If you go in illegally, and enter and leave through the same country, you're going to have extra pas

It was a great company, we stayed in Old Havana at what was then the Golden Tulip, I think it might be an Iberostar now. Once again wouldn't have been my choice on where to stay, too large and impersonal.
We went to Cuba with Insight last December and were there for New Years Eve. that is the very busiest time of the year. I also wonder how things will be due to the hurricane since some areas were destroyed. hot rod power tour We found the trip educational, the hotels they had us at were not good at all but we were not there to stay in a fancy hotel. hot rod power tour We were at the Nationale in Havana and it had lovely public rooms but the hotel rooms were early 1960's and marginally clean. Other hotels were not good at all. Meals were just ok. We were in a group on 2 busses of 15 each. One guide was exceptional and the other terrible. We felt it was overpriced, but we wanted the experience and we were glad we went.
That's disappointing. I was hoping Insight hot rod power tour would be excellent. Will start looking closely at other tour groups. They all seem to be overpriced. I would like to go in from Canada or Cancun but friends are nervous about us doing it. Anyone done Lonely planet or road scholar?
If you go in illegally, and enter and leave through the same country, you're going to have extra passport stamps for that country. Even though Cuba doesn't stamp your passport, if a sharp eyed Immigration official spots those stamps, you could have a lot of explaining to do.