Osoyoos + Watermark

Osoyoos Explorer Vacation

Our Accommodation Partner

the watermark beachfront resort

The luxurious 123 suites in the main building of Watermark Beach Resort offer a combination of studios, one, two and three-bedroom penthouse suites. Spectacular views of Osoyoos Lake, or the lovely town and surrounding mountains unfold at every window of this top rated Osoyoos resort.

Sample Itinerary

Days full of idyllic riding, stunning scenery and authentic connections with the people that call this valley home. Those are the ingredients we begin with when we create your Bespoke Giro experience. Here is one possible combination*:

  • 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 Sonora Room at Burrowing Owl Vineyards.

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

    Dinner - The philosophy of the talented culinary team at the Sonora Room Restaurant is to embrace the privilege and the opportunity to showcase many of the South Okanagan’s local producers with their array of local organic produce, fresh, seasonal fruits and artisan breads and cheeses.

  • 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!

* Our sample itineraries tend to be packed with options. As we mentioned, this is just a guide and - as such - we thought it best to give you as many options as possible.


Osoyoos offers the perfect base to explore the South Okanagan. The exceptional Golden Mile and Black Sage wine and agricultural regions extend to the north. The Similkameen Valley stretches west. And as the traditional home of the Osoyoos people, a fascinating indigenous heritage is yours to discover.

Sample Pricing

5 Days / 4 nights


$2350/p.p. quad occ.

For Studio Suite
Single Supplement $400
additional $150 per person for one bedroom suites

Includes Accommodation in 2 bedroom Suite (quad occup) or in Studio suite (dbl occup). One bedroom suites (dbl occup) available for upgrade fee of $250.

All (11) meals included

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


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