Why Cuban? There are plenty of brands that are not Cuban that smoke MUCH BETTER.
But if you must...
A real Cohiba is nice. Should be aged a few years before being smoked. 98% of Cohibas in the USA, Mexico, Canada and Europe are fake.
Bolivar, H. Upmann, Hoyo de Monterrey, Montecristo and Partagas are all fine Cubans. However, they all have non-Cuban companies making them too. Which means the ones you see at
http://www.thompsoncigar.com are not Cuban.
To get the actual Cubans (which taste remarkably like their Honduran and Nicaraguan cousins) you can go to certain web sites that actually sell Cubans. They are often based in Sweden or Hong Kong.
Expect to pay an arm and a leg. If you are getting 20 Cubans for less than $650 you are not getting Cubans. Plain and simple. You will not get a Lamborghini for $2000... Same principal.
My suggestion would be to use the URL I previously posted and get their Partagas, Padron, Rockey Patel, La Gloria Cubana or Arturo Fuente. All of which are grown in either Honduras or Nicaragua. All of them are grown from Cuban seeds (seeds that left Cuba when Castro took over). You will not perceive any difference.
All cigars should be aged before being smoked. If you smoke a $5 cigar that has been aged 5 years it will taste comparable to a $20 cigar aged 1 year.
Rocky Patel is a nice cigar to start with. The 90 and 92 series are both aged for you. So all you have to do is order them and smoke em.