Bernina express....Pontresina

I love Pontresina but it would take a lot of time back and forth. It is very to visit Lake Lugano from Lake Como to get a taste of Switzerland.

Why Lake Lugano instead? I thought the Bernina express was one of those things you had to do in Switzerland.
How long would it take to get from Varenna Italy to Lake Lugano? And how?

Yes, it's possible. If you depart Varenna at 8:24, walk quickly across the square in Tirano and connect to the 10:03 train with reserved Panorama cars, you arrive to Pontresina at 12:25. Departing an hour later is slightly faster but without Panorama cars. Return trains that get you back to Varenna with only one connection depart at 15:04, 15:21 (Panorama), and 17:04 on my test date. The Deutsche Bahn link at Looking Up Train Schedules and Routes Online has summer and fall schedules posted for this route.

This would be a lovely daytrip if you want to experience alpine Switzerland.

One thought would be to leave the train when it stops at Hotel Morterasch, before Pontresina, and have lunch there. You could then hike to a glacier or into Pontresina before boarding a train back to Tirano.

https://www.pontresina.ch/en/summer/hiking/hiking-tours/details/B00094/morteratsch-glacier-to-pontresina/?no_cache=1&cHash=66eeb72981426c7f07d3c6e157931715

Or ride into Pontresina and take the funicular up to Hotel Muottas Muragl for lunch with panoramic views:

http://www.muottasmuragl.ch/en/gastronomy/panorama-restaurant/

To get to Lugano, take the ferry from Varenna across the lake to Menaggio. Take the bus from Menaggio to Lugano. You will be dropped in the center of Lugano. It takes a little over an hour each way.

Lugano is nice enough but it feels just like Italy. If you want to see the Alps, take the Bernina train as you planned.

Our experience was that tight (under 5 minutes) Swiss train connections were not a problem. We even had a 3 minute connection return from Tirano that went exactly as scheduled.

That said, you should check the Italian train strike schedule: https://www.italiarail.com/strike-information