We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Island Sailing

#10 of 153 Tours in Naples
Open Now: 9:00 am - 9:00 pm
Open today: 9:00 am - 9:00 pm

Island Sailing
Booking unavailable on TripAdvisor

Want other options you can book now?
53
All photos (53)
Full view
Certificate of Excellence
Traveller Overview
  • Excellent99%
  • Very good1%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
“hour sail”(7 reviews)
“great sail”(4 reviews)
About
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...more
Open Now
Hours Today: 9:00 am - 9:00 pm
See all hours
Suggested duration: More than 3 hours
Contact
880 12th Ave S, Naples, FL 34102-7324
Old Naples
Website
+1 239-398-1483
Call
Improve This Listing
Reviews (110)
Filter reviews
110 results
Traveller rating
108
2
0
0
0
Traveller type
Time of year
LanguageEnglish
108
2
0
0
0
Show reviews that mention
All reviews hour sail beautiful boat great sail sailing skills captain mark light winds gulf of mexico sunset cruise city dock girls trip watched the sunset excellent trip rob dawes charter seas stories
FilterEnglish
Updating list...
1 - 10 of 110 reviews
Reviewed 4 weeks ago 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
Reviewed 25 April 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 29 April 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 17 April 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 29 April 2018

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

Reviewed 16 April 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 29 April 2018

We're so glad you had a wonderful evening!

Reviewed 10 April 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 10 April 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 27 March 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 2 April 2018

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

Reviewed 22 March 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 23 March 2018

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

Reviewed 21 March 2018 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

Date of experience: March 2018
1  Thank andrew w
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 23 March 2018

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

Reviewed 20 March 2018

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
Date of experience: February 2018
1  Thank Andy W
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 21 March 2018

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

Reviewed 19 March 2018

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
Date of experience: February 2018
1  Thank usmortons
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 21 March 2018

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

View more reviews
Nearby
Nearby HotelsSee all 61 nearby hotels
Cove Inn on Naples Bay
762 reviews
.14 km away
Charter Club Resort of Naples Bay
181 reviews
.42 km away
Trianon Old Naples
883 reviews
.88 km away
Naples Bay Resort & Marina
1,957 reviews
1.00 km away
Nearby RestaurantsSee all 1,082 nearby restaurants
Mediterrano
1,083 reviews
.82 km away
Cove Inn Coffee Shoppe
300 reviews
.15 km away
Jane's Cafe
862 reviews
.85 km away
Chez Boet-French Home Cooking
309 reviews
.23 km away
Nearby AttractionsSee all 453 nearby attractions
Cambier Park
247 reviews
.78 km away
Naples City Dock
172 reviews
.00 km away
Celebration Community Beach Church
102 reviews
.18 km away
Crayton Cove, Naples
61 reviews
.21 km away
Questions & Answers
Get quick answers from Island Sailing staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Submit
Posting guidelines