We are headed to Italy on June 26th, 2026 for a wedding in Verona on June 30th. The plan is to be in Italy for 14-15 days and below is my first draft itinerary.
Two things to keep in mind:
1) We did 14 days in Italy on our last trip-each out of a carry-on and visited Rome, Florence, Cinque Terre, Verona, & Venice - and we were fine visiting all those places in two weeks and had the best vacation ever, so for those of you who say this upcoming trip is too abmitious, I will respectfully disagree! :-)
2) We have been to Verona, Rome and Florence but will be with family who want to revisit those areas again, but we do not need a lot of time there. I am open to suggestions logistically and must see places/restaurants/wine tastings, etc..
Thank you in advance for your advice!
Below is my initial itinerary draft. Thanks to ChatGPT, it put my plan in a cute little fun outline.
Friday, June 26 – Fly from Orlando to Verona or Venice (family members flying from NYC to Verona or Venice)
* ✈️ Overnight flight
Saturday, June 27 – Arrive → Lake Garda
* 🚄 Land in Verona or Venice
* 🚗 Travel to Lake Garda (e.g., Limone or Sirmione)
Sunday, June 28 – Lake Garda (Limone Village)
* 🛶 Relax, explore Limone & lake towns
Monday, June 29 – Return to Verona – Wine tasting / Welcome Dinner
* 🍷 Travel back to Verona
* 🎉 Pre-wedding activities
Tuesday, June 30 – Wedding in Verona
* 💍 Full day for celebration
Wednesday, July 1 – Train to Bologna
* 🚄 1.5 hrs by train
* 🍝 Evening in Bologna
Thursday, July 2 – Bologna
* 🏛️ Full day for sightseeing and food
Friday, July 3 – Train to Florence
* 🚄 40-minute ride
* 🎨 Begin exploring
Saturday, July 4 – Florence
* See something here we didn't see on our last trip, or revisit our favorite places.
Sunday, July 5 – Train to Rome / Trastevere
* 🚄 1.5 hrs
* 🏛️ Visit a favorite spot or just enjoy local food and vibes
Monday, July 6 – Train to Naples
* 🚄 1 hr high-speed
* 🍕 Explore Naples or just relax
Tuesday, July 7 – Pompeii Day Trip
* 🚉 30-minute train
* 🏛️ Morning at ruins, return to Naples OR continue to Sorrento that evening
Wednesday, July 8 – Sorrento → Positano (including Praiano visit)
* 🚗 Private transfer or ferry
* 🏞️ Visit Praiano en route or as a side trip
* 💤 Stay in Positano
Thursday, July 9 – Capri Day Trip
* 🚤 Ferry to Capri, optional Blue Grotto or Anacapri visit
* Return to Positano in evening
Friday, July 10 – Travel to Naples
* 🚗 2 hrs by car or shuttle
* 💤 Stay near airport
Saturday, July 11 – Fly Home
* ✈️ Ciao Italia!