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Where to stay Val D'Orcia for 1 night? Montepulciano or Montalcino?

My boyfriend and I are traveling to Italy in a couple weeks. We're spending 3D/3N in Rome then renting a car and making our way North to Florence, driving through Tuscany and spending 1 day/night in Val D'Orcia. I'm struggling to figure out where to stay! We're hoping to stay in a nicer (updated) hotel or b&b but also in a convenient location for a few wine tastings within walking distance/ a short drive. Our budget is $400 for the room.

I really love Castillo Branfi but it's a bit over our budget and doesn't seem close to any other vineyards or wine tastings. Any suggestions? It seems like there are a lot of tastings and vineyards near Montalcino and Montepulciano but torn as to where and struggling to find a hotel/b&b that's charming but still looks comfortable and updated.

Appreciate any suggestions!!

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11367 posts

You are way out of my league, budgetwise, but we really like Montalcino. Incredible tasting room right in town. Rick Steves' guidebook should have some splurge options.