Hello! My fam3ily of 4 will be traveling to Italy in the coming year (June 2026) and I'm just trying to piece together a reasonable itinerary. We have traveled to Italy before and been to Venice and Rome and some other spots mainly in Northern Italy. We have family friends that live in Lombardy (north of Brescia). that we will be visiting at the end of our stay. Our goals are to attempt to highlight Florence, Tuscany and Cinque Terre while still giving us 4-5 days with our friends in Brescia.
I've organized this by location of activities with parenthesis as lodging location
Day 1 (may 28) - Arrival to Florence by air (Florence)
Day 2 (May 29) - Florence Sites (Florence)
Day 3- (may 30) Florence Sites (Florence)
Day 4- (may 31) Florence Sites and Transfer to Siena (Siena)
Day 5- (June 1) Siena and Transfer to Montepulciano (maybe Montalcino?) or Tuscan Agriturismo (Montepulciano/AGT)
Day 6- (June 2) Tuscany (Wine tastings - Driving (Montepulciano/AGT)
Day 7- (June 3) Tuscany (Wine tastings - Driving (Montepulciano/AGT)
Day 8 - (June 4) Tuscany and Transfer to Volterra (Volterra)
Day 9 - (June 5) Voletrra - Pisa (Vernazza)
Day 10 - (June 6) Cinque Terre (Vernazza)
Day 11 - (June 7) Cinque Terre (Vernazza)
Day 12 - (June 8) Cinque Terre and Transfer to Brescia (Brescia -- Family)
Day 13 - (June 9) Brescia (Brescia)
Day 14 -- (June 10) Brescia (Brescia)
Day 15 -- (June 11) Brescia (Brescia)
Day 16 - (June 12) Brescia (Brescia)
Day 17 - (June 13) Departure
Again - I have just started researching and think this is reasonable but I know I have a lot more details to fill in. I think this will give us enough time to see the tourist areas (Florence, Siena, Tuscany, Cinque Terre) while still affording us time to visit with our Italian friends. I know I will return at some point (God willing), but this will likely be the last time as a family of 4 (our oldest will just be graduating from college and our other finishing the 1st year of college). Is there something glaringly obvious that I am missing or overlooking. In terms of transport- likely pick up a car as we leave Florence and keep the car through the rest of the trip (find overnight parking as we stay in Cinque Terre). If I can get a timeline together, I can start filling in the details with lodging and activities. I am going to try Air BNB as much as I can to try and have our family together rather than in 2 different hotel rooms. The one night stays may be difficult (Siena & Volterra). Probably just have to stay in hotels those nights.
Does the stay over Volterra make sense? We want to be sure to stop by Pisa for no other reason than the leaning Tower but I don't think we need to spend an entire day and night there. I was anticipating a stop over on our way to parking for Cinque Terre. I assume parking is available for the Piazza dei Miracoli to allow this.
I know the "Tuscany" time could be challenging - my wife and I love wine and want to be sure to visit some wineries. We are huge Brunello fans, but thinking that from what I have read at a glance that Montepulciano is a quainter town (versus Montalcino). More recommendations in this area would be appreciated as well - maybe an AG that would be convenient for drives and allow our family to stay together. I am going to leave the Brescia time unplanned as we have made several friends through family friends there and want to afford the opportunity to be flexible.
Any wineries we should see? Would love those recommendations as well!
Looking forward to your advice and insights!!
Happy Travels!