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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, explore...so thoughts on that too would be appreciated.

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