What to expect
1. You will get to sample wines
2. The folks at the winery hope you would buy something while you're there
But they at least want you to leave with a good, memorable visit so you'll tell friends or pick up a bottle at your local store when you get home. They all have different policies--some charge for tasting, some will refund it if you buy, some limit you to a few tastes, some serve food or crackers, etc. It's their store; they get to run it how they see fit.
If they don't tell how it works you when you first arrive ask questions.
Some offer tours of the facility. Most offer a "how wine is made" tour, a few have historical or art tours. Some charge for the tour; some offer a tasting with the tour.
How to act
You can be uninformed about wine. Just say so. It helps the staff know what sort of things to talk about. There's no shame in not knowing the difference between a Sauvignon Blanc and a Cabernet Sauvignon (let alone how to pronounce them).
Just like some folks think prostitution must be legal in Vegas also think it must be OK to drink anywhere in the wine country. Nope, we have laws, too. I've seen folks walking down the street at night with a glass of wine in their hand. I've seen open bottles with wine glasses in the cupholders of their rental cars. Either can get you in a bunch of trouble.
99.9% of the people visiting are great. It's easy enough to be one of those.
When to visit
Don't like crowds? Then don't go on holiday weekends during the summer. The busiest months are July through September. The busiest day is Saturday. The busiest time-of-day is about 2 pm to 4 pm.
You'll find Highway 29 (the main drag) in Napa to be much busier than going where the wineries are more spread out. In Northern California the closer you are to San Francisco the busier the wineries will be.
So if you're coming in January you get to pick without worrying about the crowds. If you're visiting during the peak season look for out-of-the-way areas.
Best time of year? That depends. What's most important? Staying away from crowds, good weather, getting to see the grapes on the vine, seeing the harvest? You can find good weather any time of year in California, but you can also get deluged with rain or searing heat. (As I'm writing this in mid-January it's about 70 degrees outside). My favorite time, balancing all of these factors, is March-June and October-November. June is interesting as it's an in-between seasons month. Not many travellers because of graduations, weddings, or whatever, but the weather is good and there's something to look at in the vineyards.
Buying at the winery
Is it cheaper than at the store? Probably not, but it depends on where you live. You will run into many wines that are hard or impossible to find at home. Wineries may run tasting room only sales or offer quantity discounts.
Should you feel obligated to buy?
No. It's OK to shop. It's OK to check out wines you can find at home to see what you'd be interested in purchasing off the retail shelf. Heck, your trip almost pays for itself if you can stop making $30 mistakes at the local wine shop!
How about tipping? No, it's not expected. A few places have tip jars on the counter "primed" with a couple five dollar bills. It's uncalled for especially if you're already paying a tasting fee. Of course, if someone really shows you a good time...
Getting wine home
If you didn't drive your own car to go wine tasting then you can't just load up the trunk. What are your options?
1. Take it on the plane with you. If you are an international traveller you will have customs to deal with. Find out the rules first before you travel. Within the U.S. you can pack as cargo, but most airlines will charge for the extra baggage. You can purchase a wine shipping box and fill it up with your favorites. This may still be cheaper than shipping the wine.
2. Let the winery ship for you. The easiest way is to buy several bottles at a winery you like and let them ship. Mostly it depends on which state it's being shipped to (don't expect international shipping from the winery). It's up to the state's laws. It varies a lot. You may find one winery will ship to you and another won't. It's not their fault. The laws are complicated and sometimes restrictive.
If you ship from the winery see what quantity discount you get and if your state requires them to collect sales tax. You may find it reasonably inexpensive to get wine home this way.
Note: Federal law requires a adult to sign on delivery for alcohol. If you aren't home much on weekdays ship to your work or your retired uncle.
3. Ship from a UPS store or another shipping company. Collect the wines you like from all your stops, take them to a shipping company, they'll pack and ship to your home. This will be the most expensive way to get the wine home. What's nice is they can ship to pretty much any state or country.
Planning your day(s)
There are two things to watch out for: Getting drunk (duh) and palate fatigue. What is palate fatigue? Your taste buds (actually your brain) just gets tired of the taste of wine.
The best way to avoid these problems is to spread out your tasting over the day. Put in several food breaks. Some wine judges eat nearly raw beef while tasting for the protein, but something as simple as a bottle of sparkling water will help. If you are doing multiple days of winery visits take every other day off and do something else, or at least make only one or two stops on the odd days.
I've found that a nice, cold Pilsner is a great way to refresh the palate (of course you still have the alcohol issue). That's probably better left for the end of the day if you're not driving. :)
Most of all
The wine country is "Disneyland for Adults." It's a great time. Great wine, great food, great accommodations. What more can you ask for?
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