When it comes to wine, the rule of thumb is the older the vintage, the better the wine is supposed to taste. However, this is a widespread misconception and a wine’s age is not always an indicator that the wine will actually be good. This list highlights some of the oldest bottles of wine in existence, most of which are no longer drinkable. Several of the wines on this list are not only a few hundred years old, but are also some of the most expensive bottles to ever be sold at auction.

7. Chateau Lafite Rothschild

photo source: fluxmag.com

The bottle of Chateau Lafite Rothschild 1787 that was auctioned at Christie’s of London in 1985, is officially the most expensive bottle of wine ever sold at $156,450. The reason for the wine’s high price tag is that despite having no label, the bottle was etched with the initials “Th.J”, suggesting that the wine had belonged to Thomas Jefferson.

Michael Broadbent, the head of Christie’s wine department at the time of the auction, consulted with the auction house’s glass experts, who confirmed that the bottle and the engraving dated back to the 18th century. Also, the wine’s authenticity can be backed up by history as Jefferson served as America’s Minister to France between 1785 – 1789. Jefferson was also known to be a wine connoisseur and reportedly brought back with him to America about $120,000 worth of wine in today’s currency from France.

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6. Chateau Margaux

photo source: thedrinksbusiness.com

This particular bottle of Chateau Margaux 1787 is known for being the most expensive bottle of wine that was never actually sold. In 1989, wine merchant William Sokolin valued the wine at $500,000 because it was believed to have once belonged to Thomas Jefferson, but there were no interested buyers at that price.

During a party honoring the owners of the wine that Sokolin was trying to sell, the bottle of Chateau Margaux 1787 fell to the ground and was completely broken. Fortunately, Sokolin had the wine insured for $225,000 which was eventually paid out by the insurance company.

5. Massandra Sherry de la Frontera

photo source: Wikimedia Commons

In 2001, a bottle of the Massandra Sherry de la Frontera 1775 was sold at a Sotheby’s auction for $43,500 in London, making it the most expensive bottle of Sherry in the world. The wine was produced by the Massandra Winery, located in the Republic of Crimea, which is home to an extensive collection of valuable Russian and European wines.

In 1922, after the Russian Revolution, the winery was nationalized and its cellars became a protected institution. In 2015, Russian President, Vladamir Putin, and former Italian Prime Minister, Silvio Berlusconi, allegedly drank from a bottle of Jeres de la Frontera worth $90,000.

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4. Rüdesheimer Apostelwein

photo source: www.finestandrarest.com

The Apostelwein 1727 comes from the famous 12 Apostles’ cellar in the Bremer Ratskeller located in Bremen, Germany. The wine comes from 12 barrels of wines in vintages of 1683, 1717, and 1727, which were reduced in number due to evaporation – when there was only one barrel left, the wine was bottled in the 1960s.

The most expensive bottle of the Apostelwein 1727, valued at $200,000, belongs to the Graycliff hotel in Nassau and is one of the most rare wines in the world. The wine is supposedly still drinkable due to its high sugar content.

3. Tokaji from the Royal Saxon Cellars

photo source: finestandrarest.com

This bottle of Tokaji, dated between 1650 – 1690, was sold for an undisclosed amount in a 1927 auction that took place in the Saxon capital Dresden. During the auction, 62 bottles of Tokaji from the Royal cellar of Augustus II were sold. This wine is believed to be the oldest intact Tokaji bottle and was certified as authentic by the Foundation of the House of Wettin, which administrated the heritage of the former Saxon monarchy.

2. Strasbourg Wine Barrel

photo source: Wikimedia Commons

The wine cellar under the Strasbourg city hospital (Cave Historique des Hospices de Strasbourg) in France is home to the oldest barrel-stored wine in the world. The barrel is marked with a date of 1472 and the wine inside is still drinkable. The wine has been tasted only three times in its history: once in 1576 to celebrate the alliance between Strasbourg and Zurich; a second time in 1716 after the hospital burned down; and finally in 1944 when Strasbourg was liberated by General Leclerc during World War II.

The wine was most recently transferred to a new barrel in 2014 after its original barrel started leaking. A new handmade egg-shaped barrel was made for the wine by two of France’s most-respected coopers Xavier Gouraud and Jean-Marie Blanchard.

1. Speyer Wine Bottle (Römerwein)

photo source: Wikipedia

The Speyer wine bottle is believed to be the oldest bottle of wine in the world and is dated to around 325 AD – 350 AD. The bottle was unearthed in 1867 and one of 16 found in a sarcophagus in the grave of a Roman nobleman and his wife – the bottle was the only one still intact. The liquid, which is no longer alcohol, has most likely survived this long because the bottle was sealed with wax and olive oil was poured into the bottle to preserve the wine.

Since its discovery, experts have debated on whether or not the wine should be opened and analyzed. For now, the bottle remains unopened as part of the Pfalz Historical Museum collection in the German City of Speyer.