There's an AI Assistant Behind Your Enquiry
This is Kate Bot: what it does, what a person checks, and what lands in your inbox.
Kate Bot: the AI behind your enquiry
Charter Advice Backed by Experience, Checked by a Person
Dream Maker starts with an AI trained on Kate's real enquiries. It ends with a charter specialist who has been matching people to boats since 2011.
SailChecker has handled charter enquiries across more than 350 destinations for over a decade. Kate Bot puts that experience into a structured process: the AI reads your answers, briefs the team in plain language, and a specialist checks every response before it leaves. You get a direct answer about specific boats, realistic dates, and a straight read on your budget. Not a template. Not a brochure.
What just happened
How Kate Bot Works
When you submit the Dream Maker form, the process is straightforward. No black box. Here is exactly what happens between your submission and our reply.
What the AI Does
Reads your answers, scores the enquiry HOT / WARM / COLD, and drafts a reply in Kate's voice, trained on over 500,000 of her real client emails across fifteen years.
What a Human Does
A team member reads the brief, adjusts the draft where needed, and sends the response. Every enquiry is examined by a person before you hear back. The AI's outputs are also reviewed across enquiries over time to keep the model calibrated to real charter work.
What You Get Back
A specific reply: named boats, realistic dates, a straight read on your budget. Usually within a few hours.
“Kate at SailChecker did a great job preparing us and was quick with her communication. This was easily the best trip any of us have ever taken.”
Madisson Rogers · USA
Who trained the AI
Meet Kate
Kate Bot runs on Kate's professional judgement — not generic sailing content. Understanding Kate is the only way to understand why the AI responds the way it does.
Kate Ioannidou
Charter adviser and co-founder, SailChecker
- 350+ destinations matched
- Founding member, IFYA
- Bareboat, crewed, cabin, flotilla
- Greek and English
What Kate does
Most enquiries arrive with a destination in mind and not much else. Kate's job is to figure out what someone actually needs: the right size of boat, the right level of crew support, the right week, the operator worth trusting. She has been doing that for fifteen years, by email and phone, for clients across Europe, North America, and Australia.
Operators across the Mediterranean invite Kate to preview new fleets before the season opens. Other brokers route enquiries to her when a booking falls outside their expertise. Charter is not a specialism she picked up. It is the only thing she has ever done.
How the AI learns from her
Kate Bot draws on over half a million client emails and notes Kate has written over fifteen years: her shortlisting logic, the questions she asks to surface the right fit, the way she explains a price difference between two similar boats. The model has gone through multiple calibration cycles, each one verified against real enquiry outcomes. It is her professional judgement in structured form, not generic training data.
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Tell Us About Your Dream Charter
Two minutes.
Tailored options.
Kate will come back with shortlisted yachts that match exactly what you are looking for.
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Prefer to write directly? Email enquire@sailchecker.com or call +44 330 190 1260.