Song and sin in Santiago de Cuba

View from El Morro. 

It's easy to get into mischief in Santiago de Cuba.   Closer to Haiti and the Dominican Republic than it is to Havana, this city on Cuba's rugged south coast is famous for its July Carnival and the earthy Caribbean street party atmosphere that pervades year round.

La Casa de la Trova.

Son, salsa--just about every Cuban music genre originated in Santiago's narrow alleys. From Afro-Cuban drumming in Parque Cespedes to traditional trovador sessions at the Casa de la Trova, music is everywhere, harmonies rising like cigar smoke on just about every street corner.
Also on every street corner, Santiago's notorious jineteros hustling everything from black market tobacco and questionable cash exchange to steamy rum-soaked encounters with one or more of the world's savviest chicas.
You think you're well travelled.  You think you're immune to being played.  But unlike the sabre-wielding pirates who used to assail this coast, today's jinateros are typically Cuban: congenial, courteous, even sweet.  At some point you'll find you've been hustled, even if you don't realize it until a week later.
"Taxi?  No?  A dollar anyway, then?"  "Can I have your shirt? Some soap? Shampoo?"

Taxis congregate at the Cathedral.

If it all gets too much, the terrace of the Casa Granda Hotel provides a refuge, reasonably-priced drinks and a ringside seat to the street theatre playing out below.
Jinateros are not always to be avoided, though, and chatting up the right one (and many speak some English) can help streamline/maximize your experience.  If you've come to Cuba on an all-inclusive package, chances are your resort is an hour out of town.  Trying to get back to the resort late at night in an ancient Bel-Air on hairpin rural roads by no more than the light of the silvery moon is not recommended, especially after half a dozen mojitos.

So how to do Santiago on Saturday night?  Cover your resort wristband (if you're wearing one) with a bracelet or cheap watch, head for Parque Cespedes and hire a jinetero for 5 CUC to show you around several central casas particulares until you find one you like.  With the average casa particulare (the Cuban equivalent of a B&B) going for about 25 CUC, staying off the resort for a night or two works out less expensive than taking taxis back and forth.  If you're uncomfortable not having a reservation ahead of time, your resort can book a casa particulare for you.
Things have improved for Cubans since the desperate days of the "special period" when it was achingly obvious that people did not have enough to eat.  I'm happy to report that overweight Cubans are no longer a rarity, although the two-currency system has created serious inequalities.  You don't have to give a CUC or "dollar" to every rummy who asks (unless you want to get swarmed), but if someone does a genuine service, please tip.  Except for long cab rides, prices for most things (beer or coffee on the terrace of the Casa Granda about 1.50 CUC, a painting at Galeria Santiago between 20 and 30 CUC) are low so a little extra tipping won't break your budget.  Be sure to carry coins and small bills so you can spread the wealth around a little at a time, above all to the musicians.  Buy their homemade CDs, pay for a favorite song.  They, above all, create the Santiago experience.