On The Rise Ventures

Cirrus SR20 & SR22 Pilot Services

Contract flying for Cirrus owners: a captain for your trip, a safety pilot to stay current, or a ferry flight to get your airplane where it needs to go.

What We Do

Cirrus-specific contract flying

Whether you want a captain in the right seat for a trip, a safety pilot to keep you current, or your airplane flown somewhere while you're not available, we fly SR20s and SR22s specifically, and know the airplane inside and out.

Captain Services

Need a qualified captain for a trip, a business meeting, or a family flight? We'll fly your Cirrus for you, start to finish.

Safety Pilot

Working on instrument currency or proficiency? We'll fly right seat so you can log the approaches and stay sharp.

Ferry Flights

Just bought or sold a Cirrus, or need it repositioned for maintenance, an annual, or a pre-buy? We'll fly it there.

Dealer & Broker Support

Reliable pilot coverage for dealers and brokers moving inventory, demo aircraft, or trade-ins.

Why Cirrus Owners Choose Us

Real Cirrus experience, not a generalist contract pilot

A Cirrus Owner Myself

I own a Cirrus and know the line, systems, CAPS, avionics suites, and the quirks that come with the airplane, from the owner's seat, not just the pilot's.

Efficient Cross-Country Flying

IFR-capable, weather-aware routing to get your aircraft where it's going as directly and safely as conditions allow.

Careful Handling

Your aircraft is treated like it's ours: squawks documented, logbooks handled properly, no surprises.

Clear Communication

Updates before departure, during fuel stops, and on arrival, so you'll always know what's going on with your airplane.

Get a Quote

Request a Pilot

Tell us what you need (captain, safety pilot, or ferry flight) and we'll get back to you with availability and pricing.

This opens an email to us with your details filled in. Just hit send from your email app.

Need a pilot for your Cirrus?

Serving Central & West Coast Florida, with ferry flights available nationwide.