In between bites, Lot Eight's Nalini Baruch tells us the story of her 17-year journey from lawyer to one of the region's most successful olive oil producers, while the affable Tim Coney talks us through the wine matches, adding that "the point of wine is to allow people to dig themselves out from their mundane existences, talk nonsense and have a good time". I couldn't agree more.
Home for the weekend is Aylstone Retreat, the six luxury whitewashed cottages are like a slice of the Hamptons dropped into the Wairarapa.
Sadly, we've only enough time to drop off our bags before heading to the night market, where Bedouin-style canopies shelter more than 60 stalls featuring everything from mulled wine and crusty bread (slathered in the new season's olive oil) to craft stands and local musicians.
When the temperature gauge reaches zero and I can no longer feel my feet, I send a silent thanks to whoever invented the diesel heaters which are dotted around the square.
There are more than 50 olive groves in the Wairarapa, with 30 of those in Martinborough.
On Sunday morning we drive to Atutahi, where Wellington expats Ruth and Peter Graham planted 570 trees back in 1999. The region's hot dry summers and cool winter nights, coupled with rocky soil, make it similar to Tuscany, which is why, like so many around here, Ruth and Peter grow a range of Tuscan olive varietals such as frantoio and leccino.
Sitting in the sun-dappled grove, mopping up the couple's award-winning extra virgin olive oil with chunks of fluffy focaccia baked in the outdoor oven, it's easy to imagine we're actually in Tuscany.
Just down the road at Brodie Estate, we get the full Martinborough experience - wine and oil.
Artist Ann Brodie and her husband James planted half their 8ha in grapes and half in Italian and Greek olives trees back in 2001 and we wash down their peppery, buttery oil with a 2009 Brodie Estate Pinot Noir.
It would be rude not to chase this with glasses of spicy mulled wine and chunks of Ann's fruit and booze-laden Christmas cake, which we gobble as we wander through her studio.
The best comes last, though. In a stately home on the outskirts of town, food writer and caterer Ruth Pretty has her way with olive oil and more sugar than is strictly necessary in a range of delicious desserts.
It's not like I need any more calories this weekend, but the chance to sample chocolate olive oil mousse with delectable orange sugar snaps is just too good to turn down.
CHECKLIST
Getting there: Air New Zealand has direct flights from Auckland to Masterton.
Further details: See wairarapanz.com.
The writer was a guest of Destination Wairarapa.