I have travelled to Cuba and particularly Santiago de Cuba on many occasions and have discoverd the city back to front and in the process hopelessly succumbed to its charm.
A great place to visit, full of history and culture and best for those who have an ability to really get into the experience.
The guide books explain the tourist attractions much better than I can in this message. I recommend you do read up a bit on history and sights before you go as this will help you to appreciate more what you see and experience.
Santiago is Cuba's second largest city after the capital Habana but feels like a village. The centre is very concentrated and most Santiago sights are within walking distance. Do stroll and enjoy ... go off the beaten track, meet the people and get a real feel for the country and its folks. The Santiagueros are very, very hospitable and with a normal dose of precautions you should be safe in most places.
Do take water with you and don't overdo it. Santiago is hilly and to walk around in the heat is very, very exhausting !!
Santiago is culturally quite opposite from Habana, this is true for the racial mix, the music, people's attitude. It has also not yet seen the influx of investment into re-building and painting, so you get to see a very 'raw' side of Cuban life.
People are poor, but most have maintained dignity, their pride and a big smile. Lovely !! Allow yourself to be talked to, to meet the people.
You should be aware that the personal space for a Cuban is very different than for others and you may perceive their close approach as threatening. A firm 'no' is normally sufficient to keep things at bay.
All women note that Cuban men are very, very complimentary and open in their admiration and approach. This is not meant to be disrespectful and the power to take things further is entirely with the ladies !!! Don't let this frighten you, just enjoy !!
The music played in Santiago de Cuba is mainly traditional Cuban music (Son, Rumba). Listen in the Casa de la Trova during the day or in any of the many live music venues at night.
Santiago de Cuba offers many private houses renting out rooms (Casas Particulares) most of good standard and again, I recommend this as a true experience for anybody who really wants to get close and personal with the culture.
There is NO shopping ... other than food and some basic household stuff.
o.k. maybe the artisan's market in Calle Heredia being the exception.
You can undertake excursions from Santiago de Cuba into the Sierra Maestra, to the beach or to Parque Bacanao.
I recommend a trip to 'El Cobre' a pilgrim's church just outside of town (go by taxi), well worth seeing and for a Christian a very impressive exprerience.
As for beaches ... there are many around of different characteristics ... though none have white sand and are pretty-pretty as you see them in the brochures. Try 'Siboney' (by taxi about half an hour from town), it has some sand and a bit of infrastructure so that you can buy a cold drink and fruit. As it is the most frequently used beach for tourists, expect some hussling.
Not all is gold in Santiago, infact most colours are peeling. But if you look beneath the surface you will discover a real gem !!
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.