I like Padron Family Reserve Maduros and several Davidoff varieties (Nicaragua box pressed, Churchill Late Hour, and some of their limited editions). There are much cheaper options available, but those are my favorites.

One of the great things about cigars is that there are so many options and you can spend years exploring them and finding what you like. Lots of options and variety in the $10-$15 range. Once you find what you like there, it’s easy to find premium special occasion cigars that are similar but much more special. The age of the tobacco can dramatically influence the experience (and price), but when starting out it’s hard to appreciate some of those subtleties.