I believe that if you're not experienced with CC's then it's best to first make absolutely sure that you are buying from a legit source by lots of research beforehand, but secondly I would sample the staples from the bigger brands.
Therefore, not necessarily my favorites, but must try's:
1. Partagas Serie D No. 4
2. Montecristo No. 2
3. Cohiba Siglo IV or Robusto
4. Punch Punch
5. Bolivar Belicoso Finos
6. Romeo y Julieta Churchill
7. Hoyo de Monterrey Epicure No. 1 or 2
Sorry for 7 listings, but this would be a great sampler to see what Cuba offers