Family of 4 Italy itinerary - first draft - looking for feedback!

Itinerary !!MUST PROVIDE TRAVEL DATES!!

My family (2 adults and 2 boys ages 11 and 13) is traveling to Italy next June for the first time. I'd love some feedback on our tentative itinerary, suggestions for improvement, or activities we may enjoy but don't know about/aren't thinking about yet, alternative towns to consider staying in Tuscany or the Riviera. This is technically 1 day longer than we initially planned, so if you had to cut one day, which would it be?

A few details about us to help explain my thought process here:

  • Traveling to Florence and Tuscany has been a dream of mine for 25 years, ever since studying Renaissance art history in college. My family is not as enticed by the art aspect but will go along with me, within reason.
  • My kids love beaches/swimming on vacation
  • We are a very active family at home and enjoy hiking, biking, exploring while on vacation together.
  • My husband is a fly fisherman so if ever there is an opportunity to do that in a new place, he's excited to fit it in (though where we live is surrounded by blue ribbon trout fishing so it's not an activity we need to go too far out of our way to fit in)

Travel Dates: June 16 2027 - July 1 2027

June 16: Depart home in US in afternoon, travel to Rome

June 17: Arrive Rome, early afternoon

  • Travel to hotel, easy evening spent with a little wandering, maybe check out Trevi fountain, early dinner and bed

June 18: Day in Rome

  • Tour of Colosseum
  • Wandering Rome afternoon

June 19: Day in Rome

  • Catacombs of some sort (any recommendations here are appreciated!)

June 20: Travel to Tuscany

  • Train to Florence, rent a car, drive to Montepulciano
  • Stay in an agriturismo with a pool

June 21: Day in Tuscany

  • Drive around and explore other towns in Tuscany

June 22: Day in Tuscany

  • Perhaps a day my husband goes on a guided fishing trip somewhere?
  • Or, just continue to explore towns in Tuscany as a family (Siena, Pienza)

June 23: Travel to Florence

  • Return rental car
  • Check into hotel, wander Florence

June 24: Day in Florence

  • Uffizi gallery

June 25: Day in Florence

  • Accademia? Duomo climb?

June 26: Day in Florence

  • Boboli gardens
  • Maybe it would be better for my husband to catch a guided fly fishing trip that departs from Florence instead of that day in Tuscany?

June 27: Travel to Sestri Levante

  • Check into hotel
  • Afternoon at the beach, swimming, relaxing

June 28: Day on Riviera

  • Travel and explore neighboring towns

June 29: Day in Sestri Levante

  • Beach, relax, prepare to leave

June 30: Travel to Milan

  • Morning in Sestri Levante
  • Travel to Milan in evening to be closer to airport and get a good night's sleep before traveling home

July 1: Fly home from Milan

Thanks for your thoughts/help!

Posted Jun 6, 2026, 9:33 PM UTC

621
Loading comments…