Bsides swimming (just kidding) I think you can get a plane in Montego Bay to Cuba. I've heard that you pay the Cubian Immigration not to stamp your US passport. Besides that I don't know much more...

I'm not an expert at US citizens going to Cuba but I've been there twice from Canada and the officials didn't stamp my passport either time.

You can get special permission if you are a journalist, student, researcher, etc. to go from the US, otherwise you have to go from another country. You can go from canada or any of the Caribbean islands.

Be aware that once you enter Cuba in that manner as far as the US goes you don't exist. They supposedly do not stamp yoour passport and there is no record of you being there. If something happens to you while in Cuba you are up the preverbial creek.

I read in the travel section a few months ago that the spending restrictions are pretty rigid too. I think you are only allowed to spend $100 a day in the country and this includes food, lodging, and whatever you buy.

In order to travel legally to Cuba from the US, you have to obtain a waiver from the Department of the Treasury Office of Foreign Assets Control. You can only do this if you have family in Cuba, are a journalist or an academician with a very specific purpose for going to Cuba (i.e. a conference). Occasionally, the US makes exceptions, such as when the Pope visited Cuba. Once there, you can spend no more than $100/day, which includes food and lodging. No, Cuba won't stamp your passport. However, if if you get in trouble in Cuba, the US has no authority to help you. Also, if it is found that you have travelled there without a waiver, you can be fined thousands of dollars and jailed. That is because 1) you had no authority to be there and 2) it will be assumed that you have violated the economic restrictions.

Simple:
1) Read The Lonely Planet guide book for Cuba
2) As the book suggests, arrange your flight into Cuba from either Toronto, Canada or Cancun, Mexico.
3) Also as the book advises, they don't stamp American passports "so Uncle Sam is none the wiser"

There is some incorrect information on the above replies.
The best thing to do is go to the U.S. Treasury Deptartment's own page that lists the latest regulations on CUBA.

http://www.treas.gov/ofac/t11cuba.pdf

It is NOT illegal to go to Cuba, but travel is restricted. Most travelers need a license or exception, UNLESS you are going for educational, professional or humanitarian reasons in which case you do NOT need a license. If you are going purely for tourism, you may be denied the license.

Others are correct, however, in saying that you can go from Canada, Mexico, the Bahamas or elsewhere and ask the Cuban officials to not stamp your passport.

It has been widely publicized in the last few weeks that there is a new cruise going to Cuba that US citizens are permitted to take. It departs from the Bahamas, I believe.

Check dogpile.com or any newswire search under "Cuba" and "cruise".

going to Cuba as a US ciizen is no problem for the Cubans. They do not stamp your passport and you do not have to pay them for that.
from Fl., the best bet would be to check out the Bahamas. I know you can get there from Jamaica or Grand Cayman very easily. It is a great island to visit.

ARE YOU REALLY HELD TO $100/DAY WHEN YOU ARE IN HAVANA. PLEASE REPLY. THANKS.

held to that by whom? when I was there, no one checked how much I spent. we did buy some local art and they checked how much of that we bought when we left the airport. they do not want too much of that taken out, I guess.
you can live quite fine in Cuba on $100.00 a day if they do hold you to that. Things are not expensive.