Rome/Florence/Venice/Castelrotto-looking for ideas on Dolomites & Florence day trip

Your schedule is very fast-paced with lots of changing hotels. Add hot summer weather and a group of 7, even if they're all adults, and IMHO you will end up with lots of travel stress. Also, I'm thinking that you won't need a rental vehicle until after Venice; you're visiting three cities right in a row, and the train system in Italy works very well (and this is a comment from someone who likes to rent cars, and has no issues with driving in Europe). If you rent a van out of Rome (and it will have to be good-sized to fit 7 adults and their luggage, you will have to deal with parking in cities and the ZLT traffic limitation zones, which can cause the unwary to end up with traffic fines for driving in the wrong areas. AND renting a van from Rome, through Rome traffic, is no fun (I've done it, though not right into the downtown area, but it was bad enough, and I had a sedan, not a 7-person van). To make your lives easier, you could go back out to the airport to pick up the rental van, and get straight on the autostrada from there, but then you're schlepping 7 adults and their luggage back to the airport.

Doing this itinerary, keeping your current cities, I would say to take the train from Rome to Florence, take your one-day guided visit to Tuscany (for very active people, you might find riding in the tour van boring), then take the train to Venice. Pick up the rental van as you leave Venice, and keep it for the rest of the trip.

If you all are very active and enjoy hiking, I would say to leave out some cities and instead spend more time in the Dolomites; just because other people do the "Big 3" doesn't mean that you have to if your interests are different! And unless any in your group LOVE Renaissance art, I would say to leave out Florence and Tuscany, and spend more time in Rome, Venice and the Dolomites (I love the art in Florence, but the cities of Rome and Venice are like no others in the world). That honestly is still not very much time in any location, especially if your last night has to be in Milan (any way to switch that departure city to Venice?)

We did a similar trip in 2014 and after seeing Rome our sons would have preferred less time in Florence and more time in the Dolomites. As noted here we opted to use the train until we left Venice. I preferred the downtime the train afforded.

Have you considered staying in Ortisei instead of Castelrotto? Maybe its too late to change accommodations however we loved our time in Ortisei. We chose to access the meadows via gondola and hike back down into the valley. It was a spectacular few days and left us wanting.

Enjoy!

I agree with Lexma and Jean. Take the train until you leave Venice. With 7 people, you will probably need a van for 9 to accomodate luggage. Normally, a van for 7 does not have enough luggage space for 7 bags.

Good luck hiking in the Dolomites, it might be our next destination.

Thanks for the comments! My husband has been pondering using the trains and your posts convinced us to pursue that option. Jean, how many days did you spend in the Dolomites and the other cities. We had some difficulty finding lodging at either Ortesei and Castelrotto (we considered both); finding accommodations for 7 people presented a problem. We are flying on frequent flier miles so we did not have a lot of options on flights....I know the trip will be great.

You can get from Venice to either Ortisei or Castelrotto via a combination of train and bus, probably switching modes of transportation in Bolzano. It needn't take all day, either. I mention that just in case you find the cost of renting a large vehicle to be exorbitant for the little use you're likely to get out of it.

The trip back down to Milan will be 3 to 3-1/2 hours from Bolzano by train. You'd need to allow extra time to get to Bolzano, but at least the buses from the mountain villages drop you off very near the train station.

Since 1 night in Venice is not going to allow you to see much of anything, you are for the most part traveling all the way from Florence to the Dolomites and then back from there to Milan to hike for 1 day!
If that is important make the Dolomites 3 nights at least and drive from Florence directly there skipping Venice which is not on the way anyway.
You can make a stop in route to Verona if you must see something else for a few hours ; it will be a much easier city to drive into and park a van than Venice would be as well.

I also recommend the town of Ortisei ; from Ortisei there are cable car lifts on both sides one side to Seceda the other to Alpe Di Suisi both of which are incredible.

I would not want to be the one driving this van
Be sure to get specs on luggage capacity of any rental van so you pack accordingly, car types are smaller in Italy and roads are very narrow so vans can be difficult to manage

ZTL areas can be hard to avoid in Rome, Milan and Florence and parking will cost money everywhere you are going

You might try Residence Astoria in Ortisei. I think they will do three-night stays. By all means, stay three nights! Skip Venice or Florence and make 3 nights work in the Dolomites. Four nights is even better.

There is so much hiking right out of Ortisei: Rasciesa Ridge, the Alpe di Siusi, Seceda. Or take the bus (free pass given by lodging) to Santa Christina and hike from Ciampinoi to Rifugio Emilio Comici, then on the Naturonda to Passo Sella where you can take a bus back to Ortisei. Be sure to get a Val Gardena Pass for the lifts.