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I started sailing as a kid turned it into a career when I started working for an international sailing company. They have people set up all over the world, offering sailing services to travellers. Just the other month I took a tour group from the w hotel in Bali out on a boat for the day, island hopping to some beautiful beaches along the way.
I hate staying put, so the company I work for - Sail Abroad - is happy from me to jump between locations when I feel like it (with a little warning, of course). I spent the summer at club med Phuket, before travelling over to club med Bintan Island to sunbake my days away in between tour groups. It's a fantastic life and I love it.
I took a tour group out yesterday for a sail along the water. I let each of them take turns steering and showed them how to work the boat. We stopped off at a few islands so they could have a dip and cool off, when one of the guys on tour approached me and asked for my picture. I was quite taken aback.