You are the best man and you have a problem
Your best friend is getting married in six months. He has asked you to handle the cigars. You have smoked maybe four cigars in your life, three of which were at other people's weddings. You do not know what a Connecticut wrapper is. You do not know the difference between a robusto and a torpedo. You do not know whether $12 a cigar is reasonable or insulting or extravagant. You are pretty sure you are supposed to ask about ring gauges, but you do not know what they are or what number is good.
This post is for you.
We are going to walk you through the actual decisions you need to make, in the order you need to make them, with the kind of advice we would give a best friend if he called us about this. Let us use a hypothetical groom: call him Dan. Dan is 34, works in finance, lives in Hoboken, comes from a Bergen County Italian family, and is marrying a woman whose family is from Westchester. The wedding is in October at a venue in Tarrytown. About 160 guests.
This walkthrough fits a lot of weddings. The principles fit almost all of them.
Decision 1: How many cigars?
Skip the cigar bar math for a minute. Start with the gift.
The first decision is: are you buying cigars only for the groomsmen and immediate family, or are you running a cigar offering for the whole reception?
For Dan's wedding, both options are reasonable. Italian and Westchester crowds tend to have at least 30 to 40 adult guests who will gladly accept a cigar. So we will plan for both.
Groomsmen and family gift set. Dan has 6 groomsmen, 2 fathers, 2 brothers-in-law, and one godfather. That is 11 cigars at minimum. We always recommend padding by 4 to 6 for the bride's male family members who get added at the last minute. Total: 15 cigars in the gift set.
Reception cigar bar. 160 guests, roughly 60% adults, roughly 30% expected to take a cigar at a reception with cigars present. That is 160 × 0.60 × 0.30 = 28.8 cigars, which we round up to 35. Most of those will get smoked at the venue. About 8 to 10 will get pocketed and taken home.
Total order: 50 cigars. That gives Dan 15 in the gift set, 30 for the bar, and 5 spares. This is a normal-sized custom wedding order for us. It takes about 5 weeks to produce and lands at a reasonable per-cigar cost.
If you are reading this and your wedding is bigger or smaller, the formula scales linearly. 80 guests with similar demographics: about 25 cigars. 250 guests: about 75 cigars. Over 100 cigars total tips you into a "full cigar bar" situation that needs an attendant.
Decision 2: One cigar or two?
For an order of 50, we usually recommend two cigars.
Here is why. The 15 cigars in the gift set should be one specific cigar that Dan likes. The 30 cigars at the bar should include both a milder option and a stronger option, because you do not know who is taking what at the bar.
If your order is 30 cigars or fewer, one cigar is fine. The math does not justify the complexity of two SKUs at small volumes. If your order is 100 cigars or more, two is mandatory. Around 50 to 80, it is a judgment call. For Dan, two makes sense.
So we are picking three cigars total: a gift cigar for Dan and the inner circle, a milder bar cigar, and a stronger bar cigar.
Decision 3: Picking the gift cigar
The gift cigar should be something Dan would actually pick for himself. This sounds obvious. It is not how most best men shop. Most best men pick a cigar they think looks impressive, or one a sales person at a humidor recommended, or one with the highest price point in a magazine review.
Wrong approach. The cigar should match Dan.
A few questions you should ask Dan, even though he will resist answering them:
- Do you smoke cigars regularly? (If yes: ask what he keeps in his humidor and pick a step up from his daily.)
- Do you prefer milder or stronger cigars? (If he says "stronger" without context, he means medium-full. Almost no occasional smoker actually wants a full Maduro at 4 PM at his wedding.)
- Any cigars you have had recently that you really enjoyed? (Listen for brand names. Padron, Oliva, Arturo Fuente, Ashton, Davidoff. These are signals.)
- Budget per cigar in the gift set? (Most grooms underestimate. The gift set cigars usually run $18 to $30 each.)
For Dan, let's assume the answers are: yes he smokes occasionally, prefers medium-full, recently enjoyed a Padron at his bachelor party, budget is open.
For Dan we recommend the Padron 1964 Anniversary Maduro. Iconic Nicaraguan blend, recognized by anyone who knows cigars, medium-full strength, a wrapper that photographs well. Around $24 per cigar in the gift set context, which is the right price point for a meaningful groomsman gift.
If Dan wants to lean into a Dominican rather than Nicaraguan profile, we recommend Arturo Fuente Anejo. Cognac-aged Connecticut Broadleaf wrapper, distinctive, slightly more festive feeling. Slightly milder than the Padron 1964.
If Dan was open to something less common in his local humidor, Drew Estate Liga Privada No. 9 is the kind of pick that signals a step beyond the usual. Slightly off the beaten path. The kind of cigar most of his groomsmen will not have tried.
For this walkthrough, let's go with the Padron 1964. 15 cigars in the gift set.
Decision 4: Picking the bar cigars
For the bar cigars, the goal is different. The goal is breadth.
The bar will see a wide range of guests. Some will be experienced smokers. Some will be 23 year old groomsmen friends who have smoked one cigar in their life. Some will be 70 year old uncles who own humidors. You cannot pick a single cigar that pleases all three.
So we pick two cigars: a milder one for the occasional and inexperienced smokers, and a stronger one for the enthusiasts.
Milder bar cigar. We recommend Macanudo Cafe Hyde Park. Connecticut Shade wrapper, mild to medium, very forgiving. Burns clean for 45 minutes. Tastes like cedar and toasted bread. A guest who has never smoked a cigar before will not regret picking this one. This is the cigar we recommend at almost every wedding we work on.
Stronger bar cigar. Oliva Serie V Melanio. Sun-grown Sumatra wrapper, medium-full, complex. Highly rated, recognized by enthusiasts. Bridges the gap between the casual smokers and the connoisseurs. It is the cigar a 50 year old uncle who owns a humidor will actually be impressed by.
For Dan's bar, we split 30 cigars as 18 Macanudos and 12 Olivas. The Macanudo will move faster because more guests will pick it. The Olivas will get pocketed by the enthusiasts.
Decision 5: The band
Now you have your three cigars selected. 15 Padron 1964s in the gift set. 18 Macanudos and 12 Olivas at the bar. Total: 45 cigars. We bumped up to 50 with the spares.
All 50 get the same custom band.
For Dan and his bride, the band design conversation goes something like this. We usually start with a video call where Dan and the bride show us their wedding invitations, the venue style, the color palette, and any monograms they have already developed for the wedding. We extract a typeface, a color, and a small ornament from their existing wedding design language.
For Dan's October Tarrytown wedding, we expect a fall color palette: deep burgundies, golds, dark greens. We design a band that picks up one of those tones (probably a burnished gold) and pairs it with their initials and the wedding date in a serif typeface that mirrors the invitation. Maybe a small leaf motif if they have one in the wedding stationery.
You do not need to know any of this in advance. We work it out together over two or three proof rounds. The total band design process for a wedding like this takes about 10 days from first call to approved proof.
Decision 6: Packaging
For Dan's gift set of 15 Padron 1964s, we recommend a small wooden cigar box per groomsman, 3 cigars per box, with a custom-engraved nameplate on the lid. So 5 boxes for 5 of the closest guys, plus the other 5 cigars handed out individually to the brothers-in-law, fathers, and godfather in a simple branded sleeve.
For the bar cigars, no individual packaging needed. They go straight into a humidor at the bar with a small printed card describing each cigar.
If Dan's budget is tight, skip the wooden boxes entirely and use kraft cardboard sleeves with a custom printed label. This drops the gift set cost by about $30 per groomsman without affecting the cigar quality.
Decision 7: Logistics
Cigars need to be delivered to the wedding venue or to Dan's hotel room at least 3 days before the wedding. Storing them anywhere too dry (an air conditioned car for 8 hours, an overheated apartment) for too long compromises the wrapper.
We always recommend shipping to the venue's onsite contact directly, with explicit instructions to store the box in a cool dry interior room (not a basement, not a kitchen). The box we ship in is climate-protected for up to 4 days in transit. Once received, the cigars are good for 7 to 10 days unopened.
If you are running a cigar bar at the reception, you also need a humidor at the venue. Most venues have one. Some do not. Ask. If they do not, we rent humidors for $200 plus shipping, which we always include in the quote.
What this all costs
For Dan's order, here is a real-world budget.
- 15 Padron 1964 Anniversary Maduro custom-banded: $400
- 18 Macanudo Cafe Hyde Park custom-banded: $230
- 12 Oliva Serie V Melanio custom-banded: $215
- 5 spare cigars (mix of the above): $80
- 5 wooden gift boxes with engraved nameplates: $300
- Branded sleeves for the additional 5 gift cigars: $60
- Custom band design (no extra charge, included)
- Shipping with humidity protection: $80
Total: about $1,365 for 50 fully customized, hand-banded cigars across three premium SKUs, with packaging, design, and shipping included.
That is roughly $27 per cigar all-in. For a wedding gift that 30+ adult male guests will remember and that 5 groomsmen will keep on display in their offices for the next decade, that math works.
If your budget is half of Dan's, we drop the wooden boxes, switch the gift cigar to a Perdomo Habano, and use one bar cigar instead of two. Total comes in around $700 for 50 cigars. Still a great wedding offering.
If your budget is double, we substitute the Padron 1926 No. 9 for the gift set, add a third bar cigar, upgrade the boxes, and run an attended cigar bar with a brand ambassador. Total comes in around $2,800 to $3,200.
What we would tell Dan
If Dan called us directly, here is what we would tell him.
Pick the gift cigar based on what you would smoke yourself. Trust your taste. Do not try to impress the room. The room is not the audience. Your groomsmen are the audience, and they want a cigar you would smoke with them.
For the bar, two cigars beats one. A milder Connecticut and a medium-full Sumatra is the most reliable pairing we have ever found for a mixed wedding crowd. It works in October. It works in June. It works in Tarrytown and it works in Asbury Park.
For the band, give us an existing piece of your wedding design. We will work backward from there. Do not start the band brief from scratch. The band should look like it belongs to the wedding, not like it was designed by a stranger.
For timing, start six weeks out. Do not push it.
For packaging, simple beats elaborate. Wooden boxes are great. Engraved nameplates are great. Velvet linings, clasp-locked humidors, and personalized monogram cigar cutters are usually a step too far. The cigar is the gift. The packaging frames it. The packaging should not compete with it.
A small last thing
The best man job is not really about cigars. It is about being the friend who paid attention. When Dan opens the gift set and sees that you picked a Padron because he liked the one at the bachelor party, that is the moment that matters. The gift is the evidence. The attention is the gift.
If you want to talk through your specific wedding, the contact form is the fastest way to reach us. Tell us the date, the guest count, and one or two things about the groom. We will get back to you within a day with a recommended setup.
Whatever you pick, pick on his behalf. Not the room's. He will know.