Direct2 Air — Taking Chartered Flights to New Heights


(Toby Grant Woods founded Direct2 Air last May, and has been in operation out of the Bend Airport since January 1 of this year | Photo courtesy of Toby Grant Woods)

There are times in life when you need to get somewhere in a hurry, and booking a flight on the airlines just doesn’t work out the way you want it to. Be it a business meeting, family emergency or even a last-minute vacation, flying commercially is sometimes not the fastest or most efficient way to go.

Toby Grant Woods founded Direct2 Air because he was working as a flight instructor with Leading Edge Aviation in Bend for several years and noticed that the people he was teaching to fly were utilizing their own aircraft to get to a city for business, to the mountains or beach for play and for home and family life purposes. “This was the inspiration for creating a regionally focused air charter business,” he says. “I saw an opportunity there. I thought there were a whole lot of people who could benefit by modern, efficient-style aircraft for regional travel. The vast majority of people won’t be learning to fly, but some are aware of just how much of a magic carpet smaller airplanes can be. We want to bring air charter to more people at a more accessible price point.”

Woods, who has been a pilot since 2018, formed Direct2 Air in May 2021, and the business has been operational since January 1 of this year. “It took eight months to get the first aircraft functional and get the FAA approvals,” he says, adding that so far, business is going very well. “We flew about 50 hours in the first month. We had charter flights up and down the west coast and have already been to Canada. We’ve had a lot of success through word-of-mouth referrals. We feel like we are really getting some traction.”

Direct2 Air has two pilots on staff currently, and an office at the Bend Airport. Woods says the primary focus for the company in these first few months is attracting businesspeople who have business to conduct outside of Central Oregon but lack the easy and consistent means to be where they need to be, when they need to be there. “Remote work is ubiquitous now, but that doesn’t negate the fact that when you really need to get something done, you need to show up in person,” he says. “We are finding that when businesses take a minute to do the math on how much driving, or inefficient commercial flights, are costing them, the value of flying with Direct2 is clear.” He adds, “We certainly think we will see more leisure travel over time, especially during the summer season, but working with businesses who need to get to the Oregon Coast, Portland, Boise, Seattle or Northern California is what we’ve been spending most of our time doing so far. “

Woods, who grew up on the coast of Maine, came out west to go to school, and studied Environmental Science. He graduated from the University of the Pacific in Stockton, California, and played baseball at the university level. He has lived in Bend for about six years, and says, “I got into flying because I was feeling uninspired by the work I was finding with my degree. I saw planes flying around Bend and wondered if I could learn how to fly a plane. My hands were shaking, and my palms were sweating for my first flight, but I fell in love with it,” he recalls fondly. “For me, flying a plane has the same hand-eye coordination as the sports I played growing up. It’s a great challenge. Flying is inherently dynamic; the airspace, traffic and weather are always changing.”

Just before Direct2 Air became operational, Woods says the last thing he was doing as a pilot not related to his business was following a NASA drone in Alaska on a contract job. “I was way over the Arctic Ocean, mapping the thickness of the Arctic ice cap, and it was freezing. It was 30 below 0, and I was thinking that I couldn’t wait to fly out of Bend,” he says with a laugh.

Woods says his goal is to create the best-possible regional air travel experience. “What that means is growing the fleet of aircraft to include a couple of different options from a size and price standpoint, and creating experiences for people that are consistent, with exceptional customer service.” Currently, Direct2 Air operates a DA62, an unpressurized twin-engine aircraft that can accommodate a total of four passengers and has a cruising speed of 182 knots. He says he is currently in the process of securing a second aircraft, a Pilatus PC12 NG, by summer. This plane is twice as large, has a pressurized cabin, can hold up to nine passengers, has a cruising speed of 275 knots and is closer to what people are used to, he says. “We will look to multiply those two aircraft and add them in other locations to serve people not just in Central Oregon, but all over the Northwest.”

At this point, availability for flights depends upon what day you want to go, Woods says. “The sooner you can book, the better. We do have people who need to be in the air within minutes of their call. We can do that if we are on the ground at that point. Oftentimes, bookings can be very much last-minute, or are planned way in advance. We don’t see as much middle ground with charter flights.” Typically, Direct2 Air flies to destinations within 500 nautical miles of Bend. “We don’t want to be all things to all people. We don’t fly big jets. We are focused on regional travel. That is what we feel is underserved; there are plenty of big jets to fly coast to coast and beyond.”

Woods says that one of the factors that makes Direct2 Air unique is the way the chartered flights are priced. “Traditionally, air charter has been priced by the flight hour, which leads to uncertainty around what the final price will be because many factors play into just how long a flight ends up taking. We price flights by the mile, which allows us to not just give you a quote in advance, but a guaranteed price that you or your business can budget around. I believe strongly that people crave certainty and transparency, and this is a way that we can provide that.”

Moving forward, Woods says his intention for Direct2 Air is for it to be the preeminent option for businesses and people who need air travel solutions in the Northwest. “For many people, that means providing on-demand charters; for some, it means helping with aircraft acquisition and pilot services; and for others, it means aircraft management services for their own aircraft, with the ability to generate revenue by leasing the aircraft back to Direct2 for charter when it would otherwise sit idle,” he says. “Having this full ecosystem of possibilities for our clients is important so that as their needs and desires change, they can grow with us. A key part of realizing this vision is understanding that if we are in the business of operating aircraft, we are also in the business of maintaining those aircraft, so you should expect to see us have a facility for in-house maintenance in Central Oregon in the near future.”

To book a flight, call 541-569-4647 or email to To receive a quote, visit


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