Italy itinerary - input needed, please!!
 

Hello! I’m in the beginning stages of planning a trip to Italy. We’d like to go in April or May 2018. We love history, museums, architecture, art and scenery. I’ve been to Venice and Rome in the past. We will have two weeks (arriving day 1, departing day 15). I have a rough idea of an itinerary, but would appreciate any input and insight. We would like to see Venice, Florence, Tuscany (Sienna, Volterra, Cortona, Montepulciano, Etruscan sites and hot springs) and Umbria (Assisi, Orvieto).

I’d love to see the Dolomites and this is where I’m stuck. I don’t want to completely rush the trip, but I don’t think we will return to Italy in the future so I don’t want to regret missing it.

Here are my thoughts:
1 - fly into Venice, drive to the Dolomites then drive to Umbria then Tuscany, drop car in Florence and fly out of Florence
2 - fly into Venice, drive to the Dolomites, drop car in Florence, visit Florence, rent car again, drive to Tuscany, then Umbria, fly out of Florence (dropping car at airport)
3 - fly into Florence, see Florence, rent car and drive to Tuscany, then Umbria, drop car in Florence, train to Venice, see Venice, rent car at train station, drive to Dolomites, drop car at airport, fly out of Venice
4 - fly into Florence, drive to Tuscany, then Umbria, Dolomites, Venice, fly out of Venice
5 - fly into Florence, drive to Tuscany, Umbria, drop car in Florence, train to Venice and fly out of Venice – leaving the Dolomites out completely :(

Thank you for your help!

May is too early to go to the Dolomiti

... and asks for a completely different outfit than urban tourism...

problem is not only cold & muddy boots but that the risk of low cloud cover & rainy skies is strong, which obscures the peaks. You might not get to see the Dolomite spires themselves.

Thank you for your quick replies. It seems as though the Dolomites won't be included in the trip. I'm glad you told me that May is not the time to go to the Dolomites!

I will stick with Florence, Venice, Tuscany and Umbria. The next decision is whether to fly into Venice or Florence. Any thoughts of which would be preferable?

I would fly into Venice and out of Florence with that itinerary.

Is there an airport in Perugia?

Or is Rome closer from Umbria than Florence?

There are day trips from Venice to the Dolomites. It's like a 10-12 hour thing where they drive you. It's offered on sites like Viator and Getyourguide.com.

Might be something to look to book a couple of days before, if the weather looks clear.

However, a lot of services like cable cars don't open until late June.

But the weather is likely better in Tuscany and Umbria anyways.

Start in Venice, esp since you've been before. Easy entry to recoup from journey, less crowds earlier you go, weather gets nicer as you head for outdoor travel & driving in Umbria