DirtyBoat.com

The Challenge

DirtyBoat 2.0 needed a website that matched the energy of the charter itself — bold, fast, and impossible to ignore. The old site was a WordPress install that loaded slower than a drift in the doldrums. Worse, every booking had to squeeze through a third-party widget that skimmed fees on each trip, owned the customer relationship, and always looked bolted-on. The captain wanted his bookings, his customer data, and his brand back.

The Build

We rebuilt from scratch on Astro and Tailwind, then cut FareHarbor loose entirely. In its place, a custom booking engine on Supabase and Stripe — real-time availability, deposits, and every trip type (half day, 3/4 day, full day) handled in-house with zero per-booking fees. Behind it runs a full CRM: every inquiry, booking, and repeat angler tracked in one place, with automated SMS and email confirmations (Twilio + SendGrid) firing the second a trip is locked.

The headline piece is an Anthropic-powered AI agent living in the chat. It answers the questions that actually close a booking — what’s biting, what to bring, whether the weather’s holding — then checks live availability against the calendar and books the trip right there in the conversation. Claude does the talking; the booking engine does the work. The whole site still loads in under 1.5 seconds on mobile.

The Result

No booking fees, no leaked customer data, no clunky third-party widget. DirtyBoat owns the entire funnel now — from the first chat message to the deposit to the follow-up. The site ranks first page for “Islamorada fishing charter,” looks like nothing else in the sportfishing space, and the AI agent fields questions and takes bookings 24/7 while the captain’s offshore. Bleeding edge, still.