Purposeful travel.

Private and Group Tours with precision planning.

Professional Sports | Wine Tours | Golf Trips

Upcoming Events

Penticton, BC.

Saturday, October 4, 2025
Sunday, October 5, 2025

Escape the ordinary and elevate your weekend with a curated day trip unlike any other. Fly direct from Calgary by private charter and immerse yourself in the heart of Okanagan wine country. Enjoy a seamless, all-inclusive experience—where every detail, from takeoff to the final tasting, is thoughtfully designed for effortless indulgence.

American Football in Seattle-and beyond.

Multiple home games

The 2025 season schedule is out, and we want to see you in Seattle. Our primary focus is on Lumen Field, with curated group trips to catch the live action. But we’re not stopping there. We’re also planning charter experiences to other games in L.A., San Francisco, Las Vegas, Denver, and Minneapolis.

Got your eye on a different matchup? Let us know the game, the city, and your crew—we’ll build a custom trip just for you.

A packed football stadium during a game with players on the field, spectators in the stands, and injections of fire and smoke display at the sidelines.

Travel smart. Travel with Five-by-Five.

Your next journey starts here.

At Five-by-Five, we read you loud and clear.

We specialize in crafting unforgettable travel experiences for groups of all sizes—whether you're cheering on your favorite team, rocking out at a live concert, sipping your way through world-class wineries, or celebrating a once-in-a-lifetime stag event.

What sets us apart? Private charter travel designed exclusively for your group. By flying through private FBOs* (Fixed Base Operators), we eliminate the frustrations of commercial airports—no long lineups, no crowded terminals, no endless security checks. Instead, enjoy streamlined boarding, customizable itineraries, and premium in-flight amenities tailored to your group’s needs.

Our seamless, end-to-end service replaces the hassle of traditional travel with the comfort, exclusivity, and efficiency of private aviation—transforming group trips into something extraordinary.

*Some flights require a departure from an airport terminal for security or customs’ purposes.

Private & Group Tours

Carefully orchestrated.

Every detail of your group’s journey is carefully orchestrated to ensure a seamless and memorable experience. Private air charter, ground transportation, accommodations, and event tickets can all be built into your adventure, no stress, no guesswork.

And yes, there’s exclusive merch. Each guest receives a limited-edition 5x5 hat with bold super puff embroidery. It’s gear you’ll actually want to wear.

Let us handle the planning, your only job is to show up and have an incredible time.

  • We specialize in private air travel for small groups, offering convenience, exclusivity, and efficiency.

    Departing primarily from Calgary, Edmonton, Vancouver, or Kelowna, our charters are tailored to your schedule. Skip the long security lines and crowded terminals, your group will enjoy a stress-free flight with personalized service and onboard amenities.

  • Upon landing, private ground transportation awaits to take your group directly to the next destination.

    Whether it’s a stylish motorcoach, SUV, or limousine, we ensure comfort and punctuality. No waiting for cabs or managing multiple vehicles, our service keeps everyone together and on time.

  • We partner with top-tier hotels and resorts to provide accommodations that suit your group’s needs and preferences. From boutique hotels to well-known luxury brands, your stay will offer comfort, convenience, and proximity to the event venue or local attractions.

  • Whether it’s front-row seats at a hockey game, VIP passes to your favouite game, exclusive access to a music festival, or private wine tastings, we can handle all ticketing logistics. Our goal is to secure the best possible experience, so you can focus on enjoying the moment.

  • Every aspect of the trip is coordinated to create a smooth and enjoyable journey. From pre-departure communications to on-site assistance, we manage the logistics so you don’t have to. With Five-by-Five, your group can relax, knowing that every detail is handled with precision.

  • Travel with us and you'll walk away with more than great memories. Each guest receives:

    • Custom Hats
      High-quality, locally designed and embroidered with bold super puff stitching — no two tours get the same style.

    • Limited Edition Apparel (by request)
      Curated just for our tour groups, quirky, premium tees that get noticed:

    • Welcome gifts

      Trip specific items to help memorialize your getaway.

    No cheap merch here. It’s gear you’ll actually want to wear.