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# Plan a multi-week family road trip with a private itinerary site

A father used an always on Hermes Agent to plan a multi-week family road trip to Florida around his daughter's dance competition, including a private itinerary website and a calendar of bookings.

[Hermes Agent](https://www.automaticcompany.co/use-cases/agent/hermes-agent/) Added Oct 13, 2026

## What they did

Hermes runs on a Mac mini at home with cloud models, and the family reaches it over Tailscale. It recalled an existing hotel booking, mapped the route, reworked the plan after feedback for shorter drive days, checked email for a hotel check in window, researched veteran discounts and ticket rules, and built a private trip site. He pasted booking confirmation screenshots and it added them to a shared iCloud road trip calendar, and it found a new slot for an activity after the first day sold out.

## How it went

The poster says The family ended up with a usable itinerary site, a discounts page and a calendar holding every confirmation code, with drive days kept reasonable.

## Good to know

The first plan had too many stops and long drives, the first site was sparse, and he notes agents tend to please rather than push back. He made every booking himself and checked links after each change.

## A prompt to try

Help me plan a <number> day road trip from <home city> to <destination> for <who is travelling>, with no more than <hours> of driving per day and <fixed events> as fixed dates. Draft the route and overnight stops, then build a simple private itinerary page with addresses, drive times and links. When I send booking confirmations, add them to <your shared calendar> with the confirmation codes. Push back if the plan looks too packed.

## Source

[daveswift.com](https://www.daveswift.com/hermes-road-trip/) · published Jul 20, 2026 · checked Oct 13, 2026

Runs on [Hermes Agent](https://www.automaticcompany.co/platforms/hermes-agent/).

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