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Which Village in CT to stay in October, and Siena questions

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We have a trip planned for this October---Rome to Florence to CT---then work our way back to Rome through Tuscany...

I have found a B & B in both Monterosso and Riomaggiore for 2 nights...which village is "better" to stay in...we would like to relax, hike, hang out by the water, etc....Or should I keep looking...lots already booked...

As well as after we leave CT we plan to take train to Siena and rent a car...for 3 days then take train to Rome...would you recommend having Siena as the "base" in Tuscany or other places...we want countryside, wine, photography, relax, thoughts on that too would be appreciated.

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