Travel to Cuba
I didn't fly via Canada, or Mexico, or the Bahamas just kind of wandered in there :-) When I flew back to Maimi, the Immigration guy asked where I had been. I said Cuba. He responded, 'Welcome home." It is not against the law for USA citizens to go to Cuba, it is against the Helms-Burton Act (from the 60's), which is an embargo, so not legal for US citizens to spend money there, with some exceptions. The USA actually has a large building right downtown Havana, not a consulate or embassy, but something called some wierd name like "Special Interests Office." As for the embargo, I spent time with a guy who worked for a Panamanian company that bought goods, like refrigerators, in the USA, shipped them to Panama, then to Cuba. I saw plenty of Jack Daniels on bar shelves. As for bikes though, nada. The same with parts, nada. There were a couple of bikes that came in by boat to Hemmingway harbor, and I met one guy on a big bike who got his in via the diplomatic pouch (French).
One night I was invited to spend the evening with the manager and one player of the Buena Vista Social Club. He drove a Mercedes when collecting me at my place, and had toured the USA three times with the band.
On the flip side, a BSA guy I met was dying for parts for his restoration. He had a good job, but no money. One Dr. I met made $30.00 USD per month.
It's a very strange place as embargos go, but doable, and doable by motorcycle. One just needs to think outside of the box of riding your own bike, or if you want to plan on a lot of work and possible big $'s to get it in. I'd go with the 50 cc rental and swallow my ego.
I wanted to go before McDonalds and Starbucks got there, and did, but they are lining up at the border.
Dr. Gregory W. Frazier
Professional Motorcycle Adventurer/Indian Motorcycle Racer