Whether it’s game day, concert night, or wine time, we plan it like we’re going too.
Wine Tours
Discover Canada’s most celebrated wine country in one unforgettable day. Our curated wine tours offer private charter flights and luxury ground transportation to the Okanagan Valley, where you’ll enjoy exclusive tastings, vineyard tours, and a gourmet lunch — all without the hassle of overnight travel. It’s the perfect getaway for wine lovers seeking something elevated, effortless, and social.
Seattle American Football - Weekend
With the release of the 2025–26 Professional Football schedule, now’s the time to plan your bucket-list football weekends.
Our primary focus is on service to/from Calgary and Seattle but feel free to send us your request for other destinations and we will do our best to build those into our programming.
Experience professional North American sports like never before with our private charter game-day getaways. Skip the layovers, traffic, and logistics, we fly you directly to major sporting cities for top-tier matchups, with transportation, accommodation and fan-focused extras included.
Sporting Events – Adhoc Charters
Following the Edmonton Oilers’ epic run to last year’s Stanley Cup Final Game 7 in South Florida, Five-by-Five is giving super fans the chance to plan their next “Game 7” experience before it’s outrageously expensive or simply too late. Inspired by the events of a group of Oilers fans, we aim to offer reliable, well-planned and affordable travel to the most important games.
Golf Trips
Take your golf game to new heights. Our fly-in golf experiences pair private air travel with tee times at some of Western Canada’s most scenic and exclusive courses. Whether it’s a corporate outing or a weekend with your foursome, we handle every detail, flights, transport, meals, and more, so all you have to do is swing.
Feature course: Old Works, Anaconda Montana. Hop across the border to Bowman Airfield and we’ll do the rest with private ground transport to the course, tee times and if required, accommodation at the Forge Hotel.
Special Events
From sold-out concerts and food festivals to seasonal getaways and curated cultural experiences, our special event tours turn a single day into a standout memory. Fly private, travel in style, and enjoy insider access to the best events in the region, with every element coordinated for maximum ease and enjoyment.