Hey! Just another American posting a Cuban trip report. I went for 2 weeks, to Havana, Vinales, Santiago, Sancti Spiritus, Trinidad. About 30 photos posted on Instagram: https://www.instagram.com/nancyc_huang/ (but the 4 most recent are obviously not from the trip). Scroll down for general tips.
HAVANA
This is already well-covered, and truthfully I saw nearly no "sights" so I can't really contribute to that. I'll just say that it is indeed quite easy to get away from the tourists. In Viejo they're really concentrated on pedestrian streets and streets full of sidewalk cafes. People are quite open to chatting in Centro. I stayed in Centro on my first few days and on return, on kind of opposite ends of the neighborhood.
I was there during the Ciudad de Movimiento dance festival, and it was lovely to see free performances in the open. I also recommend visiting Callejon de Hamel in the evenings, and not when they have their Sunday parties. Then you can just look at stuff without being sold anything, and residents are just hanging out wanting to chat.
VINALES
It seems like normal price in a colectivo should be 20 CUC door-to-door. Unfortunately, the (otherwise lovely) casa owner in Havana owns a car and does unofficial taxi service, so he claimed he couldn't arrange a direct pick up. Had to pay him for a ride to the Viazul station and get a colectivo from there.
I stayed for two nights (arriving at 11:30AM, departing at 1PM two days later). I chose an Airbnb on the outskirts, maybe 2km out of town. I didn't really think there was a reason to see the town, and if the sights are in the countryside, might as well stay out there. Made strolling around so much easier! Only 10 USD on Airbnb. The owners--who were easily my favorite of the trip--told me Airbnb is currently the only way they find customers. Arranged the horseback trip through them, the horse "parking" spot was maybe a 10 minute walk from the casa, was told 5 CUC per hour but that wasn't exact...was definitely out for more than 4 hours but still paid 20.
Through this casa, I also rented a bicycle for 10 CUC. Rode out to La Resbolosa/El Resboloso (kinda unclear which way is correct), a swimming hole which is really lovely and the approximately 15km ride is beautiful. There's a bar on the road above the swimming hole where the owner mysteriously gave me lots of free rum (but I paid for water). There's no signage explaining the route, but ask around OR find the book "Bicycling Cuba" at your library for directions. (it's not 100% accurate, but good enough!).
If you want to look up this awesome casa on Airbnb, the owner is Leticia. They picked up from the Viazul "station" in Vinales town, but for the return colectivo they arranged a car to pick up from their house and go directly to the exact destination in Havana. I believe the only time slots are 8AM and 1PM.
SANTIAGO
I decided to fly from Havana. Oh, Cubana. With 15 people MAX in front of me in line, it took 1hr 15 min to get to the check-in counter. Then it turned out the flight was delayed 3 hours without explanation! Luckily they didn't make me check my bag.
I loved Santiago! I was there 3 nights, but the fourth day I took a night bus so I still had the full day to hang out. It's quite easy to chat with people there, everyone's friendly and it's fairly small compared to Havana. My Airbnb was 13 USD, about 5 blocks downhill from Parque Cespedes.
Mostly I just walked around, or uh, did some day-drinking with both tourist and local friends. But for sights, I highly highly recommend the Museo de Imagen. Of course, I visited the Cementerio Santa Ifgenia. There's surprisingly kind of no one visiting Fidel's grave. I also arranged a day out via motorcycle to Castillo de San Pedro de la Roca and Cayo Granma for 8 CUC (my Cuban friend felt like it should be 5, the driver wanted 10, I was OK with 8).
If possible to arrange, I'd also recommend visiting Taller Cultural Luis Diaz Oduardo. Some great art being produced there. It's not toooo too far from Museo de Imagen. I don't actually know what it's like if you just show up. Someone I met through Couchsurfing is friends with an artist there, so he showed me around the studios and introduced me to other artists.
Transportation: well, I mostly walked a lot, but you can flag down random passing motorcycles for either 1 CUC or 20 CUP to go pretty much anywhere in town. I don't really know how the license works for that. I mostly only looked for people who were clearly carrying an extra helmet, because I assumed they would be looking for passengers.
SANCTI SPIRITUS
I had chatted with someone from Couchsurfing here, so I thought it was an opportunity to just hang out somewhere non-touristy. But because the person from CS was actually a tour guide, he got called away to work in Trinidad and I joined him. We still spent one very full day in town. Mostly just walked around, climbed the church tower, hung out in the park, etc. The more interesting aspect was that this guy and his friends are mostly gay AND deaf, so we talked a lot about their experiences and ended the night at La Fiesta Gay, a huge drag show + dance party that happens every Saturday night in Sancti Spiritus.
TRINIDAD
I took the bus super-early in the morning from Sancti Spiritus with my new friend. I really just had a day and a half here, as I hadn't originally intended to come at all. I've been to lots of beautiful colonial cities, and there's so much talk about how overtouristed Trinidad is. I think if you're only seeing the town, this is actually enough. But as my friend is a tour guide, he knew more about the hikes and such in the area that he said are worthwhile.
I ended up staying at a casa belonging to someone trying to find clients at the bus station (20 CUC). It was nearly a 20-minute walk from the center, which really isn't too bad! It's a little more difficult getting away from the tourist hordes in Trinidad vs Havana just because it's so small and it seems way more people are in group tours there. But still, it just takes walking a few blocks away and it becomes just regular residential streets with people beckoning you over to chat.
One odd thing for budget travelers: the cheap peso cafeterias are much harder to find in Trinidad, relative to other cities. Especially in the touristy core. Lots of places labeled cafeterias only had drinks, or cookies/pastries, but not the egg sandwiches etc you can normally find. I mean, it exists but you just have to look harder than in other cities.
Another fun, odd bit: there's a thing with pet birds in Trinidad. Everyone has them, and they take them for walks in their birdcages. I was there on a Sunday and Monday, passing by the Santa Ana church to get to the center from my casa. There's a park by the church that on Sunday mornings, is full of dudes and their bird cages. I think they're just hanging out with the birds, like you might with your pet dogs. It's really sweet.
Returning to Havana, I got a colectivo for 25 CUC, door-to-door. I think the only time slots are 8AM and 2PM.
DEPARTURE BASICS
I had a direct roundtrip flight from JFK. For Americans, it's now just as simple as you've heard. I selected "people-to-people" when purchasing, had a fake itinerary printed just in case, even though it didn't make much sense as you sign the affidavit and buy the tourist card when you're practically one foot on the plane. And yeah, no one asked to see anything.
TRAVEL HASSLE/DIFFICULTY
This depends on your travel experience of course, but I thought Cuba was pretty normal/easy. Sure, there is a lot of waiting around, and you can't find information online quickly. But it's not like...India or anything. Most things make sense. I know this sounds vague, it's partly because I'm genuinely unclear what people find confusing or difficult about traveling in Cuba.
SOLO WOMEN
About the same as any Latin American country! Lots of catcalling, lots of approaches. Rarely frightening, I felt like most men were easily dissuaded if I didn't want to be chatted up. I never got followed in any menacing fashion as I have in some other places.
GUIDEBOOK
I used Moon. It's not that accurate, especially when it comes to pricing, despite being published just a couple years ago.
MONEY STUFF
I'm cheap and didn't like the food (and am really not picky!) so I used quite a bit of the Cuban pesos (CUP). Changed 30 CUC to CUP in total. Also, I really wasn't aware of this, but Americans CAN use their credit cards at the airport! So I ran around Havana to multiple liquor stores for rum, then didn't convert my last few CUC back to USD and spent it all on one last bottle of rum and candy at duty-free (candy was cheaper than hot food). But it turns out I could saved all the rum shopping for the airport and used my card.
I didn't plan ahead much for this trip, which means I didn't look into whether or not a double-conversion to EUR or CAD before getting CUC would have saved me much money or not.
BUDGET
I'm usually a really low-budget traveler, which is not quite possible in Cuba (although this might sound low-budget for some people). For a 2-week trip, I converted 600 USD and spent an additional 100 USD on Airbnb, and borrowed 30 CUC from my friend when I ran low and the CADECA was closed. This includes about 80 CUC spent on cigars and rum. So, not counting those non-essentials, it averaged about 37-38 CUC per day.
As probably the case in any country, the biggest budget-killer is alcohol. I normally don't drink much or at all when I travel alone, but I was with a friend for a few days, and then kept meeting up with people (although as a solo woman, I did also get a lot of drinks for free).
Lodging is just a place to sleep and the food isn't worth it (except churros, eat lots of churros), so these aren't places to spend much. But compared to a lot of budget-travel destinations, both of these PLUS transportation as wayyy more expensive. The only bus I took was a long overnight one, but even short trips like between Havana and Vinales cost 20 CUC when they'd cost the equivalent of 6-8 USD in Mexico.
INTERNET
It's really not THAT bad, and it's quite widely used. It's fast enough once you log on. It's just that logging on takes a long time and hotspots are hard to find. Outside of hotels, the hotspots in Havana seem slower than other cities (maybe too many people). Of course, there's the crazy lines to buy the wifi cards to begin with. They'll ask you for your ID but in Havana and Santiago when I said I didn't bring it, they didn't care. In Sancti Spiritus they refused to sell it to me without the ID, so my Cuban friend had to get it.
