I am always a bit surprised that there isn't more of a crossover between pipe and cigar enthusiasts. I am also heartened when I hear someone tempted to give the other a whirl. I figured I'd help the process in my own little ol' way. I'll begin by saying that if you're new to pipes, get yourself a corncob and stay there a bit. A less staunch recommendation going the other way is to start with a Robusto-sized cigar.
If you are a pipesmoker and curious about cigars, are you a fan of aromatics? If that's the case, avoid the flavored cigar temptation in order to get a better look at cigars proper. I would say that a sweetened tip might help you acclimate if you really only smoke aromatics. If not, grab a Corojo or Habano.
If you enjoy English blends for their latakia smokiness, you might want something with a bit of Fire-cured 'baccy. These are just potential starting points to be clear, feel free to frick around and find out rather quickly from go, on your lonesome. All other general pipesmokers, follow the Habano/Corojo tip unless you prefer lighter smokes--in that case dial up a Connecticut Shade.
As far as cigar smokers who are interested in giving pipes a whirl, there are blends that use cigar leaf in their recipes. You may also vice-versa the aforementioned information. Also, I'd liken the middle-of-the-road Habano/Corojos to VaPers and Burley blends.
A thing to bear in mind when picking up the pipe is that relights are par for the course and there is a learning curve of greater curviness in learning to smoke loose tobacco in comparison to simply lighting up a stogie. Be patient. Also, be excited (either way) about opening yourself up to further see what the leaf can do. There's a whole world out there. Carpe like there ain't no guaranteed diem.
::: very :::