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Italy - first trip itinerary

We got a really great deal on flight in and out of Milan ( I know t's not ideal) leaving in 2 weeks. Here's our itinerary but would love feedback and help on what to do/see in Tuscany area. Staying 20 minutes outside of Pisa in the country so we will get a rental car there.
Fly into Milan - stay 1 night - a.m. train to Venice
Venice: 2 nights
Fly out of Venice to Athens Greece for 5 nights (we have friends there so that is taken care of)
A.M Fly to Rome: 3 nights
Train to Pisa - 4 nights - need suggestions on day trips - cooking classes, wineries, coastal trip? one day more of a relaxing day and the other two can be busier - looking at Cinque Terre for a day trip
Train back to Milan: 2 nights - would love aday trip to Lake Como if weather permits

Posted by
4105 posts

If you could give us the location of your lodging outside of Pisa, you'd get a much better response. For the Cinque Terre, are you aware you would need to park in La Spezia and take the train to the villages.

Posted by
108 posts

I don’t know where you are coming from and time of arrival but if possible I would try to make it to Venice the first night. It would give you one extra day and one less hotel change. That first day is sort of a lost day anyway.

Posted by
6570 posts

Kathleen's suggestion is a good one if your flight lands early enough in the day. Though you won't save a hotel charge, you'll just shift it from Milan to Venice. Look for a hotel in Venice itself, not on the mainland, so you'll experience the city early and late in the day when it's less crowded. But give yourself plenty of time to reach the airport for your flight to Athens.

Is there a reason you don't want to spend time in Florence? Just an hour by train from Pisa. I understand your wanting a relaxing day or two, but your four nights in Pisa gives you time for that and Florence too. I'd pick Florence over CT but your interests may be different, or maybe you've been to Florence before.

Posted by
8178 posts

Pisa is just the leaning tower and a beautiful church. It has a very active airport and most travelers skip Pisa and head the 1 hr. train over to Florence--an important city.

Posted by
4 posts

In Pisa we are staying at a Hilton time share - so the dates/location can't be moved. It is located 20 minutes from Pisa going southeast. We are not able to change our flight - I thought about the train straight to Venice after landing but after a 13.5 hour flight - I wouldn't want to get on a train - we don't land until later in the day. Our plan was to land - get a good nights sleep - wake up early and head straight to Venice. It's not a lot of time but it will have to do :( I understand there is not much in Pisa so I want to get suggestions on other Tuscany towns to do day trips on - any restaurant suggestions, cooking classes, winery tours, etc would be awesome!

Posted by
4 posts

@ Gerri -I didn't know about the parking/train so thank you for that! Florence will definitely be one of our day trips - just not staying the night - does anyone know how late the train runs? Is it an easy drive?

Posted by
7347 posts

This is the Italian train website, so you can look at options: www.trenitalia.com

You will need to use the Italian names:
Florence is Firenze
Venice is Venezia
Milan is Milano
And the 5 small villages are Cinque Terre

A cooking class I enjoyed near Pisa was Extra Virgin in the town of Lucca.

Posted by
4105 posts

The drive to Florence is about an hour. Park here and take the tram into the city to avoid ZTL zones.

https://www.parcheggiovillacostanza.it/en/villa-costanza-parking/villa-costanza/

If you're staying at Borgo alle Vigne, these towns are 45-60 minutes.

Certaldo, San Miniato, Colle di valle d'Este, Volterra, San Gimignano. For a coastal experience, Viareggio, a Belle Epoch beach town.
La Spezia, is around 1 1/2 hrs.
If you've never driven in Italy, read this and download their ebook.
Edit : https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

Posted by
4 posts

Thank you for all the helpful info! Yes, the Hilton is where we are staying - it took a year to get that booked! Are there any hillside towns that really just shouldn't be missed?

Posted by
4105 posts

These three would make a perfect day trip.
I've added links to pique your interest.

Certaldo Alto Midieval hill town.
https://lovefromtuscany.com/where-to-go/small-towns-in-tuscany/certaldo-alto/

San Miniato
https://handluggageonly.co.uk/2016/11/18/beautiful-tuscan-town-san-miniato-italy/

Vinci/Anchiano.
https://www.italythisway.com/places/vinci.php
Pleasant 1/2 hour walk thru olive groves to Leonardo di Vincis' birthplace.
http://www.museoleonardiano.it/eng

These are all small towns, villages you should be able to visit all of them in a day. Total travel time R/T 2:20

Posted by
4473 posts

If you will not have time to really do anything in Milan, I would also hop on the train -- get a nap in en route, and wake up in Venice.
While staying south of Pisa, I would not go to Florence or Cinque Terre (those can be saved for a future trip and are better visited with public transport). Instead, take full advantage of a car and see things in the vicinity that would be otherwise difficult to see. Drive down the coast, etc. I loved Massa Marittima. You can see the Sam Galgano abbey, see Etruscan ruins at Piombino, nice beaches at Punta Ala.
I'd also just give Milan short shrift and only stay a night if you can add that extra night to your Tuscany stay.