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About

About The Itinerary of Regret


The Itinerary of Regret was founded in 2031 by a travel agent who noticed that a meaningful percentage of solo bookings shared a common characteristic: the traveler was not going somewhere new. They were going back.

Back to the city where they grew up. Back to the town where someone they loved is buried. Back to the street where a conversation ended badly, or never happened at all. They were booking flights to their own history, and they were doing it without support, without structure, and without anyone acknowledging that the trip they were planning was not a vacation.

We began offering planning services specifically for these journeys. The demand was immediate and has not slowed.


Our Staff

Our staff consists of four travel planners, a logistics coordinator, and a consultant with a background in conflict mediation who advises on conversation timing and structure. We do not employ therapists. We are not qualified to process your emotions. We are qualified to book your flight, reserve your hotel, and provide a suggested itinerary that gives you enough time for the conversation and enough time afterward to feel whatever you are going to feel.


Our Record

We have planned itineraries to 43 countries and every state in the United States. The most common destination is within 300 miles of the client's current home. The trip they have been avoiding is usually not far. The distance was never the obstacle.

We have a 94% completion rate. This means 94% of our clients board the plane. We do not track what happens after arrival. That is not our department.

The remaining 6% cancel. Some cancel the day before. Some cancel at the gate. One client sat on the plane, flew to the destination, sat in the rental car in the parking lot for two hours, drove to the airport, and flew home. We did not charge a cancellation fee. The itinerary was completed; the client simply chose not to use it. The choice was theirs. It always is.


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