Trip planning, advice welcome

How many days will you be on your trip? My first thought it that you have a lot of locations with long transportation time between them. If you want downtime within your vacation, that will require even more days. Your response to this question will help all of us give you better advice.

Moving between locations will take a minimum of half a day, including checking in/out of hotels. So, you will want a minimum of 3 days in Paris to have 2 1/2 days to see it, etc.

Absolutely fly into one location & out the other to gain that extra day you would have spent backtracking.

How much time are you allotting for this, at least 2 weeks I hope. Cinque Terre and Amalfi during late December would be a waste IMHO. So London to Paris (Eurostar train), then fly (Air France) to Florence (day trip to Lucca), then train to Rome. Fly home from Rome. That would be a sensible trip for 2 weeks.

Sorry, amount of time would have helped huh? We are looking at 3 weeks, roughly Dec 14-Jan 5.
As for the amount of time in each place, something like (nights): London 4, Paris 4, Florence 3, Pisa/Lucca 1, Cinque Terra 2, Rome 4, Sorrento 2, Rome 1 before flying out.

The "downtime" I expect will be in in Lucca/Cinque Terra/Sorrento areas while the other spots involve more sightseeing.
As a side point, our plan is to mostly airbnb rather than hotel.

When will you be in London? It shuts down - including virtually all transportation - into the evening of Christmas Eve, and right into Boxing Day; some central London transportation returns on Boxing Day but very few trains, and the town is basically asleep until New Year.

Nigel, the London portion would be either at the beginning or end of the trip, so hopefully miss most of the shutdown you mentioned. Thanks for the heads up.

Ron, good suggestion. I'll take another look at flights & figure out if reversing our trip makes sense. Any suggestions on places to visit are great too!

For Ron & Sam, the Lucca/Pisa portion is def optional and since Pisa is a brief stop off the train while passing through, it could mean a day or two additional elsewhere. Since my wife fell in love with some friends' photos of CT and Amalfi, I'm not sure I will win that battle, but we'll see.

Thanks everyone for the comments!

One important point to mention is that the Cinque Terre is NOT a good destination over Christmas / New Years. Many of the tourist related business shut down in about November and don't re-open again until about March. The place will be pretty much deserted and you may not even find any restaurants open. Best to stay with the larger cities at that time of year.

Yes, it absolutely makes sense to fly into one area and out from another. Those are called "open jaw" flights.

As this is your first trip to Europe, I'd suggest reading Europe Through The Back Door prior to your trip, and also have a look at the RS guidebooks for each place you're visiting. That will help you plan the sightseeing that interests you the most.

Ken, thanks for the thoughts. Since it is on the list to at least see, maybe a day/single over night would work. We're perfectly happy getting food & wine to just hang out in a room and enjoy the sights & smells, just relax. But it's a good point about not much being available to do or see. Maybe a return in warmer months would be a better plan...

The Cinque Terre are very pretty when the sun is shining. The likelihood of getting that kind of day in December is not all that high. The beautiful views are from the trails (which could well be closed if they are muddy or slippery or have been damaged by winter weather), and from the ferry which doesn't operate when seas are rough. You will use a lot of time traveling to/from the CT. It really isn't worth it.

The Amalfi Coast will be fine. There's plenty to do even in poor weather. Sorrento is the best base for a short stay. Add the 2 nights from the CT to the AC. It takes 1/2 day to get to Sorrento - it's just not worth going for less than 3 nights, and 4 is much better. Go straight from Florence, then spend the end of your trip in Rome.

And visit Lucca and Pisa as day trips from Florence. As a long-time lurker, you know changing hotels takes up a lot of sightseeing time.

Hello thecatalyst2001. You asked for suggestions of places to visit. At London, I recommend going to these places (if they are open the days you will be at London) --
First whole day in London : St. Paul's Cathedral, Museum of London, church of St. Bartholomew the Great.
Second whole day in London : walk by Big Ben Bell tower and a side of the British Parliament building, enter Westminster Abbey (church). (Admission to Westminster Abbey for tourists is expensive), walk along Whitehall Street to the place where the Queen's horse guard parade starts (be there at 11:00 a.m.), eat lunch at an eatery located near Trafalgar square, walk into three or four rooms in the British National Gallery (of Art).
Third whole day : day trip from London to Windsor Castle (a palace of the royal family) if it is open to the public. And walk through the town Windsor. Ride in a train from Paddington railway station to Windsor and Eaton central station (change trains at Slough). That train trip does not take a long time.

Let me deal with some of your specific questions --

Does it make sense to fly into one area & out from another?
We always fly open jaw. Generally it cheaper, especially when you factor the cost of returning to your starting point, more convenient and big time saver.

Any concerns with winter train travel?

Sure - ice storms can really screw up schedules since all of the trains are electric and when the ice builds up on the over head lines it is a problem. Probability is low but it can happen in the winter. Have encountered it a couple of times. You just go with the flow when that happens. Generally just causes some delays.

Without knowing your exact time line, hard to evaluate your schedule. On the surface it appears that your schedule is too much for one or two week period. Cterra, Amalfi coast at best seen sometime other than winter. And London and Paris can be a little tough in the winter. Might consider Rome and southern Italy for winter.

I would forget Cinque Terre over Xmas/New Year, and visit Venice instead. Finish with all your Rome time at once.

Dec 15 London 4nts
Dec 19 Paris 4nts
Dec 23 Venice 3nts
Dec 26 Florence 3nts
Dec 29 Sorrento 3nts
Jan 01 Rome 4nts

"maybe a day/single over night would work. We're perfectly happy getting food & wine to just hang out in a room and enjoy the sights & smells, just relax."

The important point to note is that a "day/single over night" probably won't work as the hotels will be closed. Therefore you probably won't be able to find a room to "hang out" in. The towns themselves are the attraction and there are no Museums or galleries, so there would be nothing to do. Especially at Christmas time, the locals will be busy with their traditional celebrations and likely won't be interested in dealing with tourists.

Visiting the Cinque Terre in the warmer months would most definitely be a better idea.