how crucial to plan ahead?

Thank you ... do you recommend we could go place-to-place in them? All we have booked right now is a bus ride back to Habana from Baracoa. Bookings on the Viazul are looking like nil to get us anyplace east on the 27th. I'd love to book a train ride, but wonder if it's just a matter of waiting in line? (a-la US Black Friday?)

You can go place to place in them cheap if you have the patience to wait a long time under a highway overpass with many Cubans, strong possibility that there won't be any room on the trucks or that you'll be packed in like sardines ,there's always room on the trains which the Cubans also dread because they're so slow and inefficient,watch your gear when you're on the train,not sure that hitch hiking is a practical option either. There is a transportation crisis for Cubans and to a much lesser extent tourists trying to do low budget travel across the island.

PS there is something called the Astro bus which is used mostly by Cubans,very,very slow way to travel across the island compared to Viazul,you're also taking seats from Cubans who use the Astro bus to see family ,so there's that.

Thank you all for your help. My response to this thread was to, regrettably, begin to craft an itinerary, spending most of my time seeing what Viazul trips were available, and contacting Taxi Vinales for the rest. In two weeks, it looks like we're spending only a day in several places: Havana, Playa Larga o Giron, Trinidad, Camaguey, Santiago, Baracoa (after reading a post here highly recommending it), Havana. Ending with a 21-hour bus ride Baracoa-Havana.

So ... I'm thinking I'm probably going about this all wrong, and should cut the itinerary in half. What was I thinking? Feels opportunistic, hurried, rude to travel like that. Thoughts?

Thank you so much for your help.

My thoughts are that even the worst places deserve 2 nights!
Yes it sounds like a rush but who knows what travel style suits you. Wouldn't suit us.
Fly back to Havana from Baracoa?

Otra molesta: Is it very easy, or not very easy, to find a taxi to the outskirt Viazul stations? Just worried about high season. And, if transportation is that overburdened with tourists -- travel style besides, maybe we're asking for most of our itinerary to be canceled by unpredictables. Wondering if we should stop our stay in Santiago.

Taxi prices online are going to be 2-3 times as much, you mentioned in FAQ. But I wonder, if in high season, it's worth it booking in advance. ... and we'd keep our eye out for more riders on the road who need it! We can vacate our seats for the roof if need be! They allow that, right? ;)

No probs getting taxi to Viazul but also keep in mind that Conectando goes to city centres (but can only be pre booked at least day before ONCE in Cuba).
Havana is already going to be the busiest EVER for the time you are travelling.
So although we have never pre-booked any transport or virtually any accommodation in 10 years of travel there I would be tempted to at least have Havana-Trinidad pre booked.

Some reflections on a trip ... cautions due for it being two weeks during high season, plus everything always changing. Like many others have said, unless you are going for a short time span and have your heart set on certain towns, it may not be necessary to plan travel in advance. Having heart set on certain places, also, may also not make for the most graceful and plentiful travel experience.
1. One planning-ahead highlight: taxi from Havana to Bahia de los Cochinos: main benefit here being the opportunity to stop at places along the way. Not sure if that bay shuttle is running. Cueva de los Peces was very busy, and Punta Perdiz much less so. Didn't make it to Caleta Buena We took our first (spontaneous and cheap) scuba diver ever, at the latter, after a 10-minute quick lesson. Expensive to have a personal taxi hired all day. There were others who did the same, but I'm not sure which of those was a colectivo. Ours (through Taxi Vinales) refused to pick up other travelers, regardless that we didn't need them to chip in $. Taxi Vinales did allow us to pay in full online after we asked, due to our cash shortage.
2. All other transport was fine. We got some spontaneous rides, and quickly, and generously. Who knows if you or others could count on that (we even had bikes to stow aboard), but luck and generosity does happen. "Anything is possible" and "if you keep asking..." the Cuban hope we heard. Mixed info: whether tourists are "allowed" on Cuban buses. But the colectivos across from bus stations may be worth an effort.
3. Depending on the town, a trip on Viazul may be pale in comparison (waiting in line, price, comfort) to a trip in a colectivo. We got a ride from Cienfuegos to Havana for $25 each in a classic car.
4. Snorkeling highlights: Jibacoa and Punta Perdiz
5. Close get-away from city highlight: Castillo de Jagua from Cienfuegos. A bit of classism there, and a history of such, but a scenic place to stay. Also a lovely casa there: Punta Pie. If you go on a walk, try to meet Mercedes and Leonardo's small tract of land at the northern shore side end of town. Poorer and hardworking people, and with their own little pier for swimming they say many tourists manage to find.
6. If I were to pick a "must" -- the Hershey train (maybe any train? As it will likely take you away from main roads to the back country). We disembarked at the town (renamed of course) of Hershey and got a cheap bus ride into Santa Cruz and then the Campismo at Jibacoa. Wonderful, exhilarating ride, that train. All the bucolic rural scenery you can imagine, and locals who still depend on the train for trainsport. Schedule changes, but not exasperating by any means. Just may need to wait for a few hours or until the next morning for the next train.
7. We met some bikers -- who said they camped plenty a time, even asking homeowners to let them camp out on their land (I'm sure for a small donation). While the casas were fine, and affordable for us, we would have liked to camp for that much more of a nature experience. Nice to find out that locals are okay with campers, and mystified by tents and water filters.
8. Helpful donation ideas: many asked for shirts, T-shirts. Also: maybe tools, machetes, pens and pencils. Service ideas: folks in smaller towns --even those with burgeoning new tourism, like Playa Giron -- would like English classes. One may have mixed feelings about that influence, but a thought. Also would have loved to teach and give snorkeling gear to towns kids. We met many locals who were afraid of going underwater. But what a protective mass that may be, if the locals love their coastline and want to keep it pristine.

1. If I were to pick a "must" -- the Hershey train (maybe any train? As it will likely take you away from main roads to the back country). We disembarked at the town (renamed of course) of Hershey and got a cheap bus ride into Santa Cruz and then the Campismo at Jibacoa. Wonderful, exhilarating ride, that train. All the bucolic rural scenery you can imagine, and locals who still depend on the train for trainsport. Schedule changes, but not exasperating by any means. Just may need to wait for a few hours or until the next morning for the next train.

I read this with real mixed emotions as the Hershey train and staying at the campesimo (I assume Los Cocos) in Jibacoa are favorites of mine. I am happy that some others my experience the same same delights that I have done. Yet, I have concerns that these generally undiscovered delights, once pure Cuban in nature and untarnished by foreigners, are in the process of being discovered by tourists and will ultimately change in nature.

that some others my experience the same same delights that I have done. Yet, I have concerns that these generally undiscovered delights, once pure Cuban in nature and untarnished by foreigners, are in the process of being discovered by tourists and will ultimately change in nature.>

At least you have seen them before mass tourism and modernisation will have ruined these experiences.

I'm pretty sure about the future of the Hershey train:

More and more tourists will take it. Travel agencies, cruise ships want to run special trains to accommodate large groups. The cash-starved railway operator will be only too happy to run these special trains, but they have only as many trains and no money to invest in buying new trains. Trains will be tourist only, locals will take the bus. Or a somewhat better prospect(for the long term), the railway will be modernised and the locals will travel in sleek new air-con trains, while the old trains will run tourist only services.

See it while you can!

Ruined for you,Cubans would be grateful for modern reliable transportation as they suffer through a transportation crisis.