However, if California has earned its reputation as inhospitable to lovers of the leaf, San Diego - its second-largest city, widely regarded as having the nation’s most pleasant year-round climate - has proven to be something of a cigar smoker’s oasis. First and foremost among the reasons, of course, is that climate itself; while subject to the Golden State’s strict indoor-smoking laws, San Diego area cigar enthusiasts are blessed with weather that allows them to indulge in their hobby outdoors, comfortably, for most months of the year - a contrast from their brethren in four-season towns like Boston and New York.

But it’s not just the climate. Less radical in its prevailing attitude about smoking than L.A. or San Francisco, San Diego is a city of restaurants with patios and, increasingly, open-air rooftop bars. Not all are smoker-friendly, but with a bit of homework, cigar lovers are likely to find a place that will accommodate them. You can even indulge your appetite for Cuban cigars without much hassle or subterfuge: Tijuana, Mexico, and its fine Casa del Habano shop are just 20 miles south of downtown, accessible via city trolley. Spend an afternoon on the Mexican side of the border and puff to your heart’s content. But even if your intent is to remain in the limits of San Diego County, this sunny jewel of a town is at your disposal.

Downtown/Seaport Village

“I started smoking a pipe in college,” Hunts recalls as we converse over cigars and coffee in the patio outside his shop. “Whenever I traveled, I ended up wandering into tobacco shops. Being an outgoing guy who likes to meet people, ultimately I realized this might be the ideal job for me.” The growth of Seaport Village, which kicked off the revitalization of San Diego’s entire downtown, was a boon to the shop, which now sees foot traffic of about 15 million people per year, nearly all tourists. This spawned Captain Hunt’s reputation in the cigar industry as a “tasting room,” where new brands are sent for an informal evaluation. Hunt is proud of the distinction. “We’re in walking distance of the convention center, we’re surrounded by hotels, and when the Navy ships come into port, the sailors walk past my front door,” he points out. “Someone can stop in here, try a cigar, and walk into his local tobacconist with the band and say, ‘I tried this in San Diego; order it for me.”

Hunt has raised three children, all of whom are now involved in the cigar business, and his wife also helps out at the shop. He has hosted numerous cigar events with various manufacturers, and keeps the store open every day of the year, including Christmas. It is the beautiful summer months that are his busiest shopping times, however, - with the store’s hours getting extended accordingly. “Summer,” he says with a smile, exhaling a puff from his La Flor Dominicana, “is my Christmas.”

The original location in the Gaslamp Quarter is an architectural tribute to Old Havana, with exposed brick walls, ceiling fans, and an area in the front window dedicated to cigar rolling, with a thatched roof and piles of wooden cigar molds and presses. One of the shop’s three in-house rollers dutifully makes cigars, enticing wandering tourists to stop in and check out the wares.

Cuban Cigar Factory produces an impressive output of its own domestically made brands (“All the rolling is done right here in the store,” Kalasho promises) which it sells via its shops and its website (www.cubancigarfactory.com). All made with tobacco from Honduras, the Dominican Republic, Nicaragua, Indonesia, and the Canary Islands of Spain, the lines include Natural, Maduro, an aged Vintage, and a flavored Vanilla Sweet. The tobacco is all stored in the cavernous basement, and finished cigars are aged there in a spacious humidor room. On the main floor, a walk-in humidor is stocked with numerous popular premium brands as well as the store’s in-house cigars.

A renovation of the upstairs loft area, underway during my visit, will offer even more sitting space for patrons, adding to the round tables downstairs where they can watch the wall-mounted TV or play a game of dominos or chess while indulging in a smoke.

Espinal reminisces fondly over his early days here, when the demand brought about by the boom led to a proliferation of cigar stores in the area. “There used to be about 11 stores here; people used to ask if this was a little cigar city,” he says. “Now there are only three. It’s a different city than it was in 1995. We didn’t have the condos, the ballpark… and what it cost me now for five days’ rent would buy me a whole month.”

Fortunately for Espinal and his lease, his store not only survived the lean post-boom years, but also expanded to become one of the premier destinations for Gaslamp Quarter nightcrawlers looking for a place to enjoy a premium cigar with a glass of wine or port. The walk-in humidor in the rear of the store is not huge, but carries a selection of best-selling established brands and buzz-worthy boutiques, including, of course, the Cesar brand itself - with filler and binder from the Espinals’ farm in the D.R., and Costa Rican wrapper, distributed by the family’s Tampa-based manufacturing business, Tabacalera Cesar y Familia. The house brand, Espinal says, is still the store’s biggest seller.

Espinal also takes pride in the wine selection, displayed elegantly behind the restaurant-like bar at the store’s front. Cesar’s offers nearly 150 labels, 37 by the glass. The wine list, expectedly, is about 60% California, but the rest represent a wide variety of regions, including France, Australia, and Chile. As one would expect in a cigar hangout, port is also well represented, as are Champagne and sparkling wine. Under California law, no establishment that sells cigars can be a full bar, so there are no whiskies or cognacs, but the wine-loving Southern California clientele doesn’t seem to mind. “This selection puts us at the level of a high-end steakhouse,” Espinal claims. “There are wine bars around here that don’t have nearly the selection we do.”

The ultra-modern design is highlighted by the towering wine racks that frame the entrance, and the eye-catching floor-to-ceiling waterfall that cascades into the central bar area. Stingaree’s Mediterranean-and-Asian-influenced dinner menu by Chef Anthony Friscia is alone worth the visit. After dinner, join the local scenesters as they ascend the floating staircase to the VIP mezzanine level and rooftop lounge, equipped with a reflecting pool, heat lamps, and several well stocked bar stations.

Cigar enthusiasts have been known to flock to the rooftop, often to kick back with other smokers in one of the private cabanas or around the toasty fire pit (believe it or not, San Diego evenings can get chilly in the winter months), where they can puff, converse, flirt, check out the breathtaking view of the city, or simply watch the parade of beautiful people go by.