I am just back from Cuba, I had a great time. On buying chips. There is a booksellers market around the Plaza de Armas on Obispo Street. Some of the booksellers have other items, including casino chips. Mob era chips were highly valued and you can get them cheaper on eBay. Chips from before the mob era were more reasonably priced. I did not see any that looked like counterfeits. I also found a small book store right next to Sloppy Joe's Bar. They have a display of mob era Casino chips on the wall (not for sale) and they have some additional chips for sale that were packed away in a file cabinet. Pricing was the same as in the market.
Trains ... steam era locomotives are on display in the streets surrounding the Crafts Market. I am pretty sure that whatever tour you are on will take you to the Crafts market. The steam loco's are just outside the building and there are several more in the area.
Habana is safe, lots of policeman and low crime rate. There are many beggars and street people trying to sell you something like cigars. Politely tell them "No Gracias" and they will leave you alone. You are not likely to get what you think you are getting from any of the street sellers, avoid them. You'll get better food at the private, as opposed to state run, restaurants. The best looking restored vintage American cars were in front of the Capitol building.
Absolute to do's: Cigar Factory, Tropicana Nightclub (pay for the $85 seats and you might get upgraded to the $95 seats), Buena Vista Social Club, Nacional Hotel, Habana Riviera, Park Avenue, the Malecon, Prado, Sloppy Joe's Bar, the Floridita, Obispo Street and find a nice street cafe where you can spend an hour smoking a fine Cuban cigar while sipping aged Cuban rum.
You can contact me for more info. Cuba photos on my website: http://www.ckaplan.com/mypic.php
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