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Dolomites to Tuscany Itinerary help please

We are planning a 12-14 day trip for 2 couples in mid to late September 2024. We have been to Italy several time but our friends have not. We are trying to balance places we have not been with what not to miss for our friends. Below are the places we would like to stay in, with a few days of wiggle room.

We are planning to fly in to Venice and rent a car, drive to Malcesine on Lake Garda. I know driving after a flight is not ideal, but we have done it in the past.

This is our working itinerary

Malcensine- 2 nights
Ortisei- 3 nights
Siena- 3-4 nights day trips, cooking class
Florence-1 full day and overnight to fly out

We have been to Venice, Florence and much of Tuscany, but feel like Tuscany is a must do for our friends who have never been to Italy. We want to enjoy small towns, food and wine and of course beautiful scenery, not looking for museum experiences on this trip. Any input on how to best make this work would be appreciated. Nothing is booked and I am open to suggestions.

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You can use Siena as a base for exploring the Tuscan countryside - it might require more driving time if you venture more to the south but it saves you the hassle of switching hotels. There’s no location that is perfectly situated.

A couple of thoughts:

1) Get a large-enough rental car. My wife and I did a lot of driving in Tuscany and our rental car (a small Jeep in the “Compact Elite” category from Avis) definitely couldn’t fit 4 adults plus bags. We couldn’t even fit all our bags (one backpack and one rolling bag each) in the little trunk.

2) Weigh the pros and cons of staying “in town” vs in the countryside. We chose countryside: great scenery, super quiet, parking was easy and secure. But that came at the trade off of having to drive everywhere (including home from dinner in the dark).