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Porto Ercole and what else?

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I am planning a trip for a 4oth anniversary end of June first week in July. Approximately from June 29th (arrival date) to July 7th departure date, 7 nights. I have been to Italy ( Rome, Florence, Venice, Lake Como, Milan, Perugia and one more town in tuscany.) That being said I would go back to Florence or Venice in a heartbeat ( actualy all of it!). My question is this:
Should we fly into Rome and spend most of our time in the Monte Argentario area or
Star in Venice, train down to Sienna and than on to Porto Ercole?
I am not sure if we spend the whole time in Porto Ercole which sounds fabulous if it is enough just visiting the small nearby towns and sites. I want to stay at Il Pelicano. I know it is over the top but this is special!
If anybody has any suggestions, recommendations it all would be appreciated.

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