Overview

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.

5.0

109 reviews

Excellent99%
Very good1%
Average0%
Poor0%
Terrible0%

Travelers talk about

“captain marlena” (19 reviews)

“hour sail” (7 reviews)

“beautiful boat” (6 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

Improve This Listing

Write a ReviewReviews (109)

1 - 10 of 109 reviews

steveInNY

Yorktown Heights, New York

15048

Reviewed April 24, 2018

Wonderful time, great boat and crew

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

Ask steveInNY about Island Sailing

Thank steveInNY

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

We're so pleased that you had a wonderful time and we thank you for the review! 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.

johngM4364VI

Franklin, Wisconsin

31

Reviewed April 16, 2018

Great time sailing/Sunset

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

Ask johngM4364VI about Island Sailing

Thank johngM4364VI

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

We're so pleased that you had a perfect sail! 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.

Terry C

Naples, Florida

5

Reviewed April 15, 2018

perfect sail

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

Ask Terry C about Island Sailing

Thank Terry C

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

We're so glad you had a wonderful evening!

Report response as inappropriate

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

See more reviews

robinchopra

1

Reviewed April 9, 2018

Boat Trip

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

Ask robinchopra about Island Sailing

Thank robinchopra

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

We're so pleased that you had a fabulous experience and thank you for the great recommendation. 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.

Lisa M

Raleigh, North Carolina

64

Reviewed March 26, 2018

Girls sunset cruise

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

Ask Lisa M about Island Sailing

1 Thank Lisa M

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

We're so pleased that you enjoyed your sunset sail! 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.

189don

12

Reviewed March 21, 2018

Day sail Bareboat

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

Ask 189don about Island Sailing

2 Thank 189don

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

We certainly hope to sail with you again sometime! 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.

andrew w

21

Reviewed March 20, 2018 via mobile

Chartered sailboat

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

Ask andrew w about Island Sailing

1 Thank andrew w

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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

Report response as inappropriate

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

Andy W

Boston, Massachusetts

54

Reviewed March 19, 2018

Catalina 33 Sail

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

Ask Andy W about Island Sailing

1 Thank Andy W

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

Thank you for the kind words! 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.

usmortons

Bonita Springs, Florida

11

Reviewed March 18, 2018

Family & friends sunset sail

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

Ask usmortons about Island Sailing

1 Thank usmortons

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

Thank you for the kind review and we're glad you enjoyed your sunset sail! 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.

236marylynnem

Ocean City, MD, United States

21

Reviewed March 17, 2018

Elegant boat, private charter of 6, Exceeded expectations

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

Ask 236marylynnem about Island Sailing

1 Thank 236marylynnem

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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

Report response as inappropriate

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

Previous Next

1 2 3 4 5 6 …11

Nearby