Happy New Year!
I am planning a trip for May 2016 to France and Italy. We are planning to visit Portofino from the French Riviera and then onto Milan. I know a lot of people aren't very fond of it, but this might be the only chance I get since we have a flexible budget and travel time. I have previously been to Cinque Terre and spent a few days there and had 0 regrets. Despite it being high season, I only felt like it was overwhelmed with tourists in particular places during the afternoon, but other than that the trails were great and the evenings were nice. My current travel partner isn't into hiking and prefers something more upscale like the South of France, and she wants to visit Portofino as well.
The plan is to take the Thello train from Nice to Genoa and a regional train to Santa Margherita Ligure, where we will stay. The estimated travel time (according to rome2rio.com) is ~4.5 hours and we will spend the rest of the day in SML. The next morning we want to go to Portofino by bus and around evening take an IC train from SML to Milano. We prefer the IC train because it is faster and would save us 1 hour.
It won't be tiring, even though it sounds like it - just based on previous travel experiences. But is 5 hours (9:30-2:30) in Portofino enough to wander the town, go to a bar for a quick lunch and maybe take a boat to San Fruttuoso and back (not sure about this). We aren't too interested in places like Camogli and Rapallo. I'm sure they're nice and I've seen some people prefer them to Portofino, but we are fine with just Portofino and SML.
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Happy New Year!