Good cheapish smokes that come to my mind are the 601 Blue, Man O War, and La Gloria Cubana Serie R, Oliva's, 5 Vegas Triple-A.... TBH, the list could go on and on...

I would buy some samplers before you jump headfirst into a box purchase. Would suck to have 20 cigars that you don't like.
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Read, read and read reviews. Get some samples from B&Ms or get some 5 packs online.
Start a journal with every new cigar you try, it'll help force you to sit down and focus on the cigar.
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Spend some time in the review section here and on other sites. Look for cigars that you've smoked and enjoyed and then look for other reviews by the same person. There's no guarantee that you'll like the same smokes but it could give you a lead.
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I absolutely love all things Drew Estate Liga Privada and the whole Illusione line up, both of which were already mentioned. There were many other mentions already that I agree with so I will offer a few other mentions that I smoked with great flavors that are on the more inexpensive side...

Siglo Maduro (around $6 a stick), Famous Nicaraguan Maduro (Great budget stick that you can get for $40 a bundle!), Grimalkin by Emilio (about $7.50 a stick).

If nothing else....just start smoking and you will find out what you like! Enjoy! :-)
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+1 Jake is good, Jake is wise...:-)
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If your ok with tons of great flavor without having to spend near as much money try some AJ fernandez blends.

AJ Fernandez Blends
1844
5 Vegas"AAA"
A. Fernandez Signature Series
Cigar.com House Blend Brazilian Label
Cigar.com Sungrown Label
Diesel---Unholy Cocktail,Unlimited
Double Happiness
Esteban Carreras Habano
Graycliff G2 Turbo
Gurkha--- Park Avenue,Sherpa
Gurkha Microbatch--- S-2,C-10,TPB-1
ITC 10th Anniversary
La Cuna Bin No. 85
La Herencia Cubana Oscuro Fuerte
Man O' War--- Ruination,virtue,Armada,PURO
Nica Libre
Padilla--- Achilles,Habano
Reposado 96
Rocky Patel--- Fusion,Double Maduro,Signature
Sol Cubano Cuban Cabinet
Indian Tabac Split Decision
Ave Maria
San Miguel
Moro Castle
San Lotano--- Connecticut,Habano,Maduro
:-)

I really like the 1844's, AJ signatures, MOW puro's, 5Vegas "AAA",Graycliff Turbo's.
most of these can be had for under 3.00 each.
And no I'm not affiliated with CI or AJ Fernandez.
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That seems like a great idea I put that on my list of things to do!!!
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That s a great explanation T! I cant wait to get a taste!
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Just be aware that not every employee/owner at a B&M is as knowledgeable or willing to spend the time with customers.
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I really appreciate all you guys contributing to this post! I have had the La Gloria Cubana and thought it was very tasty. Another one that I felt has a great taste is Bolivar. I want to clarify that im not a new cigar smoker, been smoking maybe 1 a week for about 5 years. Maduro and Ligero doesn't scare me either. Maybe a lil to brave there I know... But considering im smoking like 4 a week now I want to buy stuff that tastes better than the average stick. Happy Saturday guys!
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Can u elaborate on start a journal a little bit?
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That a list J!! Now I have to buy a cooler.... TY!
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One bit of advise I'd like to offer is that you should not try something new, then give up on the brand entirely if you did not enjoy that particular cigar. Remember that they are organic handmade products, and the best cigar you ever smoked may be sitting right next to the worst one you ever tried to smoke, both in the same box by the same maker, and even the same roller.

Besides, it's sort of like sex . . . you may be over- or underwhelmed with your first experience, but tastes can stabilize with repeated attempts.
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Years ago I used to write down my experiences when smoking a cigar (esp if they were a new brand for me). Think of a mini-review for yourself to keep. As someone else stated, when reading reviews and the reviewer "shares" similar tastes profile as I do, I tend to try those cigars.

I'm looking for a good iPad app for a cigar journal because now I want to rate my cigars as they age. I reviewed a cigar this morning that has been in my humi since 2007 and I wish I had written down a little review when I smoked the first one OTT in 07 (fresh). For me, it would be interesting to see how that cigar aged over the last 5 years.
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Interesting, so are you saying that if you smoked something u really didn't enjoy, you would still buy that cigar again?
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Thanks Gooner, sounds like a great idea.
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Don't just try one brand and make definitive judgement. Lots of labels share manufacturing duty's. Like AJ Fernandez makes some cigars for Graycliff, Ghurka, 5Vegas etc. He (they) don't own the entire line just make certain cigars for the other company's.

Example. I did not care for any 5Vegas I tried until the "AAA", It was totally different from the other I tried before and I really liked it. Come to find out it's made by AJ (which I have obviously recently came to love).

I have also started getting at least two of each stick to try at different times to help eliminate "a bad stick" or "bad cigar day" (Because some days I light a maduro when I really should have had a Connecticut etc.

Just smoke lots. Then smoke more.
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I could sit here and recommend cigars all day, but it's all about preference. Go to CI and purchase a lot of samplers. That will give you a decent variety so you can decide what you like or don't like.
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Image

My recent purchases...
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for what it's worth I tried to post this pic about 10 times, never had such trouble on a board trying to post a pic...
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