The Ultimate Itinerary For Three Days in Osoyoos

After a four-and-a-half-hour drive south of Vancouver, you’ll arrive in the Oliver Osoyoos Wine Country. This sun-kissed valley is sprinkled with shimmering lakes and rows of vineyards peppering the lush hillsides. Nestled along the very southern tip of Okanagan Valley, this area is home to 100+ wineries—featuring some award-winning makers—and dynamic wine-led, locally sourced restaurants. If you’re itching for an adventure filled with food, wine, Indigenous history and a touch of outdoor exploring, come along with me to discover everything that makes the Oliver Osoyoos Wine Country so special.

Day One

Lunch at Kismet Estate Winery’s Manzil Restaurant

I arrived just in time for my first culinary adventure at Kismet Estate Winery’s Manzil Restaurant. I met up with 28-year-old winemaker Manpreet Dhaliwal—the only South Asian female winemaker in North America. Dhaliwal has amassed many awards since taking up the helm in 2020. I highly recommend sitting on the patio overlooking the estate vineyards. I sipped on a glass of her 2020 Cabernet Sauvignon Reserve, which paired perfectly with the dhokla bites, kale chaat salad, blue cod pakoras and sprouted lentil salad. If you love Indian food, the diverse flavours and textures will leave you spellbound.

Check in at the Watermark Beach Resort

If you’re searching for a high-end retreat that is both unpretentious and luxe, check out the Watermark Beach Resort. The resort currently offers a Stay and Sip package that comes with a free Summer 2025 Tasting Passport that unlocks 11 of the region’s star sips (I narrowed my list down to four wineries I’d like to visit). The lakeside resort’s suites are outfitted with fully-equipped kitchens, cozy sitting rooms with gas fireplaces, ultra comfy beds and spacious patios. The resort offers an outdoor heated pool (plus a waterslide), hot tubs, a steam room, spa, fitness centre, SUP rentals and more.

Dinner at the Watermark’s 15 Park Bistro

Voted by OpenTable as one of Osoyoos’ best restaurants, make sure to snag a coveted spot at the 15 Park Bistro on the covered patio overlooking the lake, mountains and pool. Executive chef Jeffery Young brings his creativity and passion for the region to each dish, and it certainly is showcased in the herb rubbed Pacific Halibut with citrus beluga lentils and braised fennel in a white wine butter sauce. Full disclosure—it was possibly the best tasting halibut I’ve ever had. Also known for its carefully curated wine list highlighting the flavours of the South Okanagan Valley, the knowledgeable team can choose a wine that will enhance what promises to be a memorable dining experience. With a strong focus on fresh, local ingredients, a commitment to sustainable seafood and an unparalleled location, 15 Park Bistro delivers on all levels.

Day Two

Breakfast at the Barn Owl Eatery & Café

If you’re looking to satisfy your breakfast cravings, may I suggest the quaint, funky Barn Owl Eatery & Café? As one of the hot brunch spots in town, be ready for a line-up. Only a 15-minute walk from the Watermark, I enjoyed the Avo Eggy toast, two slices of sourdough French Toast topped with avocado, tomato and spinach, and a healthy mango smoothie.

A Guided Tour of the Nk’Mip Desert Cultural Centre

Discover more about the local Syilx First Nations peoples’ culture and history at the contemporary interpretive centre complete with exhibits, films, artifacts and much more. Built into the desert hillside, immerse yourself in an outdoor journey that weaves along a 2-kilometre sage and antelope brush path that takes you past sculptures, tipis and petroglyphs carved into the rock. I spent nearly two hours exploring this incredibly interesting and beautiful eco-friendly centre.

Lunch at Spirit Ridge’s The Bear, The Fish, The Root & The Berry

This gorgeous restaurant’s name reflects the Four Food Chiefs in the Syilx First Nations people of the Okanagan. A Newfoundlander, Chef Murray McDonald (who was previously at the helm of the luxurious Fogo Island Inn before coming to the Okanagan) leads the Indigenous-focussed culinary team.  The best summertime spot to wine and dine is on the large terrace overlooking the valley, lake and pool. Everything from the elevated cuisine, décor and views are some of the most stunning you’ll encounter in the Okanagan. I recommend the remarkable seafood chowder, a New England-style white chowder loaded with pieces of fresh seafood and kale.

Visit the Nk’Mip Cellars

Part of Watermark Beach Resort’s complimentary winemakers series tasting, the winery’s tasting room is located next to The Bear, The Fish, The Root & The Berry. An award-winning winery, Nk’Mip (pronounced ‘ink-a-meep’) is North America’s first Indigenous-owned winery. Firmly rooted in crafting premium wines, Nk’Mip’s premier tier of wines is named Qwam Qwmt. Ask for a tasting of the Qwam Qwmt 2020 Syrah—I went home with two bottles.

Shop Along Main Street

Main Street features locally owned and operated vintage and boutique shops featuring everything from used books, trendy clothing, handmade gifts and more. One of my favourites was Beach Chik & Island Time. With eclectic décor, clothing and accessories, it was a must-visit for me. P.S., the sales gal extraordinaire, Julie, made shopping here a truly fun experience.

Dinner at Hester Creek Estate Winery’s Terrafina Restaurant

Everything from the pergola of old vines, décor, vineyards and cuisine at Hester Creek’s Terrafina transports you to Italy. The old-world design seamlessly blends rustic warmth with earthy tones, exposed wooden beams, brick and a striking wine wall. Inspired by the previous owner Joe Busnardo’s Italian background, the menu is a love letter to Tuscany. I started with the burrata salad: The burrata sits atop basil leaves, greens, strawberries and apple slices drizzled with pure olive oil—it was a symphony of flavour that leaves you wanting more. Paired with Hester Creek’s 2021 big red, The Judge, I then indulged in the pan seared chicken entrée… heaven.

Day Three

Walk the Osoyoos Oxbows Trail

After yet another delicious avocado toast at 15 Park Bistro, I headed on the tranquil and picturesque trail winding through the Oxbow lakes, past the wetlands. From the parking lot on Road 22, walk towards the old bridge and find a path on either side that runs parallel with the channel. Past the bridge, walk past the historic Haynes Ranch, one of the oldest cattle ranches in the Okanagan Valley (circa 1915). Its crumbling barns and ranch houses are part of the Okanagan Historical Society preservation project.

Tour and Dine at Burrowing Owl Estate Winery’s Sonora Room

After a fascinating private tour into the history of Burrowing Owl Estate Winery, I was led into its award-winning Sonora Room Restaurant. The menu has been crafted with the philosophy “what grows together, stays together.” To that end, the executive team sources organic, locally grown produce as much as possible. I enjoyed a flight of its notable reds along with a charcuterie board on the wrap-around deck of the Southwestern-style winery. The winery offers several unique curated tours and tasting experiences.

Peddle Through Wine Country With Sessions Outdoor Sports

After lunch, check out the e-bikes just outside Burrowing Owl’s tasting room. Is there a better way to burn off a few calories while taking in the stunning vistas? You can cycle past several vineyards, and make winery stops along the way. Scan the QR code on the bike and you can map out your very own journey.

Enjoy the Watermark’s Stay and Sip Package: Church & State Wines, Nostalgia Wines and Black Hills Estate Winery

Nestled on the sun-soaked Black Sage Bench across from Oliver, I met up with Church & State Wines’ talented winemaker, Arnaud Thierry. Growing up in France’s iconic Bordeaux region, his bold reds definitely showcase his French background.  At Black Hills Estate Winery, I sampled some of the winery’s perennial favourites, including two that I came home with—the 2021 Tempranillo and the 2022 Nota Bene. A hidden gem, Nostalgia Wines was a pleasant surprise. In 2024, winemaker Gina Fernandes Harfman was thrilled that Nostalgia was named the third-best performing small winery in Canada and has since won numerous awards. P.S., nostalgia features free live music on Thursdays.

Dinner at Convivia Bistro Cuisine

As a last dinner in Osoyoos, look no further than Convivia Bistro. Besides a welcoming atmosphere for delicious food and thoughtful drinks, this contemporary Italian- and French-inspired bistro is just plain fun. Executive chef Romain Martinet’s French training is wonderfully evident in the cassoulet and French onion soup (which was popular among my fellow patrons). I went for the bread-dipping, mouth-watering penne al Salmone, a medley of smoked salmon in a white wine dill sauce. Located just off Main Street, the bistro’s B.C. wine and crafted cocktail program is equally notable.

Day Four

Visit Osoyoos Lake

As a last treat, take some time to dip your toes or whole body in Osoyoos Lake, Canada’s warmest freshwater lake. Right outside the Watermark, I also took the time for a lakeside walk before heading home on a scenic drive.