This was beginning as a comment reply, but as you scroll down, you’ll see that there is far too much content to fit. Therefore, it’s a whole new post.

Nothing is more intimidating than sitting down in a restaurant with your wife, friends, or both, and being presented with a wine list that comprises dozens of pages and hundreds of selections. Being given the task of choosing a great bottle or two that will please everyone – including the lucky person paying the bill – is daunting. Now, I don’t claim to be an expert on wine, but having dined out with high-profile wine critics more than 100 times in the past 3 years and having undertaken a significant amount of study in wine, I definitely have some tips.

My rules of thumb whenever I’m presented a wine list:

1) scan the list to find something something that you’re familiar with – be it Wolf Blass Yellow Label, Jackson Triggs reserve shiraz, whatever, and acquaint yourself with how much the restaurant has marked up its wines. Standard markup is double the amount you’d pay in a store. This will help you decide how inclined your are to spend your money. My wife and I went to a fancy Calgary restaurant last year where they were selling Clos de los Siete, an outstanding Argentine blend made by world-renowned consultant Michel Rolland, for $66. The wine can be found in stores for $22. Triple markup at this restaurant steered us towards cran-and-soda instead of wine.

2) think about what you and your companions are eating. If the server comes by to ask what you’ll be drinking before everyone made their menu choice, confidently state that you’re not ready. Sometimes this can create tension, as one of the customs of dining out is that you get to enjoy a glass of wine or a cocktail before your meal shows up. Cconsider ordering a glass or a bottle of sparkling as an aperitif. My wife and I always enjoy prosecco, which is an inexpensive, slightly off dry, light-bodied Italian sparkling wine.

3) once you’ve sorted out what you’re eating (I won’t get into food and wine pairings here, because even the most hard and fast rules are often called into question), pick a couple of grapes and/or regions that you’re prepared to order from. If you notice that the restaurant has put in some effort into their wine list, that you see a personal favorite you’ve never seen on another wine list, perhaps you’ll be more inclined to try something you haven’t heard of.

4) time to start considering vintages. Vintage variation can be dramatic, and manipulative restaurants will often assume consumers don’t know about particularly bad vintages. It starts to get really hard to remember not only great wines and their producers, but also their vintages. I recommend keeping in mind the really bad years – a great wine from an average year will still be a good wine, but nothing can save a great wine in a horrible year. A safe bet is to know what parts of the world consistently enjoy good weather – Australia is a great example, as is Chile, California, usually Spain and Italy. France, Germany and Canada are amongst the more marginal wine producing regions where the summers aren’t always guaranteed warm and long, so vintage to vintage, quality can be all over the place.

So now you can go into a restaurant, quickly evaluate whether or not that restaurant deserves your business, decide whether to get excited or not, and order something fun and unique that will please everyone. My last recommendation is to not take forever. Just because the wine list is 400 pages long (and believe me, they do exist) doesn’t mean you have to ignore your party and read the whole thing. If your food selections make it hard to pare down your options and the restaurant is worth its salt, it will have an on-duty sommelier whom you should definitely consult. Tell him/her what you’re eating and how much you’re prepared to spend, and let them come up with a few suggestions. Quiz him/her on vintages.

The final trick is to fit your choice within a budget. My favorite price bracket for wine is usually $35-$60 retail – that’s where you start getting into smaller production with more expensive techniques involved in making the wine (hand picked, select vineyard lots, hand sorted, higher-end oak, etc.), and more attention paid to it overall. Anything in the $10-$35 bracket is made in huge volume to cater to the masses, where usually you’ll see at least 200,000 cases produced. While there are definitely some underrated gems under $35, I find that more often than not, these wines tend to be more a product of chemistry than craftsmanship. Remember, $35-$60 retail is generally going to set you back $70-$120 in a restaurant. And yes, there are $200 bottles that present excellent value. Great wines of this price can compete with wines 4 times their price, or they’re extremely rare or old. It’s just a matter of whether or not you choose to spend that much money.

Now on to the case study.

In a previous post’s comments, my friend Jim asked me about the wine list at Sarento’s in Maui. Not having been there, I checked the internet and found it’s wine list. Always a good sign when a restaurant is prepared to put its wine list online. This is the kind of list you dream about – they’ve done a great job finding special wines. Given this effort, I would have no second thought in asking for the sommelier to choose a wine for me based upon what my party was eating. Here’s a quick review, and some idea of what my thinking would be as I went through this list:

While I wouldn’t ever pay $19 for a glass of non-vintage Champagne, I would pay $18 for the Bellavista Italian sparkling – which, if I’m not mistaken, is a Franciacorta. This sparker is fun, interesting, and you never see it by the glass. I had the Antinori Castello della Salla, just last month actually, and it’s a great Californian style chardonnay – not too oaky with good complexity. Great pedigree under the Antinori umbrella, so there’s confidence in ordering one of their wines. The Cervaro della Salla is the good stuff, but this can’t be too far behind. Haven’t had the Hall SB or the Rheinhessen riesling, but given the quality of this list, I’m sure they’re worth a gamble. Each varietal typically has lots of acid, so I’m sure they’re quite refreshing. Being German, that riesling is likely a touch sweet. What else could you possibly want to drink (except for a beer) after a hot day on the beach? The Ruffino Il Ducale red-label is Ruffino’s second-best sangiovese-based blend (#1 is the Il Ducale gold-label, produced in only exceptional vintages, like 04). If you like Sangiovese young, this will be a very good choice. Decant it (if you get a bottle), or let it open up in the glass. The A-to-Z pinot from Oregon is probably quite good – Oregon knows what they’re doing with pinot, however 05 was cooler than normal in that state, meaning the fruit might be somewhat unripe. It’ll likely be more Burgundian in style anyway, so less fruit, more compost-y, forest floor, earthy style. Good for mushroom dishes or truffled dishes. When ordering by the glass, make sure you ask the server if he’ll be opening a new bottle, or at least how long the bottle he’s pouring from has been open. If he doesn’t know, or says longer than 2 days, ask for a new bottle to be opened.

By the bottle, the Nino Franco Rustico Prosecco is a slam dunk for bubbly. Good value, great quality. My wife and I drink it all the time, and it’s fairly ubiquitous in restaurants. I’m not well versed in Italian white varietals or producers, and with a good list like this, I’d pass them by without a second thought. The rest of the list is just too good to get stuck here. The California chardonnays are well done, with the Hartford singling itself out for me. The St. Supery SB is a great value pick – over-providing for the money.

And then we end up with pages of Italian reds. The first thing I notice is the 02 Ruffino Il Ducale. 2002 was one of the worst vintages in recent decades for Tuscany. Steer clear of 02s from Italy at all costs. Consider the 2000 Tenuta Antinori, which, with 8 years of maturing would be very interesting, and also consider the Brancaia – an outstanding producer making outstanding wine. For $80 that wine is a steal. On another page, Brancaia’s Il Blu is listed for $110, and that, too, is excellent value.

I’m not overly familiar with the remaining Italian wines, particularly the Brunellos and Barbarescos, but 1997, 1999 and 2000 were great years in those regions, while 2001 was an exceptional year in Piemonte, so I’d be prepared to trust the restaurant’s selections for these vintages. The 04 Michele Chiarlo “La Court” Barbera d’Asti is a very good wine, so in a great vintage like 2001 it would be interesting to try. All of the sub-$200 super-tuscans save for the Guado Al Tasso (a spectacular wine, worth trying, but expensive) are very young, so unless you’re going to order a porterhouse for dinner, I’d avoid them. Too big, tight, jammy and tannic. These wines need time.

Looking down the list, I am not struck by anything until I get to the Californian cab-based blends. The 92 Etude is a great wine from a great vintage, and for $165, appears to provide value. For older vintages, you’re always going to pay a premium as it’s simply supply and demand. There are less and less of these wines as years pass, as they enter into their prime maturity. And remember, you’re paying partly for the restaurant to stock older bottles. Ridge Vineyards’ Monte Bello is outstanding, and 96 was a good year, so something to consider there. New vintages of that bottle retail for about $150.

The sleeper hit that most people won’t notice because they’ll have made a selection before they get to the Bordeaux, is the 1990 Leoville Barton. 1990 was an almost perfect vintage in the Bordeaux region of St. Julien, and this wine should reflect a great year like that wonderfully. With 18 years under it, I think this wine could be outstanding. While $225 is nothing to shrug at, there is potentially very good value here, and I doubt you’ll have another opportunity to try this wine again.

To end, look at the dessert wines by the glass, and be weary of any vintage ports. Once opened, older vintage ports start breaking down after only a few hours, so ordering by the glass is very tumultuous. The wine that caught my eye, and would pair perfectly with a dessert of Creme Brulee, tropical fruit-topped cheesecake, or a plate of fruit and cheese, would be the 03 Guiraud Sauternes.

Probably the biggest lesson to have learned here, is that if you can review the wine list ahead of your reservation, take advantage. It’s poor etiquette and frankly you’ll be sleeping on the deck if you put your wife, friend or party through this exasperated exercise of choosing wines.

Bon Appetit!