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Need help for Lake Como and Cinque Terre, Italy

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Four of us (late 60's and fairly fit) are planning a trip in 2017 to Milan, Lake Como, Cinque Terra, and Venice. I'd love to get your help in planning this awesome trip.
1. Which month would be better--May or September?? (we're flexible on the dates)
2. What city in the Lake Como area would be the best base for 3-4 days?
3. What village in the CT would be the best base for 3-4 days?
We definitely want to ride the ferries/boats on Lake Como and see as many sights as possible. We like to walk but are not interested in strenuous activiites (indulging in a second dessert is my idea of strenuous).
If you have any favorite sights or places to stay, I'd appreciate your input. We hope to travel by train and not have to rent a car. Is that possible/practical? Thank you!

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