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October Trip Northern Italy

We are flying into Milan mid October 2024 on our way to Trieste to join a cruise. Our current plan is to head straight from the Milan airport to Lake Como for 2 nights, then to Cinque Terre for 3 nights, Florence for 4 nights and Venice for 3 nights (then one night in Trieste). My questions are as follows:

  1. Does it make sense to go to Lake Como for only 2 nights just upon arrival? I'm debating saving this for some future trip and just staying in Milan for a night or 2 and then heading south.

  2. Has anyone stayed at the Grand Hotel Portovenere as a base for Cinque Terre? I currently have a reservation at Hotel Porto Roca (in Monterrosa) but am debating changing it to either Grand Hotel Portovenere, Grand Hotel Miramare (in Santa Margherita Ligure closer to Portofino) or Grand Hotel Bristol (in Rapallo) and just doing a day trip to some of the Cinque Terre villages. We do NOT plan on renting a car but rather taking trains/ferries etc. Would be interested in anyone's thoughts on best place to stay.

  3. Looking to do one day trip/private tour outside of Florence - probably to some wineries but would be interested in anyone's off the beaten path suggestions on this one as well as good private tour companies.

Thanks in advance for the input - much appreciated.

Posted by
795 posts

Not that I have had any experience particularly, but 2 nights give you one full day and a half of a day of possibly jet lagged fog like touring.....unless you feel like you could accomplish all that you wanted to do there in those times, it might be better to go STRAIGHT to your next destination, to give yourself more time to recover and hit the ground running there sooner (unless you are OBSESSED with Milan or need to see the Last Supper, once you arrive in Milan and are on the move, its not hard to just keep going for a bit more to get to your first REAL location)

Posted by
5649 posts

I love Lake Como, but it's more for relaxing and savoring the beauty , and a short trip won't do that. Unless you have three nights, I would skip Lake Como.
Also, many hotels have two night minimums. And- depending on when your flights arrives - there are limited trains into the evening, The Milan to Varenna train is only an hour, tho.
Enjoy this beautiful area!