I've been to Cuba a couple of times, most recently last April. I would spend more time in Havana and in my opinion, you can do Cienguegos and Trinidad with one overnight in Trinidad (or I suggest skipping them altogether as they are a six-seven hour drive both ways from Havana--which takes a lot of your short vacation)

I simply love Havana. You could easily spend eight days in Havana alone. The architecture, the music, the cacaphony of the streets. The photo oportunities are unlimited. Trinidad is a pretty colonial town as is Cienfuegos, but they are a long way to travel for such a short visit.

I'd do Havana and Varadero and savor the island culture. There are so many different parts of Havana and so many fabulous Paladars which have cropped up in the last two years, that food is now really good. I'd save Trinidad for another trip.

Last thing: Here are some photos that will give you a flavor of the opportunites you will have in Havana. there are Trinidad photos here too, but I had a lot more time in Cuba than you will have. Great cars. Great people. Great vistas.

https://www.facebook.com/media/set/?set=a.10150894989862959.478118.589287958&type=1&l=8e38cf7c50

BostonHarbor - thank you! I take it you are American? I am considering traveling illegaly through Canada..
Any suggestions on agents? I found one agent - cubatravelus.com , however I want to make sure they are legit and wont be scammed in any way.
Thanks

Hi Apatinage, Yes, I am an American. I went legally in April with 12 photographers on a photography trip under the auspices of the US "cultural" program. There are lots of legal trips right now, but the agenda is very strict. If you are a photographer I would recommend the group I went with. The groups are small, the photography classes terrific, and the experience amazing. Because our focus was photography, we had a lot of flexibility. The photographer's name is Lorne Resnick and he is an amazing teacher. www.lorneresnick.com

There is another non photography (Legal) group going in mid January with a woman who knows Cuba like the back of her hand. She does luxury trips--the best hotels, food and experiences. I know she just had her license renewed (some, including Nat Geo are having problems getting their State Dept licenses renewed) . If you would like her contact information, let me know and I'll post it.

i have not been to varadero, but spent 3 days on the beach outside of trinidad. the best of both worlds: you have a heritage site with friendly people and a casa de la musica for dancing with the locals and a beautiful beach w/ only two hotels. the beach is about a 1o minute shuttle from town

cheers
AndrewDavid

Yes, given the short nature of your trip, I'd skip Varadero altogether. Really, while Varadero has a nice beach, it's the "Cancun" of Cuba and you won't experience much of Cuban culture or life. Far better would be to plan a few days at Plays Ancon, which is on the Caribbean side of Cuba, about 8 km away from Trinidad. Then you can get some beach time, but also spend time exploring the UNESCO heritage town of Trinidad.
Havana is wonderful, in a chaotic, crazy, unique way. Since 1998, I've probably totaled 7 or 8 months total time in Havana and I'll be back again in December.
Here's a few slideshows of my photography in Cuba. Also, one specifically on Trinidad.

Havana - Dusk to Dawn
http://s3.photobucket.com/albums/y55/Steve_YYZ/Habana%20-%20Dusk%20to%20Dawn/?albumview=slideshow

Cuba Images Slideshow (Havana, Vinales & General)
http://s3.photobucket.com/albums/y55/Steve_YYZ/2008_Trip/?albumview=slideshow

Trinidad Slideshow
http://s3.photobucket.com/albums/y55/Steve_YYZ/Trinidad-1/?albumview=slideshow

BostonHarbor I would be interested in the womans name who is going in January can you please post her contact info.

Hi Acme. Her name is Batia Plotch, Email globalgallop@nyc.rr.com. Her trips are so great. She stays at the best hotels (Iberostar Parque Central in Havana and the Iberostar Grand in Trinidad). Yet her prices are comparable/less than those staying in 3-4 star hotels. She is also very smart and super connected in Cuba. She's been going to Cuba for 30 years and seriously knows everyone there. I would have gone on this tour, but I am going back with a photography group in April.

I could not recommend her more highly. Her trip price includes airfare and visa and almost all meals.

Sorry I didn't see your note earlier. It might be getting too late to get a visa, but she goes to Cuba a couple times a year, so send her a note.