Some US rides I've done over winter months include:
- Key West, FL to Savannah, GA
- Brownsville, TX to Dallas, TX
- "The Christmas Ride" in San Diego
- One lap around Big Island of Hawaii

This year my plan is to drive myself one way to Brownsville and spend a week slowly getting myself back to Austin by way of the Rio Grande valley. Southern Texas can be occasional hit and miss - with 80F temperatures or a freezing ice storm. Not real winter like those of you in north, but still enough that I'll keep some flexibility in my schedule if I decide to take a shorter ride one or two days.