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30th anniversary trip - Umbria, Marche, Puglia - help wanted!

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I'm starting to put together a trip for our 30th anniversary (yes, time flies!) and could really use help. We are zeroing in on Italy but nothing is booked. We can spend around 2 weeks in early to mid-June but that's flexible. We can't leave until June 8th and would like to be somewhere lovely for our anniversary on June 11th. I had been thinking Umbria and the Marche but then I made the mistake of reading astonishing trip reports on Puglia. Yum. Thank you ekscrunchy!

In past trips we've spent time in Umbria and the Marche and LOVED the countryside and the towns. Our favorites were Spoleto, Assisi, Norcia, the Plano Grande, Castelluccia, and Urbino. We love Rome, Bologna and Ravenna but not this trip. We've been to Tuscany, including Siena and Florence, northern Italy including CT, Trento, Lago di Garda and Venice and don't want to return this year. DH is a geologist so he loves CT but will never set foot in Venice again! He's not a fan of crowds.

We love hilltowns, small and delicious restaurants, wine, finding amazing food in markets and sometimes making dinner or lunch. We go to any and all museums and most churches we see but most of our days are spent wandering around towns or hiking.

I'm roughly thinking about 4 or 5 days in a rental near Spoleto or Assisi, a night in Norcia, then a few days in a rental near Urbino. After that (or before that) I'm open. We could spend more time - longer stays - in Umbria and the Marche or we could decamp and head south to Puglia. Or vice versa, as we could fly into Brindisi.

No plane tickets yet. I'm looking at flights out of Vancouver BC as they're around 950 right now, RT to Rome in early June. That seems to be a good price for June.

I'd appreciate any thoughts on how to pull these random ideas together. And if anyone can recommend the perfect rental in Umbria or the Marche where I can sit on a terrace with a view of valleys before me, drinking wine, watching the sun set and sketching (I'm a landscape painter, I definitely need those views!) - that would be MUCH appreciated.

And of course, restaurant recommendations are welcome. I'm a little food obsessed. DH is not but he accompanies me!

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