HI SweetDA1,
Here how it started all for me, I'd suggest the same approach that we could call the "crescendo approach"
It all began when I tasted a Barros Vintage 1985 in 1994. I was just blown by this fermented grape juice. But it wasn't until my brother gave me a Taylor 10 years old that I really start having a real interest for Port. So I start buying books and Ports.
To start I would suggest the Tawny and Colheita range as they are easier to understand their taste and structure. A good book of reference to start is the one from Godfrey Spence, defining what all the style of Port, some history facts and at good space for the caractheristics, history and tasting notes from a lot of houses. Taste a few Ports and try to associate what you drink with what you read in the books, this way you are going to understand what are your taste and if they fits with the recommendations of the author. If its a yes, then try some of his recommandation as your taste are compatible, you should not be deceived.
My suggestions would be these to start:
Tawny 10 years old : Fonseca, Smith Woodhouse and Taylor
Colheita : Try to find some 10-15 years old Colheita from these houses: Niepoort, Noval, Barros and Dow's.
Then I would move on the LBV to start experiencing raw power and extraction in Port. Some nice effort have been made recently, Niepoort and Sandeman 99 are nice example. Noval 96-97 are also really good. The LBV stated earlier are traditionnaly made LBV's, bottled without filtration. It is my preference, Fonseca is one of the best when it comes to filtered LBV. Smith Woodhouse and Warre's release their LBVs 10 years after the harvest to prove that traditionnal LBV can mature in the bottle, but command a higher price. Long dicussion could be made about these two style of LBV
Then threat yourself and open up a nice mature Vintage Port. You'll notice how charming it is, more like the tawnys, and how its fruit is still young, more like the LBV but more silky, balanced and less alcool is felt. This is all about harmony and complexity. The 83 Vintages are drinking perfectly right now.
Graham 83, Still a baby but so much pleasure drinking this monster
Ramos Pinto 83, fully mature a great effort from this house
Offley 83, also fully mature at a fraction of the price from bigger houses.
Smith Woodhouse 83, a second label from the symington's but is really showing in this vintage.
Cockburn 83, never tasted but a lot of great comments are made on it.
Well, now you are free to do what you feel and your taste should find a preference on what style of Port you like the most. Don't hesitate to try the Tawny 20,30 and 40 years old. My favorite are the 20 and 30 years old, there is far less good example of 40 years old as not all of the house have enough quality grapes able to age 40 years old in cask.
Some suggestions : 20 years old: Ferreira, Sandeman, Noval, Taylor
30 years Old :Dow, Taylor
40 years Old: Sandeman,Rozès
Also you should try to taste at least once in your life the taste of a young Vintage Port. A real monster of fruit intensity. Not as complex as a mature one and for me also less pleasure, but just as with wines, it is always a good indicator on how your Port will turn out in 20 years +
Recently I had great pleasures drinking the 2000, especially from
Niepoort Spicy and powerfull
Noval More classic with fruit purity
Fonseca Having nice chocolate flavor
Vesuvio Its a jar of jam, concentration and extraction at the front row!
Welcome to the magnificient world of Port and don't hesitate to port many more questions so many people are shy to ask, because these are the kinds of discussion that will drive this site, Port tasting comments don't generation as much intervention from people.
Cheers
Fred