Two Weeks is good time for getting to know Cuba a little better. As in other posts I recommend don’t put to much places and things in your agenda. Of course this is just an idea of what you could visit in two weeks, there are a lot of different options.
This route contains some of the main sights and beaches in Western Cuba. Of course you can change the route in a different way or stay a different amount of days, this is just a suggestion.
Day One – Day Four
Discover Havana. Of course if land in Varadero or some of the other airports the route changes a little.
I think to enjoy Havana the most you should stay there some days at the beginning and some days at the end of the trip. Havana is a loud, hot and sometimes a little bit crazy city, so if you come back after a a trip to other places in Cuba you will see it differently.
Day Four – Day Six
Go on and go to Viñales, as I recommended in this post: One Week: Havana and some nature, I suggest to visit Soroa on your way.
Take a walk in the valley of Viñales, go climbing or horseback riding.
You also could think about staying a day longer and taking a trip to Cayo Jutías or Cayo Levisa
Day Six – Day Ten
Go to Cienfuegos. Take the bus or a Taxi at the Busstation in Viñales and go down south. The trip takes a while (about 7 hours) but it’s the longest distance to travel in this route suggestion. If you don’t want to sit in a car or bus that long, make a stop in Havana and travel to Cienfuegos from there.
In Cienfuegos there are a lot of excursions you can do for example to the Nicho waterfalls or to Rancho Luna. I also to visit recommend Guanaroca to see flamingos in nature.
I Usually suggest to do Trinidad in one day as an excursion from Cienfuegos. You can go there by Taxi and for 40$ the driver takes you there, waits for you and take you back to Cienfuegos.
Of course you could also go to Trinidad for one or two nights and enjoy sights like the Casa de la Música or the Playa Ancón close by.
Day Ten – Day Fourteen
You could split the last days up and go to Trinidad for one night and than head back to Havana, or simply go back to Havana and enjoy more of the cities cultural life.
You also can think about making stops at Paya Giron or Santa Clara on this route.