Island Sailing
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Island Sailing
The original name for a new generation of yachting. Outstanding yacht charters, the best sailing destinations in the Mediterranean and the Caribbean and the widest choice of thoughtfully selected modern yachts. Whether you're planning a sailing getaway with friends or family, or looking to discover the most stunning yacht charter destinations with a professional skipper or crew, we can design a yacht charter that's perfect for you.

Discover stunning destinations with a professional & friendly skipper. Ideal if you are new to sailing, having a special celebration or just want more time to relax with family or friends. Larger, more luxurious yachts and catamarans with a skipper/captain plus 1-2 extra crew including a cook or host.
Services
The Island Sailing team combines unrivalled experience with specialist expertise in every area of yachting to provide a first-class, personalised service. When it comes to our approach we're proud to say we're different to your average yacht charter company. We offer something a little more special.
A yacht charter is the perfect way to experience ultimate freedom to explore some of the most beautiful parts of the world, that are often only accessible by yacht. Discover the sun-kissed Mediterranean or visit a Caribbean tropical paradise. Choose your great escape; sail yourself bareboat, take a skippered charter or have a crewed yacht.
We have the widest choice of thoughtfully selected modern yachts to charter in the Mediterranean and the Caribbean, built by Beneteau, Bavaria, Jeanneau, Dufour, Hanse and catamarans from Lagoon, Fountaine Pajot, Bali, Nautitech and Sunreef. We're defined by the quality of the yachts.

We know from experience what makes a great charter experience and that's why we carefully choose only the best yachts available to charter, in the best sailing destinations around the world.We only offer the latest yachts from the world leading yacht builders, all renowned for excellent quality, safety, performance and specifications.
A yacht charter is the perfect way to explore some of the most beautiful parts of the world. Encompassing some of the world's most iconic yachting destinations, the east and west Mediterranean offers a diverse mix of culture, fantastic cuisine and beautiful coastlines. With so many sun-kissed destinations perfect for sailing the possibilities to explore them are endless.
The Island Sailing team has unrivalled experience organising corporate and group yacht charters and special celebration and multi-generational yacht charters. We bring together an enviable mix of talent from the corporate and sailing world to organise successful events in the best sailing destinations worldwide.
Reviews (13)
Susan Junge
Susan Junge
Nov 06, 2021
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Rob, took out a crew of Veterans from Woodsmoke Camping Resort, Saturday. They had a great time.. Everything was Excellent!! Would highly recommend this company & crew!!
Thank you Captain Rob⛵️⛵️ Thank you from the Woodsmoke Sailors..⛵️⛵️
Carl Santos-Ocampo
Carl Santos-Ocampo
Sep 28, 2021
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My parents did a 3 hour sunset cruise with their friends and Captain Paul and they loved the whole experience. Budget friendly for a private charter. The meeting point at the Naples dock was convenient. Boat was large, clean. For their friends from out of town, a trip out of Gordon Pass to see Naples from the water and the Port Royal houses is a treat. Then when they got out to the Gulf, he turned off the engine and let the sails out. A way more peaceful experience, if you're into that, compared to the louder boats with engines. They will definitely be returning to do another sunset sail in the
Kaley Nemeth
Kaley Nemeth
Jun 26, 2021
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Had such an amazing time! Will definitely be coming back for another sail with them! Loved captain Paul, views were amazing, great sailboat!
Alan Epstein
Alan Epstein
Apr 11, 2021
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This whole operation is tremendous. We had Captain Mark and when we come back we'll ask for him again. Mark was engaging, fun, accommodating, and an incredible host and guide. He knows the area and tells great and funny stories. Our whole family had a special and great time.
Julie Payne
Julie Payne
Feb 25, 2021
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We chartered their Catalina for a few days (Naples to Marco Island and back). The boat was clean, sails were in good shape, easy to handle. We got some great local info about where to go. The owners were easy to work with and do right by their customers. Thank you from Julie & Andy.
Simon De Labilliere
Simon De Labilliere
Aug 14, 2019
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Excellent support from Isaac, Cameron and Tristan on the lead boat and the Ionian is a beautiful place to sail. Thank you!
Alexander Devey
Alexander Devey
Jul 15, 2019
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Just finished a week long flotilla in the Ionian. What an amazing experience with amazing people. It was our first time and they all made us feel so welcome and comfortable. I would highly recommended Island sailing! Thanks Cameron,Tristan and Isaac!! ☺️☺️☺️
Margaret Eldridge
Margaret Eldridge
Oct 19, 2018
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Nice folks. We stopped by to inquire about bareboat charter of their Catalina 31. They showed us around the sailboat, which is roomy and nicely outfitted, including a mast furling mainsail. Looks like an easy, comfortable boat to sail.
Chris Basten
Chris Basten
Jun 27, 2018
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One of , if not the best bare boat charter companies. Will we go with Island again? Most definitely.
Donovan Hervig
Donovan Hervig
Sep 08, 2017
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Our half-day yacht cruising experience with Island Sailing on New Year's Eve day 2017 was fabulous. Thanks to Rob for being responsive and assisting with the last-minute booking, even though he was traveling. And a special thanks to Captain Marty. With a friendly and helpful demeanor, excellent sailing skills (which made you feel safe) and a wealth of local knowledge, he helped make the experience some something special to remember. Next time the family is in Naples, let's do it again!
Rob Giles
Rob Giles
Aug 04, 2017
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Highly recommend! Thanks to Ruth who helped us select (and answer my contstant emails very quickly), book and make all the arrangements for an amazing week on a chartered Lagoon 39 Catamaran with a superb skipper - Mikey! Only 2 nights left but our family holiday with Island Sailing has been fantastic! Thank you Mikey, Ruth and Johnny.
Nickola Clarke
Nickola Clarke
Sep 01, 2014
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Thanx to Ruth and Johnny for an amazing holiday , it was our first sailing holiday but sure it won't be our last. Thanx also to Sam , billy and Becky for all their help xx
Cameron Block
Cameron Block
Feb 20, 2014
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Had a brilliant season with these all last year! Hope this year is as busy as last year for you!