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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.
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Hours Today: 9:00 AM - 9:00 PM
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Island Sailing
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carl683 wrote a review May 2022
1 contribution
We went out for half a day on "Island Time". The owner and captain were very friendly and on top of last minute weather changes. I would highly recommend Island Sailing for a private sailing adventure departing Naples. We plan to do a multi-day sail with them in the future.
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Review collected in partnership with this attraction
Date of experience: April 2022
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christopherT515TB wrote a review Apr 2022
1 contribution
As locals, my girlfriend and I were in awe of this experience. We've both had our own boats with ex-marriages, still have boats and/or experienced the SWFL Gulf just about everyway possible with our separate families during our adulthood lives; but this was a hidden gem. Finding Capt. Rob and Island Sailing was like finding a $100 bill in a pair of shorts worn last week.. Capt. Paul couldn't have been more professional and made a surprise romantic sunset private cruise, completely top notch. My girlfriend and I have raved about our experience and will definitely being doing business with Island Sailing many more times in the future!! We are looking forward to a future overnight sailing charter with friends. 100% Satisfaction!!!! Thanks for making a good night, great!!
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Review collected in partnership with this attraction
Date of experience: April 2022
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Diana wrote a review Apr 2022
Prior Lake, Minnesota4 contributions
We truly enjoyed our day sailing with Captain Mark from Island Sailing out of Naples. So relaxing and adventurous. If you're into sailing or want to learn more about sailing this is a great excursion and I highly recommend it!
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Review collected in partnership with this attraction
Date of experience: March 2022
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Apr 14, 2022
We’re so very excited to hear that you enjoyed your sail and we do appreciate Capt Mark. Thank you for sailing with us!!!
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bobwerner73 wrote a review Apr 2022
22 contributions1 helpful vote
Had an awesome sunset sail out of Naples into the Gulf. Captain and sailboat were great. Brought a bottle of wine and sat on the deck up front. Lots of dolphins to keep us company. Can’t wait to sail again. Highly recommend.
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Review collected in partnership with this attraction
Date of experience: March 2022
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Apr 14, 2022
We’re so very excited to hear that you enjoyed your sail and look forward to seeing you again. Thank you!!!
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Natalie P wrote a review Mar 2022
27 contributions5 helpful votes
We had an incredible time on the sail. Boat was amazing and the Captain was great. Perfect evening out on the water. Would highly recommend.
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Review collected in partnership with this attraction
Date of experience: February 2022
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Response from IslandSailingNaples, Owner at Island Sailing
Responded Apr 1, 2022
We’re so pleased that you had a wonderful sail!
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