One of the most stressful moments for a lot of business travelers is not when the client has an objection or asks a difficult question but when they are handed the wine list. Depending on where you are dining this can be a selection of a few dozen to several hundred choices or even more in some cases. And since wine is a profit center in restaurants (at least here in the U.S.) you will often pay two or three times the retail price for what you select. Since everyone wants a good value whatever their budget, here are the factors I consider before selecting a wine in a restaurant.
Rule Number 1: Don’t buy wine by the glass
Unless you are only drinking one glass at a table where no one else is enjoying wine then wine by the glass at most restaurants is not a good deal. Sure, they let you skip around and try new wines but rarely is that worth the $12-25 charged per glass. Instead look to see if they stock half bottles or sell wine by carafe. In some cases, you will get a better deal by choosing a full bottle and just drink half leaving the remainder or, where the law allows, taking the unfinished bottle with you after your meal. 
Rule Number 2 – Don’t buy the least expensive wine on the list
All restaurants have a price floor for wine and generally pick some pretty poor values to populate the bottom of the list. I always look $5-10 from the price floor when assessing the selection in a restaurant. Most times, this is where the best values are to be found. At the other end of the spectrum, higher priced wines tend to get lower markups unless they are one of the famous brands (see below) so also check out the higher priced selection if your budget allows.
Rule Number 3: Find out what the wine buyer likes
On most restaurant lists compiled by a wine buyer or sommelier you will get a sense for what they personally like from the selection. For example, if they have a lot of Rhône varieties on the list, I would narrow my selection down to these. Same for Burgundy, Cabernets or Italian wines. Chances are the buyer is able to find more interesting wines for the price if they know more about a region.
If you don’t feel like actually asking, much can be learned from just looking at what the selection is and narrowing the choices based upon what appears most from a region or variety perspective, then factor in your budget.
Rule Number 4: Ask the sommelier for advice
If you are in a restaurant with a sommelier ask them for a few picks. Give them an idea of what food you will be eating, what type of wine you usually enjoy, and then put them to work. After-all, you are paying for their services in the marked up bottle price. I know a fair amount about wine but often get some great values I’ve missed on the list by just asking the sommelier.
Rule Number 5: Tell the sommelier what your budget is
In addition to letting your sommelier know what you are eating, and what types of wines you usually like – it is really important that you tell them how much you want to spend on wine. Trust me, they have heard every budget level, and they will be glad to help you regardless of how deep your wallet is. Often, it can even be a more fun challenge to find a bottle that fits both your palate and your wallet than just opening “any expensive bottle”.
Rule Number 6: Look to non-mainstream regions and varieties
Instead of ordering that Napa Chardonnay, Chilean Merlot or red Bordeaux blend look beyond the well known varieties and regions. Like Pinot Noir? Look for them from emerging regions like New Zealand, try an Oregon Gamay Noir or Beaujolais. Instead of Chardonnay try Viognier, Marsanne or Roussanne. Many times the best values on a restaurant wine list come from these slightly “off-the-radar” varieties or regions.
Rule Number 7: Don’t buy brand names
Scan a wine list and you will see a lot of brands with big reputations. Opus One, Domaine de la Romanée-Conti, Château Pétrus, Dom Pérignon. While these might be nice wines to have with dinner they are likely to be the worst values on the list. Instead look for lesser known names or second labels of more famous producers. Leave the famous wines for billionaires and celebrities to splurge on.
Rule Number 8: Use the technology at hand
These days most business travelers have some sort of smartphone with a web browser. If you have an iPhone or Android smartphone apps such as Vivino can be used to narrow down your choices. Both Wine Advocate and Wine Spectator have useful mobile-friendly websites for subscribers, as well.
These are not hard-and-fast rules, as I still order my share of wine by the glass, but if you follow one or more of these suggestions you will likely end up with better values.
Bookmarked, coming back to this! Great guide.