Portrait of Catherine de Médicis and her children (c. 1561) by the workshop of François Clouet. Private collection.
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Portrait of Catherine de Médicis and her children (c. 1561) by the workshop of François Clouet. Private collection.

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George Vertue FSA (English, 1684-1756) The royal progress of Queen Elizabeth I, ca.1740
How would a lord decide which of his vassals to visit, and when? During Littlefinger's negotiations with the Lords Declarant, the Declarant tells Littlefinger that Sweetrobin will visit the castles of the other lords eventually. We also hear of Eddard Stark visiting his vassals, and numerous other examples throughout ASOIAF. Would it start with an invitation from a vassal? Or would the Lord write to the vassal that he was visiting? How frequently would these visits occur in European history?
Technically speaking, as a king, a royal progress can go wherever the king wishes, as all land is held by the king. In practice, kings chose vassals either to honor them with the royal presence and strengthen feudal ties or bankrupt them by forcing them to put up the king's party. Usually the king would plot out the course of their progress, although a vassal throwing a tournament or other game might write to invite the king for the event. The progress's frequency would depend on the monarch - the Tudors held a progress annually in the summer, while early Middle Age kings had an itinerant court.
Thanks for the question, Anon.
SomethingLikeALawyer, Hand of the King
Hi I was wondering about the travel time between King’s Lansing and each of the seats of the Great Houses for a full party similar to Robert’s party travelling in AGOT. How much time would be cut without a Wheelhouse?
Good question! I’ve talked about it here, but I’ll show my work.
WARNING: A HISTORIAN IS DOING MATH.
King’s Landing to Casterly Rock:
Wheelhouse: 83 days. (avg speed)
Riding party: 40 days. (avg speed)
King’s Landing to Highgarden:
Wheelhouse: 76 days (avg speed)
Riding party: 36 days (avg speed)
King’s Landing to Riverrun:
Wheelhouse: 74 days (avg speed)
Riding Party: 35 days (avg speed)
King’s Landing to the Eyrie:
…this one is complicated, because it makes way more sense to take ship to Gulltown and then go west to the Eyrie (450 miles by land) than to go from King’s Landing to the crossroads and then ascend the High Road through the Bloody Gate (640 miles by land, and rough miles at that.)
So I’d call it 5 days by ship and then either 45/21 days by land.
King’s Landing to Storm’s End:
Wheelhouse: 38 days (avg speed)
Riding Party: 18 days (avg speed)
King’s Landing to Sunspear:
Wheelhouse: 205 days (avg speed)
Riding Party: 97 days (avg speed)
Ship: 10 days (avg speed)
King’s Landing to Winterfell:
Wheelhouse: 146 days (avg speed)
Riding Party: 69 days (avg speed)
Ship: 16 days (avg speed)
George Vertue FSA (English, 1684-1756) The royal progress of Queen Elizabeth I, detail, ca.1740

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If the king and his entourage came to stay with one of his vassals, would the vassal be expected to foot the bill or would the Crown pay some? What about one lord staying with another?
The king would absolutely not pay the bill. Indeed, half of the point of the king going on royal progress and crashing at his vassals’ houses was to gently bankrupt them so they didn’t have enough cash on hand to rebel against you.
I’m not familiar with sub-infeuded examples of the same process. I’m guessing it depends on the terms of the feudal contract, because some of them could be very specific about the responsibilities of the vassal to provide various services and goods when the liege lord came to visit:
Moreover I acknowledge that, as a recognition of the above fiefs, I and my successors ought to come to the said monastery, at our own expense, as often as a new abbot shall have been made, and there do homage and return to him the power over all the fiefs described above. And when the abbot shall mount his horse I and my heirs, viscounts of Carcassonne, and our successors ought to hold the stirrup for the honor of the dominion of St. Mary of Grasse; and to him and all who come with him, to as many as two hundred beasts, we should make the abbot’s purveyance in the borough of St. Michael of Carcassonne, the first time he enters Carcassonne, with the best fish and meat and with eggs and cheese, honorably according to his will, and pay the expense of shoeing of the horses, and for straw and fodder as the season shall require…
(Feudal Contract of Bernard Atton, Viscount of Carcassonne, 1110 CE)
So if there’s a similar clause as the one bolded above, then the vassal would be obligated to provide those services, but otherwise probably not.Â
Given the "gentle bankruptcy" aspect of a King's visit, were there any particularly . . . unusual ways that they tried to get out of such visits?
Well, A. it wasn’t easy to get out of them, and B. it actually was a social cachet to host the king, and often honors could flow from said visits, so if you could afford it, it wasn’t a bad way to try to win royal favor.Â
However, there are more than few cases of rich people pleading poverty (”my estate without my undoing cannot bear it…my land sold and debts not small; how this will agree with the entertaining of such a Prince your wisdome can best judge.”) and other such excuses, especially towards the end of a monarch’s reign when political incentives start to shift.Â