Which cigars would you give serious contemplation to spending $100 USD upwards on?

[Havanaaddict]

I have lived through the days of buying great cigars at great pricing from the early 90's till the boom. So I have a very hard time justifying paying $100 for anything fresh. Vintage 70's 80's and Davidoff's, Dunhill's, Humidor release stuff is another story. 😛

[habanohal]

None for me. In reality they are just rolled up leaves...even though I spend maybe 2k a month on cigars but to me, no cigar is worth $100.

[Çnote]

Maybe vintage Dunhill, Davidoff. A 1980 birth year box. Something Double Corona-ish in CC at 20 years, but even then $100 is a hard number to justify for single. For relevance, I can justify a $300 bottle of Champagne or Burgundy and maybe a $1000 of aged claret or birth year dessert wine. It's just money, honey, but we all have emotional limits.

[smashed]

11 hours ago, griller said:

This is pretty much my context for spending that kind of money on a single cigar, too. Very reliant on the situation, store, age, etc. Back in the early 2000s, I spend $500 for 4 Davidoff Chateau LaTeurs (sp?) that I planned to smoke for the birth of children, which I did get to enjoy in 2004 & 2009. Figured the other 2 would find the right life moment and I'm down to just one. No regrets with that purchase.

Now, I'd say $100+ could be valid for me should the timing & situation arise with the following:

QdO Imperiales

Punch Churchill (if available, maybe a situation in London could manifest the opportunity?)

Upmann Sir Winnie

Trinidad Fundadores

EVERYbody who has smoked a QdO Imperiales keeps raving that this is some sleeper hit. That good huh? I gotta find a box, as I love QdO in general. QdO honestly never misses with their tight knit offerings.

[gormag38]

Siglo VI

Espy

Those may be the only two I've ever paid more than 100 a stick for. I had the opportunity to buy some 2015 BCG for 100 a stick a while back and declined...definitely a chased after stick for me personally, but still thought that was a little too excessive, in my opinion. 

[Ruggerpgh99]

If I could get my hands on an Edmundo Dantes, I would probably drop the coin for that, the other one is a CoLa. 

[Head83]

Cigars and whisky are two luxury items that I have spent a lot of money on in the past. Every time, I am left thinking the cost was not worth the taste, but it was worth the experience. Like most regular folks, I can't afford to enjoy the higher ended options often lot but every now and then, its worth the experience. With that said, the only cigar that I would be willing to pay over $100 for fresh/new would be a BHK. If I could get a 20+ year aged Monte #2, Fundie, Esplindido, or Sig 6 then I would jump all over those as well.     

[WestCoastSmokin]

Vintage Davidoff, Aged Lusis, Aged Fundadores 

[madandana]

On 12/15/2025 at 3:04 AM, Chas.Alpha said:

Espy

CPE

Behike 52 (just to say I’ve had one).

I might send you a 52 for a block of cheese…Just to say that I got to try your cheese 🪤

[Wiclovis18]

Madandana- As your Wisconsin neighbor, I will gladly send you a block for a BHK 52😆

[BrightonCorgi]

It would have to be good size cigar no matter what.  I don't want a $100 cigar and it's smoked in 45 minutes or less.  That being said...

Cuaba or Partagas Salomones

Montecristo A

Punch DC

Cuaba Diademas

I think you get the idea.