South Okanagan

Spring Cycling and Winery Tour

With the wild success of our 2020 Harvest Tour, we’ve upped the ante, engaging some of British Columbia’s finest chefs and wineries to deliver a truly outstanding gastronomic cycling tour.

Dates: May 15-21, 2021

“We have fond such memories of our Okanagan Wine Tour.  Matt  is a wonderful, genuine, dedicated host and provided us with an amazing experience. The cycling was challenging at times but it was breathtakingly beautiful and we always ended our days with a 5 star dining experience. Already looking forward to our next Magic Places Tour.”

  • Steve and Kara, 2020 Okanagan Wine Tour


Narrow ribbons of asphalt winding through vine-clad hills, breathtaking vistas of the Okanagan Valley while sipping a perfect pinot, and gourmet farm-to-table dinners highlight an unforgettable week in the sunny Okanagan. Boasting over 180 wineries, an ideal spring and fall climate, and hundreds of kms of immaculate, winding country roads, the South Okanagan offers a clcle vacation experience that rivals France and Italy, yet it is in our own backyard!

We’ve painstakingly curated our 6-night, 7-day South Okanagan tour to showcase stunning cycling routes, beautiful accommodations, and wineries and restaurants that have quietly gained a cult following among wine and food enthusiasts.

Each day will see you riding some of the most iconic and picturesque cycling routes in Canada, and with a spring and fall climate perfectly suited to cycling, you’ll be in short sleeves while much of the rest of Canada is bundled up. Beautiful rides are only half of the experience! From a chef’s table dinner at Row Fourteen (voted BC’s best restaurant by the Globe and Mail), to dining amidst the vines at Church and State vineyard, we’ve created a tour that combines the most scenic rides with the best food and wine in the country.

Tour Highlights:

  • Climbing out of Okanagan Falls along quiet, winding Green Lake Rd and watching the vineyard-clad valley unfold beneath you;
  • Sipping an award-winning Syrah while watching the sun set from your patio overlooking Burrowing Owl vineyards;
  • Summiting Richter Pass, and riding along the infamous Seven Sisters, made famous in Ironman Canada;
  • Dining al fresco at an exclusive long-table dinner in the vineyard of Church and State Winery;
  • Touring the vineyard with the winemaker of one of the Okanagan’s best kept secrets, before enjoying the best of his cellar with local charcuterie;
  • Discovering the best roads, the best wines, and the best cuisine BC has to offer each and every day of your tour.

Package Includes:

  • Six nights double-occupancy accommodation in Penticton, Oliver, and Cawston;

  • Six fully guided, van supported daily rides;

  • Four chef-prepared gourmet dinners:

  • Poplar Grove Winery dinner

  • Church & State vineyard long table dinner

  • Row 14 chef’s table dinner

  • Naramata Inn Chef’s Feast private dinner

  • Six delicious breakfasts and gourmet picnic lunches, along with ride nutrition and drinks along your rides;

  • 1 set of Magic Places professional-grade cycling bibs and jersey;

  • Our friendly and attentive customer service.

Optional Services Include:

  • Single occupancy room supplement: $900

  • Transport of your bicycle from Vancouver to Penticton return: $75

  • Road bike rental: price upon request


Day 1: Arrive at E’Laysa Vineyard Retreat in Naramata and check into your private suite. Once settled, relax in the garden or join us for a short afternoon shake-out ride along the peaceful Kettle Valley Rail Trail to Naramata and back. Dinner overlooking the sunset across Okanagan Lake awaits at a Poplar Grove’s lovely winery restaurant. Ride distance: 20km

Day 2: After a delicious breakfast in the garden, we’ll head south along Skaha Lake before turning up into the rolling semi-arid desert hills of the White Lake grasslands where we’ll stop at Nighthawk Vineyards for a delicious picnic lunch showcasing local wines, charcuterie, salads and baked goods. We return to Penticton in time to enjoy your afternoon relaxing at E’Laysa or exploring great wineries within walking distance. Dinner sees us at Hillside Winery, boasting great wines, beautiful garden seating, and a delicious menu. Ride distance: 72km

Day 3: Bound for Oliver’s Black Sage bench, we load your luggage for transport to award-winning Burrowing Owl estate winery. Your ride takes in the beautiful ranch lands of McLean Creek valley, before descending into Canada’s premier wine terroir as you ride through vineyards with incredible valley views. A delicious lake-side picnic lunch awaits before we’re back on the bikes, bound for the famous ‘golden mile,’ so named because this stretch of land consistently produces Canada’s most award winning wines. We’ll arrive at Burrowing Owl early afternoon, and after checking into our stunning rooms at the winery, you’ll have ample time to enjoy a wine tasting, relax by the pool, and enjoy the stunning views. We’ll enjoy dinner tonight in Burrowing Owl’s renowned dining room, taking in the sunset over the vineyards and valley below. Ride distance: 55km

Day 4: Today we explore the vineyards and orchards around Oliver, bound for Covert Farms, an award-winning family run winery. A guided tour of the farm and winery is followed by a private tasting of their finest wines, sampled alongside locally sourced… artisanal cheeses, cured meats, pickles, olives, crackers, and fresh produce and edible flowers grown on the farm. Save room for desert, as we’ll make a stop in Oliver at Medici’s for the best gelato and espresso in the Okanagan. Dinner tonight is one of the tour highlights – a long-table chef’s feast amidst the vines in Church and State’s Coyote Bowl vineyard.

Day 5: After a leisurely breakfast, we load up the trailer and hop on the bikes for another stunner of a ride, this time along a stretch of the famed Ironman Canada course to Cawston, the organic farming capital of Canada. After a riverside picnic, we’ll ride through orchards and farms, making our way to the the Klipper’s Organics farm and their beautiful guest lodges located in the middle of the orchard, where you can put your feet up and relax for the afternoon. Dinner tonight will make it onto most people’s lifetime highlight reels – a Chef’s Table dinner at incomparable Row Fourteen where chef Derek Gray pairs immaculately prepped local fare with the distinct wines of the Cawston bench.

Day 6: Our final ride sees us riding north from Cawston, through the rich fruit orchards of Olalla, before turning north onto Green Mountain Road. Here, we leave the lush valley floor and climb up a narrow, winding canyon into thick pine forests and ranch land along the flanks of Apex Mountain. A fun, swooping descent takes us back to Penticton where where jump onto the Kettle Valley Rail Trail for our final stretch into Naramata, and it’s beautiful heritage hotel, the Naramata Inn. To celebrate the end of our journey, we’ve arranged a private dinner, prepared by celebrated chef Ned Bell and paired with the finest wines from the Naramata Bench.

Day 7: After a delicious breakfast at the Inn, we will shuttle you back into Penticton and wish you farewell with a warm smile and hope of riding with you again soon.


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