Everyone who gets into wine eventually feels an itch to drink a truly great bottle. But there's a big price difference between a 2005 Château Pétrus for about $4,000 (no exaggeration) and a 2005 Vieux Château Certan for $200. With that in mind, here's my list of truly great wines that are all less than $250—not cheap by any means, but at least in the realm of super-duper-special-occasion rather than holy-Moses-I-can't-breathe. For fun, there's also a map of the world's most expensive wines, as well as a glance into the diamond-encrusted world of wine bling.
Expensive White Wines
1998 Veuve Clicquot La Grande Dame ($120) There may be other top Champagnes that will be better in 10 or 20 years (Dom Pérignon and Cristal come to mind), but for drinking right now, this release of Grande Dame is hard to beat. The 1998 Champagne vintage was warm and generous, and that shows through in this rich, lusciously toasty sparkling wine.
Loire Valley, France
2008 Didier Dagueneau Silex ($120) Didier Dagueneau, the prodigiously bearded wildman of the Loire, made some of the best Pouilly-Fumés and Sancerres ever. He died when his ultra-light plane crashed in 2008, but his son, Benjamin, has kept the wines at the same level. This lovely Sauvignon Blanc, with its minerally grapefruit-peel scent, is his first solo vintage.
Related: Best $15-and-Under White Wines
Sonoma Coast, California
2008 Littorai Thieriot Vineyard Chardonnay ($60) It will take some work to find a bottle of this—collectors pounce on winemaker Ted Lemon's brilliant Chardonnays and Pinots with raptor-like ferocity. This single-vineyard white's creamy texture and bright citrus fruit hide a tensile strength that suggests it will be able to age for years.
Mosel Valley, Germany
2008 Egon Müller Scharzhofberger Spätlese Riesling ($115) True, Egon Müller IV's middle-tier bottling costs more than other Mosel producers' top wines do. But the Scharzhofberger vineyard was famous for its wines as far back as the 1300s, and Müller is a master at channeling this great vineyard's distinctive essence. Slate-inflected, powerful, delicately sweet and able to age for decades, this is truly profound Riesling.
2008 Domaine Leflaive Puligny-Montrachet Les Folatières 1er Cru ($220) Burgundy fanatics love to argue about all things Burgundian. But one thing that's universally agreed is that Domaine Leflaive is one of the region's greatest white wine producers. This $220 premier cru bottling, with its round, almost honeyed density and seductive spice notes, is spectacular.
2007 Prager Grüner Veltliner Achleiten Stockkultur ($68) Toni Bodenstein, the impressively talented winemaker at Prager, makes this concentrated and complex Grüner Veltliner from a single-acre plot of 70-year-old vines in the renowned Achleiten vineyard. It's one of those rare wines that seem to smell and taste different with each sip: lime, wildflowers, wet stone and more.
Expensive Red Wines
2007 Gaja Barbaresco ($210) Italy's Angelo Gaja has received so much acclaim that one might assume the hype about his wines exceeds the quality. It doesn't, especially with his basic—if that's the right word, given the triple- digit price—Barbaresco. Fragrant raspberry notes and incredible poise are the hallmarks here.
2007 Sassicaia ($220) Sassicaia was the first of the Super-Tuscans, which broke Tuscan wine regulations by using Bordeaux varieties like Cabernet Sauvignon (and, in this case, a touch of Cabernet Franc). It remains one of the few that actually deserve the term "super." The '07, from a very good year, is a bit more opulent than usual but lacking none of Sassicaia's trademark finesse.
Napa Valley, California
2008 Spottswoode Cabernet Sauvignon ($135) Year after year, Spottswoode goes on making one of the best Cabernets there is from America's defining Cabernet region, the Napa Valley. And while their wines do sell out swiftly, buying them isn't a mailing-list-only waiting game. The '08 recalls violets along with blue- and blackberries, knit up by fine-grained tannins.
2006 Jasper Hill Emily's Paddock Shiraz ($125) Take one of the Heathcote region's greatest vineyards, farm it organically, then add owner Ron Laughton's brilliant winemaking. The result is this intensely aromatic (mint, tea leaf, wild blackberry) Shiraz, an Australian icon.
2005 Bodegas Roda Cirsion ($249) While Rioja traditionalists may be skeptical about Roda's modernist winemaking practices, they should open their minds and taste this wine. Exotically perfumed and elegantly structured, it's a knockout Spanish red.
2007 Concha y Toro Carmín de Peumo Carmenère ($120) Many countries, including Chile, make exceptional Cabernet. Only Chile makes great Carmenère. This wine's velvety richness, black currant fruit and green-olive-plus-herbs aroma are as good as Carmenère gets.
2007 Nosotros ($100) Susanna Balbo is one of Argentina's best winemakers, and Nosotros is her best wine. It's almost over-the-top—like black raspberry confit but more luscious—yet its tingling acidity keeps it from being overbearing.
Expensive Wine: Billionaire Bottles
Chambord by Donald Edge Chambord: $30. Chambord with 1,100 diamonds set in 18-carat gold? Ouch. Personally, I'd rather have a private island.
Macallan Lalique Cire Perdue Sixty-four-year-old whisky, extraordinary decanter—and the money all went to charity.
Hennessy Beauté du Siècle Stunning Cognac, but how about the unique, artist-designed, glass-and-aluminum chest that holds it?
Rémy Louis XIII Diamant Édition Précieuse Louis treize is expensive enough. Add a stopper with a big diamond and it quadruples in price.
Courvoisier Erté Collection ($10,000) The seven bottles in this collection of cognacs were created by the Art Deco artist and designer Erté, and illustrate seven steps in the cognac-making process. The liquid inside is a special blend, including cognacs dating back to 1892, the year of Erté's birth. First released one by one in the 1990s, the remaining bottles were released by Courvoisier as a set, for a cool ten grand, in 2009.
Expensive Wine: Stars' Bottles of Choice
Jacob the Jeweler
Jacob Arabov sells diamond-encrusted watches to everyone from rap stars to, oddly enough, Rudy Giuliani. So why not a vodka in a bottle faceted like a diamond? Called Bocaj, it's perfectly OK—but it's also $80.
Armand de Brignac Brut Gold Champagne, with its metallic gold bottle, flew off shelves after Jay-Z featured it in his video for "Show Me What You Got." It's quite good, in a rich style, but for $250? Hmmmm.
Hip-hop star Chris Bridges actually helps blend Conjure Cognac, a rarity in the world of celebrity-promoted products. It's a lush, vanilla-and-spice spirit, a crowd-pleaser, and at $30, it's fairly priced, too.
A Treasure Map to the World's Most Expensive Wines
Perhaps only millionaire wine maniacs are buying these expensive wines, but—much like window-shopping at Harry Winston—it's fun for the rest of us to see where the bottles come from. For a reality check, each is matched with a less shockingly pricey alternative.
For the Crazed Collector: 2005 Domaine de la Romanée-Conti Romanée-Conti ($4,000)
For the Would-be Connoisseur: 2007 Domaine Dominique Mugneret Vosne-Romanée ($55)
Ribera del Duero, Spain
For the Crazed Collector: 2007 Pingus ($695)
For the Would-be Connoisseur: 2007 Hacienda Monasterio Reserva ($80)
For the Crazed Collector: 2005 Château Pétrus ($4,000)
For the Would-be Connoisseur: 2005 Vieux Château Certan ($200)
For the Crazed Collector: 1995 Krug Clos d'Ambonnay ($4,200)
For the Would-be Connoisseur: NV Vilmart & Cie Grand Cellier ($45)
Rhône Valley, France
For the Crazed Collector: 2003 Jean-Louis Chave Cuvée Cathelin Hermitage ($2,550)
For the Would-be Connoisseur: 2005 E. Guigal Hermitage Rouge ($90)
For the Crazed Collector: 2007 Tenuta dell'Ornellaia Masseto ($475)
For the Would-be Connoisseur: 2007 Le Macchiole Rosso Bolgheri ($29)
Douro Valley, Portugal
For the Crazed Collector: 2003 Quinta do Noval Nacional Vintage Port ($950)
For the Would-be Connoisseur: 1996 Dow's Quinta do Bomfim Vintage Port ($50)
Napa Valley, California
For the Crazed Collector: 2006 Screaming Eagle Napa Valley Cabernet Sauvignon ($1,100)
For the Would-be Connoisseur: 2006 Dalla Valle Napa Valley Cabernet Sauvignon ($150)
Eden Valley, Australia
For the Crazed Collector: 2006 Henschke Hill of Grace ($500)
For the Would-be Connoisseur: 2006 Yalumba Hand Picked Shiraz+ Viognier ($30)