Luckily I don't suffer from nausea, so the semi-suicidal 2,000-foot climb to Montalcino rewards me with stunning views of Tuscany's grandeur. "That's where I live," Yoshi mentions casually with just a hint of pride. I follow his gaze up the mountain to the rustic hamlet now barely visible behind its wall. A few church towers rise above the crowded maze of tenant buildings. A woman opens the red shutters of her rustic apartment. March in Montalcino is a long, lingering month. With that in mind, I feel the urge to kill Yoshi and steal his job and life when I'm suddenly quelled by some amalgamate image from childhood: the Italian equivalent of Julie Andrews running down a green, mountain pasture, arms aflight, Ave Maria wafting in the background. I relax and enjoy the scenery with only mild pangs of jealousy.

We're in southern Tuscany -- the place Adam and Eve had to leave after Eve bit into that ripe sangiovese grape. Here, there's no shortage of excruciatingly quaint hilltop towns; no problem making you feel like writing home to say, "Sell everything. Never returning." Southern Tuscany is wine country, is Italy, is civilization at its very best. And if southern Tuscany is all that, Montalcino (Moan-tall-chino) is the capital in my eyes -- what most Americans must envision when they think of Italy. Picture the medieval burg clinging to its pinnacle, the serpentine cobblestone streets and squat grandmothers who negotiate them. Churchbells can be heard from anywhere in the city. Good wine is a given. Here, the pace is slower, the olive oil greener, and the entire town seems to reek of the perfection of daily life.

"There's not much to do in Montalcino," Yoshi says. But he says it in such a way that leaves me thinking "nothing to do" in Montalcino is most definitely a good thing. Here, hours are stretched free of charge. Wineglasses swell with content, and like the mythic Hydra, dishes of savory pasta seem to regenerate threefold every bite you take. There are no teenybopper discotheques, no cheesy trinket venders peddling their weary wares on the streets. Not even the Let's Go and Rick Steves backpacker hordes find their way up the mountain (often), as it's a bit difficult to reach. No train braves the perilous climb up to Montalcino's summit. Without a car, you're better off taking the one-hour bus ride from Siena.

Once at Montalcino, you're greeted by a perfectly preserved medieval hamlet. Start with a walk to the far end of the city where the fortress, or Rocca, lies. Familiarize yourself with the one main street. This requires little effort and will also let you kick off your stay in Montalcino at its Rocca. Walk the grounds, take a stroll along the catwalks, or cruise inside the turrets. And though the views from just about anywhere in Montalcino are truly inspiring, those from atop the Rocca feel somehow even more regal. Plan secret attacks on neighboring villages, wax philosophic, or just suck in the mountain air.

Although constructed in the 14th century, the Rocca has been "modernized" inside with the addition of its own wine bar, or enoteca -- arguably the first Italian term you should memorize. These blessed creatures, these enoteche, curiously absent (or at least endangered in America) thrive in Montalcino. And enoteche make me very happy. This particular one allows you to sample not only some of Italy's finest wines ($1.50 to $5 a glass) but also local meats and cheeses, like the indigenous wild boar sausage and the smooth Pecorino cheese.

Someone dead and famous once said, "To truly appreciate someplace, go there poor." That sums up my travel philosophy as much in principle as out of necessity. And while northern Italy is no budget traveler's dream, we will endure. Believe me, you'll feel better spending money on a truly memorable Tuscan experience -- like a few glasses of wine in the Rocca -- than you will getting your caricature taken outside the Duomo in Florence for triple the price.

If you're looking for something a little less, well, fortress-like and expensive, check out Enoteca Franci, one of Yoshi's hangouts. You'll find it in the main piazza to the side of the clock tower on Via Mazzini. Enoteca Franci is the Cheers of the city, attracting every living inhabitant in Montalcino, young and old, hip and otherwise. During sunny days, get a bottle of great Montalcino wine, sip a cappuccino or snack on some rustic salami and Parmigiano cheese. At night, the atmosphere is right out of a Hemingway novel: red vinyl benches; mirrors; chandeliers; and a dark, cavernous back room full of wines to choose from or to ogle, or both. Sound expensive and chic? Nah. Plus you get the whole "ex-patriot, grainy black-and-white" feeling to boot.

And there's plenty of great wine to go around. First and foremost, the top wine, the black rooster of the town: Brunello di Montalcino. Actually, its reputation doesn't just apply to Montalcino, Tuscany or even Italy. In the world of wine, Brunello is a big boy. A strain of the more familiar sangiovese grape of Chianti, Brunello (so named because of its brownish hue) is responsible for Italy's finest red wine alongside Barolo. With a minimum aging of four years -- six months of which must be in bottle -- Brunello is a dark, dry, potent wine that goes with anything it wants. For that reason, it's, well, a bit expensive. A bottle will start around $20 and run as far as your credit card can. And further. And faster. Keep in mind, though, that the same wine in America -- provided you can even find it -- costs much more. From the little investigating I've done, you're looking at around a $10 to $15 price hike in America on Brunello. In addition, you have the usually insane "dock fees" or whatever American restaurants call their premiums. Translation: if you feel like doing it up in Montalcino, Brunello is the one.

But I have good news for those who don't want to mortgage their mothers for wine: Rosso di Montalcino. This wine is made from the same sangiovese strain. In many respects, it's the same wine, the only difference is the aging time and price tag. And sure, I could probably tell the difference between Brunello and Rosso. But I can also tell the difference between a Mercedes and a Honda. And which is better for the money? Rosso starts at $5 and runs to about $10 for the top producers. Don't sweat these big names, though. Every bottle I had was a lesson in how to enjoy life. And if you're not a total wine geek, Rosso, in most cases, is a much better choice than the far pricier Brunello.

The more established wineries in Montalcino excel in most all the varietals, though. Apart from the slew of red wines, you can peruse anything in white from sauvignon blanc to the syrupy sweet moscato. In short, Montalcino is a wine town. You merely need to visit Enoteca Franci or any one of the some thirty million bars or enoteche (or so it seems, as potential wine pit stops appear with blissful regularity). And when drinking wine in Montalcino remember: being snobbish with wine doesn't come naturally to Italians. Wine is their mass consumption, normal beverage which, for most Italians, still comes in a water glass. As such, wine drinking seems a touch more genuine, more enjoyable. No pedantic rigamarole, just good wine and, of greater importance, kind, witty people.

If you're itching to taste the proverbial "fruit of the vine" and want to experience what really put Montalcino on the map, go to the tourist office and get a bus schedule for the wineries themselves. They're located outside the city, it takes a vehicle, a Japanese friend with a vehicle, a bus, a taxi or a long thumb to get there. For a taste of the original Brunello, head toward Biondi Santi. Clemente Santi was responsible for isolating the Brunello strain of the sangiovese grape in the last century. Since then, Biondi Santi has claimed awards around the world for its Brunello. Good for them. Also good for us -- if we want to spend around $40 a bottle. Prices and standards are high. However, if you're a Brunello freak, or plan on becoming one, this wine is a "must taste;" and the winery, a connoisseur's "must see."

I also highly recommend Banfi: one of the most established yet progressive wineries in Montalcino. You can enjoy the views from the tasting room, the Banfi Villa, the Banfi Castle and, most importantly, slurp some vino with Yoshi. (Tell him I sent you. Heck, it might be good for some perks.) You can even eat at the winery, if you want to drop some major cash and really impress your significant other. However, any type of winery experience is possible. Montalcino has everything from space age, stainless steel producers, to old school brothers with unpronounceable names.

Just about any type of winery experience is possible, though. Montalcino has everything from space age, stainless steel producers to old-school brothers with unpronounceable names. The smaller estate of Campogiovanni, for example, doesn't have the esteemed reputation and, therefore, must make quality wine at the lowest cost possible. Although owned by the larger San Felice, Campogiovanni is fighting to make a name for itself in the highly traditional ground of Montalcino And in this category, there's a plethora of great wineries ready to sell you on wine before non-existent, or at best, respectively small, reputations. Apart from Campogiovanni, definitely try Marchesato degli Aleramici, Col d'Orcia, Castelgiocondo, Mastroianni and la Poderina. Brunello from these producers usually runs in the $18 to $30 range; Rosso from $6 to $10. Though their wines are easy to acquire, information on most of these wineries is scarce. Check with the tourist office, or call directly upon arriving.

"But we must eat," you say. "We can't live on wine alone." Sadly, this is true. Have no fear, though. If the Montalcinese know anything beside wine, they know food. And the question is not where or what to eat, but how to sample everything without breaking your budget or your new Italian leather belt. Yoshi and I checked out his favorite place, Osteria di Porta al Cassero. From the street it may not seem like much. The actual surroundings are quite simple and unpretentious -- my favorite style. But the smell alone is enough to merit a try. I almost floated in on a wave of heavenly aromas a la Tom and Jerry. Definitely try anything with wild boar, usually prepared as a stew or ragù. And if tripe is your game, it's also the specialty. Yoshi partook. I did not. If you're like me, check out Pici -- thick, worm-like spaghetti -- or Pappardelle -- big ribbons. Both are traditionally served with one of many rustic treats from meat lover's heaven and come almost attached to a bottle of Montalcino vino.

For espresso, cappuccino and every derivative thereof, stop by Bar Mariuccia, sort of across from Enoteca Franci. I never asked, but the elderly couple who slings the java must be the Mariuccias. A real mom-and-pop operation complete with sweets from another Mariuccia who runs a pastry shop and rents rooms down the road. Stunning views of the countryside await in the backroom of the bar. There is no charge to sit down or be waited on as there is in the bars of some of the more touristy hilltop towns.

Now you're beat. You pounded out the last drop of your Brunello and went for the after-dinner grappa. Feeling oh so Italian, you even stopped for the late-night espresso. Where to stay? Hotels are scarce and expensive, but fortunately rooms abound. While taking your non-goal-oriented strolls, you probably saw signs here and there saying: "camere/zimmer/rooms." These could be anything from private rooms inside family houses to quasi-condos.

The best I found was a place called Il Moro. Also located on Via Mazzini but away from the main piazza, Il Moro is attached to the trattoria of the same name. There are four double rooms, beautifully refinished with wooden interiors, superb views and a combined kitchen/dining room/sitting room downstairs. I was there in March, and my girlfriend and I had the whole swanky place to ourselves. A room will run you about $40 a night, but it increases to $60 from Easter to the festival month of June. Well worth it, even if you have to bend, twist or otherwise alter your budget. If Il Moro doesn't turn your crank, check with the Mariuccia family or the tourist office by the main piazza for listings. Otherwise, take another leisurely stroll around the city inquiring about prices when you see the sign "camere/zimmer/rooms." Nothing could give you a better feel for Montalcino and its inhabitants.

More rustic getaways are also possible. If you're bent on getting away from everything, try an agriturismo: usually a rural hotelesque setting on the road less traveled. Being that Montalcino is already a tad "out there," agriturismo offers you the possibility of stretching your days even further. For a really different take, try Abbadia Ardenga. This ex-abbey now rents entire apartments at reasonable prices (starts at about $20 per person per day). This is particularly worthwhile for larger groups. A minimum stay of three days is required.

If Il Moro and the rustic hideaways don't turn your crank, there are, of course, the star clustered hotels. Montalcino's best -- Hotel Bellaria and Albergo Ristorante Il Giglio -- boast three stars and have all the amenities. Get the full treatment and opt for "full pension" -- two square meals along with the room, all at the same place for around $85 per person.

If you go for a posh pad, save money on eats by grabbing some sausage, cheese, good Tuscan bread and wine from the COOP supermarket. Have a picnic on the church lawn at the opposite end of the town from the Rocca. And don't worry if you find yourself becoming more Montalcinese than you thought possible: hanging out in bars when you're not thirsty, chatting with locals when you don't speak Italian. I was even eyeing Yoshi's overtly Italian shoes and coat thinking, "those are pretty sharp." Just enjoy these metabolic changes -- what I group collectively as "The Montalcino Syndrome" -- while they last.