Whether it’s kickoff, first pour, or the opening act, we plan it like we’re going too.
Upcoming Wine Tours
Penticton, BC.
Saturday, October 4, 2025
Sunday, October 5, 2025
Escape the ordinary and elevate your weekend with a one-day getaway like no other, a seamless, all- inclusive wine tour that whisks you from Calgary to the heart of Okanagan wine country by private charter. Touch down in Penticton and spend the day sipping award-winning vintages, indulging in a gourmet winery lunch, and exploring some of the most scenic vineyards in Canada, all without the hassle of driving or overnight stays. With luxury ground transportation, curated tastings and stunning views at every turn, this is wine touring done right, smooth, social and unforgettable.
Seats are limited, book your spot and experience wine country with Five by Five.
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Departure City: Calgary or Edmonton
Destination: Penticton, BC
Tour Duration: Approx. 11 hours (door to door)
Ground Time in Wine Country: ~9 hours
Group Size: approximately 100 passengers
Air Travel: Private Charter (Various Operators depending on group size)
Ground Transport: Luxury Coach (Traxx Coaches)
Meals Included: Lunch
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07:00 – 07:30: Check-in & Welcome.
Guests arrive at private charter terminal
Greeted by 5x5 tour hosts.
Light refreshments and trip briefing.
08:00: Wheels Up
Depart Calgary
Private charter flight to Penticton
In-flight coffee and breakfast snack
08:30 PST: Arrive Penticton Regional Airport
Meet and board luxury coach
Begin scenic drive through Okanagan wine country
09:30 – 12:00: Morning Tastings – 2 Boutique Wineries
Guided tastings and vineyard experiences
Optional behind-the-scenes tours
12:30 – 14:30: Lunch with a View
Seasonal, locally inspired lunch at a winery restaurant
Optional wine pairings with lunch
14:45 – 16:30: Afternoon Tastings 2 More Wineries with Wine tasting
Exploring Naramata Bench region
Return to Penticton Airport
Farewell toast on the coach
Final scenic photo ops
17:00 PST: Depart Penticton – Private Charter Flight Home
19:00 – 19:30 MST: Arrive Back in Calgary
Optional ground transfers available
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Non-stop roundtrip flight aboard a private chartered aircraft from Calgary or Edmonton to Penticton
Luxury ground transportation on a Traxx coach with a professional driver and dedicated 5x5 tour host
Private tastings at four to five hand-selected Okanagan wineries, with optional cider or beer alternatives
Locally inspired gourmet winery lunch, with optional wine pairings
In-flight snacks and beverages, plus refreshments throughout the day
Scenic photo opportunities and time for shopping at boutique tasting rooms and winery shops
Special guest appearances — winemakers, sommeliers, or culinary experts may join select departures
All tasting fees, transportation, and taxes included (GST applied at checkout)
5x5 Welcome Gift — a small keepsake to remember your day
Hassle-free luxury — no driving, no planning, just show up and enjoy
