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How to Get into Cigars for the First Time

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The Basics:

So, you’re looking to get into the world of premium cigars? Maybe you’ve never had a cigar before, or maybe you enjoyed one at a wedding recently and are looking to dip your toes into the deep end a bit. Whatever the case, we’ve got the selection and knowledge you need to guide you through the world of handmade cigars. Cigars are a fantastic hobby, encouraging you to take time to sit down and relax while enjoying some time for yourself, or with close friends.

Before we jump into our cigar selections, let’s make sure you have the right tools for the job. If you’ve never enjoyed a cigar before, check out some of our beginner tips here:

Okay, ready to get started? Let’s dive in!

For our beginner cigar recommendations, we’re going to take a tour of the whole industry. Many people recommending first cigars will stick to really mellow stuff, or classic brands like Romeo y Julieta or Macanudo. We’re going to do things a little bit differently.

Our list covers a range of price points, body, and flavor profiles, starting with mellow, beginner-friendly options and ending with full-bodied powerhouses. We’ll enjoy some classic brands, some truly top-shelf options, and a nice variety of offerings from boutique cigar makers.

All of these cigars are available in our upcoming Ultimate Beginner Cigar Sampler (Check back sampler coming soon!)


Ten fantastic cigars, available for a great price, that’s sure to get you into cigars the right way. I’d recommend this to anyone who wants to learn more about the cigar industry, or as a great gift. Once the sampler is in your hand, check out our rundown of each choice below.

Top 10 Beginner Cigars:

1.      Southern Draw Rose of Sharon Robusto


  • Body: Mellow – Medium
  • Country of Origin: Nicaragua
  • Price Point: $10.25
  • Main Flavors: Cream, Nuts, Slight Pepper

The first cigar in our line-up is one of my personal favorites, the Southern Draw Rose of Sharon. This mellow to medium-bodied blend is approachable and incredibly flavorful. Rose of Sharon is crafted in Nicaragua with a Connecticut wrapper leaf (something you’ll find a lot of in the beginning of our list). This is a great introduction to the joys cigars have to offer, and I’d confidently recommend this to anyone as their first cigar ever.  

2.      Black Label Trading Co. Royalty Corona



  • Body: Medium
  • Country of Origin: Nicaragua
  • Price Point: $8.50
  • Main Flavors: Earth, Sweetness, Spice

For our second cigar, we’re going down to Nicaragua to visit another up-and-coming boutique cigar maker: Black Label Trading Company. Started by husband-and-wife James and Angela Brown, Black Label has quickly become a very well-respected brand with a large portfolio of highly sought-after releases. Traditionally, they’re known for super full-bodied blends, but Royalty takes a step back on the body and instead, presents a balanced, medium-bodied blend with spicy and sweet nuances that will have you coming back for more.  

3.      Cohiba Connecticut Robusto


  • Body: Mellow - Medium
  • Country of Origin: Dominican Republic
  • Price Point: $21.50
  • Main Flavors: Toast, Nuts, Cedar

For our third cigar, we’re going to take a trip to the top shelf. Cohiba Connecticut. Cohiba is one of the best-known names in cigars due to their beginnings as a Cuban brand. The Cohiba Connecticut is a US version of the cigars made in the Dominican Republic, but its one of the finest Connecticut offerings available. This is our most complex blend so far, with five different countries making an appearance: Ecuador Connecticut on the wrapper, a Mexican binder, and a combination of Brazilian, Dominican, and Nicaraguan fillers. Enjoy!

4.      Foundation Charter Oak CT Rothschild



  • Body: Medium
  • Country of Origin: Nicaragua
  • Price Point: $5.70
  • Main Flavors: Bread, Charred Oak, Peanuts

Alright, we’ve gone through the mellowest cigars on the list, and now it’s time to step it up to the medium-bodied realm. The next four cigars will be slightly fuller than the ones before, but none will overwhelm you. To start, we’re going to ease in with a smaller cigar from a great boutique brand: Foundation. This cigar is a rich, complex gem with a fantastic price point – in fact, Charter Oak CT was named the #1 Value Cigar over at Cigar Aficionado!

5.      ADVentura The Explorer BP Gran Toro


  • Body: Medium
  • Country of Origin: Dominican Republic
  • Price Point: $12.00
  • Main Flavors: Cocoa, Black Pepper, Fruit

For Cigar #5, we’re going to enjoy our first non-Connecticut blend. And, we’re going to step things up in terms of size. ADVentura The Explorer is presented here in a 6”x56 box-pressed Gran Toro and finished with an Ecuador Habano wrapper leaf. Make sure you have plenty of time to enjoy this complex gem, and if you’re a fan of pairing, you’ll find a cigar like this will go nicely with a good bourbon. For future pairing ideas, the general rule of thumb is to match the body and contrast the flavor. A mellow cigar with nice sweetness goes great with a light cup of coffee that’s nice and acidic. Similarly, a full-bodied cigar with tons of spice wants a hearty liquor with some rich caramel sweetness.

6.      Davidoff Winston Churchill Commander


  • Body: Medium
  • Country of Origin: Dominican Republic
  • Price Point: $20.50
  • Main Flavors: Sweet Floral, Wood, Dried Fruit

Named after one of the most famous cigar smokers in all of history, we’re going to enjoy a treat now with the Davidoff Winston Churchill. Davidoff makes some of the finest cigars you can find, and the Winston Churchill line is no exception. This cigar features an Ecuador Habano wrapper leaf over Dominican and Nicaraguan filler tobaccos. A cigar like this is worthy of celebration – make sure you’ll find some uninterrupted time to really soak it in.

7.      Sobremesa El Americano


  • Body: Medium
  • Country of Origin: Nicaragua
  • Price Point: $12.50
  • Main Flavors: Caramel, Baking Spice, Salt

We’re going to wrap up our tour of medium-bodied cigars with the Sobremesa by Dunbarton Tobacco & Trust. Dunbarton is operated by Steve Saka, a legendary blender in the cigar industry. For years, Saka worked at Drew Estate, creating the famous Liga Privada blend. Dunbarton is Saka striking out on his own, and the Sobremesa is his first offering. Enjoy the attention to detail here and resist the urge to burn this down too fast – Saka’s creations are best enjoyed nice and slow.

8.      Drew Estate Undercrown Gran Toro


  • Body: Medium to Full
  • Country of Origin: Nicaragua
  • Price Point: $9.00
  • Main Flavors: Leather, Chocolate, Coffee Bean

Speaking of Drew Estate, let’s move into the medium to full-bodied realm with one of the classic Maduros on the market: Undercrown. This may be the cigar that I’ve personally enjoyed the most of in my life – it’s just a blend I love keeping around in a wide variety of sizes. Undercrown features a Mexican San Andres wrapper and a combination of Brazilian and Nicaraguan leaves inside. If you love this cigar, make sure you check out the Undercrown Sun Grown and the Liga Privada No. 9.

Tip: As we move into the fuller-bodied side of the sampler, set yourself up for success. None of these cigars are going to be “too much” if you approach them correctly. Enjoy fuller cigars after a full meal, and if you like, with a sugary beverage – a Rum & Coke or a Dr. Pepper works well. 

9.      Guardian of the Farm Campeon


  • Body: Medium to Full
  • Country of Origin: Nicaragua
  • Price Point: $9.50
  • Main Flavors: Almond, Cinnamon, Cream

Guardian of the Farm is a blend from Aganorsa – an incredibly important factory to the current Nicaraguan boutique cigar game. Aganorsa grows tobacco and produces cigars for both themselves and many other craft Nicaraguan producers. With Guardian of the Farm, they’ve collaborated with Kyle Gellis from Warped Cigars to create a Nicaraguan “puro” – a cigar containing 100% Nicaraguan tobacco. This size also features Aganorsa’s signature rounded torpedo cap, a nice stylistic touch.

10.  Oliva Serie ‘V’ Double Robusto


  • Body: Full
  • Country of Origin: Nicaragua
  • Price Point: $9.50
  • Main Flavors: Dark Chocolate, Leather, Cedar

You’re ready for the last cigar in our list, a true full-bodied creation from Oliva. Serie ‘V’ is one of the most consistent cigars in Cigar Aficionado’s Top 25 Cigars of the Year. The Serie ‘V’ features a healthy kick of ligero within the blend. Ligero is one of the top leaves on the tobacco plant, and receives the most sunlight and nutrients, making it incredibly flavorful and robust. If you like this cigar, and I’m sure you will, make sure you check out the Oliva Serie ‘V’ Melanio the next time you grab some cigars. This sequel cigar switches out the wrapper and box-presses the blend to make a truly perfect smoke – one that’s won the #1 Cigar of the Year award from numerous outfits.

Next Steps

So, you’ve worked through our entire sampler. Congratulations! You now have a great range of blends, cigar makers, and styles under your belt. Chances are you liked some more than others – that’s natural. Cigars, like food, wine, or beer, are a very subjective hobby.

The first thing I’d do in your position is rank the cigars you have already enjoyed, particularly noting any favorites, and any you did not care for. Then, do a little research. Do the cigars you like have something in common? Is it the wrapper leaf, the country, the flavors, the body? Look for more cigars like that as you continue to explore.

You could also more cigars from the same brand – if you loved the Davidoff Winston Churchill, pick up some other offerings from Davidoff and see if you like them more or less. While the cigars within a brand will taste very different, you’ll often find that particular cigar makers or factories have a signature “style” you can latch on to.

And finally, our best advice: ask other cigar lovers! Post in our community and tell people what you’ve tried and what you’re looking for, and see what people recommend.