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I am aware of travel agencies catering to US citizens visiting Cuba, but are those services really worthwhile? If so, how does one go about vetting them?

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I know they charge large fees to exchange American money. You'd be best off changing your money to Canadian dollars before going down, even though we're above par with you at the moment. – Matthew Read Jun 21 '11 at 21:20
Could you provide more information about the services you're talking about and what services they provide? – Christine Letts Jul 7 '11 at 4:21
Unverified anecdote: I heard years ago from travellers in Mexico that it's not illegal for US citizens to visit Cuba according to US laws but that if you spend any money there it is technically "dealing with the enemy". – hippietrail Oct 5 '11 at 7:10

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I don't know about the services these agencies provide, but visiting from Mexico is fairly straightforward. All you need is a plane ticket. WikiTravel Americans in Cuba article provides more details and some of the risks involved.

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If you (or anyone else) would like to extrapolate from the information provided behind that link, that would be a great way to provide a much more thorough and interesting answer for this site. – Robert Cartaino♦ Jun 22 '11 at 18:00
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I think Americans who have been to Cuba, may be unwilling to talk about their trips very publicly. – user27478 Jun 25 '11 at 17:39
up vote 8 down vote

You don't need much to visit Cuba, most Americans get in via Mexico or another country in Central America and then just get the next plane.

Border control in Cuba will not stamp your passport, so there is no evidence that you have ever been there. Instead you have to fill out a Tourist Card, which allows you to stay in the country for 90 Days. Keep in mind that they ask for you hotel address on this card, so should have at least a booking for one night... or know a valid hotel address before you arrive.

gocuba.ca has more general tips for north-Americans visiting Cuba.

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For the tourist card, address of a casa particular is good too (way better value than hotels in Cuba). – Jonik Oct 4 '11 at 22:03
Even if your passport doesn't get stamped when entering Cuba, you still have the problem of getting a stamp when returning to the country you entered Cuba from. For example, if you fly USA-Mexico-Cuba-Mexico-USA you're going to end up getting two entry stamps into Mexico and when you return to the USA a clever immigration officer might wonder why you got two entries into Mexico without a stamp for another country in between. Two solutions are to ask Mexican immigration not to stamp you on your second entry or to have a passport so full of other stamps it's too difficult to tell what happened. – user27478 Dec 9 '11 at 11:09
up vote 5 down vote

My friend just went to Canada earlier this year and then flew to Cuba. No hassle, no tourist agency required.

Depends what sort of traveller you are, but I definitely wouldn't bother with an agency when there are such easy flights from other countries.

(Fun fact: the flight he was on was the first I've ever heard of that allowed smoking on board!)

However, he was a Kiwi. For US Citizens, I recommend Chris Guillebeau's How to Travel to Rogue States and other Interesting Places article:

Cuba – The U.S. embargo prohibits American citizens from going to Havana without a good reason. Naturally, this only applies to Americans, so everyone else can freely travel to Cuba. For its part, Cuba is happy to welcome American travelers, and in fact they’ll go along with the ruse by not stamping your passport if you ask upon arrival.

You can get to Cuba by:

a) Flying to Jamaica (or elsewhere in the Caribbean) and then taking Air Jamaica

b) Flying through Mexico (Aeromexico), Canada (Air Canada and several charter companies), or the U.K. (Virgin Atlantic and others)

c) Going through the process to get “permission” from the U.S. government to visit Cuba. This can be done through a university exchange, a journalist visa, or a few other approved exceptions.

As for me, I’m waiting it out because there are a lot of other places I need to go first, and since I come and go so often, I don’t want to get put on some kind of TSA terrorist list because my passport was scanned in Havana. Of course, if you’re not a U.S. citizen, then it’s not difficult at all to get to Cuba.

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Was your friend a US citizen? – hippietrail Oct 7 '11 at 21:01
to be fair, no, but if I was a US citizen attempting it I'd be wanting as little of a paper trail as possible ;) – Mark Mayo Oct 7 '11 at 21:03
I think you should mention that in your answer. I haven't been to Cuba but I've been in Mexico where travellers get to Cuba from, and the Americans were always pretty apprehensive about the implications where the rest of us weren't at all. – hippietrail Oct 7 '11 at 21:07
Primarily because it's 'illegal' for them to visit. I'll adjust though, as I've just remembered a link which may be useful. – Mark Mayo Oct 7 '11 at 21:09
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Asked! – hippietrail Oct 7 '11 at 21:15
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