The Itinerary
of Regret
We do not arrange vacations. We arrange reckonings.
Since 2031, The Itinerary of Regret has provided full-service travel planning for journeys that should have been taken years ago. We handle the flights, the hotels, the ground transportation, and the suggested timing for the conversation you have been rehearsing in the shower since 2014.
We do not provide the words. We provide the plane ticket. The words have always been yours. You have been carrying them long enough to know what they are.
What We Do
Every itinerary we plan begins with a destination you already know. You know the city. You know the address. You may know the apartment number, or the name of the restaurant, or the bench in the park where it happened. You have thought about going back. You have not gone.
We make the going possible. We book the flight. We reserve a hotel close enough to walk but far enough to collect yourself. We build a schedule that includes time for arrival, time for the conversation, and time afterward for whatever you need; a long walk, a drink at a quiet bar, a bench in a park that is not the same park but serves a similar purpose.
We do not guarantee outcomes. We guarantee logistics.
Featured Packages
Two nights. One conversation. Airport transfers included.
Our most requested package. Designed for the apology that is overdue by years but could be delivered in an afternoon if you could just get yourself there. We get you there. Suggested itinerary includes arrival Friday evening, the conversation Saturday, and departure Sunday after checkout with an optional detour to a place that used to matter.
Three nights in the town you left.
For the person who moved away and never looked back, or looked back constantly but never returned. We book accommodation in the part of town you remember, not the part that has been redeveloped. Itinerary includes time for driving past the house, time for the diner that may or may not still be there, and time for the cemetery if applicable.
Five nights. Multiple stops. For the person who owes more than one conversation in more than one city.
We plan multi-destination itineraries with appropriate spacing between reckonings. We recommend a minimum of 36 hours between difficult conversations. You will need the time. We have learned this from experience; not ours, but the experience of clients who did not take our advice on spacing.
The destination has always been known. The departure date is the variable. Begin planning your return.