As with any activity, and especially with flying, risk is present. One must decide what their risk tolerance is, the inherent risk of their activity, circumstantial risk, and strategies for the mitigation of risk. For this trip, the most salient risks specific to this trip are:

Weather

The weather in Alaska and Northwest Canada is notoriously treacherous. There are two concerns in particular: One is coastal fog, the other is icing.

To mitigate these risks, we've designed our trip with flexibility in mind. This is a particular challenge for Katie, who normally plans our trips down to the hour. We have only three major activities scheduled, and they're in the middle of our trip. This will give us the freedom to skip a day or two of flying if the weather isn't cooperating.

Furthermore, Will is an instrument-rated pilot, and we will be filing and flying the trip under instrument flight rules.

Finally, our plane is equipped with a non-hazard icing protection system (using TKS fluid). This is not a system that you can rely upon (legally, or practically), but if we end up in icing it will buy us some time to turn around and get out.

Terrain

This is high country. Denali is a stupidly tall mountain (around 20,000'). A lot of the mountains out here are huge. One problem this poses is that the weather and the terrain may push us to fly higher than is safe given the "thinness" of the atmosphere at altitude. Another problem is the potential for lack of situational awareness while in instrument meteorological conditions (IMC) and finding some terrain by surprise.

For the first problem, we mitigate it by choosing routes by looking at the highest MEA of the journey for each leg. In our case, the highest MEA is 11,300'. Will is a fit, relatively young, non-smoker. We routinely fly at ten, eleven, sometimes twelve thousand feet without supplemental oxygen. We have a pulse oximeter onboard, and check our SpO2 frequently on these flights, and make sure that it's at least 90%.

Regarding the unexpected encounter with terrain, the mitigation here is to use the technological tools at our disposal, including the aircraft's multi-function display (MFD), the terrain awareness and warning system (TAWS), and backup from the Foreflight synthetic vision system. Also, we will be avoiding IMC wherever possible, and my personal minimums for the ceilings at the destinations will be much higher than charted.

Facilities

Ketchikan and Juneau are not accessible by road. Take a minute, and let that sink in. The implication of this is that these very small towns (by normal standards) need to get everything shipped in via air or boat.

Simple things like aviation fuel may be difficult to come by. The FAA advises that you call ahead to each port that you intend to receive services from, prior to departure, to make sure that they can actually provide them to you. The biggest worry is fuel. We intend to bring a few quarts of oil with us, and a few spare spark plugs.

Additionally, many Alaskan airports don't have precision instrument approaches. I suspect that this is due to the nearby terrain, in many cases. For at least Ketchikan and Juneau, these airports are nestled in deep canyons. It's hard to have a miles-long straight shot to a runway, to say nothing about a missed approach procedure in this case.

For the instrument pilots reading, check out the approach for Juneau shown above, notice how different many things are relative to the lower-48, even the mountainous west. First of all, the missed approach point (MAP) and minimum descent altitude (MDA) are relatively far away from the airport and higher than normal. Also, if you reach MOLRE, and don't see the airport, you had better be turning without delay!

Mechanical

While our plane is in excellent condition, and there are no known issues, anything could happen. We're flying over a lot of desolate land, and the endpoints may have limited mechanical service available.

There's really no mitigation available other than to address anything that comes up as soon as its detected, especially if there are services available on the field. This even applies if it means that we may miss an appointment or booking because of it. It will be tempting to defer issues if it's inconvenient to have them addressed.

Procedural

Things are different in Canada. Things are even different in Alaska. These procedural differences are at best annoying, but at worst could lead to loss of separation with other aircraft.

The mitigation strategy for this risk is to read up on the procedures, and try to understand them as best as possible. I've got the Canadian Airman's Information Manual, and I've been reading through it.

Risk Tolerance

Phew, that's a lot of risk!

Or is it?

Ultimately, we decided that the risks are fully outweighed by rewards. We planned 4 days in Juneau, that gives us a bank of days that we can use to stay safe in the case of weather. On the way home, we don't have any appointments, Will has two days of PTO to spare, and we're taking the safer interior route.