South Okanagan

Cycling and Winery Tour

September 19 -25, 2020


Boasting over 180 wineries, a semi-arid desert climate, and hundreds of kms of immaculate, winding country roads, the South Okanagan offers a cycle vacation experience that rivals France and Italy, yet is in our own backyard!


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 Canada’s desert playground.

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 fall climate perfectly suited to cycling, you’ll be in short sleeves while much of the rest of Canada is bundled up. And don’t worry, following each ride your tastebuds will be rewarded for the efforts your legs and lungs put in! From a chef’s table dinner at Row Fourteen (voted BC’s best restaurant by the Globe and Mail), to a wine tasting amidst the vines at Painted Rock vineyard, we’ve got the inside scoop on the best wineries and restaurants in the entire region.

Tour Highlights:

  • Climbing out of Okanagan Falls along quiet, winding Green Lake Rd and watch the vineyard-clad valley unfold beneath you;
  • Sipping an amazing Pinot Noir while watching the sun set from the deck of Poplar Grove winery;
  • Summiting Richter Pass, and riding along the rolling Seven Sisters, made famous in Ironman Canada;
  • Play bocce and sip a cool drink on the lawn of Tinhorn Creek Winery, before sitting down to a gourmet dinner overlooking the South Okanagan at Miradoro restaurant;
  • Share stories and laughs with your fellow riders over a casual, yet gourmet farm-to-table dinner at BC’s finest restaurant.

Package Includes:

  • Six nights double-occupancy accommodation in Penticton, Osoyoos, and Cawston;
  • Seven fully guided, van supported daily rides;
  • Six delicious breakfasts and gourmet picnic lunches;
  • Celebration Harvest Dinner at Row Fourteen (alcohol excluded);
  • 1 set of Magic Places professional-grade cycling bibs and jersey;
  • Our friendly and attentive customer service.

Optional Services Include:

  • Single occupancy room supplement: $770
  • Transport of your bicycle from Vancouver to Penticton return: Free
  • Road bike rental: Price upon request


Sept 19: 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 beautiful Okanagan Lake to Summerland.  Dinner overlooking the sunset across Okanagan Lake awaits at a beautiful winery restaurant.

Sept 20: 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 a delicious picnic lunch awaits showcasing local wines, charcuterie, salads and baked goods.  We return to Penticton on the west side of Skaha, in time to enjoy your afternoon relaxing at E’Laysa or exploring great wineries within walking distance.  Dinner sees us at Elma, Penticton’s newest culinary experience, on the shores of Okanagan Lake.

Sept 21: Today’s ride sees us riding the Naramata Bench, one of Canada’s premier terroirs, studded with many of the countries best wineries.  A jaw-dropping ride with expansive views down onto Okanagan Lake takes us to Indian Rock, for a beach-side picnic lunch.  Our return trip takes us through the quaint village of Naramata and along the famed Kettle Valley Rail Trail, before a tasting of Lock and Worth wines paired with Poplar Grove cheeses.

Sept 22: Bound for Osoyoos, we load your luggage for transport to the Watermark Resort on the shores of Osoyoos Lake, but you’ll travel via a wonderful route through the Canada’s premier terroir as you ride through vineyards with incredible valley views.  We’ll stop for lunch overlooking the valley at the famed Burrowing Owl winery on Black Sage bench, before continuing on to Osoyoos.  We’ll enjoy the evening tasting wines and relaxing in the outdoor amphitheatre of Tinhorn Creek Winery before dinner at the award-winning Miradoro restaurant.

Sept 23: An optional rest day today, you have the option of spending the day relaxing on the beach, exploring Osoyoos and nearby wineries, or if you’re up for a challenge, follow your guide for the iconic climb of Anarchist Summit.  The best part of this climb is that you can turn around whenever you’re ready, take in the vast expanse of the valley spreading out beneath you, and coast all the way home!  Dinner tonight is a more simple affair, so you can extend your rest day without having to load into the shuttle for a set dinner.  The Watermark Restaurant, at our hotel is award winning, of if you’re up for a quiet evening with someone special, we have many great recommendations for you.

Sept 24: After a leisurely breakfast on the lake, 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, in the Similkameen Valley.  After a picnic along the meandering Similkameen River, we’ll head to fun and funky Crowsnest Vineyards, our home for the night, where you can wander the vineyard and enjoy a tasting with the vineyard owners, or 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.

Sept 25: 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 into thick pine forests and ranch land along the flanks of Apex Mountain, before a fun, swooping descent takes us back to Penticton and the end of our journey together.

TRIP PRICE: 1990 pp + GST

September 19 - 25, 2020