september 30 - october 5

Our Giro Retreat at Watermark Resort in Osoyoos

Join us for a very special week of cycling in the South Okanagan. We’ve chosen the Watermark Beach Resort as our base. From this central location, great cycling stretches in every direction.


Giro Explorer Retreat Extras

Retreat Pricing and Itinerary

5 Days / 4 nights


$2640/p.p. dbl occ.

Single Supplement $600

Includes Accommodation in One Bedroom Suite.

All (11) meals included

Guided Tours and Shuttle Services
(Airport Transfers available for extra fee)

Day by Day:

  • Day One

      Day One - After your check in at the Watermark Resort, join us for a welcome reception where you’ll be introduced to the Giro Team. After the reception, you'll have dinner at Watermark's own restaurant. After dinner, stroll back to your suite and have a nightcap as you enjoy an Okanagan sunset. Tomorrow, we begin riding!

      Dinner - With a focus on fresh, regional ingredients, Watermark's Chef Adair Scott incorporates the varied and rich flavours of the Mediterranean with the highest quality seasonal fare of the Okanagan.

  • Day Two

      Day Two - This morning, enjoy breakfast in your suite while we load up your bikes and get ready for your first ride. We’ll meet you at the resort and take the Giro shuttle to Penticton. Today’s ride climbs through the pine forests of Green Mountain towards the Apex Alpine Ski Resort. Then we descend down to Highway 3 for another climb to Yellow Lake, then ride through the Okanagan Highlands to Oliver and Black Sage Road. Lunch today is at Covert Farms. After you freshen up after your ride, the Giro shuttle will pick you up for a guided tour at the Nk'Mip Cultural Center. The dinner destination tonight is a quick walk from the resort, Convivia Bistro in downtown Osoyoos"

      Lunch - A gourmet al fresco charcuterie lunch will be served at Covert Farms

      Dinner - Dinner tonight is at one of Osoyoo's favourite restaurants, Convivia. Choose from Mediterranean classics in this charming family-run bistro.

  • Day Three

    Day Three Today, we explore the incredible Similkameen Valley. We'll shuttle you to Princeton and we'll ride along the Similkameen River to Hedley, where we'll learn more about the mining history of this town. Then we continue to Keremeos and Cawston and the emerging stars of it's wine region. The Giro Shuttle will pick you up in Cawston and take you back to the Resort where you can refresh yourself before our supper adventure in nearby Oliver

    Lunch - An al-fresco lunch at the Grist Mill in Keremeos

    Dinner - First, we do a private brewery tour and tasting at Firehall Beer and then we enjoy an al fresco dinner catered by the Vagabond Kitchen

  • Day Four

    Day Four It’s our last day of cycling and we’ve put together a spectacular itinerary for you. After breakfast at the Resort, we'll take the shuttle to the Kettle Valley Rail Trail at Glenfir. We'll ride down to Naramata, where we'll visit a few of our food artisan and winemaker friends. Then, we continue to Skaha Lake for a ride down to Okanagan Falls, wrapping up at scenic Blue Mountain Winery. For dinner, we'll join you for a spectacular hosted dinner at the Chef's Table at Backyard Farms

    Lunch - today we'll stop at one of our dining partners in downtown Penticton

    Dinner - Chef Chris and his team at the Chef's Table have been redefining excellence in sustainable cuisine for the past 3 years now. Dinner here is a spectacular "meal of a lifetime" experience. (Minimum group size of 8 for the Chef's Table)

  • Day Five

    Day Five This morning, enjoy a leisurely breakfast at the Resort before your travels home. If you’re not quite ready to leave the Okanagan, ask us about other ideas to extend your stay!

  • 4 Nights Accommodation

  • 11 meals (4 dinners, 3 lunches, 4 breakfasts)

  • Welcome Reception and Wind Up Evening Event

  • Fully Guided & supported Rides

  • Bikes, helmets and repair kits

  • Complimentary jerseys and water bottles

  • All free time options

  • All tasting fees at winery stops

  • Shuttle Transportation as Required

Our Retreat Accommodation Partner

  • Licensed Restaurant & Patio

  • Full Gourmet Kitchens

  • Condo-Style Resort Amenities

  • 24-hour Guest Services Team

  • Picture perfect views from your private balcony

  • Outdoor Saltwater Pool and Hot Tubs

  • Walk to cafes, restaurants, and unique shopping boutiques

Watermark Resort

“The Watermark Beach Resort is a gem in this lovely little town. You are right on the beach with spectacular views and access to everything! The service was beyond compare, everyone friendly and helpful.”

TripAdvisor Review

Discover the South Okanagan “good life” at the Okanagan resort that defines easy living, where attention to detail and personal service is as unmatched and unique as the experience and amenities at Watermark. Experience the Watermark difference. You’re steps to everything: beach, dining, shopping, marina, and groceries for your full gourmet kitchen.  Come see what makes Watermark a top-rated choice for Osoyoos hotels and accommodation.


Itineraries shown here are examples and may be subject to change. For a detailed itinerary request a planning guide: