the best ever! it was much so much fun, beautiful areas where they take you, clean, awesome customer service! overall, it was such a great experience. I did not expect it to be so fun & interesting... our captain gave us so much history about the beautiful surroundings. Coming here again!!
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Date of experience: May 2020
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Marilyn1320 wrote a review Mar 2020
Naples, Florida1 contribution
This was our 2nd time taking a sunset sail with Island Sailing. We had a different Captain each time and both we amazing. They each were informative and fun. The sailboat was perfect for our group of 5 and our group of 3. We were able to bring snacks and wine and they have a table. I am looking forward to doing this again sometime soon! If you have out of town guests, it's a perfect activity!
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Review collected in partnership with this attraction
Date of experience: January 2020
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Mar 9, 2020
We’re so pleased that you enjoyed your sail! Thank you for your continued patronage and we look forward to sailing with you again!
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Jim R wrote a review Mar 2020
13 contributions
6 of us went on a 3 hour sail. Captain Marlen greeted us onto their sailboat. She was so laid back like an old friend and made us feel right at home. The cruise out to the gulf was under power but was enjoyable seeing all the other boats. Once at the gulf we were under sail. Anyone who wanted to steer could try steering. It was a beautiful day on the water. Coming back in the channel, i was allowed to steer most of the way back. We all think is was probably the hi point of our time down here in Florida. Thanks again, Marlena
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Review collected in partnership with this attraction
Date of experience: February 2020
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Mar 9, 2020
We’re so pleased that you enjoyed your sail! Thank you for your patronage.
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Explore11757234240 wrote a review Mar 2020
1 contribution
Simply good all around - excellent vessel, full facilities at Naples City Dock. This is an organized and capable bunch. Very knowledgeable about local waters, simply an enjoyable experience that we'd plan to do again upon another visit.
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Review collected in partnership with this attraction
Date of experience: February 2020
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Mar 9, 2020
We’re so pleased that you enjoyed your sail! Thank you for your patronage and look forward to sailing with you again!
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Naples wrote a review Mar 2020
Naples, Florida3 contributions
Island Sailing is the best! The captains are extremely personable and knowledgeable not just about sailing but the area too. They know the boats, winds, swells etc to make sure you have the best type of sail you want. We have been out with them multiple times and would not go out with anyone else.
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Review collected in partnership with this attraction
Date of experience: January 2020
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Mar 9, 2020
We’re so pleased that you enjoyed your sail! Thank you for your continued patronage and we look forward to sailing with you again!
Read more
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