aiofthe.day
Subscribe

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

Hermes AgentUser story

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.

First reported
daveswift.com · 20 Jul 2026
Added
13 Oct 2026
Source checked
13 Oct 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.

What happened

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.

Keep in mind

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.

Try it with your agent

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.

Replace the <angle brackets> with your own details.

Original source

daveswift.comUser story

Someone who uses the agent described their own setup. Figures are theirs.

More from Hermes Agent →More in Personal errands →Get five like this every day