Headcanon that as soon as Caleb buys a house to settle down with in Rexxentrum, he begins working on creating a brand new teleportation circle that connects to nowhere else in the world, and painstakingly carves it into the floor of his living room.
Once that's finished, he starts every day for an entire year by picking up pastries from a nearby bakery and then casting the same three spells: scry, teleport, teleportation circle. The first two bring him safely to Fjord's boat, The Nein Heroez. He stays for an hour, enjoying the company of Jester, Fjord and Kingsley, then casts teleportation circle to return to his home and continues his day teaching at the Soltryce Academy.
When you cast teleportation circle in the same place every day for a year, it becomes permanent. After 365 days of pastries and friendship, there is a teleportation circle that connects Fjord and Jester (and Kingsley, for as long as he stays) directly to Caleb's home.
After that first year, he repeats the process with The Blooming Grove, with the strangest plants and seasonings he can find in the market instead of pastries. Caduceus is delighted to have company, and Caleb finds that tea at the temple is a wonderfully relaxing way to begin the day.
Both of those first two years, he has weekly dinners with either Beauregard and Yasha or the Brenatto family. The third year, he dedicates to connecting his home with Veth and Yeza's new seaside house in Nicodranas.
Beau and Yasha are tricky for a while, because Beau has a tendency to be constantly moving around. But eventually they settle down in Zadash, and Caleb happily christens their home with a circle as well.
By the fifth year after Caleb buys his home, it takes him only one 3rd level and three 5th level spells to assemble all his friends in one place. One 3rd level Sending to Jester reaches everyone else, as she is more than happy to expend almost all of her spell slots spreading the word. She and Fjord usually arrive without his help, aided by Orly who had surprisingly picked up the spell at some point in his travels. In the same boat are Veth and Yeza, with our without Luc in tow depending on whether Marion was busy. Veth is quite accomplished at magic by then and can cast the spell on her own. A little over an hour before they all arrive, Caleb uses his own spell slots to travel to Beau and Yasha, takes an hour to restore his spell slot, and brings them along to the Blooming Grove to collect Caduceus and the dinner he's cooked before finally returning to a living room that is invariably newly packed with life and cheer.
He starts a roaring fire in the fireplace, serves them his best wine while Caduceus sets the table, and sends a message to Essek to come downstairs before the soup gets cold.
It's not something they can do every day, but it's something they all do at least once a month for as long as they can manage it. Everyone stays the night in the bedrooms Caleb set aside for that express purpose, and in the morning Veth takes her family home and Caleb teleports Caduceus and Jester and Fjord back to their temple and ship respectively. Beau and Yasha stay a few days so Beau can check in with the Rexxentrum archives, before Caleb takes them home as well.
Professor Caleb Widogast has a teleportation circle in his living room and a heart full to bursting with the love of his friends.
