"Which of you guys is Miles?" everyone wants to know when they hear our plan. My friend Kelley and I are re-enacting the movie Sideways, in which two buddies – one a failed writer coming off a divorce, the other a sex addict on the brink of marriage – take a road trip to Santa Barbara, visit wineries, drink prodigious amounts of wine, and have adventures along the way.

I'm a writer, but I hope I'm not as pathetic as Miles, who dumps a spit bucket of wine over his head when he learns that his novel has been rejected. Kelley's in the market for a new woman in his life, but I trust he'll be more discriminating than the abhorrent Jack.

In any case, we've made a few changes to the script. Instead of Santa Barbara, we're in Bordeaux, the world's most renowned wine region. (Kelley happens to be one of the American representatives of the Bordeaux Wine Bureau, so he'll act as tour guide.) We won't be drinking to forget our problems, but to taste and compare wines in the majestic setting of Bordeaux's chateaus. Except at meals, we'll be spitting, not swallowing, since DUI stops have replaced soccer and cycling as France's favorite sport. And unlike Jack, we're not looking to drive into any trees.

I've chosen seven of my favorite producers, one in each of Bordeaux's top appellations: St.-Estephe, Pauillac, St-Julien and Margaux of the Medoc peninsula west of the city; Pessac-Leognan to the southwest; and Pomerol and St.-Emilion across the river to the east, the so-called Right Bank. We'll be tasting everything from still-unbottled samples of recent-vintage, Cabernet-based wines of the Medoc to lush Merlot and Cabernet Franc blends from older vintages as made on the Right Bank. (There will be no Pinot Noir, a grape that in France is grown almost exclusively in Burgundy, Sorry, Miles.)

Another difference from Sideways: You can't just throw on shorts and a t-shirt and set out in the car. A visitor to the fine chateaux of Bordeaux has to dress appropriately. That means long pants and a sportcoat for men. Even a tie wouldn't be going too far.

In addition, appointments must be arranged in advance. The usual drill is to call or write expressing your profound admiration for the property and its wines. Identify yourself as a consumer who has a consumed the wine in question on several special occasions, or has a case or two sleeping in his cellar. Ask if you can be received on a certain date at a certain time, then make certain to follow up a week or so before arriving.

This region is often considered stuffy because you can't simply show up, rap on the door, and get served a range of wines by a fetching barmaid. But that's because these properties have no starter wines, and they're not in the business of retail sales. Nearly all of Bordeaux's wines are sold through an arcane system of middle-men which is unique in the world. It leaves the wineries with little knowledge of who is actually drinking their wines – which is another reason they like to entertain consumers who make the effort to establish contact with tastings and even meals.

I set out alone on a humid June morning. I've arranged to meet Kelley at our first stop, Chateau Cos d'Estournel in St. Estephe, Bordeaux's northernmost appellation. I pull up and notice without surprise that his car isn't there. I know that he was out past four in the morning at a formal dinner and its aftermath, doing who knows what. That makes him Jack. But he's also habitually late, like Miles.

"Start without me," he says when he calls on my cell phone a moment later. "Traffic."

* * *

Cos d'Estournel is my favorite Bordeaux wine. I've tasted every decent vintage since 1961, but I've never visited the chateau. As I drive through the iron gate, I feel like I'm entering the stadium of my favorite sports team. So the first thing I do when I walk through the courtyard and into the reception area, of course, is fork over $54 for a Cos d'Estournel polo shirt.

Soon I'm joined by Jean-Guilliame Prats, a man in his thirties wearing a conservative suit. His father, Bruno, used to own the chateau but sold it several years ago. It has been sold again since, but Jean-Guilliame – who seems to have more lives than Rasputin – has managed to survive as the managing director through all the changes.

One reason is that perhaps no Bordeaux winery has put together the streak of fabulous wines that Cos d'Estournel has since 2000. Prats is setting up a tasting of the three most recent vintages when Kelley arrives. Together, we sniff, swirl and sip the 2002, 2003 and 2004. The 2003 is very ripe, the result of an extraordinarily hot European summer that year. But unlike the over-extracted wines made by many Bordeaux producers, it is firmly in balance. It is the best wine from that vintage I've tasted. Still, at half the price, the almost-as-good 2002 Cos is the better value.

There's nothing to see at Cos, Prats tells us. A new cellar is being constructed, and several of the existing buildings – dating back a century and more – will be demolished. I feel like I've made my first visit to Ebbets Field a week ahead of the wrecking ball. I'd love to soak up the atmosphere, but we have three more visits scheduled before dinner. We jump in our cars and move on.

Pauillac is just south of St. Estephe on the D2 road, which runs past most of the most famous chateaux in Bordeaux. On our way to Chateau Pichon-Longueville-Baron, we stop at Au Baba d'Andrea, a deceptively simple, wood-fronted bakery that serves the best bread in the area. We buy noisettes fresh from the oven, and souvenir jam. Then we pass Mouton-Rothschild and see Latour and Pichon-Lalande out the window as we turn into the driveway of Pichon-Baron, which looks like a picture-book castle.

Owned by the French insurance company AXA, Pichon-Longueville-Baron is the archetype of a Bordeaux chateau, with its turreted front and expansive lawn. It's also a little bit of Napa Valley on France's Atlantic Coast – though unlike in Napa, tastings here are free. A gift shop sells shirts, books, even an umbrella. Appointments aren't necessary (though you'll get treated better if you write ahead.) "We have no gates around the property, and that's deliberate," says Christian Seely, who runs AXA's dozen or so wine estates in Bordeaux and beyond. "If someone has even a single bottle of Pichon at home, I don't want him to feel like he's not welcome."

Seely shows us vineyards – "I don't want people coming here thinking it's all about buildings," he says – then guides us through the cellar. We learn that the fermentation tanks are computerized and connected to an alarm system, so if the temperature inside them rises or falls even one degree, a call is automatically made to the cellarmaster's mobile phone. We taste recent vintages at a long glass table, and I'm especially taken by the 2002. It has a core of dark fruit, tannins that will allow it to age effortlessly for at least another decade, and a $40 price that I find immensely appealing.

Then we sit down to lunch with Seely in a parlor in the chateau, and dine better than Jack and Miles ever did. We have beef grilled over vine cuttings alongside roasted potatoes and carrots, and drink three superb older Pichon-Barons, the 1988, 1989 and 1990 – about $600 worth of wine at current retail cost. Kelley and I take this as a complement. The quality of the wine served with meals in Bordeaux usually reflects the host's reading of his guests' sincere level of interest in their wines. In this case, Seely is right. I've long been a fan of Pichon-Baron's '89 – and with this lunch, the '90 tastes even better.

Our third stop, Chateau Gruaud-Larose in St.-Julien, isn't as picturesque as our first two, and it doesn't entertain nearly as many visitors. But because Kelley and I both enjoy its long-lived, classically structured wines, the owner himself is there to give us a tour. He takes us up a tower for a view of the area, and then to the wine library where we touch bottles of Gruaud-Larose from 1815. (Let's see them try that in Santa Barbara.) And because Gruaud-Larose has no formal tasting room, we stand with him in the cellar, beside the oak barrels full of aging wine from the 2004 and 2005 vintages, and taste wines back to 1989.

For our last visit of the day, we drive to the bottom of the Medoc and the commune of Margaux. The fairytale castle of Chateau Palmer might well be the most beautiful structure in the entire region. Until recently, though, it was falling apart. Under the management of Thomas Duroux, who used to work at Italy's Ornellaia, it is being renovated and the wines are being restored to their former luster. (The 1966 Palmer is one of Bordeaux's greatest wines of the last half-century, but more recent efforts haven't come close to hitting that height.)

We sit on walnut chairs, amidst marble columns. Duroux serves a purplish wine to us without announcing the vintage, and Kelley and I make our guesses. I note the lightness of the color but the amount of rich glycerine in the glass and choose the 1999 Palmer – and I'm right. "Some have called it the wine of the vintage in Bordeaux," Duroux boasts.

When Duroux arrived in 2004, he organized a tasting of old vintages of Palmer in order to understand the place and its wines. "I was surprised by the finesse and elegance of vintage after vintage," he says. "My first reaction was that we were much closer to Pinot Noir than California Cabernet. The property is very, very rich in history, and you can taste that in the wine. When you arrive at such a place, you have to make a contribution, but you have to respect the history."

The upper floors of the chateau are still in a state of disrepair, but Duroux tells us there is another part of the property's history that he wants us to see. We walk up a rickety staircase and step into an abandoned room.

The Nazi army occupied Palmer during World War II, Duroux tells us. They didn't do much damage – they believed they were going to win the war and wanted the wine industry to thrive once hostilities had ended – but they did drink nearly all of the accumulated vintages. Duroux translates what one soldier has written on the wall in German:

FAR FROM THE BATTLE
STAYING HERE IN THE GARRISONS
WE WANT OUR SALARY TO BE TRANQUILITY

I stare with a lump in my throat at the thoughts of an enemy soldier who felt much the same as I would've, under the circumstances. I won't look at a bottle of Chateau Palmer the same way again.

* * *

That night, I sleep at Les Sources de Caudalie, which is owned by the daughter of the owners of Smith-Haut-Lafitte, the chateau we will visit in the morning. The hotel is a stunning spa and resort, done up in country-cottage fashion but with all the amenities, including Michelin-starred cooking and a range of body treatments and massages.

Smith-Haut-Lafitte is a five-minute walk through the vineyard. Kelley is late again, so a beautiful young woman named Virginie guides me alone through the fermentation tanks, the barrel room, the tasting. I can't help thinking that this was the visit he should have been least inclined to miss.

He finally arrives, and we drive together across the Gironde river to the Right Bank. Pomerol's Petit-Village is bordered by famous names Petrus, Cheval Blanc, Figeac and others. It used to be owned by Bruno Prats, Jean-Guilliame's father. We meet Serge Lay, who runs the property. He's wearing a simple blue shirt, not a coat and tie like the four proprietors we saw the day before. That's the difference between the Medoc and the Right Bank, Kelley says. Plots of land in Pomerol and St.-Emilion tend to be far smaller – Lay makes 45,000 bottles of Petit-Village annually, about a tenth of what Pichon-Baron makes – and the people who run the properties and make the wine are, first and foremost, small farmers.

Lunch with Lay in St.-Emilion at L'Envers du Decor – literally, "Behind the Scenes" – is outside in a garden, under the tower of a stone church. It's something of a clubhouse for area winemakers, and the bar is made from the ends of wooden wine cases. A woman named Jana, an American who works for the St.-Emilion tourist office and an old friend of Kelley's, has joined us. "We needed a woman on this trip," he says. I eat red mullet, a Mediterranean fish, served with a tapenade of black olive, followed by a confit of rabbit, and I drink several glasses of 1990 Petit-Village. The wine is astoundingly good, even outside in the summer heat.

At the next table is Patrick Beaudry, who gained renown as the first French astronaut. ("Has there been a second?" is the question that comes to my mind.) Lay whispers the story of how Beaudry at first refused to visit the Russian space station where he was scheduled to live for several weeks. "If I have to eat that crap food, I'm not going," he'd reportedly said. After my last bite, I lean back in my chair and contemplate the steeple of the church rising above me. Life feels good.

After lunch, the group divides for the afternoon. Jana and I stroll the Medieval village of St.-Emilion, probably the most beautiful wine town in the world. Set on a steep hill, it looks the way it must have several hundred years ago. I stop in at a wine shop, Comptoir des Vignobles: one of the few in the area that offers old wine at good prices. I contemplate buying a bottle of Palmer from the 1950s, but I have nowhere to keep the wine for the rest of the day, and the temperature is nearly 100. Even the best wine in the world swiftly becomes undrinkable without proper storage.

Then we walk up the street to the Hostellerie des Plaisance for 5 o'clock tea. That's more a British custom than a French one, I know – but after so much wine, I need a caffeine lift. The hotel is owned by Gerard Perse, who also has the St.-Emilion chateaux Pavie, Pavie-Decesse and Monbousquet. Perse has named each of the rooms in the hotel after area wines, and he caused a sensation when he priced the one called Pavie higher than the one called Cheval-Blanc. Rumor is some producers have stopped speaking to him because of it.

It is six o'clock, and we have to be at Chateau Angelus, our last stop, in half an hour. Jana proposes we walk there, and we do – a delightful stroll down a country lane. We sit under a tree beside a gurgling fountain and a bed of white roses, waiting for Hubert de Bouard, the owner and winemaker, to arrive – and for Kelley, who actually gets there more or less on time. Hubert gives us a tour of Angelus, a modified version of the organized tours (complete with picnic lunch) that come through once a week courtesy of the local tourist office.

Four hours later, we're still with him. De Bouard lives next door to the chateau, and he has invited us to stay for dinner. The meal is simple – fish with a salad, followed by steak cooked on a very hot grill – except for the bottle of 1955 Angelus he has opened. The astoundingly complex wine is the best of our tour. When I consider that the bottle has existed six years longer than I have, I understand why the Bordelais say that to truly appreciate the wines of the region one must have a sense of history. I use the moment to call home and talk to my family.

The weekend ends without much of a movie plotline – no sex, no fistfights, no weddings – but with our announced intention to repeat our trip in a different wine region at the earliest opportunity. We toast Bordeaux, then "Sideways" for getting us there, then sip the '55 Angelus and consider where to go next.

 
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