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Nine Cities in 9 months!

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I'm taking a pause from working and traveling 9 months. Gonna make this happen. Always wanted to live abroad, at least 3 months straight, but could never pull the trigger because of school, money, work, family, obligations, the list goes on. This time I'm going to make it happen!

I'm not sure how to go about it though and need advice. I'm allowed 3 months in the Schengen zone and 6 months in the UK. If I leave the US in November, where would you start and which cities would you pick? It doesn't just have to be in Europe but airfare would definitely be cheaper if I stayed within.

Snow is fun but realistically I prefer a not so bone chilling environment. I can't stand the heat either. Somewhere that isn't completely dead at night. Nice scenery, good food and art options whether that's visual or performing, preferably both.

Some water mid way in to the journey, I've been to Venice, in awe of its beauty, but where else? Also thinking of 3 weeks in a wine region either Tuscany or France?

Budget including housing, flights and all other expenses, 6K a month for 2 people, less would be even better.

I will be doing this trip with my hubby to be, my biggest supporter, who can thankfully work anywhere in the world.

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