guest reviews
for Island Sailing
Reviewed Jan. 2017
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 they definitely delivered. Captain Mark clearly is an expert and his interactions and sailing skills were perfect for our needs. I'd highly recommend this outfit if you're wanting the real deal at a fair price and with competent staff. Hope to use them again on our next visit to Naples.
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Sunset Sail in Paradise"
Reviewed Nov. 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.
Reviewed Nov. 2017
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 again. Rob was professional, knowledgable, chill & likable.
Reviewed 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 never knew. A delightful sunset experience! We look forward to sailing on Island Time again next season.
"A perfect day in every way"
Reviewed April 2017
A perfect day in every way. how could you not have a great time on a beautiful day in the Gulf of Mexico Sailing along with no worries! It is a must do on a visit to beautiful Naples.
Reviewed April 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 knowledgeable. The experience of sailing out of Naples into the Gulf of Mexico was memorable...and our afternoon adventure with our great friends was unforgettable. Many thanks to Captain Gerard and Island Time!
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"Sailing to Cuba"
Reviewed April 2017
Awesome! Amazing! An experience of a lifetime!
Captain Rob Dawes and his wife Rachel provided me a "once in a life time" experience planning a sailing trip from Naples Florida to Havana, Cuba. I spent 14 days and nights aboard their sailing vessel "Island Time" a 47 foot Beneteau. From my initial call, Rob planned and created a detailed itinerary that met my needs perfectly, and more importantly, executed the trip to perfection. And the "icing on the cake" was Captain Vinny Checa, who took this landlocked Texan for 2 weeks under his wing and sailed over 400 miles roundtrip to Cuba and back. Vinny, who is fluent in Spanish, made the journey extremely pleasant, comfortable and most essential, "FUN". After such an adventure, it is an honor to me to consider Vinny as a close friend. Vinny and Rob were extremely responsive, conscientious and went "over the top" to ensure my sail was everything I expected. Finally, without being redundant, I would like to thank Rob, Rachel and Vinny in providing me an adventure that I will cherish and never forget. Also, one last note, besides exceeding every expectation, Island Sailing delivered real value.
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Reviewed March 2017
Outstanding sail. Perfect wind and water. 4 hours went by in a flash. We all got helm time and line time. Tacked, jibed and even raced another boat part way to Marco. Captain was great to sail with, be with. Next time, the Bahamas!!!
Reviewed March 2017
Beautiful boat, professional crew and over all great time. Captain was well informed and very knowledgeable.
"Serenity on the water!"
Reviewed March 2017
Rob Dawes (owner) was a pleasure to work with. He was very accommodating and answered all my questions on a timely basis. Captain Jerry was very friendly, with a good sense of humor. He made our sail relaxing and enjoyable. This was the second time we have used Island Sailing and will continue to do so in the future.
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Reviewed March 2017
Both the captain and first mate were Fantastic! The captain explained everything and involved us as we wanted. I would highly recommend them. We had a great time.
Reviewed March 2017
This is the third time I have sailed on Island Time and each time the captain was friendly, the boat was clean, the weather was great, and the overall experience was fantastic. What a wonderful way to spend a day on the water. I would highly recommend this charter service.
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"Sailing is fun!"
Reviewed March 2017
Great sailing adventure on Island Sailing! The boat the captain, and of course the beautiful waters of Naples and Marco Island made this a wonderful trip for everyone! Highly recommended!
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"Canadians enjoy fabulous sunset cruise & green flash!"
Reviewed March 2017
Beautiful sloop Island Dreams with Capt. Gerry at the helm provides outstanding sailing experience for party of six Canadian snowbirds. Clean, comfortable vessel offers perfect views of harbour and gulf shores. Our third time chartering this beautiful sailboat and we will be back again.
"Great experience"
Reviewed February 2017
Easy to make a reservation. Responsive office. Boat was clean and very well-maintained. The chart briefing was thorough and meaningful without being overly long. We had a great day at sail. Will charter with this company again!
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"Valentines Day Sail"
Reviewed February 2017
We had a great time sailing on the gulf with Captain Mark. 2 of us were experienced sailors and one was thinking about going on a sailboat with friends for 2 weeks but she has never sailed. Captain Mark was patient and an excellent teacher when Barbara took the helm. I would recommend this company to both the sailor and the adventurer who wants to be on the water. WInd and water are good for the soul
"Great Time with Captain Vinny"
Reviewed January 2017
We very much enjoyed our day on the Island Sailing boat. The boar was very clean and Captain 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 Sailing.
"Key West Adventure"
Reviewed January 2017
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!!!
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Island Sailing is Excellent
Reviewed Dec. 2016
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 we booked to the end of our sail. We wouldn't hesitate to book through Island Sailing again ourselves and highly recommend them. Thanks for everything!
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"Incredible Experience"
Reviewed Dec. 2016
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 broke out his acting skills to help trick my fiancé into believing that our ride took place by chance--instead of being an obvious proposal opportunity. She had no idea it was coming! He also gave us a wonderful bottle of champagne on the house to enjoy. I could go on, but suffice it to say that the group at Island Sailing are true professionals and will bend over backwards to accommodate their clients!
Captain Vinny and Captain Jim also helped to make the whole experience very enjoyable and did an excellent job. We hope to come back to Naples and sail with you all again soon!
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Sailing getaway!"
Reviewed Nov. 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 pre-planned to have groceries delivered to boat for us. Next trip we would plan to get out further out, more adventurous trip. Overall, an excellent time!
"The perfect way to enjoy a sail in Naples."
Reviewed Nov. 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.
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Island Sailing - Naples"
Reviewed Nov. 2016
A great time and an outstanding value! Beautiful boat and Captain Mark was outstanding. Very knowledgeable, competent, and entertaining. Highly recommended.
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Reviewed Nov. 2016
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.
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Reviewed October 2016
Island Dreams was great. Clean top to bottom. Very user friendly even single handed. Staff was informative and extremely through. "I'll be back"
Reviewed 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.
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Reviewed 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 name key- swam with and fed the pigs!! and last stop Abaco Mariana where I exited the beauty and went to the airport 10 min. away to return home in West Palm Beach. Each Island had its own beauty, for Capt Rob was able to give us the history and tour that is not known by many travelers. AS we would take the dinghy from the beauty (island Time) to shore of theses magnificent Islands, to look back at this beautiful ship in clear blue water, with just the sound of silence, that alone is memorable! AS we sailed, with a glass of wine in hand, and delightful bites, at sunset, it made the day complete. From the steak and lobster dinners on board, and french toast, with bacon and eggs in the am with the smell of salt water in the air and the gentle movement of sailing, was ever so peaceful. My six day trip with the beauty and the staff was a definite choice I would recommend. Each day was a memorable one!! I am sure I will be Sailing with the BEAUTY again! Thank You Capt Rob!!
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Reviewed 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, knowledgeable and friendly captain, beautiful sunset out in the gulf of Mexico. I highly recommend Island Sailing and will definitely be booking another trip.
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LADIES DAY PER PERSON SAIL
Join Captain Marlena for a Ladies Day Sail on Saturday, January 27th, from 12-3 p.m., for a *per person* ladies day sail. This 3-hour sail is a *per person* sail, meaning the price is per person, rather than securing the entire vessel. Ladies only :)
When: Saturday, January 27
Time: 12-3 p.m.
Cost: $75/person
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PER PERSON SUNSET SAIL
Join us on Saturday, January 27th, from 4-7 p.m., for a *per person* sunset sail. This 3-hour sail is a *per person* sail, meaning the price is per person, rather than securing the entire vessel. Join us as we watch another amazing SWFL sunset.
When: Saturday, January 27
Time: 4-7 p.m.
Cost: $75/person
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PER PERSON FULL MOON SAIL
Join us on Wednesday, January 31st, from 5-8 p.m., for a *per person* full moon sail. This 3-hour sail is a *per person* sail, meaning the price is per person, rather than securing the entire vessel. A full moon sail is an amazing experience as we sail out watching the sun set in the west while the full moon rises in the east.
When: Wednesday, January 31
Time: 5-8 p.m.
Cost: $75/person
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Summer trip to the Exumas, Bahamas!
This summer,
Island Time
is going on a journey to the Bahamas, The Exuma Cays to be exact! The Exumas are a tract of islands and cays that stretch for over 150 miles south of Nassau to Great Exuma Island. This could be you relaxing on the bow of Island Time as we slide past crystal clear waters and white, sandy beaches on the way to places like the waterslide at Shroud Cay (pictured above). Visit (and feed!) wild hogs on sandy beaches, visit the Thunderball Grotto of James Bond fame, snorkel with colorful fish, submerged planes and coral, and then spend a lot of time doing....nothing at all...but enjoying water, beaches, and the pace of island life.
Fly in to Nassau, Bahamas to meet the captain and vessel. We will have guests board on Saturday, June 2nd at noon and will stay in Nassau through the rest of the day for sightseeing. We will set sail the next morning for Nornan's Cay, Staniel's Cay, Great Guana Cay, Shroud Cay and then return to Nassau Friday evening for the last night in the Bahamas. Guests will disembark on Saturday. All navigation will be over the Exuma bank, not open ocean.
Charter Information:
- Charter Dates: June 2-June 9, 2018 (other dates may be available in July)
- Charter Costs: This charter is on a per cabin basis at $300 per cabin, per night. You may fit up to two guests in each cabin.
- It is customary to give a tip for the captain as well.
- Want the vessel for yourself? All three cabins for $700 per night!
- Other Costs: Food and drink
- We cover all port, marina, and mooring fees, as well as fuel and water. We also provide all linens and beach towels, snorkeling gear, A/C in all cabins, Bluetooth stereo, completely covered cockpit, two heads with showers, a full galley, grill and coffee maker! Come relax with Island Sailing!
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Bareboating and our Boat Club!
Bareboating
Want to go sailing but don't want to pay the costs of owning a sailboat? You can! We can get you on the water for less than you would pay for dockage.
Experienced sailors can bareboat Island Dreams, our 31' Catalina, for a half or full day sail. Enjoy cruising along Naples' sugar white sandy beaches aboard a fun and easy-to-sail yacht. Our bareboat sails cost $400/half day and $600/full day. Or, join our boat club and save thousands!
Boat Club
Through our boat club, we offer two packages:
* 5-day packages: $2,000
* 10-day packages: $3,500
How does the boat club work? To begin with, we evaluate your sailing and local navigational skills to ensure that you can set up the vessel and navigate through the channel and in the local sailing areas (Naples, Marco, Fort Myers, and Sanibel). Next, we show you how to set up Island Dreams and how to stow her away at the end of a sail (docking and putting away the basics).
Now that you are ready to sail, just let us know when you wish to reserve Island Dreams. We only accept ten boat club members at a time to ensure availability. Boat club members have priority over captained charters.
Want to string days together for overnight or extended sails? Trip to the Keys? You can do that with the boat club at no extra cost!
Island Dreams is a 31', 2007 Catalina 309, with roller furling main and jib, two cabins, head, galley, stove, refrigerator, color chart plotter, autopilot, stereo, and inverter.
WARNING: Bareboating can be a dangerous hobby and can lead to boat fever! We should know, we used to belong to the bareboat club with Island Dreams ... and then we bought the business!
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Engagement Photos!
Did you know we provide special events that we customize for our guests, such as engagements and small weddings?
These lucky couples were recently engaged and hired their own photographers to capture their private/special moments.
Congratulations to these couples!
We're proud to announce our 100% success rate!
Photo credit:
Aimee Rossi Photography (local photographer)
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Photo credit:
Anastasiia Photography
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Island Time |
Extended Sailing Excursions!
Looking for an amazing getaway that's unique?
Sail aboard one of our vessels for an extended trip and allow one of our
experienced captains to charter you on a memorable trip along the Florida gulf coast, the Keys, or the Bahamas.
Need a float plan? We're happy to help you design your itinerary.
Island Time
- 47' Beneteau
- 3 cabins, 2 heads
- air conditioning
- comfortably sleeps 6 guests
Island Dreams
- 31' Catalina
- 2 cabins
- comfortably sleeps 4 guests
For overnight trips, our boats come fully stocked. You bring the food and we cover the rest. We have linen, pillows, pots and pans, coffee maker, plates/bowls/utensils, etc. These overnight trips give our customers the feel of live-aboard life without the added expenses of actually owning a boat.
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