Did a Cyclades trip in mid-August and must say it was awesome. I came in with 0 sailing experience and wanted to learn the basics in a social setting, which also has enough relaxing bits. Our skipper Adam got me exactly this experience!3-6 hour sailing bits sometimes with swimming/paddle board surfing pauses in between and the rest of the day secluded bays, relaxing, small hikes to sunset points, Greek towns and ancient ruins for ourselves. Be prepared to really experience sailing which means likely things will break. In our example: Plumbing broke and our skipper Adam had to fix it - literally, a very shitty situation but this is what sailing can be like and it was "perfect" since it taught me all the things that can happen and how a good skipper reacts to this: Calm, collected, problem-solving. It's definitely not a cheap holiday, but it is worth the price. One tip: the itinerary on the website is a suggestion, so don't expect to see exactly those spots. So manage your expectations or communicate them early.
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