Good idea.
Back in November I smoked a La Flor Dominicana with my brother-in-law in San Antonio at the Menger Hotel (google it). That was a damn fine cigar. I also smoked a Fuente Hemingway Masterpiece in the same bar that Teddy Roosevelt used to recruit his Rough Riders in. Smoked a great Illusione in Silverthorne, Colorado with the same brother-in-law.
But perhaps the best cigar I ever smoked was a Habano RASS with my dad on his back porch a few years ago. He passed away a little over a year ago. I'd like to burn one with him now.
Ambience and company make all the difference in a cigar. It can make a crappy cigar good, and a good cigar superb.
DL