travelmiss

I recently chatted with a friend about going to Cuba for a long weekend, 4 nights, in January or February as flights are so cheap from New York and it's been a dream destination for some time.

With the restrictions for Americans, I'm compiling a list of museums, day tours, cooking classes, salsa classes, etc. Do you have any specific recommendations for affordable educational activities, workshops, or tours to fulfill the requirements? I always love walking tours and I'm interested in art, food, music, and culture. I really WANT the required 1 on 1 cultural exchange, but without the confines of a formal tour group. Advice on how to achieve this?

We were hoping to go as a group of 3 or 4, but our travel hungry group of friends were also excited by the idea that it looks like 6 are interested. Is this going to be an inconvenient number for doing activities together? I imagine we'll need to split into 2 taxis to get around, but hoping a big group of 6 won't be obnoxious otherwise? We are all women in our late twenties. Two speak fluent Spanish. We plan on booking an AirBnB.

SambaChula

The requirements are a sham. Yes, you must choose one of the 12 OFAC categories on a form that the airline seems to be keeping, but no OFAC staff has inquired about proof in quite some years apparently. On return, the border staff are simply wishing travelers welcome home. So go do whatever you want that you can manage to set up.
IMO it would take the whole long weekend to even make the contacts you'd need to set up the kind of "tour" you are talking about. Maybe hiring a private guide (about 29 CUC per day) might get you around more efficiently.
AirBnB charges much more than the casa particular owner receives. Book direct through CubaJunky or similar site,
Best Cuba info is on the forum of Lonely Planet's Thorn Tree forum, with many posters who've been going for decades.
Have fun.

Lois2

For Americans (given the cash only situation) Air BNB is a very good choice...good feedback and availability usually accurate. A long weekend from NYC sounds like alot of fun with the nonstop flights now offered. Do check out the recent post on here by WelltraveledBrit...has a link to their planning and other important details....often if staying at a Casa with english speaking staff onsite they can organize some tours in advance including maybe a "classic car". No reason a well thought out long weekend could not be very fun. You can check out TA and Lonely P but many of those travelers seem to be less tourists and more visiting people etc. and I don't find the sites helpful..but of course check them out. It is really just as simple as booking the casa (in your case you will probably need something with 3 bedrooms) and then some tours with lost of time for wandering about. Good luck...and also I would suggest based on so many comments if you want to go to some of the better non government run restaurants you will need to get those booked in advance too...again Casa owners usually can help with suggestions and bookings.

SambaChula

Casas (including double bed room with separate entrance, and double with single in living room apt, which we had) run U$25-30 per night, paid in cash when there. Larger apt maybe slightly more, maybe 70. Not such a lot of "extra" cash to be carrying for a long weekend, to justify paying more to AirBnB to use credit in advance. Many cases owners speak English, so easy to communicate by email.
Rides in classic cars in Havana can be arranged on the spot. Casa owner can point out the central square where the nicest ones park and wait. Plenty of them. (Note this does not technically count as a people to people activity. )
There is also a hop on/off bus (actually 2 routes) that gets you around the city cheaply to understand the geography.
One night you might like the cannon firing at 9pm. There's a good jazz club with a killer virew of the harbor too. Rumba on Sunday at Callejon do Hamel.

welltraveledbrit

TravelMiss - we did it on our own at the end of May and had a great time. I posted a trip report here and you can find pictures and link to restaurant reviews on my blog..
.
http://www.somuchmoretosee.com/search/label/Cuba

Be aware that a six women in your late twenties you'll get ALOT of attention. I'm sure the case owner will be only to happy to organize tours, transfers and restaurant reservations for you - I'm sure you'll have a great tim .