It is 5:58pm as we walk back out into Causeway Bay’s crowded streets. Feeling bleary-eyed in the cool December air, at first it takes us a moment to re-establish our bearings amid the chaos of Tang Lung Street. People are everywhere; buses and taxis shoot past. One of the group should have been on his way to the airport 30 minutes ago: “I really need to get going, otherwise I am a dead man”. And with that, like Keyser Söze, he’s gone.

Five-and-a-half hours earlier, the four of us had taken our seats at Wooloomooloo Prime on the 27th floor of the Soundwill Plaza building (above), for what would be an epic journey through eight terrific wines from around the world. The lunch would be a Christmas social, a recap of the year, as well as an eccentric celebration of our common backgrounds. All being British, the lunch would serve as a nostalgic – but perhaps more relevantly, comedic – backdrop to a conversation about The Old Empire.

In keeping with the spirit of the event, we start with arguably the greatest Brit of all time: Sir Winston Churchill. The Prime Minister had drunk Pol Roger Champagne since the 1920s, but it was not until he attended a dinner at the British Embassy in Paris at the end of the Second World War, where he was seated next to the beguiling Odette Pol-Roger, his predilection for the famous Épernay house was sealed. Their close friendship (right) lasted until Churchill’s death in 1965, and in 1984 Odette decided to name their prestige blend in his honour, launching it at Blenheim Palace, the place of his birth.

We drink the 2000 Cuvee Sir Winston Churchill. A shimmering golden colour with only minimal bubbles, its nose was beautifully layered: first toast and vanilla, it moved on to stewed apple before taking on somewhat of a mineral note, typical of a younger wine. Still very fresh. On the palate it was enormously rich and full-bodied, less fruit but delivering biscuity autolytic cues as well as more of that oak influence. A long finish confirmed its undoubted quality – what a start.

We then moved through some awesome food to go with our chosen bottles: Fines de Claire oysters and Iberico ham while we considered the menu (and drank the SWC); scallops and crab cakes as starters, before a selection of meats from the butcher’s block including a superb bone-in ribeye Tomahawk.

This was how we found the wines:

2013 Greywacke Pinot Gris

• Cloudy Bay founder and photographer Kevin Judd set up his own label in 2009, and this past couple of years has seen the fruits of his labour rewarded with real quality. This one was pale lime-green in colour; a quirky aromatic wine with a complex nose of white flowers, stone fruit (esp. peach) and a slight candied note. Very enjoyable, and a perfect way to kick things off post-fizz, this off-dry wine had a full-ish body with refreshing acidity and a nice green fruit finish

2010 Domaine J-M Boillot Batard-Montrachet Grand Cru

• A deep gold colour, this Premier League chardonnay from one of Puligny-Montrachet’s Grand Cru sites was mineral, rich and toasty. Surprisingly, not much fruit there but a Chablis-like steeliness instead. A perfect accompaniment, as well as a stylistic contrast to the Greywacke, for our starters

2008 Dry River Pinot Noir

• Following the recent tasting, we decanted for well over an hour and it made a big difference: more primary fruit on the nose, especially strawberry and raspberry, as well as sweet spice and a touch of white pepper, it was pleasant but still somewhat closed. All the elements of tannin, fruit, acidity and alcohol were balanced enough though, to suggest this should be long-lived (damn: only two bottles left)

2000 Domaine Leroy Pommard “Les Vignots”

• What, hopefully, the Dry River will taste like in 8 years’ time. Beautifully perfumed, it has trademark Pinot red fruit, but now perfectly integrated with a savoury character, best described as “meaty”. On the palate it was delicate and balanced, medium-bodied with nothing out of place. A pleasure to drink, and an outstanding example of premium aged red Burgundy

2001 La Rioja Alta Gran Reserva

• For a 14-year-old, this Spanish favourite seemed remarkably young on the nose. A Tempranillo fruit bomb of blackcurrant and black cherry jumped out of the glass, and it was only when tasted that some of the more secondary (winemaking) character – oak, vanilla – started to come through. Fruit forward with plenty of soft tannin, it was perfect with the Tomahawk

2000 Chateau Haut-Bailly

• A classic Claret from a brilliant vintage. Sweet spice, oak, blackcurrant and graphite on the nose, followed by mellow tannins and lovely red fruit on the palate. We were starting to flag after the previous six wines, but still lucid enough to appreciate the quality of this excellent wine

2007 Klein Constantia Vin de Constance

• Worth reading the history of this famous wine. A terrific way to end our vinous odyssey, this sweet wine from South Africa was a deep, coppery-gold colour. Rich, full-bodied and unctuous (but not cloyingly so), it had cinnamon and clove, orange marmalade and tropical fruit attacking the senses…fantastically matching our apple crumble and cheesecake desserts

It is fair to say that by the time we had worked through the above, with darkness starting to fall, we had long since moved away from discussing the virtues – or lack thereof – of Britain’s rich and varied history. Instead, our long lunch turned into what the best social events always do: outstanding food and wine serving as a canvas for friends to share hour after hour of great conversation.

Roll on Christmas!