Check the latest status for U.S. citizens traveling to Cuba. Some restrictions eased earlier in 2009. state.gov
Fly through Mexico, Canada or the Bahamas. Since 1961, the U.S. gov’t has prohibited Americans without special licenses from spending money in Cuba (in theory limiting tourism). Despite the threat of fines and even imprisonment, however, thousands of Americans travel to Cuba every year through a third country.
Stay at Hemingway’s old haunt, Hotel Ambos Mundos (rooms start at $110), a wonderfully colonial hotel (his room, 511, has been made into a small museum), hotelambosmundos-cuba.com. Rooms are small and simply furnished in the heart of Old Havana. Request an outside room; interior rooms don’t have windows. Hotel Los Jazmines (rooms start at $65) a few miles outside the tourist town of Viñales has the best panorama of the valley with its picturesque limestone mountains. The rooms in the new wing have balconies & picture-postcard views. Casa Emilia (run by Doña Emilia, ask anyone for directions) rents out rooms in her home for $30 and cooks fresh lobster dishes. There’s only one resort at Maria La Gorda, the Villa Maria La Gorda Hotel and International Diving Center (rooms start at $65). villamarialagorda.com
Sip a mojito with fresh mint leaves and lime, available anywhere, anytime. Frozen daiquiris run a close second. You’ll pay $4 a drink.
Puff a handrolled puro. Cigars are available everywhere (prices start at $5), but the best come from cigar shops in Havana or directly from tobacco farms in Piñar del Rio. Homemade puros won’t have labels, but make sure they’re fresh (the cigar should give just a little — and not feel dry and crackly — when pinched).
Spend Cuban convertible pesos (referred to as CUC or “kook”). U.S. dollars can be converted on arrival, but a 10 percent tax is imposed. A better option is to bring along plenty of Canadian dollars and change those into CUC. Change from banks to avoid being duped into buying Cuban pesos (the local currency, worth far less). Your American credit and debit cards will not work in Cuba, so be sure to bring plenty of cash.
Hop on the Havana Tour Bus, an open-air double-decker bus that circulates through old and new Havana. For just $5 you can hop on and hop off all day.