Whether it is safe to drive from Denver to Breckinridge in winter depends entirely on the weather that day. In good clear weather, no problem.

Second option: Fly to SLC and then take the CZ through Ruby Canyon (in coach) to Glenwood Springs. If on time it is in Glenwood about noon. Take the Roaring Creek bus line up to Aspen.
Whether you take the California Zephyr east from Glenwood Springs or take the Bustang is up to you.
I would not try to fly to Glenwood Springs (Aspen).
Vail is served by the Bustang. Winter Park/Fraser is served by the train (daytime arrival).
Ruby Canyon and the Glenwood Canyon (east of Glenwood Springs) are the most scenic spots on the California Zephyr route IMO.
There's plenty to see in Chicago without going outside the city.

Hi,

You can easily fly into Glenwood Springs via the airports at Vail or Aspen. Some of the richest people in the world use these airports and these airports mostly only operate in winter when there is peak demand.

I have flown into Vail in wintertime, and it is a great little airport and I wouldn't think twice about it. My friends steered me toward Vail over Aspen--they like that airport better. So I can't help you with Aspen.

United Airlines and American Airlines both serve Vail. Sometimes tickets can be spendy, and that will be your only issue. I

You would need a shuttle or a car rental to get to Glenwood Springs. The ride from Vail was really pretty in the snow.

Here is a link to the airport:
https://www.flyvail.com

Here's a very extensive list of shuttles, limos and rides:
https://www.flyvail.com/parking-tran...es-limos-taxis

Hi, I realize I never addressed your itineraries and your question.

#1--It appears you plan to ski at Tahoe and skip Colorado. Makes sense, since you will be in California already. Stay 3 nights (2 full days of snow) or 4 nights (3 full days of snow). Skip either Boston or New York to make room for that. New York hotels are very, very expensive in December so for value, I would pick Boston, or more time in San Francisco and Chicago.

#2 Also doable. That seems more the speed of a vacation to me. You could add more "city time" in San Francisco or Chicago. (2-3 days of either).

#3 You will spend more time in airports than enjoying yourselves.

You asked about whether the roads to Breckenridge or Estes Park are treacherous. I really would encourage you guys to take shuttles since you are not used to driving in snow. Someone who is inexperienced in snow driving can spin out and end up in a ditch even in a "nontreacherous" spot.

>>1st option:
- We will rent a car from SFO
- Carmel? (1 night) <<

>>2nd option:
- Carmel? (1 night)<<

Not a good idea in either option. You are flying in VERY long haul. By the time you clear immigration, and collect a car you will likely be exhausted. But even if you are totally rested -- on night in Carmel merely to pack up the next morning to leave again makes no sense. Forget about Carmel/Monterey unless you spend a minimum of 2 nights there.

I love Sacramento (I live just outside the city) but you have very limited time I would not spend time there.

I wouldn't go to Napa either -- December none of the vines will be in leaf and vast areas of Napa/Sonoma are just beginning to clean up from the huge fires. You can do wine tasting in the Carmel area.

I would do Carmel/Monterey for 2 or 3 nights, then either Lake Tahoe or Colorado for skiing. Since you won't know the road conditions much ahead of time I'd personally choose Colorado since you can fly there (I LOVE Lake Tahoe but I have the luxury of deciding at the last minute whether it is safe to drive up.

I just reread the original post. I would.NEVER count on being able to ski in Lake Tahoe before Christmas, or really even until the middle of January. Been too many times when there’s been very little snow. May have plenty, may have none.

Really appreciate for all the suggestion.
Tomfuller, you said "I would not try to fly to Glenwood Springs (Aspen)". May we know the reason?
Between Vail & Breckenridge, which one is prettier and easier to reach by public transportation?
Thank you.

I hate flying into small airports and they tend to more expensive to fly to. If I'm not in a real hurry to get to a destination, I'll take a train or drive.
Tomorrow evening I'll be parking my 4WD at the Amtrak station and heading to Santa Clarita CA.
Vail is served by the Bustang either from Denver or from Glenwood Springs.

OP Are you spending NO time in San Francisco?
Tahoe skiing has now been ruled out for the time.
In Option 2--your are already IN Colorado ski country if you fly to Glenwood/VAil. Ski in that area at Aspen Highlands (not sure what the name is now but it is an EASY mountain and you could really enjoy it).
Then if you want to go to Denver, good. But don't go back to Breckenridge.
Otherwise, fly to Denver and go to Breckenridge.
Even if there is snow on the ground, unless it is actively snowing, driving to Breck would be fine.

Thank you Tomfuller for your info, yes the air ticket to Aspen/Vail is very expensive in Dec.
Therefore, we will fly to Denver then go to Breckenridge as suggested by Gretchen.

To answer Gretchen's question, yes 3 of us will spend 3 days in SF before 4 of us start our 16 days trip.

We are thinking to also skip Napa as suggested by janisj.

How does it look if we do:
-Sausalito, Sacramento, driving (2 nights)
-Carmel, driving (2 nights)
-Fly to Denver (1 night)
-Breckenridge, driving/public transport (2 nights)
-Boulder, Denver, driving/public transport (2 nights)
-Any suggestion for another place before we heading for 2 nights in Chicago? We still have 4 nights open.

We will only spend 2 nights in Chicago because we did visit the city some time before.

Thank you.

>>Sausalito, Sacramento, driving (2 nights)<<

Why???

Sausalito is just over the bridge from San Francisco so you can easily visit it from the city -- even by ferry.

Do you not want to see <i>anything</i> in San Francisco? I personally would not spend time in Sacramento in the winter -- use those two days for SF car-less to get over the jetlag, then go to Carmel/Monterey, then fly to Colorado.

Once again janis beat me to it - why Sacramento? It is backtracking to go east from SF area (Sausalito) to Sacramento, then drive west back to Carmel. It also used to get pretty cold there in the winter, my late husband has family in the area and we drove up after Christmas at least 3 times to visit them.

Sacramento isn't that cold by say midwest or snow country standards. But cool, often quite damp, and definitely the chance of serious fog. If it is going to be cool/wet I'd rather it be on the coast instead of in he Central Valley/Sacramento.

If you are going to ski in Breckenridge, it will take more than 2 nights. Please read my scenario of what it will take to get ready to ski in a post above.
NO to Sacramento.
Drive down the coast to Big Sur or Monterey. Drive up the coast to Muir Woods and Eureka. That will add a couple of days at least.
YOur days are too "compact". When you are flying there is a lot of lost time in airports also to factor in.

Agree with Gretchen on just about everything. And thanks to sf7307 for the snow season at Tahoe.

Most especially I would emphasize Gretchen's point about the number of days skiing. Plan on 3 nights/2 full days. Any snow sport takes time. Between getting gear fitted and taking a ski lesson that you reserved ahead and eating lunch, only one day on the slopes won't give you that much time.

If possible try to find a place in Breck (or Winter Park) to stay. Can you get a cancellable reservation soon? (Pay attention to the date you must cancel by.)

Here is why: The American holiday Thanksgiving is tomorrow. More Americans will begin thinking Christmas plans after tomorrow will also start reserving.

Hi,
Sorry we did not write clearly.

"Sausalito, Sacramento, driving (2 nights)" ---> It means we'll drive & stay there for 2 nights :)

Since it is backtracking & seems not the good timing to go in winter, we will skip Sacramento.

"Do you not want to see anything in San Francisco?" ---> we will have 2 full days after our arrival at SFO to enjoy the city before we start our 16 days trip.

We would like to have any recommendation for the good accomodation & restaurants in SF, Sausalito, Carmel, Denver, Breckenridge, Chicago.

Also, any suggestion in which town/city we need to rent a car.

Thank you.

Thanks all for the suggestion, it's really helpful.

We are interested in going to Muir woods, but is it good in winter?

Which places nearby SF (within 2-3 hours drive) that is worth to do/see before we fly to Denver?

Thank you.

>>"Sausalito, Sacramento, driving (2 nights)" ---> It means we'll drive & stay there for 2 nights :)<<

I understood what you meant and I responded with "why?" Now you are skipping Sacramento which is a good thing.

Now . . .

>>We would like to have any recommendation for the good accomodation & restaurants in SF, Sausalito, Carmel, Denver, Breckenridge, Chicago<<

You do not need accommodations in Sausalito. Sausalito is directly across the Golden Gate Bridge from SF. You should stay in San Francisco for about 3 days and visit Sausalito for a few hours on one of those days. You can take the ferry across.

What is your budget for accommodations? . . . it is pretty late to be looking for places to stay in SF, Carmel, and Breckenridge but you should be able to find something. However we can't recommend any places without knowing how much you want to pay.

Thanks a lot janisj for the info.

Our budget for the accomodation is about usd200/night room only.

In Denver The Crawford Hotel in Lodo is new and in the heart of Denver's Lodo district. Lots of restaurants and shops in the area.

Normally it's outside your budget but I just got an email from them and they are having a "Black Friday" sale. If you book within the next three days you might be able to just stay within your budget and get a very nice room:
http://www.thecrawfordhotel.com/denv...k-friday-2017/

We stayed there earlier this year and enjoyed it.

If that's too expensive then there is a Hotel Indigo, part of the Holiday Inn chain, that's just a few blocks and should be cheaper. There are a few other hotels nearby as well.