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4 Days in Tuscany in mid October for Honeymoon

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Hello, I am starting to plan our honeymoon (I will be 34, my wife to be 30) for October, 2013, and is our first trip to Tuscany. Starting to do my homework, and just overwhelmed with the possibilities in Tuscany.

We will be arriving in Florence on Monday morning. Our plan is to decompress, relax, enjoy the wines and food of Tuscany, and explore the Tuscan country side for 4-5 days before heading to Venice. During these 4-5 days in Tuscany we will NOT be going into Florence, as we are going to return to Florence after Verona.

I am thinking of spending our first night (Monday) just outside of Florence in Bagno a Ripoli at Villa Olmi as would be a good starting point for Tuscany. We would go directly from the Florence airport to Bagno a Ripoli. This way we could relax after our flight (coming from NYC) and enjoy the grounds and get our bearings.

Our ideal time in Tuscany (Tuesday-Thursday or Friday) would be spent exploring (we will rent a car) the countryside, stopping at small villages/towns, enjoying the vistas, wine tasting, olive oil tasting and enjoying the food.

We definitely want to visit Siena and Greve and do a Chianti tour. I expect that we stay in at least 1 (possibly 2) other hotels during our time in the Tuscan countryside as it is too big of an area to have just 1 home base.

We are not the type of people that like to have a concrete itinerary where we have to stick to a schedule and can't spend an afternoon sitting at a cafe or wandering thru a small town that we discover. Basically, I am trying to get a rough idea of itinerary suggestions - restaurants, vineyards, towns, etc.

A loose itinerary I was thinking was the following:
Monday and Tuesday nights staying in Bagno a Ripoli
Wed night stay in Cortona
Thurs and Fri nights stay in Siena

Sat wake up and drive from Siena to Verona (or drive from Siena to Florence, return the rental car and take the train to Verona).

Does this itinerary allow us to immerse ourselves in the Tuscan countryside and experience some of the countryside without too much travel?

Would you recommend taking a tour or just doing everything on our own (with rental car)?

Would you recommend leaving rental car in Florence and taking train to Verona or to drive from Siena to Verona?

Sorry for the length of this post - but it is overwhelming planning to see and experience just a small part of the Tuscan countryside. Thanks in advance for taking the time to read this and to offer your suggestions!

Ryan

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