Florida to Oregon in 2007
Join Date: Oct 2005
Bikes: LeMond Buenos Aires, Trek 7500, Scattante CFR, Burley Hudson
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Don't worry about the winds. They will be headwinds no matter which option you choose. Yes, the prevailing winds favor the west to east routing, but trust me, the local weather pattern that you encounter is the only thing that matters. Having just done the southern tour last year, west to east, beginning in mid March, your plan sounds good. Either direction is fine.
The route to San Diego will be mostly desert/high desert until you get to the mountains near San Diego. Lots of stuff to see and there will be other riders on the route as well.
The route to El Paso will put you into the mountains first and then flat lands to finish. If it is really cold/snowing in the mountains you can depart from the route at Safford, Ariz and head to Lordsburg, N.M. Or you can bail out of the mountains and go south to Deming as another option. You can use I-10 to get to Las Cruces for these options.
The Adventure Cycle maps are good assets for the trip. One map covers San Diego-Phoenix and a second map covers Phoenix-El Paso.
Good Luck and have a great ride.