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Island Sailing

880 12th Ave S, Naples, FL 34102-7324
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Review Highlights
Great time sailing/Sunset

We truly enjoyed our sunset sail. The weather was perfect and the sunset awesome! Our captain was... read more

Review collected in partnership with this attraction

Reviewed 4 days ago
johngM4364VI
,
Franklin, Wisconsin
perfect sail

Great sail, awesome crew, it was a wonderful evening with Island Sailing. I would recommend for any... read more

Review collected in partnership with this attraction

Reviewed 5 days ago
Terry C
,
Naples, Florida
Read all 108 reviews
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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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Travellers talk about
“captain marlena” (19 reviews)
“hour sail” (7 reviews)
Open Now
Hours
Hours Today: 9:00 am - 9:00 pm
Suggested Duration: More than 3 hours
LOCATION
880 12th Ave S, Naples, FL 34102-7324
Old Naples

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Write a ReviewReviews (108)
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"captain marlena"
in 19 reviews
"hour sail"
in 7 reviews
"beautiful boat"
in 6 reviews
"sailing skills"
in 3 reviews
"sunset cruise"
in 9 reviews
"gulf of mexico"
in 8 reviews
"light winds"
in 2 reviews
"wonderful sailing"
in 2 reviews
"city dock"
in 3 reviews
"girls trip"
in 2 reviews
"amazing experience"
in 3 reviews
"saw dolphins"
in 2 reviews
"helm"
in 10 reviews
"dawes"
in 6 reviews
"sailors"
in 7 reviews
"charter"
in 9 reviews
"vessel"
in 5 reviews
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1 - 10 of 108 reviews

Reviewed 4 days ago

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
Thank johngM4364VI
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 5 days ago

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
Thank Terry C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 1 week ago

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
Thank robinchopra
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 1 week ago

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

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Reviewed 3 weeks ago

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
1  Thank Lisa M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 2 weeks ago

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

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Reviewed 4 weeks ago

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
2  Thank 189don
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 4 weeks ago

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

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Reviewed 4 weeks ago via mobile

We chartered a five hour sail and had the best time possible. Captain Rob made my family feel completely at ease (my wife was nervous) and safe. Knowledgeable and charismatic, Captain Rob regaled us with stories about the local communities and pointed out wildlife. We...More

1  Thank andrew w
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 4 weeks ago

Thank you for the kind words and we're so very happy that you and your family enjoyed the experience. We look forward to sailing with you again! Best wishes, Capt. Rob and Rachel

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Reviewed 4 weeks ago

Island Sailing's Catalina 33 is extremely well outfitted with both jib and main roller reefing, strong diesel engine, very good nav set; wheel rudder control; comfortable seating on seat cushions for 6; well stocked fridge with water and an assortment of soft drinks; prompt meeting...More

Review collected in partnership with this attraction
1  Thank Andy W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 4 weeks ago

Thank you for the kind words! Best wishes, Capt. Rob and Rachel

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Reviewed 4 weeks ago

Fabulous evening, sunset sail. Beautiful boat, so shipshape and well outfitted. Captain was excellent & well informed but not intrusive. Thanks again Island Sailing!

Review collected in partnership with this attraction
1  Thank usmortons
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 4 weeks ago

Thank you for the kind review and we're glad you enjoyed your sunset sail! Best wishes, Capt. Rob and Rachel

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Reviewed 4 weeks ago

Stunning 41 foot sailboat, long ride onto gulf, through the beautiful homes of Port Royal. The captain selected delicious cheeses and we brought our own small cooler full of wine and beer, and our own cheese and veggies. The sail was so intimate...we went until...More

Review collected in partnership with this attraction
1  Thank 236marylynnem
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 4 weeks ago

Thank you for the kind words and we're so happy to hear of your great experience with us! Best wishes, Capt. Rob and Rachel

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Reviewed 4 weeks ago

My husband and I enjoyed a half day charter during our February trip to Naples. Captain Gerry was very skilled and professional, and allowed my husband to brush up on his sailing skills. The boat itself was very clean and in great condition. We would...More

1  Thank Penny133
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 4 weeks ago

We're so happy that you enjoyed yourselves aboard our vessel! Best wishes, Capt. Rob and Rachel

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This response is the subjective opinion of the management representative and not of TripAdvisor LLC
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