This is primarily a question of logistics. It is not much more difficult to tow a trailer in winter than in summer as long as the weather cooperates. I would not want to be towing in a snow or freezing rain event however. We haven't towed as far south as Disney, but have a lot of trailering experience (we are in an HTT too), including cold weather travel.
Some of the logistical questions:
- Will you have access to your trailer to hitch it up? Where is it parked, and will it be snow bound? Ours is at a storage lot, and though the roads are plowed, the trailer is behind the accumulated snow bank from the plow.
- You will not be able to de-winterize until you hit warmer climate zone. So no water for a good chunk of the trip. (Making an assumption here as I don't know of any hybrids with heated underbelly and tanks).
- You will need to re-winterize before you hit colder weather. Are you prepared to do this on the road?
- Standard issues with border crossing (regardless of time of year), careful what fresh food you are packing, no firewood allowed, etc.
I did actually consider this once when we had our old pup camper, but decided that with the hassle and extra gas for towing that it would be easier to rent a trailer there, and then DW got a killer deal on a timeshare stay, and the end result is we've been doing timeshares ever since; still haven't stayed at FW.
One bonus - just think of the size of souvenirs you can bring back with a trailer in tow!
