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Address: 880 12th Ave South, Naples, FL 34102
Phone Number: +1 239 398 1483
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9:00 am - 9:00 pm
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Hours:
Sun - Sat 9:00 am - 9:00 pm
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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Naples 3 Day Sailing Excursion

The international sailing experience, stories and hospitality of Captain Marlena put a smile on our faces and the left the planning and worrying to her. The timely communication... read more

Review collected in partnership with this attraction

5 of 5 starsReviewed 4 weeks ago
karyng2016
,
Birmingham, Michigan
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43 Reviews from our TripAdvisor Community

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Birmingham, Michigan
1 review
5 of 5 stars Reviewed 4 weeks ago

The international sailing experience, stories and hospitality of Captain Marlena put a smile on our faces and the left the planning and worrying to her. The timely communication with business owner Rob, made for easy chartering and planning. The 47' Beneteau 'Island Time' is spacious, well maintained and comfortable for 6 adults. It was a memorable and thoroughly enjoyable three... More 

Review collected in partnership with this attraction

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

Thank you Karyn and we're so very pleased that your family had a memorable experience. We look forward to seeing you soon! More 

A TripAdvisor Member
5 of 5 stars Reviewed November 26, 2015

Totally enjoyed our sail. Our captain, Vinnie, was very skilled at sailing the boat and was entertaining and informative. We already booked another sail!

Review collected in partnership with this attraction

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

We certainly appreciate your patronage and look forward to sailing with you again soon! More 

Marlton, New Jersey
Level Contributor
16 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed May 12, 2015

My wife and I recently took 2 friends for a sunset cruise with Captain's Vinny and Jimmy. While the service is under new ownership . . . the service and hospitality still remains fantastic. New owner Rob Dawes has kept old customers happy with the same attention to detail that Captain Marlena insisted on. I will be calling on them... More 

Helpful?
2 Thank Michael P
IslandSailingNaples, Owner at Island Sailing, responded to this review

Thank you Michael for the kind words as we certainly strive for customer service. We look forward to sailing with you again. More 

1 review
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed April 8, 2015

Great sail and Captain Eric made the sail even more special. Kids really loved it. We planned for a 2 hour sail and had so much fun we extended it to a 3 hour sail.

Helpful?
2 Thank Rosemarie I
Rob D, Owner at Island Sailing, responded to this review

Thank you for the review and glad that Captain Eric made your day enjoyable. We hope to see you back again! More 

Arlington, Virginia, United States
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed April 2, 2015 via mobile

Perfect ending to a wonderful vacation on a 47 ft sail boat in mint condition. Pure luxury. Highly recommend the private, chartered sail with Rob and Marlena.

Helpful?
1 Thank Kitty N
Rob D, Owner at Island Sailing, responded to this review

Thank you for the wonderful review and being the first guests out on Island Time. Marlena and I both enjoyed having you out with us. Enjoy your future sails! More 

Bonita Springs, Florida
Level Contributor
29 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
5 of 5 stars Reviewed March 29, 2015

My family and I enjoyed a beautiful sail for 3 days, starting off at Naples stopping at Sanabel, then Fort Myers before returning to Naples. My whole family had lots of chances to take the helm, and we all loved it! Marlena was the perfect host, and made us all feel very at home on the beautiful boat (Island Dreams.)... More 

Helpful?
Thank Y W
toronto
Level Contributor
701 reviews
148 attraction reviews
common_n_attraction_reviews_1bd8 293 helpful votes
5 of 5 stars Reviewed March 23, 2015

Six of us took a three hour sail with Marlena. She was so much fun . The sail was delightful and will provide us with warm memories for years to come. Malena has just sold the business but she assured us that the new owners will also be providing memorable cruises. Next time we are with friends looking for a... More 

Helpful?
Thank worldwatcher
New York City, New York
1 review
5 of 5 stars Reviewed March 11, 2015

I booked a 3 hour cruise with Marlena with the intention of proposing to my then girlfriend. Marlena was awesome. She took us out and gave us some information about the surrounding area as we headed to the Gulf. We were able to bring some wine with us (fridge and bathroom on board big plus!). Ahead of time I asked... More 

Helpful?
Thank Michael R
Arlington, Massachusetts
1 review
5 of 5 stars Reviewed March 2, 2015

On a recent trip to Naples, my husband and I went on a two hour sail with Marlena. We chose to go during the morning with the hopes of seeing some dolphins and other wild life. Marlena was the perfect captain and tour guide. She knows the waters and surrounding area exceptionally well, and gave us a lot of interesting... More 

Helpful?
Thank Tyhler R
1 review
5 of 5 stars Reviewed December 12, 2014

If you're looking for a first-rate sailing experience in the Naples, FL area, "Island Sailing" is just the ticket. Without being over the top, every detail and customer need is taken care of by the Captain. The tone of the cruise is up the the customer - everything from a leisurely cruise to a sailing lesson and everything in between.... More 

Helpful?
Thank Alan M

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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?