In a restaurant in Palo Alto with great friends from Chicago and it was just dazzling. At 19 years old (and from a relatively earlier drinking good vintage) it was beautiful and made the gathering extra special.
(Oh and I had bought that magnum at retail when it cost something like $160.)
Love that story! I did something similar for our 15th anniversary, with a magnum of 1988 (our wedding year) Beaucastel and a Rolex.
Various ‘88 Bordeaux for other anniversaries have also been sentimental favorites, with Lynch Bages, Haut Brion, and Yquem standing out for also being excellent wines.
Other than that, I tend to like Bordeaux at 20+ years, and would say most of them were worth the wait.
I am like David. I drink an awful lot of older wines and most of them are worth the wait.
Brought a 2001 Truchot GC Combottes to a restaurant for dinner for our anniversary a couple of months ago and it was perfectly mature and wonderful.
Went to my wine group dinner in June and brought a 2001 Clos des Lambrays that was fantastic. There were a lot of wonderful aged Burgundies from vintages around 2001-2006 that others brought.
As an outlier that night, one friend brought a 1979 Ridge Langtry Road. Wow was that interesting and fascinatingly good. It is amazing how good Ridge Zins from the 1970s can still be (assuming good storage).
About a year ago, my same group had old Piedmont wines that included 1964 Marcarini Barolo Brunate, 1998 and 2004 G. Mascarello Barolo Monprivato, 1974 and 1979 Produttori del Barbaresco Barbaresco and 1967 Cappellano Barolo. These wines were magical.
And, just this weekend I had a 2011 Ridge Klein Cabernet that was perfectly at its peak. Probably not as good as some of the wines I mentioned above but still quite good.
Older wines should not be a once in a lifetime thing. There are great older California Cabs, Bordeaux, Burgundies, Barolos and Barbarescos, Chenin Blanc whites from the Loire, German wines, Sauternes and Barsacs and wines from many, many wines from the world, including Champagne (try a 2006 or 2007 Taittinger CdC for example).
The two keys IMHO is finding wines with a track record for aging and proper storage.
And, there is no one right special moment (unless that is a moment in your life). Most good wines stay at their peak for quite a number of years.