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MassHole Militia
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In Boston, the best IMHO is L J Peretti. An old school place, the owners are *tight* with the Fuentes, and they have a phenomenal selection. You can't compare Massachusetts B&M prices with the online vendors because of the 25% excise tax, but when you want to find a cigar, Peretti will usually have it. The space is small and there isn't a smoking lounge, but there are a couple of chairs if you want to sit back and enjoy your purchase.
Next best is Gloucester Street Cigar. They've got a great selection, too. A couple of chairs, but no lounge. CigarMasters has a big selection and a nice lounge, but the prices are extra high and there's a fair bit of attitude. My favorite hangout is Churchill's Lounge, near Quincy Market. Selection is mediocre, but you can bring and smoke your own without any hassle, frowns, or lighting fee. It's a really comfortable place with a very friendly staff and great atmosphere. I try to get there a few times a week.
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