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2 week Italy trip - Input Requested

Posted by on

Hi All,

We (husband and wife coming from the U.S.) are looking to visit Italy for 2 weeks in late May 2027. Part of the reason for the trip is celebrating 30 year anniversary. Here is the tentative starting itinerary we are thinking. Would love to get input from others if this is too many stops, not enough time in certain areas, and flow or logistics of getting around.

  • Arrival Florence (FLR), spend 2 days here
  • Grab rental car from FLR then head to San Gimignano area for 3 days at an Agriturismo location
  • Return rental car to FLR location then take train to Bologna, spend 2 days here
  • Take train to Bellano/Varenna/Bellagio area, spend 4 days here
  • Quick train down to city of Como itself for 1 day, maybe catch Como 1907 Serie A match
  • Head to Milan for 1-1.5 days before departing back home

Any input would be appreciated. Thank you in advance

Posted by
10206 posts

Congratulations!

Do you have the flexibility to add a couple of days? If so, I’d add at least one more to Florence. You’re arriving with jet lag, so it will feel like a quick 1 full day stop and you’re off to the next location.

Posted by
2277 posts

Quick tip - most people here count nights rather than days. The helps by denoting where you are going to sleep each night (and so need lodging) and which days are travel days. You get 1 less full day someplace than the number of nights stayed. So 3 nights is 2 full days and 2 nights is one full day with travel days on either side. I find this the most clear way to spreadsheet out where we are each night, what travel we have on which days and what lodging is booked where.

Your plan looks reasonable and well spaced out. FLR is very close to the city you can grab a cab or take the tram into town depending on where you are staying. You can take the tram to the train station after you drop off the car at the airport and then onto Bologna.

Fast trains come in at Level -4 in Bologna so it will be trek to get up the surface and out of the train station. It is unusual among Italian train stations that way.

Be sure you have International Drivers Permit for all drivers before leaving the states. Read up on ZTLs before you go and read up on each touristy town before you drive there. Add at least 25% to Google maps time estimates for rural roads and driving.

Have a great trip,
=Tod

Posted by
1993 posts

Dropping the car off in Bologna will save a transfer and time.

Posted by
752 posts

I’m assuming when you say two days, you mean two nights.

I guess it depends on your interests, but I think a slower pace is a more enjoyable way to travel. I’m not a fan of going to Florence, Bologna, and Milan and spending just one full day in each. I would skip Bologna and Como (city), add two nights to Florence and one to Milan.

If you go to Como, the ferry ride down to Como is scenic and worthwhile, maybe do that instead of the train.

Posted by
239 posts

I would drop off the car rental in Bologna rather than Florence. This will save you time having to navigate Florence local traffic/ZTLs, getting from the car rental to the train station, waiting on your train, etc. You'll already be on the A1 anyways, why not keep driving?

You'll probably be dragging Day 1 in Florence, so be sure you can see what you want to see in 2 days.

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