4 of us recently returned from a sherry trip to Jerez. I don't have too much time for a complete posting but wanted to give a few recommendations.
First, if you're going to make a trip to Jerez, do buy the book "Sherry, Mansanilla, and Montilla" that Peter Liem and Jesus Barquin published recently. You will learn all you need to know about sherry as well as recommendations on how to travel around the region. Most of our sherry trip were based on the book.
We stayed at Casa Grande (recommended in the book). It is a charming hotel with quaint rooms run/owned by a very sweet German lady named Monica. Well priced (breakfast 12 Euros) but you may hear the echos from the central interior courtyard if people are loud in the evenings and if you're a light sleeper. There are 3 rooms on the roof (I had one) which are very cool. I would recommend getting one of those rooms.
Eat at Tabanco San Pablo. Great little locals hangout that is open Sundays, which is key!!! Try the various sherries, and notice that some of the barrels are labeled Valdespino, which means that it is a must-try. It is an incredibly very well reputed Sherry House. The tapas are generally good, and when you consider that this is a local bar hangout, the food is outstanding!!
The other place to try is Bar Arturo. Seems like everyone in Jerez knows it. Awesome place for seafood, both fried and grilled. It is located in a non-touristy part of town, so take a cab to get there. Pepe runs the front of the house and he is full of energy, just like the Tazmanian devil. What a great guy! Don't wonder about what to order. Just order the seafood, but try it both grilled and fried and if you don't know Spanish, there are sheets of paper Pepe has that Monica (from Casa Grande) has translated into English. Definitely a must try and when you get the bill, you'll laugh and then cry from the memory of some of the other outrageous bills that you've paid for seafood in Spain. (I can honestly say that I have some knowledge about that, having been up and down the Galician coast, and I've done my share of crying......)
In terms of sherry houses, we skipped the large, more commonly known bodegas in the center of town and went to Fernando de Castilla and Valdespino. I don't know how difficult it is to set up tastings, but you can certainly purchase the sherries at both bodegas, but IMHO, if you really want to bring back some sherries, buy the ones from Fernando de Castilla that are harder to find outside of Jerez and buy their sherry vinegar, which is very very hard to get.
Now regarding Valdespino, just get a cab and go there. It's an impressive bodega and again, I don't know how easy it is to set up a guided tour, but we got lucky. The prize is that the wine shop there sells the high end rare sherries. These are incredibly difficult to find (and pretty much almost impossible to find outside of Spain). AMONTILLADO COLISEO, PALO CORTADO CARDENAL, OLOROSO SU MAJESTAD, PEDRO XIMENEZ LOS NINOS, and the ultimate prize Moscatel Toneles. Be warned, these are expensive, but it's cheaper than buying them in whatever country you're from and if you are realistically not travelling back to Jerez, then you'll never be able to pick up these sherries again. But that's my opinion. All 4 of use went nuts buying sherries, so much so that we had to purchase an extra suitcase and bubble wrap to accomodate those bottles.
More later...........hope this was somewhat informative and entertaining.....