Itinerary Ideas - June 2018

Unless you are experienced motorcycle riders, using a motorbike in Italy is 'tutti pazzi'

"take it day by day" ..... does that mean not making hotel reservations ahead of time? You may find the selection limited.

Just a very good idea when travelling from Rome to Tuscany choose to drive Cassia old Roman way heading to Siena, from there to Firenze Chiantigiana local way and from Florence to Pisa don't forget to bike thru Lucca.
If not in a hurry local road are best onestamente. Last suggestion drive from Siena to San Gimignano and then to Volterra and on your way back thru the geothermal Hill area South of Volterra up to Massa Marittima. Dramatic driving and sights!

Travelling by motorbike? Are you experienced bikers? Are you renting bikes that will also accommodate your luggage? Are you knowledgeable about Italian traffic laws? ZTLs? Are you planning on driving these in the cities as well as between them? And what are you going to do with them in Venice? If you only want to visit the places you listed, I'd really reconsider your choice of transportation. All are easily reached by comfortable, frequent, inexpensive, and safe trains.

Aside from the problem of luggage on a bike, Italian drivers are aggressive. Don't expect them to respect motorbikes as equal vehicles on the road the way US drivers do. And other bikers are likely to be worse, especially if you aren't as aggressive as they are on the road.

I agree with the others, you are going to popular places in high season, you should probably reserve rooms. Then you might as well buy train tickets to get the early purchase savings.

Pisa is an easy 1/2 trip from Florence by train.

The best itinerary is to fly into Venice, then Florence, then fly home from Rome. With 2 weeks you could add one more stop. Bologna is between Venice and Florence, well known for its food and wine. It's also a good base for day trips to surround towns by train - Modena, Ferrara, Ravenna, Padua . . . Orvieto is an Umbrian hill town, take the train from Florence.

Agreeing with the rest: your trip will be much easier and safer by train versus a motorcycle. Traffic laws - both written and unwritten - are different than in the U.S. plus you don't want to do any sightseeing with belongings left on the bike, riding in the rain, after wine, etc. You also can't ride a motorcycle and pay attention to a map at the same time.

Virtually all of Venice is pedestrianized as are parts of central Florence. Rome? Not so much but dodging traffic is crazy enough on foot let alone on wheels! Trains are great; learn to love them. :O)

One exception might be to rent wheels for a day in rural Tuscany but best have someone who has done it give you some pointers there. Pretty sure the previous poster who recommended "to bike thru Lucca" meant on a rental bicycle and not a motor-driven bike. Pedaling the old walls of the city is a much-recommended activity in Lucca.