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Best city to go on a cigar vacation?

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I am looking to go on vacation some time next year in the US, but wanted to choose a place that is great in general, but also a city that is great for cigar smokers. Does anyone have place in mind they really like, and why? I've been to Vegas numerous times, and might be going there for the IPCPR next year so that is out of the question.
 
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For cigars? I have a feeling you would be hard-pressed to find a place better than Miami!
I live in South Florida already, and find Little Havana to be a disappointment. I am looking for a city that is great for cigars, but offers a lot more in other things. I enjoy sports, nice restaurants, and sight seeing when I am on vacation.
 
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Chicago is great for cigars as far as quality shops go...but you wont be able to smoke indoors anywhere besides the shops. If you are also looking for good eats, sports, sight seeing and tourist stuff then Chicago may be an ideal spot for you. Just don't come in Dec-Feb or you will be miserable coming from a warmer climate.
 
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I was actually at a wedding in Tampa a few months ago, and was extremely disappointed by Ybor City's cigar selection. I work for a cigar company, and someone in my company told me to go to Tampa Humidor instead of Ybor. Unfortunately, I didn't listen to their advice, and went to Ybor instead. I fel the hand rolled cigars they make in Ybor are made with crappy tobacco, and the stores did not have a good selection of brands.
 
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Chicago is great for cigars as far as quality shops go...but you wont be able to smoke indoors anywhere besides the shops. If you are also looking for good eats, sports, sight seeing and tourist stuff then Chicago may be an ideal spot for you. Just don't come in Dec-Feb or you will be miserable coming from a warmer climate.
Chicago is definitely a place I am looking at as I've never been to the city, love that it is a sports town, has a lot of history, great restaurants, and great cigar lounges. I am also looking at San Francisco/wine country, Washington DC, NYC, and others.
 
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I hear that New Orleans can be nice. Great food, sights and music. I don't know how they feel about public smoking but there are some nice shops like Cigar Factory. My wife brought home some of their cigars, which they roll on the premises, and they were very good.
 
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Chicago is great for cigars as far as quality shops go...but you wont be able to smoke indoors anywhere besides the shops. If you are also looking for good eats, sports, sight seeing and tourist stuff then Chicago may be an ideal spot for you. Just don't come in Dec-Feb or you will be miserable coming from a warmer climate.
I agree, haven't gone personally but have heard great things. Plus in Maryland we can't smoke indoors except for cigar shops so I'm not at a loss there, haha.
 
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Charleston, SC - Classy lounge....very good hand-rolled shop.....good weather and decent enough sight-seeing

Couple of other favorites: San Diego (cigar friendlier than you might think - and LCdH TJ is only couple hours round-trip), Jacksonville/St. Augustine (sights, weather, lots of comfortable smoking spots)
 

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Edit: just read all of the first post, sorry, nothing of any value to add
 
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New Orleans, just stay off bourbon street, unless frat boy type shennanigans are your thing.
 
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Couple of other favorites: San Diego (cigar friendlier than you might think - and LCdH TJ is only couple hours round-trip), Jacksonville/St. Augustine (sights, weather, lots of comfortable smoking spots)
I've actually lived in San Diego, and moved away about five years ago so I know that they have to offer.
 
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Charleston, SC - Classy lounge....very good hand-rolled shop.....good weather and decent enough sight-seeing

Couple of other favorites: San Diego (cigar friendlier than you might think - and LCdH TJ is only couple hours round-trip), Jacksonville/St. Augustine (sights, weather, lots of comfortable smoking spots)
Dave where in Charleston? I was just there this time last month and only found 2 shops (Tinder Box and Smoking Lamp) both had little to no inventory but did have a decent looking lounge area.
 
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