Does anyone know if you can stand with one foot in Italy and one foot in Switzerland in this border town? I've heard you can and would love to do so when visiting there soon. Also, what hotels would you recommend when staying in Chiasso that would be close to the train station?
Thank you for your input.
You can stand on any two bordering countries simultaneously if they are part of the Schengen Zone in any border point, not just Chiasso.
Chiasso is in Switzerland, the section of Como municipality close to the border is Ponte Chiasso.
The border passage point is extremely trafficked - there are literally thousands of persons living in Italy and working in Switzerland that commute across the border twice per day - so I do not know if custom inspectors will turn a blind eye to people playing games across the border. Apart from the passage point, the border is marked by mesh fences to avoid unauthorized crossing.
I just drove through Chiasso and had read your question this morning. It looks doable at the border crossing. But I didn't see any distinct mark of the border. You would likely need to not attract the notice of the border people, though. It's definitely not picturesque and is amazing how the city changes when one crosses into Italy. It's worth going to the border just to see the contrast between the two countries.
My objective at Chiasso has always been to get out of town, and the associated traffic backups, as soon as possible. I've never had anything approaching pleasure there.
Pick another place.