Valparaiso tour guide
 

I am looking for recommendations to tour Valparaiso/Santiago. We dock at 8:00 on the 20 December and fly out at 22:00. Can anyone suggest a tour or tour guide, or, is it possible to tour on our own and how do we go about it?

You will get much more out of your visit if you use a guide. Since the number of cruise ships started growing, a lot of people have set themselves up as "guides" but they are more entertaining than knowledgeable. Whoever you use, make sure you are using a registered service.
The best way to see Valparaíso is on foot. My recommendation would be for http://www.apatita.cl/. These are half day walking tours run by local architects who know the history of the city well. Their English is actually better than the website would lead you to believe!

We used a guide from Darwin's Trails who was OK, nothing special though.

Thanks for your replies but we can't do a walking trail as we're disembarking and will need to get to the airport that night. Any recommended tour guides?

Look at Darwins Trails webistes. They offer different tours of Valparaiso. However, the narrow streets are best seen on foot. Our walking tour guide worked with a drivre who would meet us at the end of a street and take us to another area, etc.

My husband and I traveled in the Crown in 2005, we made our transference with www.enaturchile.com , the cost was less that portCompass, in the route we visited a vineyard, we made a trip for Valparaiso, it is an interesting city, with a harbour atmosphere and with many hills, we made one stop where, we saw the city from the heights, it was a beautiful landscape. Our driver and guides gave the opportunity us to visit the house of the Chilean Poet Pablo Neruda (museum) was something of our interest.
Vina del Mar; is clean, very tourist, modern and beautiful city. You cannot let visit this city. we had an pleasant lunch with food of the sea, this company could please all our requests