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Lake Como, CT & Tuscany

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We'll be celebrating our 40th anniversary with a two week Sept. trip to Lake Como (Varenna), Cinque Terre, and Tuscany. Flying into Milan, train to Varenna for 2 day/3night stay, train to Monterosso via Milan, stay in Monterosso 2 more days with not much hiking, but leisurely enjoying the five towns and Portovenere. (Why Monerosso? Because it seemed the fewest train and transportation transfers after coming from Veranna.) I'm considering adding another day in Monterosso for a day-trip with 1.5 to 2 hr. train ride going to Pisa and/or Lucca. This stop might also be made en route to Siena (probably train) but makes for a long day and luggage issues. I'm getting mixed opinions about Lucca and this seems like a lot of travel time getting there w/o actually staying and adding another hotel. Any thoughts on this? We're trying to limit the number of hotel changes since we'll have one more in Tuscany and the last night near Florence airport to catch an early flight. I'm also a little wary of the train system since we've only used it once when we recently visited lovely Verona from Venice where our cruise ship was docked. Unfortunately, we also don't speak Italian. But we managed years ago when we drove from Venice to Florence (3 days), saw the major sites in Siena on our way to Assisi and continued our trip with a white knuckled drive on the Amalfi Coast to Positano, back through Pompeii and ended in Rome. We always said we would like to spend more time in Tuscany and Siena. With a car we could possibly visit San Gimignano (Monteriggioni and/or Colle di Val d' Elsa on the way). Perhaps another day we would drive to Pienza and Montepulciano. Last year we drove through beautiful Provence enjoying many small towns, each with their unique characteristics. I'm sure Tuscany will be delightful as well. Any suggestions for this itinerary, hotels recommendations, would be appreciated.

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