If you have 2 weeks (early-June) in Italy, how would you plan it? (Bonus point if includes wineries :))

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In no particular order
Rome 2/3 days
Venice 3/4 days -2024 is art biennale
Both cities are both rammed with tourists - take a step back and include watching the tourist show and you can hover above the chaos

Rest of the time split between Tuscany and Puglia 
 
Maybe one day and night in Naples to mess your head up

Working on Farcaster and Warpcast. Longer thoughts at https://dwr.email

When I’m with my parents, it’s mostly about food and interacting with locals, eg discovering this local escargot bar in Paris and mingling with locals there was the most memorable. Usually, they enjoy mixing waterside experience eg thinking lake como. But no outdoor activities like hiking.

Beyond wine, what else is interesting to you on a vacation?

Tuscany all the way!!
You can start from Florence, the Siena, Pienza the “chiantigiana” road (Chianti wine). You can enjoy Umbria and then go for Rome, continuing to south towards Naples and the Amalfi coast. 
Then the southernmost part of Puglia: the Salento where you can enjoy Primitivo wine, good sea and food

(Fly into Rome)
5 days in Sicily (Palermo and Taormina) or explore Puglia region
3 days in Florence
2 days in Lucca
2 days in Tuscany (Sienna, Panzano, Pienza)
2 days in Rome
(Fly out Rome)

Engineer @farcaster. Founder bountycaster.xyz

Ex Phantom, 0x Project engineer.

From Italy originally, currently live in NYC