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

880 12th Ave S, Naples, FL 34102-7324
+1 239-398-1483
Call
Website
Save
Review Highlights
Beautiful boat

"Island Time" is a beautiful boat and Captain Marty did a great job for us, he is very... read more

Reviewed 3 days ago
Margaret S
Everything I hoped it would be

Made a last minute request to sail and they were able to accommodate me without any issues. Very... read more

Reviewed 4 weeks ago
HappyRock75
,
Ames, Iowa
Read all 96 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
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.
  • Excellent98%
  • Very good2%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain marlena” (19 reviews)
“hour sail” (6 reviews)
Closed Now
All 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
CONTACT
Website
+1 239-398-1483

Similar Things to Do in Naples

Write a ReviewReviews (96)
Traveller rating
Traveller type
Time of year
Language
All reviews
"captain marlena"
in 19 reviews
"hour sail"
in 6 reviews
"beautiful boat"
in 4 reviews
"gulf of mexico"
in 7 reviews
"city dock"
in 2 reviews
"amazing experience"
in 3 reviews
"saw dolphins"
in 2 reviews
"helm"
in 10 reviews
"dawes"
in 6 reviews
"sailors"
in 6 reviews
"voyage"
in 4 reviews
"cruise"
in 15 reviews
"vessel"
in 5 reviews
"sunset"
in 11 reviews
"chartering"
in 2 reviews
"adventure"
in 6 reviews
"stories"
in 5 reviews
Filter

1 - 10 of 96 reviews

Reviewed 3 days ago

"Island Time" is a beautiful boat and Captain Marty did a great job for us, he is very knowledgeable and interesting to talk to. The boat is beautiful and just as pictured. We sailed in light winds so we didn't get the full experience of...More

Thank Margaret S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 4 weeks ago

Made a last minute request to sail and they were able to accommodate me without any issues. Very easy process to reserve and the ship was great and easy to access. I was wanting a “real” sailing experience and not just some lame cruise and...More

1  Thank HappyRock75
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 pleased you enjoyed your "real" sailing experience with us :) We certainly hope to sail with you again. Best wishes, Captain Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 31 December 2017

We really enjoyed our time sailing with Captain Mark. He was extremely fun, knowledgeable and professional. We will definitely do it again.

Review collected in partnership with this attraction
1  Thank shaner220
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 January 2018

We're so happy that you enjoyed your time!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
See more reviews
Reviewed 31 December 2017

We chartered a 30' Catalina from Island Sailing for an afternoon. The boat was in perfect shape and Captain Marty was very good at getting us acclimated and ready to go. We had a great day of sailing and then dropped the boat off again...More

Review collected in partnership with this attraction
Thank kiva60
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 January 2018

We're so pleased that you enjoyed bareboating Island Dreams! Best wishes!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 28 November 2017

Thank you Captain Rob for the clear scheduling, directions, etc., you made the preparation for our sail very easy. Thank you Captain Rob for the wonderful sailing experience, we had a lovely afternoon and saw a beautiful sunset.

Review collected in partnership with this attraction
Thank FinickyFoody
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 30 November 2017

We're so very pleased that you had a lovely sail and greatly appreciate your business. Best wishes, Capt. Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 25 November 2017 via mobile

A several hour sail on the majestic Island Time with Cap’n Rob Dawes was heaven. Saw huge sea turtles & many dolphins. Anchored and swam in to a deserted beach for shelling. All ages had the most wonderful day. Highly recommend and would definitely do...More

Thank Lillian L
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 26 November 2017

Lillian, Thank you for the kind words and it was a pleasure to have you aboard. We greatly appreciate your patronage. Best wishes, Capt. Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 5 May 2017

Captain Rob took us on a memorable, informative and fun sail. Not only was he an excellent captain but a well informed tour guide as well. We have been in the area for 15 years and he shared information and facts with us that we...More

Review collected in partnership with this attraction
Thank css517
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 6 May 2017

We're so pleased you had a memorable experience and enjoyed your sailing adventure. Thank you kindly for your patronage and we look forward to seeing you again! Best wishes, Captain Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 4 May 2017

Met Capt. Jerry at the dock on time and was invited on board. Boat was clean & ship shape. Got underway and " motored" out to the Gulf. Took over the helm at the invitation of the Capt. was a bit rusty at first but...More

Review collected in partnership with this attraction
Thank kpmintosh
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 6 May 2017

We love it when the customers take over at the helm, such fun for them! We're happy that you enjoyed your experience! Best wishes, Captain Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 1 May 2017

Our Naples Sailing adventure was just wonderful. Captain Gerard was excellent, as was the weather…and the sailboat was beautiful! Our captain was friendly and knowledgable. The experience of sailing out of Naples into the Gulf of Mexico was memorable…and our afternoon adventure with our great...More

Thank FoodWineTravel2015
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 May 2017

We're so pleased that you had a wonderful adventure aboard Island Time and we certainly thank you for your business. Capt. Gerard has been a superb asset to our team and we're glad that your trip was memorable! Best wishes, Capt. Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 27 April 2017 via mobile

Sailed with Captain Marlena. Very knowledgeable skipper, great personality, the 47' boat was pristine and the sunset was amazing! We were two couples, brought wine and cheese and had a most enjoyable experience. This is our second time out with Marlena - last time was...More

Thank Walter K
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
IslandSailingNaples, Owner at Island Sailing, responded to this reviewResponded 30 April 2017

Thank you sir for the kind words and we're extremely pleased that you enjoyed yourself on both of our vessels and are beyond grateful for your repeat business. Best wishes, Capt. Rob and Rachel

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
PreviousNext
12345610
Nearby
Nearby HotelsSee all 59 hotels in Naples
Cove Inn on Naples Bay
735 reviews
.12 km away
Charter Club Resort of Naples Bay
163 reviews
.41 km away
Trianon Old Naples
811 reviews
.85 km away
Gondolier Apartments & Inn
34 reviews
.93 km away
Nearby Restaurants
Mediterrano
832 reviews
.73 km away
Jane's Cafe
776 reviews
.76 km away
Campiello
1,351 reviews
.77 km away
Tommy Bahama Restaurant & Store
2,529 reviews
.79 km away
Nearby Attractions
Cambier Park
217 reviews
.71 km away
Naples City Dock
146 reviews
.11 km away
Celebration Community Beach Church
97 reviews
.07 km away
Crayton Cove, Naples
51 reviews
.11 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.
Posting guidelines
Submit