Upsail is a maritime charter booking platform connecting customers with charter companies worldwide. Our challenge was to transform the booking experience from a fragmented, email-heavy manual process into a real-time conversational experience powered by AI - one where customers can discover and book a boat simply by describing their ideal trip.
The boat charter industry runs on fragmented systems and manual coordination. Charter companies manage availability across multiple platforms, while customer inquiries arrive by email, requiring staff to interpret requests, check availability, calculate pricing, and respond entirely by hand. Junior staff spent hours triaging emails, and traditional booking platforms had no integration with the conversational AI interfaces where customers increasingly wanted to search and book.
Upsail needed an end-to-end platform that could handle the full charter lifecycle automatically, from natural language search through to payment confirmation, while keeping charter companies informed at every step.
We built a fully automated, serverless booking platform on AWS. We focused on:
Native ChatGPT integration: Customers can describe their ideal trip directly in ChatGPT - “a sailboat for 6 people in Croatia next July” - and get real-time availability, pricing, and a booking confirmation, all without leaving the conversation. Authentication is handled seamlessly via OAuth 2.1.
AI email triage: An Amazon Bedrock AI agent reads and classifies every inbound email automatically — answering routine customer questions instantly and routing anything complex to the right person, with no manual review needed.
AI-powered knowledge base: Amazon OpenSearch keeps the AI assistant up to date with current company policies, procedures, and boat rental information — new documents are uploaded once and indexed automatically, no maintenance required.
End-to-end email automation: Every customer enquiry, charter company notification, and admin alert is handled automatically via AWS SES — the AI reads, interprets, and responds without anyone touching a mailbox.
Secure, observable infrastructure: The entire platform is deployed as infrastructure-as-code via Terraform, with enterprise-grade security and real-time dashboards giving full visibility into bookings, email volumes, and system health.
We delivered a production-ready marketplace serving 100+ verified charter companies with 1,000+ boats across 50+ destinations. Customers can now describe their ideal trip to ChatGPT and receive instant availability and pricing, reducing average booking time from hours to minutes.
The majority of customer support inquiries are now handled automatically, without any manual intervention. Charter companies receive booking notifications immediately, reducing response delays and enabling them to scale globally while significantly cutting operational overhead.
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