I was in Cuba summer 2001.
I am an outlaw, sinner, pinko leftist, liberal, heathen, and example of the moral decline of our God fearing nation!
But boy oh boy did I have a ball in Havana!
The best thing for you to do is go through Toronto or Cancun.
From Toronto (YYZ
) you have a 50/50 chance of getting a cheap A320 or a magnificent IL
Here is a website that tells you everything you need to do in terms of getting to Cuba.
I used their services.
You need to have a passport to show before entering the country. You could request that your passport not be stamped or staple an extra sheet to your passport for them to stamp. Then rip it out as you leave Cuba.
Your friend from Pakistan shouldn't show his U.S. passport while entering Cuba.
Bring an old extra suitcase you want to get rid of and put lots of bottled water, condoms and clothes you don't want in it. Mainly sandals, shorts and t-shirts you don't want. You can use those to barter and exchange for dinners and tours from the locals. The drinking water may not be good for Americans who haven't had all of there shots. You will get thirst in the hot humid climate.
I am sure you'll know what to do with the condoms.
The rates go from $10-$20.
Hotels are cheap and so are the restaurants and bars.
You are going to have a great time!