*This post was written in collaboration with Visit Penticton.

The South Okanagan has everything you need for a weekend break: vineyards, expansive views, warm lakes, farm-to-table restaurants, and breweries. The only challenge will be fitting it all in. Staying in Penticton provides a central home base for our guide on how to spend a September weekend in the South Okanagan.

View of Okanagan Lake from the Naramata Bench.

Night 1: Dinner Downtown Penticton

If you arrive in time for happy hour, head to Chulo Tapas on Estabrook Avenue. Enjoy a Spanish vermouth and soda while chatting with the bartender at their outdoor window. Finish the evening a couple of blocks away at Cannery Brewing, a 24-year-old institution in Penticton. Settle into their laid-back patio and share a plate of chicken nachos with your beer(s).

Day 1: Wine Tasting on the Naramata Bench

Image courtesy of @wayneandfreda.

Start your morning with coffee and breakfast at Wayne & Freda, a Penticton staple known for its breakfast sandwiches and bright atmosphere.

With a full belly and a caffeine boost, stroll two blocks over to the Penticton Farmer’s Market, a bustling market packed with fresh produce, local wine, spirits, ciders, crafts, and more. Next up—Ad Hoc, a boutique shop whose allure comes from its curated mix of clothing, shoes, accessories, and home goods by independent designers and artisans. You'll find Canadian-owned Bare Knitwear sweaters, Rachel Comey dresses, body care from Sḵwálwen Botanicals, and more.

With the morning behind you, it's time to start your tour of the Naramata Bench—a wine region celebrated for its full-flavoured white varietals and earlier-ripening reds. Begin at Nichol Vineyard in Naramata, home to the oldest Syrah vines in Canada. Here, owner and winemaker Ross Hackworth takes a minimalist approach, allowing the natural qualities of the grapes to shine through without unnecessary intervention. From there, head toward Penticton to Creek and Gully Cider, where you'll go from some of the oldest vines to the oldest apple trees in the area. Cider-maker Alyssa Hubert crafts wild-fermented ciders that represent a new era of cider-making. By now, you’re probably feeling hazy, but don’t miss a stop at Roche Wines for an intimate, guided tasting.

Come dinner time, eschew wine altogether and opt for cocktails at Elma, a Turkish-inspired restaurant in Penticton. Not to miss are the lamb dishes or a pide (a Turkish flatbread) to soak up an afternoon well spent.

Day 2: Wine Touring in Oliver

Image courtesy of @checkmatewinery.

Today is a day to explore other pockets of the South Okanagan. Start at Crêperie Ooolala on Okanagan Lake with a cappuccino and a crêpe before diving into another day of wine touring.

On route to Oliver, stop in Kaleden at Black Market Wine Co. for a seated tasting overlooking Skaha Lake, where owner and winemaker Rob Hammersley uses minimal-intervention techniques to produce terroir-driven wines. From there, continue to Checkmate Winery in Oliver for a canapé-paired tasting of a select lineup of library Chardonnay and Merlot—the only wines made on the property. Your final stop is District Wine Village, where you can explore eleven different wineries. On weekends, bands take to the outdoor stage in the center courtyard.

Spend your final evening in a relaxed setting at Tratto, a Neapolitan pizzeria many now consider a Penticton staple. The wine list rolls deep with international offerings but also gives nods to nearby producers.

From the bustling weekend energy of Penticton’s downtown to the vine-covered hills of Naramata and Oliver, September in the South Okanagan offers an array of experiences (many not mentioned here). Here’s to a weekend well spent and the many reasons to return.

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