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Italy Itinerary

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Hi! My husband & I (27 years old) are planning a trip to Italy from around October 1st - October 12. The 9-12 will be spent in Val D'orcia for a wedding. We are looking for itinerary suggestions.

We honeymooned May 2025 in Italy (Rome, 1 night Sorrento, day trip to cinque terre (LOVED!) and Florence). We didn't love Florence but would be open to spending 1-2 nights in any of the other locations & then explore more of where we haven't visited. We would love to explore the Tuscany region and/or Umbria (but also don't love wine a ton lol). Would also love to be around some sort of water at some point.

Thank you so much!

Posted by
6801 posts

I’d first drill down on the Tuscany wedding details, like will you need a car to get around while there, are you comfortable with driving in general (as it will determine your Tuscany and Umbria stops), then you can get to the fun part of choosing destinations. If you do a coastal stop. I’d do it first, then choose somewhere convenient to the jumping off point to the wedding.

Posted by
1135 posts

So much of Italy is easy to move around by train or bus. That does take away some of the tension that can come with driving, parking and getting lost. Have you considered Siena? Lucca? Verona? Venice? Assisi? You don't have time to visit them all, but a couple of nights in a couple of them might be rewarding.

Posted by
10018 posts

Didn't love Florence!!!??
What did you see there?

Other places in Tuscany in Umbria are Siena, Lucca, Pisa, Voltera, San Giminancio, Gubbio, Spoleto, Assisi, Perugia, Spello and Orvieto.

Personally, loved the Amalfi Coast more than Cinque Terre.
You didn't mention Venice, which is very special. Also, nearby Bologna and Ravenna.

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