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Address: 880 12th Ave S, Naples, FL 34102-7324
Phone Number: +1 239-398-1483
Website
Today
09:00 - 21:00
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Hours:
Sun - Sat 09:00 - 21:00
Recommended length of visit: More than 3 hours
Description:

Go sailing with Naples' premier sailing charter company ... 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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TripAdvisor Reviewer Highlights

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Sailing getaway!

Booked Island Sailing for a 50th bday trip.3 nights /days with 4 adults. Not knowing what to expect with the whole idea of "sailing" this was a perfect introduction! Marlena, our... read more

Review collected in partnership with this attraction

5 of 5 bubblesReviewed 1 week ago
laura e
,
Denver, Colorado

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61 Reviews from our TripAdvisor Community

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Showing 61: English reviews
Denver, Colorado
Level Contributor
18 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
5 of 5 bubbles Reviewed 1 week ago

Booked Island Sailing for a 50th bday trip.3 nights /days with 4 adults. Not knowing what to expect with the whole idea of "sailing" this was a perfect introduction! Marlena, our Captain was fantastic! She truly made our experience! It was a simple little jaunt, not to far off land. Docked for dinners on shore. Boat was very nice. We... More 

Review collected in partnership with this attraction

Helpful?
Thank laura e
IslandSailingNaples, Owner at Island Sailing, responded to this review

Thank you Laura and we're pleased that you had an excellent experience. We'll be happy to serve you again, any time :) Best wishes, Rob and Rachel More 

Naples
1 review
5 of 5 bubbles Reviewed 2 weeks ago

Couldn't have been more enjoyable. Captain had a million stories, or just let you enjoy the sail. If you want to take the helm, you can do that, too. A perfectly planned and executed experience sailing.

Review collected in partnership with this attraction

Helpful?
Thank RaphaeldeEpicure
IslandSailingNaples, Owner at Island Sailing, responded to this review

We're so happy that you enjoyed your sail with us and hope to see you again soon! Best wishes, Rob and Rachel Dawes More 

Marlton, New Jersey
1 review
5 of 5 bubbles Reviewed 3 weeks ago

A great time and an outstanding value! Beautiful boat and Captain Mark was outstanding. Very knowledgeable, competent, and entertaining. Highly recommended.

Review collected in partnership with this attraction

Helpful?
Thank BobMarlton
IslandSailingNaples, Owner at Island Sailing, responded to this review

Thank you so much for your kind review. We love our captains and are very pleased to hear that you enjoyed your trip! Best wishes, Rob and Rachel Dawes More 

Naples, Florida
1 review
5 of 5 bubbles Reviewed 4 weeks ago

We had a wonderful afternoon sail, ending after viewing the sunset. It was so peaceful to be sail under wind power alone if we wanted it. Shelling on the island and viewing dolphins all around really rounded out the experience for our European guests. Captain Vinny was a great host. We booked another cruise a week later.

Review collected in partnership with this attraction

Helpful?
Thank 764lawrence
IslandSailingNaples, Owner at Island Sailing, responded to this review

We're so excited to hear that you had a wonderful sunset sail and are honored to have you back! Best wishes, Rob and Rachel More 

Naples, Florida
1 review
5 of 5 bubbles Reviewed 5 weeks ago

Island Dreams was great. Clean top to bottom. Very user friendly even single handed. Staff was informative and extremely through. "I'll be back"

Review collected in partnership with this attraction

Helpful?
Thank mattmP2777CQ
IslandSailingNaples, Owner at Island Sailing, responded to this review

Thank you, we strive to keep our vessels sparkling :) More 

Kansas City, Missouri
1 review
5 of 5 bubbles Reviewed 27 October 2016

I've worked with this company twice and both times had an amazing sail. One was just a couple trip and the other was a girls trip. They will let you have whatever type of trip you desire in a safe and fun environment.

Review collected in partnership with this attraction

Helpful?
Thank laurenleighschuster
IslandSailingNaples, Owner at Island Sailing, responded to this review

Thank you Lauren and we're so honored to have you sail with us again! Best wishes, Rob and Rachel More 

Winter Springs, Florida, United States
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 27 July 2016

I flew into Marsh Harbor, Bahamas, from West Palm Beach and meet the beauty called ISLAND TIME, a 46 ft Sailboat that gave me an experience of a lifetime! Three bedroom two bath, great galley, with easy access on and off the ship! Capt. Rob brought us to many beautiful islands, Munjack, Powell, Treasure Key, Guana Beach, Tahiti Beach, No... More 

Helpful?
Thank JoAnne A
IslandSailingNaples, Owner at Island Sailing, responded to this review

JoAnne, We are beyond grateful for your kind words but more importantly, are overjoyed that you had an amazing experience aboard Island Time and enjoyed your vacation in the Bahamas! Thank you so much for choosing Island Sailing and will look forward to having you aboard soon! Best wishes, Rob and Rachel Dawes More 

Boston, Massachusetts
1 review
5 of 5 bubbles Reviewed 2 June 2016

I had been on a sunset sail with Island Sailing before and when I was returning to Naples with 2 friends who had never been I knew it would be the perfect excursion to take them on. The trip did not disappoint, clean boat, knowledgable and friendly captain, beautiful sunset out in the gulf of Mexico. I highly recommend Island... More 

Review collected in partnership with this attraction

Helpful?
Thank jameef328
IslandSailingNaples, Owner at Island Sailing, responded to this review

How exciting to hear that you introduced your friends to a sailing excursion and very pleased that everyone had a great time! We certainly look forward to seeing you again! -Rachel and Robert Dawes More 

Hickory Corners, Michigan
1 review
5 of 5 bubbles Reviewed 30 May 2016

Six of us went out for a sunset cruise- and it was wonderful! Took a picnic dinner. Enjoyed highlights of the area-saw dolphins and an eagle. We plan to do this again! It was magical

Review collected in partnership with this attraction

Helpful?
Thank rawskya
IslandSailingNaples, Owner at Island Sailing, responded to this review

Love that you brought a picnic dinner for your sunset sail and that everyone had a wonderful evening! Thanks for sailing with us! -Rachel and Robert Dawes More 

Burlington, Ontario
1 review
5 of 5 bubbles Reviewed 29 May 2016

Well presented from the beginning. Excellent contact with description of the sail and expectations. Information left us well prepared and able to enjoy a wonderful experience. Captain was super!, knowledgable and friendly.

Review collected in partnership with this attraction

Helpful?
Thank krbbrk
IslandSailingNaples, Owner at Island Sailing, responded to this review

So happy to hear that you had a wonderful experience. We feel our captains are the best in the business! Thanks for your patronage. More 

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Questions & Answers

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?