A sailing holiday that fits you.
We help families, friends, and first-time sailors find the right boat, the right region, and the right week.
Always with a skipper.
You tell us about your group, your dates, and what you're hoping for.
We reply within a day, by email or WhatsApp, with a real recommendation — region, boat type, timing, and honest tradeoffs.
You decide whether to take it further. No pressure, no follow-up sales.
We won't quote a price we can't stand behind. We won't promise weather. We won't recommend August in the Cyclades to a family with small children. We'd rather lose your booking than put you on the wrong week.
What does a sailing trip actually cost?
Short answer: it depends. But we can give you a realistic range in under 30 seconds.
The people behind SimpleSail
We're Sofia and Mikael. We sail in Greece with our own kids, and we've helped other families and first-time sailors get on the water for years.