Despite my advanced years, I've managed to get a good level of fitness (today I'm focused on completing a 40 km stroll complete with all my long distance gear) with two hillocks of 150 m asl to get over. My home, at 90 m asl, is just on 2 km from the sea. Other features close by and a bit further afield make for a great training ground.
I was booked to return to the VF in March 2020, but ...
Thanks for your notes on the approach to Siena.
When I leave San Gimignano I propose turning left, follow up a valley, then over a hill down to Florence, this being the route taken by the New Zealand army in July 1944, for a lay day. Then by train to Siena.
Kia kaha (take care, be strong)