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Family winter holiday

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We are a family of four adults from SEA country planning to have holiday in USA from the third week of December for 16 days (excluding the international flying time).
Our arrival is in San Francisco and departure from Chicago.
We would like to go to San Francisco nearby area, maybe Sausalito, Napa valley also Lake Tahoe if possible then take California Zephyr to Colorado (stop at Glenwood Springs or Denver). We want to visit a Christmas picturesque/winter wonderland town and would like to try skiing.
Boston & New York are in our mind too if time permits (and worth for this trip).
We prefer to use public transportation instead of driving in the mountainous snowy area if possible since we are not used to it.
We are looking forward to have any suggestion for our itinerary so that we can enjoy the trip.
Thank you.

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