OK, I can speak from experience. I hosted the cigar bar for my niece at a wedding of about 200 people. I personally paid for the whole thing as my wedding gift for them as I really like her and her husband.
1) Buy cigar bands with the couple's name, initials, or something. Wrap each cigar with this as a second band. Leave the originals on. It takes forever to label the cigars LOL. I think I had 5-6 boxes.
2) Buy boxes of matches with their name, monogram, or something. I think the ones I bought had their names and the wedding date. EVERYONE, non smokers included, will want a box to take home as a souvenir. They are cheap and easy to have made. There are companies all over the internet that do it. Also, this will keep you from having everyone steal your lighters. PEOPLE WERE SUPER IMPRESSED WITH THIS.
3) Have a ton of cutters. They were too expensive to have monogrammed, so I just brought a bunch of generics. Alot of the drunk **** will take them and not return them. Offer to cut their cigars as most wont know how much to clip off anyway.
4) Buy 5-6 silver Big Stinky Ashtrays and put them around the area you will be smoking. They look classy and the guests cant really hurt them Buy the big ones because they will be filled with mostly unsmoked cigars. When the night is over, I kept one and gave one to the groom and the rest went to anyone else who was an actual cigar smoker. And you will know who they are as they will want to hang out and talk about it with you.
5) Be prepared to see about 100 cigars in ashtrays that have about 1/4" smoked. 99% of the people will do this. Most will have never tried one and a little alcohol makes them adventurous. Dont buy expensive cigars. It will make you sick to look at it.
As for cigars, here is my advice...
Macanudos. Cheap, very mild, and most people have seen/heard of them. Trust me, people cannot handle strong cigars. Buy different sizes.
Buy 2-3 boxes of DECENT cigars. Give these to the people who think they know cigars and are loud mouths. Then, make fun of them when it is too strong for them and they hack up a lung trying to inhale it LOL
Cubans - Buy a couple of boxes. The above mentioned in the other posts were good choices. I had R&J and the people loved them. These are for the groom / groomsmen / REAL cigar smokers/ and family who are genuinely nice people. Keep them under the table. People will come back for seconds of them to "take home and show people".
That beings me to the last category which I've touched on throughout the post. These are the people you will encounter:
Tipsy Female: Never had a cigar and will go share it with a friend. Expect 1/4" smoked.
Loudmouth Douchebag: Wants the biggest strongest smoke. Will have admittedly smoked tons of boxes of glass-toppped Cubans smuggled from Mexico. Will clip 1" off and will light the cedar on the cigar if it has any.
Freeloader: Will come by and put 3-4 in his pocket. Will possibly come by multiple times. He just wants free stuff.
Genuine Cigar Smoker: Will look around and pick the best smoke on the table. Will clip it, leave the cutter, and take a box of matches and go outside the enjoy a smoke for an hour. This is a good candidate for a Cuban.
Total Newb: Wont have a clue and will genuinely ask for advice. Be prepared to clip and potentially light the cigar. Same rules apply as Tipsy Female. Give them a Mac and they will probably be in heaven. Might make a cigar smoker out of them. This is a good choice to give a cutter to at the end of the night.
Groomsmen: They could fit into any of the above categories, but give em a Cuban. They had to pay $150 for a damn tux. Plus, they will be there the latest partying and you might be smoking cigars with them later.
Good luck and I can help you out if you need anything.
