745 Boylston St., Boston
Cigar Masters is by far the most luxurious of Boston’s cigar bars. It has the finest cushy leather couches, vintage liquors, and, of course, cigars to be had this far north of Cuba. Highly recommended by Hans Rickneit of Leavitt and Pierce, as well as Cigar Afficionato, this is the best smoke in town for a young beginning smoker. Although this establishment does feature a physical bar, the real scene can be found in the back lounge. The lights are warm and low, and the dark wood paneling evokes an Old World ambiance. Choose from a wide selection of ports, sherries and wines brought to you by scantily clad waitresses. Light fare such as quesadillas or hummus and pita bread are also available.
But let’s face it—you came here to smoke. So head over to the huge walk-in humidor—a climate-controlled room where all the cigars are kept—and ask the friendly, knowledgeable staff for a recommendation. They will happily respond with more questions than an overzealous mother-in-law: Do you want something light or heavy? Big or small? Cheap or expensive? Are you new to cigars?
There is a point to this well-meaning barrage, as you will realize when you’re smoking the cigar of your dreams.
Vittorio's Stanza dei Sigari
292 Hanover St., Boston
Welcome to Boston’s premier Mafia hangout. Descend three floors below Vittorio’s proper to enter an unmarked door that seemingly leads to the janitor’s closet. Sweep straight past the stone-faced bouncer and smile for the thirty pairs of eyes suddenly fixed upon you. Before you hit the bar up front, make sure you know what you want, because nothing is on display. If you made it this far, and found a cigar and a seat, congratulations – you’ve reached people-watching Valhalla. Even if psychology is not your forte, you’ll be drawn in by the social machinations around you. Of course, if you are female, you’ll get to participate first-hand. Over the course of an hour, FM met three different men, all of whom were named Guido. Yes, you will find una bella fuma (a good smoke) here, but the real reward’s the company.
Gloucester Street Cigar Company
34 Gloucester St., Boston
Although it’s an old boys’ club, Gloucester Street Cigar Company is rather welcoming. This establishment is more of a cigar shop than a cigar bar, but the roomy seats in the warm, simple front room do encourage loitering. Packs of regulars make a quick trip to the large humidor in the back before settling in for the morning to chat. At night, a back room is available for group rentals. For example, the Boston University Cigar Afficianato Club holds regular meetings here. While barman Justin Held insists that the Gloucester Street Cigar Company is “a very male environment [where] testosterone levels get going,” there is a small but growing group of female regulars. Want to know how to break into the inner circle? Pierre Rogers, a patron of five years whose beagle Louie freely roams the shop, jokingly says that becoming a regular depends on “how many hours a week you put in.” But between the affable crowd and the quality product, making this your fifth class might not be too difficult.
Five Steps to Cigar Expertise
1. Request something mild, smooth and light-colored, such as a Davidoff or an Ashton, to start.
2. Ask the establishment to trim the cigar for you in either a wedge cut or a straight cut. Unless you’re a connoisseur, it doesn’t really matter.
3. Same deal with label-on, label-off—it’s really up to your discretion.
4. Hold the flame to the end of the cigar and keep puffing. Don’t inhale into your lungs; you get enough toxins from keeping it in your mouth.
5. Don’t tap off the ash too frequently—it’s the mark of a newbie.