Glad you enjoyed your trip.

If you travel on a "Support for the Cuban People" OFAC reason for travel, though, which implies that you will support independent Cuban business people, why put money into the hands of an American based company (AirBnB)? If prices are the same, as you write, the Cuban business is getting less since AirBnB takes a substantial cut. (Also for a time, maybe even still, AirBnB were not paying hosts in a timely manner.) As far as "carrying extra cash", a casa is $30 per night x 7 nights is $210., nbd IMO, and it helps the private economy and promotes.closer friendships dealing personally with hosts in this way. (I am comfortable carrying big cash in other parts of the world though, and have never had a problem over decades of doing so.) Cuban businesses don't usually give receipts, and the chances of getting audited, as you said, is pretty much nil.

Here, for any future readers, is a list of CUBAN casa agencies. Very easy to use one of them. I have had good experience with Cuba Junky and my repeat host likes working with them. Some of them have European billing, so you can use your US based credit card to pay in advance.
However, your initial host can help you find a comfortable casa in your next stop.
Casa Agencies
http://www.tour4cuba.com
http://www.casasdealquilerencuba.com
http://www.alquilerencuba.com
http://rental.point2cuba.com/
Websites to help find Casas in Cuba - Cuba - Debbie's Carribean Reviews Forums
Cuba-Junky - All About Cuba Traveler's information and Reviews
http://www.casasdecuba-en.net/
casa particular cuba .org - Casa Particular organization for renting private rooms in Havana and all Cuba
http://havanacasaparticular.com/
CasaParticular.org - Organization of casas particulares in Cuba - Online Bookings
https://www.mycasaparticular.com/en/
http://www.cubaccommodation.com/
bedincuba.com
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http://www.casaparticular.com
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http://yourcasaparticular.com/
Casa Particular Cuba 2018 ~ Stay in a Casa Particular Havana and all Cuba with CubaParticular.
www.bbinnvinales.com
[email protected] (Dalia)
www.Cubabookingroom.com
www.cubacasas.net

Bucking US sanctions, American Airlines expands flights to Cuba
22 May 2019

American Airlines, the leading international carrier serving Cuba, said Wednesday that it intends to offer additional flights to the island despite moves by the United States to tighten its economic embargo against Havana and further restrict travel between the two countries.

Early this month, President Donald Trump's administration activated Title III of the Helms-Burton Act, a 1996 law that intensified the embargo the US imposed in 1962.

https://www.efe.com/efe/english/busi...000265-3982716

Any of us can make guesses about the impact Bolton's recently-announced travel restrictions will have on Americans visiting Cuba, but AA is putting real money behind its guesses. The airline seems to be guessing that there is less here than it might appear.

Seeking advice on Cuba itinerary
 

My wife and I (Americans) and another couple (Brits) are planning a trip to Cuba in late February. Due to work schedule restrictions, it will only be for six nights/five days (though perhaps an exploration for future visits). We'd arrive in Havana from Miami at about 5 pm on the first day and fly out to San Francisco (via San Salvador) at about the same time on our last day. We wouldn't be staying in any resorts, but rather casas.

This would be our first visit to Cuba. We're mainly looking to experience the culture, meet the people and learn more about the country in our brief time there. So getting to a beach isn't a priority unless it somehow fits into those priorities. We all speak a bit of Spanish to varying degrees. Given our backgrounds in international development and journalism, we've traveled to many other countries (including in Latin America and the Caribbean), but we realize Cuba is unique in some ways.

With all that said, we're thinking of the first three nights in Havana, and the last two in Pinar del Rio, most likely in Vinales, due to it being just a few hours away, the scenery there and other nice things we've read and have heard about it from friends who've gone there.

So, some questions:

1. Would it make sense to spend the first three nights in Havana and the last two in Pinar del Rio, most likely Vinales?
2. If not, any other recommendations on the timing or other places to go?
3. If we do go to Vinales from Havana, best to book a car ahead or just arrange a taxi when we leave Havana?
4. Same question as #3 , to get from Vinales to the airport on the day of departure?
5. The way the schedule could work out, we'd be in Havana a Wednesday through Sunday and then in Vinales Sunday through Tuesday. Am I correct in assuming that this works out well in terms of Vinales possibly being a bit less crowded then as opposed to the weekend? Any particular reason to try to be there over a weekend?

Of course, any other advice and suggestions are very welcome. Thanks.

Have you read the wiki for this thread? As I understand it, you are flagrantly violating the law. Many of us enjoyed self-licensed, people-to-people exchanges during the prior administration. While hardly an expert on the subject, I would consider the itinerary described above (solo, extensive travel within the country) to be a flagrant violation of even the prior regulations.
As indicated in the wiki: American citizens are required to maintain a detailed diary, detailing all activities, how they conform to current regulations, subject to Treasury Department audit. If you are serious about attempting such a trip, I would avoid online message forums, find a real expert who can advise you how to avoid substantial fines, CBP issues when attempting to return to the US - or at least understand the risks before proceeding.

Thanks very much for the reply and the cautions it contained. Especially given our professional backgrounds and interests, and other qualifications I didn't bother to put in my original post, I'm less concerned than you are about current regulations and about posting questions regarding potential Cuba travel. Perhaps I'm missing something, but in reading the wiki and post #153 , I'm not seeing the regulations as being changed in ways that would preclude our travel or put us in a position to fail potential post-travel audits, should those really occur. But still, with new regulations still to be promulgated, it is certainly something to keep track of.

And if I'm in fact missing something that precludes such a trip, I'd welcome more information on that. I will seek it out independently of FT, of course.

There have been threats, for political reasons, by the Trump administration, but not to worry. You will be fine. I travel to Cuba often, and am always greeted with a nice "welcome home" by the U.S. immigration authorities when I return (with rum and cigars!). I could expand on this, but just get yourself a good current guidebook and any fears you may have will be allayed.

On your questions: Your itinerary looks just fine. Definitely Vinales. I recommend however that instead of a casa you book the Hotel Los Jazmines. It sits on a promontory overlooking the valley of Vinales, fertile tobacco fields, and the beautiful mogotes (look this up). The views from your room balcony will be surreal. The hotel has a pleasant swimming pool, small store, excellent concierge who an arrange a horseback ride--CUC 5 per hour, riding through the countryside with stops at a local tobacco plantation/cigar operation and a pina colada). The hotel food is mediocre, but there are excellent private restaurants just a short walk away, also overlooking the valley and in a jungly setting (La Terraza and Balcon del Valle are my favorites--ask the concierge). BTW, the concierge, a lady, is married to a taxi driver (his name is Hornan, accent on the a) who, for 40 CUCs or so, will give you an excellent guided tour of the principal sites (look them up in a guide) in his 1952 air-conditioned Chevy.

Your casa host will surely have contacts for transportation from Havana to Vinales (should cost more or less 120 CUCs). There is also a "conectando" bus, state of the art coach, from Havana to Vinales. They pick up at hotels, and surely you will be close to a hotel (14 CUC/person Hav-Vinales) If you arrange for a driver instead, you could use the same person for the return, or again, the Jazmines concierge can arrange for your transportation Vinales-Airport on the last day.

Thanks very much for this useful info and much appreciated advice, catcher1.

A few more questions:

No sooner did I post my original questions than our friends (i.e., the other couple) asked about spending the nights this way:

Two in Havana
Three in Vinales
One in Havana

One thing I forgot to mention in my original post is that our friends will be flying to a different destination (to be determined, but likely in Florida or somewhere else in the eastern USA) than San Francisco at the end of the trip, so it's possible that they'll need to spend the last night in Havana to catch an early or mid-day flight the next day.

That factor aside, any particular reasons for or against splitting the nights evenly between Havana and Vinales, in the ways they suggested?

My approval of your travel directly from Vinales to the airport presumed a 5 p.m. flight. Under your circumstances though, your alternative plan is fine--although splitting your Havana stay could create a problem for your casa. And BTW, I'd stay at a hotel in Havana, and I recommend the Hotel Sevilla, which is a historic and colonial but very comfortable hotel, well placed in Habana Vieja where most of the attractions are located, with live music playing throughout the day in the lobby/bar area. If you prefer a casa, look for one in the Habana Vieja neighborhood and not the modern Vedado, so you can walk around to the major sights.

Forgot to mention: I think two nights in Vinales is plenty, and Havana has sooo much to offer. Perhaps you can do 3-2-1, or 2-2-2?

Too much to experience in Havana on a first trip to spend more than overnight in Vinales.
But I wouldn't want to be driving to the airport from Vinales on the same day as departure flight either.

Thanks a lot for this additional information and advice, folks. I need to run this by our friends, but I think we'll indeed spend the last night in Havana and split Havana/Vinales 4/2.

Hotel Sevilla looks very nice, but beyond our friends' budget. In addition, I'm under the impression that staying in a casa, in addition to being more affordable, brings us more into contact with very nice and helpful hosts. Please correct me if I'm wrong about that.

That's ok, but look for a casa in Habana Vieja, close to the major attractions, and you won't have to be taking taxis all the time.

Well, first of all, you seem to be from the US. You will likely use the OFAC reason for travel Support for the Cuban People, as most do these days. That reason implies that you will be on a "full-time" schedule of activities that put money in the pockets of independent Cuban entrepreneurs. Hotel Sevilla, or any other hotel, is hardly an independent Cuban entrepreneur, so how would you legally or morally/ethically justify spending money there in lieu of a casa? And secondly, yes, from personal experience, staying in a casa gets you the knowledge and help of a local, and most interestingly, adds the opportunity to get to know the life and perhaps the thinking of a "regular" Cuban family. Just don't expect much luxury unless you lose part of those benefits by staying in some foreign-funded (US relatives or foreign spouse who have access to higher quality imported home furnishings) fancier private apartment just serviced by the owners.