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By the way... there's no weird paperwork, visas, etc. for you to visit Cuba.

All you require is your US Passport and a Cuban Tourist Card which you acquire right at the departure airport in Canada/Mexico/Caribbean/Central or South America. Sometimes it's included in the price of your ticket (Canada) and other times you have to purchase it (most other departure points.) Everyone on your flight will be doing the same, you can't board the aircraft to Cuba without it. No big deal.

Cheers,
Terry

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This topic has also been discussed here many times before, I suggest you do a search.

Also, if Nassau/Bahamas, we would have 2 1/2 hours in total to connect with the flight to Havana...Is this correct & if so, does 2 hours give us plenty of time to do this?

You will have enough time to get through on the way TO Havana. The problem is always on the WAY BACK. Whether your return flight leaves Cuba and arrives in the Bahamas on time is another thing. Chances are it will not, and if you live on the east coast of the US like I do, you will probably miss the last flight, depending on the number of flights you have to take. It takes me 3 flights from Havana to my home town, and on more than one occasion I have missed the last flight home and had to be rescheduled for the next morning. Spending a night in Nassau can be an expensive option, so I have spent nights in Miami, my connecting city.

Granted, it is not always Cubana's fault. On one occasion, US Customs in the Nassau was seriously understaffed, to the extend that the airlines sent staff down to the customs desk. They spent some time helping sort out people by departure time of their connecting flights to the US. Good luck!

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If near future means before March 2013 you better start making bookings ASAP.

I always recommend Cancun or Mexico City as the gateway to here.

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I fly from Canada every year and have not even seen a raised eyebrow at the US Customs re-entering USA in the last five or more years- as Terry and others say, a non-issue just buy the tix and go! Breath deeply and have a great trip!

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The best gateway depends entirely on where you're situated in the US.

Mexico usually offers the best options for west coasters and southerners, but if you're in the northeast don't ignore Canada. Last month you could fly New York/Toronto/Havana return for less than $850 all taxes in. Prices/routing/convenience varies wildly depending on where you're departing from in the US.

Cheers,
Terry

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Other sensible gateways include Grand Cayman - both legs on Cayman Airways, so less risk of a missed flight. (That connection is tight, but Grand Cayman airport is tiny.) - a popular route for Cubans with Spanish passports.

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Sincere thanks to all of you, ... your responses rocked!! : ) Quiet thorough Mr. Terry & very helpful (hats off also to bahaman, dMac, Jorge, & Beardo for all your inputs) since we came up on this as somewhat of a last minute idea & also happen to have finals week approaching next week.

"embarrassing and immoral piece of US foreign policy." Couldn't have said it any better myself Terry. I knew the Cuba side was not a problem, but have not been through Bahamas & just in case there was a delay out with our connection ... didn't know if we had to step outside the airport to a travel kiosk for the travel card, or just received it upon boarding ... thanks for verification.

Got a decent fare for less than month out. Just under 1k through Nassau from Northeast. Cancun was ridiculously expensive, $800 just for that segment plus flight from East Coast down (likely because of New Years wknd). Nassau quiet a bit more reasonable & although an expensive overnight, with two people, it was a significantly better price to overnight there & fly back on Monday. Surprisngly it was cheaper to fly out of a smaller airport nearby than NY or Boston as a hub.

Didn't mean to sound paranoid with the question ... but if you can relate, I grew up here as an "illegal alien" (can't think of a more Martian like labeling Lol) for 8 years during my upbringing in teen years. Being in the states at that time, I was even paranoid to go to a hospital when I got a broken nose playing winter baseball, no papers, no insurance, etc ... that type of societal behavior here, frames ideals in your mind when you have an arrogant government with arrogant international policies, who uses suppression of immigrants to keep cost of labor at what it is for those who do the brunt of our hard labor. In addition, with exception of N Korea, I have stamps in my passport from handful of other countries that we label evil, so wanted to get a consensus on here.

So deep breath it is DMac : )

Wish all of U a healthy new year in advance,
Peace

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Have fun !

Come back and tell us how it all went afterwards.