Spent the last couple of weeks doing a lot of research on here and elsewhere and have finally come up with what I think is a workable itinerary for a first visit to Cuba in August. I wish we had far more time - a few weeks at least - but with my wife working in the corporate sector it's all she can manage to even get a 6th day off from work to try and make the itinerary a bit more workable. The one thing we have in our favor is that we live in Orlando, Fl. so it won't be too hard for us to go back again and fill in the gaps. So first time out we're just going to go the more or less standard first time route of Havana, Vinales and Trinidad, though in our case we're doing it in reverse by flying into Santa Clara and exiting via Havana.
Here's out 10 day stay -
Fri - Depart Orlando – Arrive Santa Clara mid afternoon (head straight to Trinidad by taxi?)
Sat - Trinidad
Sun - Trinidad
Mon - Trinidad (Day in Cienfuegos) – alternatively overnight in Cienfuegos.
Tue - Drive to Vinales as early as possible
Wed - Vinales – mid afternoon drive to Havana
Thu - Havana
Fri - Havana
Sat - Havana
Sun - Depart in the morning for Orlando
A few questions.
Firstly, as we'll be arriving in Santa Clara around 3:15pm and will hopefully clear customs around 4 is there a possibility we could get a taxi/collectivo at that time of day for the trip to Trinidad, perhaps with someone still hanging about looking for a return fare? If not I guess we'll be visiting Che's memorial for the afternoon and staying overnight!
Secondly, because we're so pressed for time I'm essentially trying to squeeze a 24 hour stay in Vinales over two days by leaving as early as possible from perhaps Cienfuegos (5 hour road trip to Vinales according to one of the taxi sites) and hopefully getting to Vinales around midday, then staying overnight and leaving for Havana in late afternoon. I'm hoping that's enough for a quick overview of the area. One issue is that Vinales seems to be a place that's obviously geared to exploring by simply just getting 'out there', but we have a problem in that my wife's knees are pretty well shot and she can't take too much rough terrain or going up and down hills. Nor does she like horse-riding, which seems to be a popular means of exploring the area. The best for her situation would be some kind of driving tour of the area, but every time I put in a search for tours by vehicle of the region, all I seem to get are tours exiting out of Havana, rather than anything local. Any suggestions?
As far as Trinidad is concerned, I'd like us to be able to spend a half day perhaps exploring some of the natural highlights of the area - are any of the waterfalls easily accessible for my wife?
Finally, though I've traveled extensively in my life, Cuba will be just about the first country I'll be visiting where a lot of the standard measures for financial security aren't going to work in that it seems we'll have to take a wad of cash with us and hope all will be well, because we won't be able to use our American credit cards at any place other than the airports in an emergency (that's if what I recently read on here is correct). It seems kind of weird to think that every time you see a tourist or traveler wandering about they've probably got a hefty sum of cash hidden on their person - especially if they're American - because there's no other option. Thankfully Cuba seems to be a relatively safe place, because when you think of the fact that the average tourist is undoubtedly carrying at least a year's worth of income for the average Cuban on their person it would seem a recipe for disaster. With that said, I'm tempted to minimize the risks by paying for as much as possible beforehand by booking things like accommodation through Airbnb, but it kind of rankles taking that option as I'd much rather go the direct route and see the money go to the local people and casa networks. We could do the same for taxis to out various destinations with companies like taxivinalescuba.com, though I'm assuming it would be substantially cheaper to do it all locally. Guess I'll have to trundle out my old money belt! :)
One last point. If we were to use a company like taxivinalescuba.com to book our drives between Santa Clara-Trinidad, Trinidad-Cienfuegos, Cienfuegos-Vinales, and Vinales-Havana are there any protocols in place as far as trying to find other people along the way to split the costs of the rides - will the company kick up a stink if we try? I've thought about simply hiring a car but all I keep reading is what a nightmare it is simply trying to get one unless you book months in advance, plus all the standard concerns about insurance in the event of an accident. I typically do hire cars when possible, and if you can survive driving in the chaos of downtown Athens or some parts of Asia you can survive anywhere else, but in this case it just seems simply to taxi around - or use a collectivo.

