Your worst enemy is sitting in the rich leather seat right next to you. And the smell of car exhaust and back-alley private commerce is everywhere.
The front cover of the box is about as misleading as it can get.
In Santiago, there are no smiles. No companionship. No bicycles, either. There is a musician, but he exists only as a person to shake down for money if he gets too close to your car. Which is probably why he's hiding out on the balcony.
Instead, you and your opponents are "black-market wheelers and dealers" who try every hook and crook (in the book!) to acquire resources to supply a waiting cargo ship. You will wish failure and disappointment down on your adversaries every turn. You will fight tooth and nail. But there is a twist to this competition.
You and your opponents must share the same car.
I'm surprised this hasn't been turned into a reality show yet.
The board is a simple track. Around the track are randomly placed Cubans and special-ability Buildings. The various stops around the track give you fruit, sugar, tobacco, cigars, rum and wood. At the end of the track is the cargo ship, waiting expectantly for the goods you're picking up.
The track moves in one direction, like Monopoly. So after reaching a destination, you have to wait to come all the way around for a return visit. There is an additional "pesos" resource which you must continually pay your driver with, otherwise he robotically stops at each destination like a sabbath-mode elevator.
The randomly placed buildings mean every single game plays completely differently. You can't internalize any particular route because next game all the synergies you've grown used to are gone. The tobacco guy who lived next door to the cigar factory could just as easily be the fruit seller who lives next to the rum refinery.
I love games where you can really mess with the other players. Resource collection is normally pretty boring, luckily Santiago de Cuba has many tools for the enterprising saboteur.
There are three minor and one major sources of shenanigans.
This leads to the next shenanigan. One of the special-ability buildings is the "newspaper publisher".
Next we have Alonso the Lawyer.
Finally, we have the Customs Office.
Driving around the board with somewhat experienced players quickly transforms into a delicate dance by automobile around the great harbor of historic Santiago de Cuba. You might start leaning toward resource acquisition, switch to dishing out as much hate as possible to the other players, then switch back to resource acquisition once the boat gets reloaded. Figuring out the new points of synergy between people and buildings is also a big part the overall strategy.
The biggest secret just seems to be to keep your options open and use what's easily available from your somewhat unpredictable car stops. One of the sellers is a "lumberjack" who gives you wood. The cargo ship is always hungry for wood, and accepts in place of any other resource (and only giving you 1 victory point as a penalty). But if you don't think you're going to be able to make the sugar seller, wood is definitely better than nothing.
Santiago de Cuba at Board Game Geek
Santiago on-line game playable for free at Yucata.de