Revised Itinerary 16 days Veneto, Florence, Rome

What time of year?

Early June. Getting ready to press buy on the airline tickets. I tried to do multi-city but much more affordable to do Milan both ways.

Visiting the Dolomites as a daytrip from Vicenza is a stretch without a rental car.

I think your time is pretty well divided, but it is a lot more daytripping than I would enjoy. Personally I think Siena deserves a night at least, and I would consider going there for two nights and then straight on to Rome. ( I'd skip Pisa). I've not been to Vicenza, but wonder if Verona or Padua might have a bit more to do if staying for 5 nights, as I think they both have a few more sites.

Yes, getting a rental car for the Dolomites.

If we should give up on a day trip then that is something. Maybe we drop Sienna?

I'd do multi city to save time. I'd fly into Venice and out of Rome. I'd skip Milan all together. I'd also save the Dolomites for another trip - do them with Northern Italy & Switzerland - you will want 1-2 weeks in that area alone. I'd also skip Pisa - Florence needs 3 full days to barely scratch the surface. I'd do a day trip with WalkAboutFlorence - their BEST OF TUSCANY TOUR takes you to Siena, Pisa, San G w/a great lunch. Italy is meant to be savored & enJOYed, not rushed.

Folks who go to Venice for one day often seem to dislike the city. It's my theory that, having such an inadequate amount of time, they have to spend nearly all their time around the Rialto Bridge, Rialto Market and Piazza San Marco. That area is totally mobbed and Disneyland-like. It's really important to have enough time in Venice to wander the atmospheric, uncrowded back canals.

Day-tripping to Venice from Vicenza would be even worse than spending one night in Venice or in Mestre. It's at least a 45-minute train trip from Vicenza to Venice, and that doesn't count the time you'll spend getting to the train station in Vicenza from your hotel. The train station in Vicenza isn't terribly close to the historic center, so I imagine you won't be staying really close to the station.

I'd agree that Verona or Padua should be considered as an alternative to Vicenza. I liked Vicenza, but the other cities have a lot more sights. On a trip of this length intended to cover so much of Italy, I wouldn't consider Vicenza a required stop unless you have a special interest in Palladian architecture. To me, it's more the sort of place one might go on a second or third trip. Certainly, I'd prefer more time in Venice than a day in Vicenza.

Time in Venice seems short given the fact you intend to visit as a day trip from Vicenza. It’s doable, but…

Dolomites as a day trip from Vicenza is a bit too much. You have 5 nights in Vicenza. How about spending only 3 nights in Vicenza, and 2 somewhere in the Dolomites? You can return the car in Bolzano or Verona and take the train to Florence from there. You could even drive all the way from the Dolomites to Florence and return the car in Florence. Given my wife’s inability to pack light, that is what I would probably do (and actually done), but I will admit it is a long and very boring 5-6 hour drive (depending in departure point) on the freeway from the Dolomites to Florence.

You have too many daytrips from Vicenza. I would not visit Venice as a daytrip because you will see it at its worse with tons of other daytrippers. Last May we spent 4 nights in Venice, and it is now one of my favorite cities. Venice truly is magical and unique, but I probably would not feel that way if I saw Venice as a daytrip. We had enough time to wander and explore the less crowded back canals, take a gondola ride in the Dorsoduro neighborhood where we stayed (much less crowded), and visit some highlights. I think you are trying to see too much on this trip. I would spend 3 or 4 nights in Venice to fully appreciate and enjoy this amazing city.

I also don't like the idea of visiting the Dolomites for a day. You won't see much at all. This is another area where you need more time. We spent 4 nights in Merano last May, and we did see some amazing scenery, but just a tiny slice.

Florence needs at least 3 full days as well to see its amazing art and architecture. And Florence will be extremely crowded so you need to account for the crowds. And Siena deserves more than one day. I would drop one of the daytrips from Florence. Overnighting in Siena on the way to Rome would make sense.