Best Cigars for Beginners: A Guide For Your First Smoke
Walking into a cigar shop for the first time can feel overwhelming. Hundreds of options, all different sizes, wrappers, and price points — and everyone in the room seems to already know exactly what they want. We get it. We've helped thousands of first-time cigar smokers at our shops in Southern Arizona, and the advice is always the same: start mild, keep it simple, and don't overthink it.
This guide breaks down everything you need to know to pick your first cigar with confidence.
Start Mild — You Can Always Go Stronger
The single biggest mistake beginners make is grabbing a full-bodied cigar because someone told them it was "the best." A full-strength cigar on an empty stomach with no tolerance is a fast track to feeling sick. It's like jumping straight to black coffee when you've never had caffeine.
Start with mild or mild-medium strength cigars. These let you actually enjoy the flavor without your body fighting the nicotine. Once you've smoked a few and developed a palate, you can work your way up to medium and eventually full-bodied cigars.
Understanding Cigar Sizes and Shapes
Cigars come in a range of sizes, measured by two numbers: length (in inches) and ring gauge (the diameter in 64ths of an inch). A 5 × 50 cigar is 5 inches long with a 50 ring gauge.
For your first cigar, aim for something in the Robusto or Corona range:
- Robusto (roughly 5" × 50) — The most popular size in the world. Takes about 45 minutes to an hour to smoke. Not too long, not too short.
- Corona (roughly 5.5" × 42) — A classic, slightly thinner shape. Maybe 30–40 minutes. Great if you're not sure about committing to a longer smoke.
- Toro (roughly 6" × 50) — A step up in length. About an hour. Good if you want a bit more time to explore the flavors.
Avoid anything over 6.5 inches or above a 54 ring gauge for your first time. A Churchill or a Gordo is a lot of cigar for someone who's never smoked before.
What the Wrapper Tells You
The wrapper is the outer leaf — it's the first thing you see, and it gives you a solid clue about what to expect in terms of flavor and strength.
Connecticut — Light tan, smooth, and golden. This is the classic beginner wrapper. Expect creamy, mild flavors with notes of cedar, vanilla, and toast. If you see a light-colored cigar, it's almost certainly Connecticut.
Habano — Medium brown with a bit of sheen. A step up in body. Adds some pepper and spice to the mix. A good second or third cigar once you're comfortable with mild smokes.
Maduro — Dark brown to almost black. Despite the dark color, Maduro doesn't always mean strong. Many Maduro cigars are medium-bodied with rich, sweet flavors — chocolate, coffee, molasses. Don't be afraid of the color, but check the strength rating first.
Our Top Picks for Beginners
These are cigars we consistently recommend to first-timers at Anthony's. They're all widely available, reasonably priced, and forgiving enough for a new smoker.
Oliva Connecticut Reserve — The Easy Choice
This is the cigar we hand to someone who says "I've never smoked a cigar before." The Ecuadorian Connecticut wrapper is silky smooth, and the Nicaraguan filler keeps things interesting without overwhelming your palate. Light, creamy, with a touch of sweetness. The Robusto is the best starting point.
Strength: Mild-Medium | Wrapper: Connecticut | Price range: $7–10
Shop Oliva Connecticut Reserve →
Arturo Fuente 8-5-8 — A Dominican Classic
Arturo Fuente has been making cigars since 1912, and the 8-5-8 is one of their most approachable blends. The Connecticut wrapper delivers a mellow, nutty smoke with a bit of sweetness on the finish. It's a cigar that practically smokes itself.
Strength: Mild | Wrapper: Connecticut | Price range: $6–9
Macanudo Café — The Gateway Cigar
If there's one cigar brand synonymous with "beginner-friendly," it's Macanudo. The Café line uses a Connecticut shade wrapper and Dominican filler for a smooth, easy smoke with hints of cream and roasted nuts. It's not flashy, but it's consistently good.
Strength: Mild | Wrapper: Connecticut | Price range: $5–8
Perdomo Champagne 10th Anniversary — Smooth Operator
If you want something a little more refined for your first smoke, the Perdomo Champagne is hard to beat. Aged in bourbon barrels, it's incredibly smooth with notes of cream, vanilla, and a hint of honey. The Connecticut wrapper keeps it solidly in mild territory.
Strength: Mild | Wrapper: Connecticut | Price range: $7–10
My Father Connecticut — When You're Ready for More
Once you've smoked a few mild cigars and want to push into mild-medium territory, My Father Connecticut is the bridge. It has a bit more complexity — some pepper, leather, and cedar alongside the cream. Still very approachable, but it gives you a taste of what fuller cigars are like.
Strength: Mild-Medium | Wrapper: Connecticut | Price range: $8–12
How to Smoke a Cigar (Quick Version)
- Cut it. Use a cigar cutter — a straight cut just above the cap line is the easiest method. Don't bite it.
- Toast the foot. Hold the flame about half an inch below the foot of the cigar and rotate it slowly. You want an even, glowing cherry before you start puffing.
- Don't inhale. This is the most important rule. A cigar is not a cigarette. Draw the smoke into your mouth, taste it, and let it go. Inhaling cigar smoke will make you cough and feel terrible.
- Take your time. Puff every 30–60 seconds. If you smoke too fast, the cigar gets hot and bitter. Let it breathe.
- Don't worry about the ash. Let it fall naturally — a long ash is actually a sign of a well-made cigar. You don't need to constantly tap it off.
A Few More Tips
- Eat something first. Don't smoke a cigar on an empty stomach, especially as a beginner. The nicotine will hit you harder than you expect.
- Pair it with something sweet. Coffee, cola, or even a sweet bourbon or rum smooth out the edges and make the experience more enjoyable.
- You don't have to finish it. If you start feeling dizzy or nauseous, put it down. No shame in it. Cigar smoking is supposed to be relaxing — if it's not, stop.
- Store cigars properly. If you buy more than you'll smoke in a day or two, keep them in a humidor or a sealed bag with a humidity pack (like a Boveda). Dried-out cigars taste terrible.
Ready to Try Your First Cigar?
Browse our full cigar collection or filter by mild strength to find your starting point. We ship nationwide, and every cigar leaves our humidor fresh.
Not sure where to start? Contact us — we've been helping first-time smokers pick the right cigar for over 15 years.