Now he has added Nelson's thriving arts community to the mix, with a tour designed to introduce visitors to the things that make this small seaside city special.
Kennedy's Wine Exposed art/wine tour starts with a pause at a hilltop lookout to admire the view over the poetically named The Haven and the boulder bank which has created this pretty harbour.
The bank is a rare geological feature - one of only three in the world, created by tidal currents. It stretches for 13km across the Nelson waterfront, and the sandbar, where the lighthouse still stands picturesquely against the sea, is still dotted with a few baches, the work of lucky folk who built years ago, before such things were banned.
From there it's on to lunch, prepared by Kennedy and eaten in the home of well-known local artist Anna Leary.
Before lunch, Leary walks us through her home and studio, with its epic views over the harbour and valley, talking about the art on display and of her inspirations, which so often come from her Nelson environment.
On the balcony, Leary points out the homes belonging to different artists that are dotted around the valley. It's a neat physical representation of this tight-knit but still open artistic community.
The idea of dropping into an artist's house or home studio may be a little strange for many visitors and in a lot of towns, but in Nelson it just seems to work that way.
"It would be weird if it wasn't like that," Leary says.
That kind of attitude also makes the Nelson region an excellent place to explore independently. Take a tour like this to get your bearings, then hop in a rental car and explore on your own. It's a follow-your-nose kind of place. Back roads and main highways are dotted with signs advertising art, olives, wine, cheese and plenty more.
In most instances, visitors are welcome to roll up and admire or buy.
But for now, Kennedy is navigating his Mercedes people-mover down Nelson's narrow winding alleyways, some dating back to the town's settlement.
Then it's out through Tahunanui and Richmond to the wine country that sits between Nelson and the summer beach meccas of Golden Bay, Kaiteriteri, Abel Tasman National Park and Farewell Spit.
Kennedy keeps up a fascinating commentary on the wine region's social history (settled by the Germans) and geographic make-up (surrounded by forests and national parks that - except for today - keep the storms at bay, providing its famously stable weather) until we arrive at Neudorf Winery in Upper Moutere.
The rain is still driving down but owner Tim Finn (no, not that one) dusts off the gas heater and we sit admiring our surroundings. Here again, art is never far from the wine, and sculpture is dotted through the winery's public areas. It feels more personal seeing this place on a wet but calm late winter's day rather than with the summer crowds.
Kennedy fires up the gas cooker to prepare delicious hot smoked salmon as we settle in for a lesson in food and wine matching. The rule is there aren't any rules... except for all the rules.
Everything I think tastes good together seems to give everyone else some sort of sour-cat expression - except for the Marlborough mussels with the Neudorf pinot gris, which everyone agrees is a triumph.
Food matches aside, I've fallen in love with Neudorf's famous chardonnay. Anybody who insists chardonnay is yesterday's grape has never tasted this.
Hours, possibly weeks, could be whiled away like this but we have a pressing date with Kina Beach winery, a short drive up the road, towards the coast.
Kina Beach owner Dave Birt, formerly an oil company executive, spent 10 years looking for the right spot to settle his vineyard - he had a list of 10 criteria and waited until he found them all before buying.
Crucial on that list was a coastal breeze to cool down the fruit come summer and slow the ripening process. And it's hard to argue with his choice, the wine is excellent - particularly the pinot noir - and the idyllic location is even better.
Birt has also made over an old schoolhouse on the property into an exclusive, reclusive B&B. It's the perfect romantic hidey-hole. Although within easy reach of beaches, wineries and gorgeous places to eat, it's hard to imagine why you would tear yourself away from the gorgeous cottage with its beautiful views from the master bedroom.
The wintry day is getting short so we head back towards Nelson via the coastal enclave of Mapua.
Here among the wharfside cafes is the Coolstore gallery - yes, in what was once a coolstore - which exhibits a range of fantastic paintings, sculptures, ceramics and jewellery.
And it has an excellent opening-hours note on the door which reads something along the lines of "open from 11ish" - life here is, apparently, one endless summer, rain or shine.
Kerri Jackson was a guest of Heritage Hotels and Air New Zealand.
