Havana [1] has about two dozen Casas del Habano (the official cigar stores), with more being added all the time. Buy at an official store. If you buy off the street, you’re almost certainly going to be sold fakes, although you’ll be hard-pressed to know this.
For more information about what to look for and what to avoid when shopping specifically for cigars, see the Cigars [2] page in the Essentials section.
The airport departure lounge has the best-stocked rum and liquor stock in town, as well as a fine cigar selection and a full range of Cuban and import scents and colognes, though don’t expect better prices.
The best cigar store is the Casa del Habano (Industria #520, e/ Barcelona y Dragones, tel. 07/862-0086, Mon.–Fri. 9 a.m.–7 p.m., Sat. 9 a.m.–5 p.m., Sun. 10 a.m.–4 p.m.) in Fábrica de Tabaco Partagás. It has a massive walk-in humidor, plus a hidden lounge with a narrow humidified walk-in cigar showcase for serious smokers.
My other favorites are the Casa del Habano (Mercaderes #202, esq. Lamparilla, tel. 07/862-9682, daily 10:30 a.m.–7 p.m.) in the Hostal Conde de Villanueva and Salón Cuba (Neptuno, e/ Prado y Zulueta, tel. 07/866-6627, daily 8:30 a.m.–9:15 p.m.), in the Hotel NH Parque Central. Each has a sumptuous smoker’s lounge.
The Casa del Habano (Mercaderes #120, esq. Obrapía, tel. 07/861-5795, daily 9 a.m.–5 p.m.) has a limited selection.
And the Casa del Ron y Tabaco (Obispo, e/ Monserrate y Bernaza, tel. 07/866-0911, daily 10 a.m.–6 p.m.), above El Floridita [3], has knowledgeable staff. This store also lets you sample the rums before buying, as does the Fundación Havana Club (Av. del Puerto #262, e/ Churruca y Sol, tel. 07/861-8051, daily 9 a.m.–9 p.m.), adjoining the Museo de Ron [4].
Taberna del Galeón (Baratillo, esq. Obispo, tel. 07/33-8476, Mon.–Fri. 9 a.m.–7 p.m.), off the southeast corner of Plaza de Armas [5], is well-stocked with rums.
Fábrica de Ron Bocoy (Máximo Gómez #1417, e/ Patria y Auditor, Cerro, tel. 07/877-5781, Mon.–Fri. 7 a.m.–5 p.m., Sat. 9 a.m.–3 p.m.) has a well-stocked store, plus a bar for tasting as a prelude to buying.
The Casas del Habano in the Hotel Nacional (Calle O y 21, tel. 07/873-3564), Hotel Habana Libre Tryp (Calle L, e/ 23 y 25, tel. 07/834-6100), Hotel Meliá Cohiba (Paseo, e/ 1ra y 3ra, tel. 07/833-3636), and Hotel Habana Riviera (Malecón y Paseo, tel. 07/836-4051) are well-stocked.
Miramar [6] has some of the best cigar stores in town. The Casa del Habano (5ta Av., esq. 16, tel. 07/204-7975, Mon.–Sat. 10 a.m.–6 p.m.) boasts a vast humidor, executive rooms, bar and lounge, and good service.
Club Habana’s Casa del Habano (5ta Av. e/ 188 y 192, tel. 07/204-5700, daily 9 a.m.–5 p.m.) is run by Enrique Mons, who for most of the 1970s and ’80s was in charge of quality control for the Cuban cigar industry.
Other sources include Tabaco El Aljibe (7ma Av., e/ 24 y 26, tel. 07/204-1012), Tabaco La Giraldilla (Calle 222 y Av. 37, La Coronela, tel. 07/33-1155), and the tobacco stores in the Hotel Comodoro (1ra Av. y Calle 84, tel. 07/204-5551), Hotel Meliá Habana (3ra Av., e/ 76 y 80, tel. 07/206-9406), and Hotel Occidental Miramar (5ta Av., e/ 72 y 76, tel. 07/204-3584).
Links:
[1] http://www.moon.com/destinations/cuba/havana
[2] http://www.moon.com/destinations/cuba/essentials/shopping/cigars
[3] http://www.moon.com/destinations/cuba/havana/sights-habana-vieja/monserrate/el-floridita
[4] http://www.moon.com/destinations/cuba/havana/sights-habana-vieja/plaza-de-san-francisco/museo-de-ron
[5] http://www.moon.com/destinations/cuba/havana/sights-habana-vieja/plaza-de-armas
[6] http://www.moon.com/destinations/cuba/havana/sights-playa/miramar