Who we are

The journey started way back in 2017, when Richard, Kiran and some friends went on their first sailing holiday to Croatia. They soon caught the bug, delighting in the unrivalled variety afforded by a holiday on the water. Waking up each day to a fresh sea breeze, deciding on the day’s itinerary over breakfast on deck and anchoring at night at whichever secluded bay looked most appealing, they soon realised that more of their friends needed to know about sailing holidays. Share the love! And so, the following year, they returned to sample more of the Mediterranean, this time with three sailing yachts full of feverish friends. Thus SailSterling was born and the vision was simple: to deliver memorable holidays at sea. We know what makes a great holiday and we certainly know how to have a good time! Join us on board so that we can show you just how fantastic a SailSterling holiday really is.

Boats Available
Nautical Miles Covered
“It is not that life ashore is distasteful to me. But life at sea is better.”

- Sir Francis Drake

Meet the Founders