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Address: 880 12th Ave S, Naples, FL 34102-7324
Phone Number:
+1 239-398-1483
Today
09:00 - 21:00
Open now
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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

Read all 68 reviews
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  • 66
    Excellent
  • 2
    Very good
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Great Sailing Experience

We thoroughly enjoyed our sailing adventure with Captain Vinny on Island Dreams. There were five of us and it was a beautiful day although not much wind - nonetheless, everyone... read more

Review collected in partnership with this attraction

5 of 5 bubblesReviewed 6 days ago
Mike S
,
Columbus, Ohio
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68 Reviews from our TripAdvisor Community

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Showing 68: English reviews
Columbus, Ohio
Level Contributor
3 reviews
5 of 5 bubbles Reviewed 6 days ago NEW

We thoroughly enjoyed our sailing adventure with Captain Vinny on Island Dreams. There were five of us and it was a beautiful day although not much wind - nonetheless, everyone enjoyed the sail and the time with Vinny. He's knowledgeable, engaging, and just a great person to spend your day with. We would do it again for sure.

Review collected in partnership with this attraction

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

Yes, Captain Vinny is certainly a favorite amongst our guests and we're so happy that you enjoyed your trip. Thank you for choosing Island Sailing. Best wishes, Rachel and Rob Dawes More 

Naperville, Illinois
2 reviews
5 of 5 bubbles Reviewed 1 week ago

We very much enjoyed our day on the Island Sailing boat. The boar was very clean and Capitan Vinny made it a very fun day. My kids (13 and 10) both enjoyed sailing and did some crewing on the boat. I also enjoyed talking to the owner Rob and it was very easy to set up. I would recommend Island... More 

Review collected in partnership with this attraction

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

We always love to hear from our guests and are especially pleased that the kiddos enjoyed the sailing trip! We appreciate your business and thank you for choosing Island Sailing! Best wishes, Rachel and Rob Dawes More 

Level Contributor
16 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
4 of 5 bubbles Reviewed 1 week ago

We had fun sailing with Captain Mark. We asked him if our three teenage kids could take part in helping him sail and he was very accommodating. I think our kids, once we were out to sea, got to steer the boat 90% of the time. Captain Mark was very fun for our kid's sailing experience. The boat was clean,... More 

Review collected in partnership with this attraction

Helpful?
Thank W2495TNmikew
IslandSailingNaples, Owner at Island Sailing, responded to this review

We're so pleased that the teenagers enjoyed their experience behind the helm and that Captain Mark was so accommodating. Thank you for the positive feedback on our customer service as we strive for the best, particularly with our customers. Unfortunately, we cannot shorten the time it takes to reach the gulf, so we attempt to make the best of that... More 

Birmingham, Michigan
2 reviews
5 of 5 bubbles Reviewed 1 week ago

We had a fantastic trip cruising from Naples, FL to Key West, FL over 4 days with Captain Marlena. Rob Dawes went out of his way to ensure that we had a great experience. Thank you all again!!!

Review collected in partnership with this attraction

Helpful?
Thank karyng2016
IslandSailingNaples, Owner at Island Sailing, responded to this review

Karyn, Sounds like the extended trip to the Keys was amazing, and we're so happy that you enjoyed your experience. Thank you again for sailing with Island Sailing. Now how about that trip to the Bahamas? :) Best wishes, Rob and Rachel Dawes More 

Warwick, Rhode Island
1 review
5 of 5 bubbles Reviewed 1 week ago

Rob was there waiting to greet me on Island Dreams. He ensured the boat was ready to go and he made sure I had the info to enjoy the sail. He also was there when I returned the boat and he was very helpful. I would highly recommend.

Review collected in partnership with this attraction

Helpful?
Thank wilsonmath101
IslandSailingNaples, Owner at Island Sailing, responded to this review

Thanks for the recommendation! We hope you enjoyed your bareboat experience and thank you for sailing with Island Sailing. Best wishes, Rachel and Rob Dawes More 

Naples, Florida
2 reviews
5 of 5 bubbles Reviewed 3 weeks ago

We found Rob from Island Sailing to be very nice and highly professional. We had a group of 6, with 5 sailors and while we had more wind than expected, we learned the boat fairly quickly and had a great sail. The boat itself had everything we needed and Rob was an excellent person to deal with from the time... More 

Review collected in partnership with this attraction

Helpful?
Thank 708lorie
IslandSailingNaples, Owner at Island Sailing, responded to this review

Lori and Jim, It was great having you aboard and we're pleased to hear that you enjoyed your day. Best wishes, Rob and Rachel Dawes More 

West Palm Beach, Florida
1 review
5 of 5 bubbles Reviewed 4 weeks ago

I chose Island Sailing to help me pull off one of the most important events in my life: proposing to my now fiancé. I'm happy to say that the entire experience was nothing short of perfect, all thanks to their help! The owner, Rob Dawes, personally helped me plan and prepare for the big event via many emails. Rob even... More 

Review collected in partnership with this attraction

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

Wow, bring us to tears! Thank you kindly for your incredible feedback. Congratulations again Jim and Kristi. We are so very happy for you and are excited for what the future holds. You rocked the proposal and can't wait to see the rest of the pictures. Best wishes always, Rob and Rachel More 

Denver, Colorado
Level Contributor
18 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 9 helpful votes
5 of 5 bubbles Reviewed 21 November 2016

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 16 November 2016

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 12 November 2016

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 

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  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
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