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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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Naples, FL
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Reviews (113)
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All reviews hour sail beautiful boat captain mark great sail sailing skills light winds gulf of mexico sunset cruise city dock girls trip watched the sunset excellent trip fort myers rob dawes charter seas
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Reviewed 1 week ago

My siblings and I surprised our parents with a sunset cruise and it was perfect! The boat was the perfect size and it was such a fun and relaxing sail. I would definitely recommend this service!

Review collected in partnership with this attraction
Date of experience: December 2018
Thank Road57049932031
Reviewed 1 week ago

Our family took a 4 day sail out of Naples with Island Sailing on Island Time (47 foot Beneteau) and could not have been more pleased. Rob was extremely helpful and nice to deal with in the planning of the trip, and Mark was our...More

Date of experience: December 2018
Thank bsettle2016
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 1 week ago

Thank you, and we're so pleased that you enjoyed your multi-day sailing trip!

Reviewed 3 weeks ago via mobile

My now fiancé and I went on a sunset charter with Captain Mark and we could not be happier with the experience. I popped the question on this charter and both Capt. Mark and Capt. Rob knew the drill and helped me coordinate it. The...More

Date of experience: December 2018
Thank Khris_Miami
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 1 week ago

Congratulations again and thanks for sharing this special moment with us!

Reviewed November 13, 2018 via mobile

I booked a sailing adventure as a surprise for my wife's birthday. We could not have had a better time. Captain Rob was great to deal with before our sail. Captain Marty was fantastic as our skipper. Everyone we dealt with couldn't do enough for...More

Date of experience: November 2018
Thank Brent C
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 1 week ago

We're so pleased to hear this, and thank you for choosing us!

Reviewed April 24, 2018

This is the boat you want to be on. Everything was clean and beautiful, the crew were amazing and fun to be with. The sailing and sunset were spectacular. I highly recommend sailing aboard Island Time.

Review collected in partnership with this attraction
Date of experience: April 2018
Thank steveInNY
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded April 29, 2018

We're so pleased that you had a wonderful time and we thank you for the review! Best wishes, Capt. Rob and Rachel

Reviewed April 16, 2018

We truly enjoyed our sunset sail. The weather was perfect and the sunset awesome! Our captain was very accommodating and interesting. Loved it!

Review collected in partnership with this attraction
Date of experience: March 2018
Thank johngM4364VI
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded April 29, 2018

We're so pleased that you had a perfect sail! Best wishes, Capt. Rob and Rachel

Reviewed April 15, 2018

Great sail, awesome crew, it was a wonderful evening with Island Sailing. I would recommend for any occasion. Birthday, anniversary or just a fun date night out!

Review collected in partnership with this attraction
Date of experience: April 2018
Thank Terry C
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded April 29, 2018

We're so glad you had a wonderful evening!

Reviewed April 9, 2018

Excellent trip. Fabulous experience. We did a four hour boat trip and watched the sunset. People were very friendly and helpful. Trip was tailored perfectly to what we wanted. Beautiful views, had a wonderful time. Would highly recommend.

Review collected in partnership with this attraction
Date of experience: April 2018
Thank robinchopra
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded April 9, 2018

We're so pleased that you had a fabulous experience and thank you for the great recommendation. Best wishes, Capt. Rob and Rachel

Reviewed March 26, 2018

We were recommended to call Island Sailing for our Sunset Cruise. We had a great experience as well as wonderful hospitality. Our Captain was very knowledgeable about the area and sites. They offered us non alcoholic beverages (as we could byob). He has interesting stories...More

Review collected in partnership with this attraction
Date of experience: February 2018
1  Thank Lisa M
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded April 1, 2018

We're so pleased that you enjoyed your sunset sail! Best wishes, Capt. Rob and Rachel

Reviewed March 21, 2018

The crew at Island Sailing were great very easy to deal with would have no problem going back and sailing with them again.

Review collected in partnership with this attraction
Date of experience: March 2018
2  Thank 189don
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded March 22, 2018

We certainly hope to sail with you again sometime! Best wishes, Capt. Rob and Rachel

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