The Okanagan region of British Columbia comprises the wine (and fruit) growing areas surrounding Osoyoos, Oliver, Penticton and Kelowna. With a semi-arid climate, the area boasts long warm summers and eternal sunshine. Numerous fresh-water lakes (including the namesake ‘Okanagan’) compliment the stunning desert topography making it an attractive destination for cycling. Swank and hip accommodations and restaurants with outstanding cuisine await.

Only Great Explorations:

  • Small groups, extraordinary guides, and authentic experiences
  • Dinner at acclaimed Miradoro, with panoramic views over vineyards
  • Wine tastings at top wineries
  • Order off the menu at restaurants you won’t find in guidebooks
  • Distinctive, charming hotels too small for larger groups
  • We design and operate our own trips so there are only good surprises!



Osoyoos, BC, Canada

Day 1+2


Oliver, BC, Canada

Day 2+3


Summerland, BC, Canada

Day 4


Penticton, BC, Canada

Day 3+4+5

What’s Included in the Cost of Your Trip?


Services of one or more experienced Great Explorations guides
Support vehicle
5 nights lodging
All breakfasts, 2 lunches, and all dinners but 1
Entrance fees for selected historical sites
GPS instructions
All baggage transportation
All transportation from initial meeting point to final drop-off




Jun 3-8
Jun 10-15
Jun 17-22
Jun 24-29
Jul 1-6
Jul 8-13
Jul 15-20
Jul 22-27
Sep 2-7
Sep 9-14
Sep 16-21


Jun 2-7
Jun 9-14
Jun 16-21
Jun 23-28
Jun 30-Jul 5
Jul 7-12
Jul 14-19
Jul 21-26
Sep 1-6
Sep 8-13
Sep 15-20

Trip can start at any date. Custom trips also available. Call or email for details.


4-16 participants


6 days / 5 nights


Osoyoos / Penticton


40-50+ kms daily
(25-31+ miles daily)
Van supported




Land Cost:
CAD $2,850 pp*
Includes 5B/2L/4D

Single Supplement:
CAD $730*

Bike Rentals

Hybrid or Racing Bikes: US$230

E-Bikes: US$400

E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.  

*Prices subject to British Columbia GST tax (5%).

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services.
Due to the nature of our business and exchange rates, prices are subject to change. All our trips in Canada are quoted in Canadian Dollars (CAD) but we gladly accept payment in U.S. dollars (USD) also. Due to cancellations and waiting lists, trip availability fluctuates daily.
If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at or by telephone at 604 730 1247 | +1 800 242 1825.

Getting there
Our trip starts in Osoyoos which can be reached from Vancouver by driving or you can fly to Kelowna and transfer from there. Details in your pre-departure package.


Day 1


Your trip starts in Osoyoos. We will meet at 2pm at the hotel and transfer to the Grist Mill and Gardens historic site in Keremeos. Ride as far as you like– it’s a spectacular introduction to south Okanagan and the descent into Osoyoos is sublime. After our customary wine welcome, we will enjoy a casual dinner at the hotel restaurant.

Ride distance: up to 30km; elevation gain TBC depending on your route


Day 2

Osoyoos to Oliver Loop

From Osoyoos we will ride north passing Burrowing Owl Winery and then in Oliver, enjoy coffee at an eclectic bakery. At Tinhorn Vineyards, taste some of the local wines over lunch. The afternoon ride passes countless other wineries on our way back to Osoyoos. This ride is moderately rolling with a few steep but short climbs. Dinner will be at Hester Creek’s Terrafina Restaurant.

Ride distance: 48km; elevation gain 378m


Day 3

Oliver to Penticton

We transfer today to Oliver to ride north to Okanagan Falls, where we will picnic on Skaha Lake. Late afternoon, stop to taste wine at Painted Rock vineyard with its contemporary tasting room. Arrive to Penticton, and the south end of Okanagan Lake. Stop at Wayne & Freda an eclectic coffee shop and bakery for a post-ride treat or one of the craft breweries downtown. Dinner is OYO tonight and there are many options walking distance from the hotel.

Ride Distance: 45km; elevation gain 435m


Day 4


Today, we’ll transfer to the town of Summerland allowing you a fantastic descent to start the day. After a mid-morning stop at a popular cyclists’ coffee shop, we will continue along the east side of Okanagan Lake to Naramata, with lunch at an eclectic spot near the lake. There are of course, more wine tasting options in the afternoon including Poplar Grove, just a few kilometers from our hotel. Arrive back to Penticton.

Ride Distance: 35 up to 50km; elevation gain up to 504m


Day 5


You have a choice today, to cycle from the hotel south along Skaha Lake, turning up past See Ya Later Ranch on Green Lake Road to connect with White Lake Road, a local’s favourite. Alternatively, transfer south to Oliver and ride a classic section of the Axel Mercx Gran Fondo route along the White Lake Grasslands Protected Area. Arrive back to Penticton in time to relax lakeside and dinner at a surprise destination in Naramata as we toast our days cycling together.

Ride Distance: TBC by your guide depending on the option you choose


Day 6

Departure Day

After our last breakfast together, you may leave Penticton at your convenience.

Watermark Beach Resort, Osoyoos

Located on a sandy beach in Osoyoos, this 4-star hotel with full-service spa and marina is well located, steps to town and many restaurants. The restaurant, wine bar and patio options are great.

Ramada by Windham, Penticton

Located close to town and with the Penticton Golf & Country Club next door, the Wyndham managed property restaurant, the Station Public House and many amenities. Many of the guest rooms have recently been renovated and there is a pool and hot tub etc.