Actually, this used to be a requirement (Bush era). My wife, who takes Americans to Cuba, had each passenger keep a detailed diary of the day's activities (not expenditures), which corresponded with the detailed itinerary she prepared for them to comply with the U.S. Government restrictions on travel activities. Over the years, several travelers were asked for their records by U.S. authorities of various sorts (e.g., Global Entry applications).

AA has some good fares this summer. I'm seeing ORD-HAV-ORD $340 RT in Y, and $650 in J. I'd like to be able to take advantage of that.

I know the Grand Hotel Kempinski Manzana is on the restricted list for US Citizens.
However, I'm a bit confused about the provision below. Does this mean if I prepay a travel agency not on the list for a night's stay at the hotel rather than the hotel directly, I'm not in violation of OFAC's rule?

Section 515.421 of the CACR contains an interpretive provision for incidental transactions where OFAC has clarified that authorized transactions ordinarily incident to licensed transactions exclude direct financial transactions with such entities and subentities if the terms of the applicable general or specific license expressly exclude such direct financial transactions. For a complete description of the scope of the interpretive provision and the restrictions and exceptions that apply, see 31 CFR § 515.421. [09-06-2019]

There is a "third party" factor. For example, there is a brand of rum that Americans are not supposed to buy from the manufacturer. However, if it is purchased from the corner liquor store, no problem. So perhaps that can be applied to booking and paying for hotels through an agency.
However, IMO, the issue is not so much being in violation of OFAC's rule, but a moral one. We Americans who are traveling to Cuba on the "Support of the Cuban People" reason for travel should indeed be doing so, maximizing the support by staying with a Cuban family in a casa particular, getting to know them and encouraging their entrepreneurship. If you can't see that as an essential factor of your trip to Cuba, (IMO) pick another destination.

No matter what the ownership or management of the Cuban hotel you stay at, you are supporting the hotel staff by staying there — ordinary Cubans. I don’t see any moral difference in staying at a hotel or a casa particular.

I fully agree. The Cuban people are in dire economic straits, principally as a result of the U.S. blockade as well as actions and threats by the Trump administration that chill Cuba travel by Americans. To purchase just five liters of gasoline, there are waits of three and up to four hours. There are food scarcities, even of essential products, especially in the provinces. We should encourage Americans to travel to Cuba, for a wonderful experience and money spent that helps the Cuban populace.

But how much of the cost of your stay is actually going to the staff, and how much is going to the military/governmental ownership or management? If you stay at a casa particular, essentially ALL of your money is going to "ordinary" Cubans.

Not necessarily; many of the properties are owned - at least indirectly - by family in the US, who are also often involved in the reservation process, take some portion of the rent. All private enterprise is also heavily taxed by the government, local party representative may also get a cut.

We too stayed at a casa particular, I am all about supporting private enterprise, but it is still a communist country, there are many interests benefiting from such business activity.

Well, not all of the money (commissions and maybe some other reductions), but you're right that more of the money would go to the casa particular owner than would go to the staff at the hotel. Sill, hotels are very labor-intensive operations. I don't think the difference is ultimately stark enough to make this a moral dilemma for the traveler intent on helping ordinary Cubans.

Guide advisable for going outside Havana?
 

As I'd previously posted, my wife and I and another couple will be in Cuba in late February/early March, for four nights in Havana and two in Vinales. I just received this email from that other couple: "Some friends came over yesterday who toured Cuba in 2017. Their opinion is that even for a short trip out of Havana it’s best to hire a guide; that even simple tasks like getting a taxi, locating the casa you booked etc are very difficult when you try to do it as a non-Spanish speaker etc."

Do you agree? For what it's worth, we're all pretty experienced travelers who generally don't use guides and we speak a smattering of Spanish. We'll be staying in casas particulares in both places.

Thanks for any advice.

The Support for the Cuban People OFAC reason for travel specifically mentions supporting independent Cuban entrepreneurs (cuentapropistas), like owners of casas particulares, by giving them your business as a part of a "full-time" schedule of support. The point is to foster an understanding that the capitalist system works, even in Cuba.
OFAC regs mention NOTHING about employees of hotels owned by the government in partnership with a foreign entity (as most are) qualifying under support from US based travelers..
So yes, it is a moral issue, and in the (unlikely) event that an audit were done on any traveler in future, possibly a legal one.
As I said before, Cuba is unique. If your primary preoccupation is your own
comfort on a tropical vacation, over contact with the Cuban culture, find another island that will cater to you.
__________________________________________________ ____
Guides:
"four nights in Havana and two in Vinales"
There are lots of guides to take you around Havana, although you can just as well jump in a taxi to wherever yo need to go or walk to many places. There are regular taxis or classic car tours/rides.Try Strawberry Tours for free walking tours (tip the guide afterwards) in the historic neighborhood(s) and some other paid tours. Get yourself a good guidebook at home. I recommend "300 Reasons to Love Havana" to start with, to decide your priorities. ( )
As far as getting to and from Vinales, that is another advantage of staying in a casa. The owner will undoubtedly have a friendly taxi driver in mind, who can get you there at a reasonable price. Your casa owner in Vinales can arrange for the return trip. Most classic cars are not so comfortable, but some have been done over very well, have air conditioning, and would hold 2 couples and luggage comfortably on such a trip (several hours). You can ask to stop at Las Terrazes for lunch and a swim in the river on the way. Or there is a bus.
You don't have to be fluent in Spanish to get around. Cuba is also very safe, so you don't need a pseudo-bodyguard either. Some people like to have their hands held though. Not at all a necessity however.
And yes, maybe a taxi driver from Havana also has to ask for directions to a certain address of a casa in Vinales. No big deal.

Thanks very much, VNP! Great info and advice.

My wife and I travelled throughout Cuba as independent travelers in February 2019. Part of our trip covered the same itinerary you posted about. We had the host of the AirBnB we were staying at in Havana arrange for a taxi to take us to our next AirBnB stop in Vinales. He got us a ride with a friend of his who happened to be a 65+ year old couple. The man usually runs the taxi by himself but it was Valnetines Day so he had his wife come along. Taxi was a mint condition 1955 Chevrolet with a new Mitsubishi engine and ice-cold air conditioning.

WIth the help of Google Translate on my smartphone, we were able to converse on the long ride. As it was Vanetines Day and near lunchtime, I offered to treat them to a lunch if they knew a good spot to stop. We ended up having a delicious lunch at an open-air restaurant in the middle of nowhere. Valentines Day is a big deal in Cuba so the place was packed with couples wearing their best suits and dresses.

The taxi driving team took us right to our casa particular in Vinales. Through AirBnB, we booked some excursions including a wonderful horseback riding adventure in Vinales. Here's where we stayed in VInales: https://www.tripadvisor.com/Hotel_Re...ince_Cuba.html Wonderful place, super friendly hosts and delcious breakfast. The casa particular host also set us up for a taxi back to HAV airport when it was time for us to head home.