Your trip, already planned
Text Caddy the idea. It builds the itinerary.
Booked. It’s on your calendar now
An illustrative conversation with Caddy in iMessage
From a rough idea to a trip you can take
Chicago, three easy days
Good food · One museum · No early starts
A plan that fits your kind of trip
Share your dates, budget, and must-dos. Caddy researches places that fit and groups the days around where you’ll actually be.
Dinner booked for 7
Plus two hotel picks near River North
The useful options, pulled together
Ask Caddy to compare flights, look into places to stay, or find dinner near your hotel. Get a shortlist for the next decision.
Museum booked
Saturday at 1 · On your calendar with the tickets
Booked and on the calendar
Ask Caddy to book the museum, the table, or the tour. It checks with you before paying and adds it to your calendar with the confirmation.
Give Caddy the trip you have in mind
Tell Caddy the dates, who’s coming, and the few things that matter. It researches the options and builds the days around them.
Your questions, answered
Where do you want to go?
Tell Caddy the dates and a rough idea. It takes it from there.