Part Time Wine Tour Guide or Shuttle Driver

Are you witty, charming, sociable, and selfless? How about courteous and charismatic? Are you a “people-person”? Do you like to have a lot of fun? Maybe you’re tired of being retired? Are you a non-smoker? Are you neat, tidy, and "put-together"?

People say you’re fun and interesting. Some would also say, caring, reliable, genuine and principled. Your natural wit and humor are appreciated by others – not just yourself!!!

You have excellent driving habits and a near-perfect driving record. (Driving vehicles, not golf balls silly! :)

Daily physical requirements of this position include excessive smiling and laughing, lifting up to 40 lbs., repeated driving, standing, walking, talking, ascending or descending stairs and ramps along with intermittent kneeling, pushing and pulling. Not unlike spring cleaning or a round of golf.

If I’ve described you – you are in for the time of your life! We have way too much fun and zero drama – except for sharing our wittiness and storytelling.

Our goal is to build the most recognized team of customer-focused professionals in the industry. An unstoppable force. Personally engaging, knowledgeable, professional raconteurs and true service aficionados who share colourful local history and interesting information (E.g. why Kal Lake’s colour ranges from cyan to indigo, about grape farming, wine making, distilleries in the orchards, real estate prices, extinct volcanoes, and local legends – not just your golf handicap!)

About Us

THE COMPANY

Highly respected within BC's Tourism, Transportation, and Wedding Industries, Cheers Okanagan Tours and Transportation was founded in 2016 and quickly vaulted from 124th to first place on TripAdvisor® for exemplary experiences. Modelling on Canada's Best Managed Companies and Top-Ranked Employers, we’re building an uncommon company culture that focuses on the care and success of our 1) employee-partners, 2) customers, 3) vendors, and 4) neighbors. Helping people thrive differentiates our business.

THE UNIQUE SELLING PROPOSITION – WHY CUSTOMERS TRUST US AND BUY FROM US

Customer loyalty, an unblemished safety record, and consistent accolades for our friendly, knowledgeable team—all supported by clear, proactive communication—reflect a culture of uncommon (shameless) customer enthusiasm. Relentlessly caring, going the extra mile, and continually improving, with an unwavering commitment to safety, set us apart and make us the best choice.

THE OWNERS

Married 47 years, seasons of volunteering our time in remote developing countries plagued by conflict and natural disasters assisting victims rebuild their lives was intensely fulfilling. Adopting Haitian brother and sister twin orphans, training them up and watching them volunteer in orphanages in Zambia and Haiti as adults was inspiring. Helping people to feel cared for, valued, and respected permeates the Cheers! culture.

THE COMMUNITY

Our employee-partners share the bond of caring deeply for humankind and we’re pleased to support kind and compassionate organizations such as Freedom’s Door, Mamas for Mamas, Dreams Take Flight, Cops for Kids, and others with our time, talent, and treasure.

ABOVE AND BEYOND

Cheers! has been known to all of a sudden rescue over 155 forsaken travelers on Christmas Eve from the Vancouver Airport and safely deliver them to the Okanagan as seen on Castanet. We’ve swiftly delivered a local nurse practitioner from Oyama to the Calgary airport to catch a flight to the Northwest Territories so that the remote community's healthcare facility wouldn’t be closed for weeks. We’ve abruptly drove to the Kamloops airport from Kelowna to rescue 5 marooned Heli-Skiers, and safely delivered them 6 hours to the East in Kaslo, BC. We’ve suddenly driven 13 hours from YLW to Mike Wiegele Helicopter Skiing in Blue River, BC and back to rescue 20 isolated Heli-Skiers. Dashed to Vancouver from Kelowna, picked up a stranded Australian family, and then safely deliver them to Sun Peaks Ski Resort and return to Kelowna – all in one fell swoop – on Christmas Eve. All of a sudden we were transporting Vernon’s W.L. Seaton Secondary School’s choir on the eve of their performances at Black History Month celebrations in Vancouver when their transportation abruptly cancelled on them at the last minute.



We’ve instantly rescued numerous engaged couples whose wedding transportation never showed up. Expeditiously rescued an Ottawa family of 7 that urgently needed to go to the Vancouver Airport from West Kelowna due to an unexpected, last-minute flight cancellation. Spontaneously driving 13 hours to help 16 US golfers get to Seattle to catch their flights home because the Kelowna airport suddenly closed due to wildfire smoke in 2018. All of a sudden we safely transported 8 Edmonton school teachers who were stranded in Penticton due to extreme wildfire smoke and delivered them home to the ones they love – a 12-hour drive away. Erin commented the next day, “I have never been so happy to hug my kids!” Overnight in August 2021 we suddenly began shuttling dozens of RCMP every day between their Kelowna accommodations and the Vernon Detachment as the White Rock Lake wildfire levelled structures in Ewings Landing, Killiney, around Monte Lake and in the Paxton Valley. And again, in 2023 we suddenly pivoted to transporting busloads of RCMP for three weeks between their Kelowna accommodations and the Kelowna, Lake Country, and West Kelowna Detachments due to the McDougall Creek Wildfire. Just a few examples of when our business has gone above and beyond to help.

TRANSPORTATION & TOUR SERVICES OVERVIEW

· Sports Teams

· Golf Transfers

· Airport Transfers

· Corporate Meetings

· Event Transportation

· Dinner Transportation

· Wedding Transportation

· DIY & Guided Wine Tours

· Long-distance ground transportation (Vancouver, Seattle, Calgary, etc.)

· Ski Transfers to 50+ Heli-ski, Cat-ski, Ski resorts, and airports throughout southern British Columbia

A LEGITIMATE OPERATOR

We're properly insured and compliant with the law, so Cheers Okanagan Tours and Transportation is a legitimate operator. We are BC Passenger Transportation Licensed (PT 72224), National Safety Code, and Transport Canada Certified (202445168). Moreover, we take our guests' and employee-partners' safety and travel comfort very seriously. Please review our fleet and safety program here.

COMPENSATION

Our tour guide and shuttle driver compensation package begins with a base $19 an hour wage plus guaranteed gratuities, and shift differential. In 2026 the average hourly compensation equalled $35 per hour. PLUS there’s uncalculated cash gratuities at our guests’ discretion.

WORK-LIFE BALANCE

We understand the importance of a flexible schedule for work-life balance. For every tour or trip, we email you an invitation first – you accept or decline according to YOUR schedule.

At Cheers we have a lot of fun, laugh a lot and enjoy the benefits. We guarantee improved health! The Mayo Clinic says, “Laughter enhances your intake of oxygen-rich air, stimulates your heart, lungs and muscles, and increases the endorphins that are released by your brain, the body’s natural feel-good chemicals. Laughter relieves your stress response and soothes tension. Laughter decreases stress hormones and increases immune cells and infection fighting antibodies, thus improving your resistance to disease. Endorphins promote an overall sense of well-being and can even temporarily relieve pain.” https://www.mayoclinic.org/healthy-lifestyle/stress-management/in-depth/art-20044456 or consider the ancient proverb, “A happy heart is like a good medicine and a cheerful mind works healing.” Circa 700 BC

ABOUT YOU

We’re looking for exceptional people, the right people, people who are self-motivated and self-disciplined. People who wake up every day with an innate urge to do their best - to achieve excellence.

We’re looking for people who want to be a part of building something great while helping other people to feel cared for, valued, and respected.

The right people are our most important asset. The right person has more to do with character traits and innate capabilities than with specific knowledge, background, or skills.





We believe that when you have disciplined people, you don’t need hierarchy. When you have disciplined thought, you don’t need bureaucracy. There’s no need for micromanaging when everyone has their act together.

Perhaps a little brusque or insensitive in his delivery, but the sentiment is expressed well by U.S. Army Delta Force founder Colonel Charlie A. Beckwith, “I’d rather go down the river with seven studs than with a hundred sh*theads.”

This is not the place for pitiful, timid, ineffectual, fainthearted, half-hearted, wishy-washy, time-wasting, and lazy, cowards, or narcissists with an unwarranted sense of entitlement who are easily offended and unable to deal with opposing opinions. It’s okay if those are a person’s character traits – they'll just want to avoid this place.

“This is no place for a confidence problem” Peter C. Tour guide & driver since March 2018

As far back as you can remember you have demonstrated an obsession for delivering exceptional customer service and hospitality.

HOW TO APPLY

1) SEND AN INTRODUCTORY LETTER OR, A “PERSONAL VALUE PROPOSITION”

Please attach a memorable introduction letter to you, your character traits, and innate capabilities, describing how they would prove advantageous to our customers and the company.

You don’t need to, but if you want to go “PRO”, check out this article “Personal Value Proposition Example (With Template)” If unable to go direct, search the title in your browser.

Although conveying your pride, self-respect, self-esteem, honor, privilege, and dignity is somewhat of an art, nevertheless, we need a fascinating reason to consider interviewing or hiring you. Now is the time to break out the accolades, testimonials, and references. What have other people said about you? “Let another praise you, and not your own mouth; a stranger, and not your own lips.” Ancient Proverb.

2) SEND A RESUME

In addition to your introductory letter or “personal value proposition”, please include a copy of your resume. A simple resume is adequate. However, if you want to go “PRO” and craft a results-oriented resume that focuses on quantitative (measurable) accomplishments, please do.

Check out this article from INDEED on What Is a Results-Oriented Resume? (And How to Write One) If unable to go direct, search the title of the Indeed Article in your browser.

3) SEND A COMMERCIAL DRIVING RECORD AND INSURANCE HISTORY or a Class 5 driving record if you don’t yet have a Commercial Driver’s Licence

For your Class 1, 2, or 4 Unrestricted BC Driver’s Licence Go to: https://onlinebusiness.icbc.com/clio/ Follow the prompts on each page. On the “Request document(s)” page, under section, “Select the document(s) you need” Check: “Commercial driving record (National Safety Code abstract)”

If you don’t have a commercial driver’s licence, go to: https://onlinebusiness.icbc.com/clio/ and follow the prompts on each page.

Attach your 1) letter, 2) resume, and 3) driver’s abstract to your application.

Successful applicants will be required to get their BC Class 4 Unrestricted Driver’s Licence — and be able to prove they can have fun – all day long.

“Outstanding companies don’t hire skilled people and motivate them, they hire motivated people and inspire them.” Simon Sinek

Job Types: Part-time, Casual

Pay: $19.00-$35.00 per hour

Benefits:

- Flexible schedule

Application question(s):

- Firsthand knowledge of the Okanagan Valley is advantageous for this position. How many years have you lived in the Okanagan, please?
- For the best fit, our employee-partners must possess our core value of I CARE. Are you known to be a kind, caring, compassionate, charitable, selfless, bighearted humanitarian? Please explain.
- 3) In the “How To Apply” section towards the bottom of the Job Advertisement, it clearly states you must send an 1) introductory letter OR, a “personal value proposition”, 2) a resume, and 3) a commercial driving record and insurance history. Your application may be rejected immediately if the requested documents don’t accompany it. Have you attached/submitted the 3 required documents?

Experience:

- Driving: 10 years (required)

Language:

- English (required)
- French (preferred)

Location:

- Kelowna, BC V1X 1V8 (preferred)

Work Location: In person

📌 Shuttle Driver (Canada)
🏢 Cheers Okanagan Tours and Transportation
📍 Canada