Summer Updates - June 2026

Happy summer, this is a big one, so here we go.

We are making changes to how you interact with Penobscot Island Air. Since the beginning of time, you’ve made a phone call to book a flight or track a package. As long as you called during business hours and we weren’t overly busy, this system worked. We learned last summer that this system falls apart under heavy load. There will always be a ceiling on how many phone calls a single dispatcher can handle, and if you can’t reach us, you'll make alternative transportation plans.

We are moving reservations and freight tracking online, so you can book flights and track packages 24/7, 365 days a year. First, a little backstory.

Sortie

Sortie is a venture-backed company building software for remote operations. It’s a team of 7, I’m one of them, that is building the underlying technology for a very underserved market. If you have spent any time on these islands, you know that most operations technology is built for urban settings. From the Waymos to the DoorDashes to Jobys, they are built for population centers, not the ends of the network.

While PIA is unique to the Penobscot Bay, the problem of remote logistics is not. Sortie is building a platform to support operators who fly planes, deliver freight, and pilot water taxis. I’m telling you this because Sortie is PIA‘s operations platform. It’s not a piece of software that we bought. It’s something that we built from the ground up to solve the needs of PIA and the islanders. Software is not static. It’s always improving, changing, and sometimes breaking. This is our opening volley, but we’ll need your feedback.

FAA

The FAA has three broad categories of flight operations, all named after the section of the code. Part 91 applies to anyone with a pilot's license who isn’t being paid to provide services. Part 135 is for small-scale commercial operators. Part 121 is Delta, United, American, etc. Within Part 135, there are on-demand and commuter operators. PIA is an on-demand carrier, and Cape Air is a commuter carrier. The regulatory hurdles for each are different.

The FAA doesn’t want on-demand operators acting like commuters without the oversight and has put strict rules in place to prevent this. Holding out is the common term used. If you hold out, i.e., display/advertise the origin, destination, and time of more than 5 legs a week, you need to be a commuter operation. Because of this, all air taxi and charter services operate on a request/quote process. When you call PIA, that’s the request that we then quote. If you want to do this on the internet, though, then it gets a little sticky about what you are allowed to show to the customer. PIA used to advertise the mail flight as a reduced fare, and the FAA had us take it down because it’s a scheduled flight.

A lot of the design decisions for online booking are driven by the FAA’s holding out principles. We are allowed to price flights however we see fit, but we are not allowed to show the underlying schedule. So while pricing will seem like it’s a black box, it’s by design to avoid the ire of the federal government. We will, however, explain the principles of how it works.

Online Booking

We started this journey over a year ago to reach the launch of online booking, so I’m very excited to see this live and in customers' hands. You can book online at flypenobscot.com; just select your origin, departure, and date, and you’ll get sent over to Sortie to complete your booking. If you have been flying with us recently and log in, your saved passengers and billing information will be available to make booking faster.

And now we're talking about everyone’s least favorite topic: pricing. Well, it’s mine, because I’ve always hated how we handled shared pricing. There were two core principles when designing pricing:

1. What you pay at checkout won’t change, no matter what.
2. Price is based on where a plane will be at a given time.

The first question we will ask you is whether you are willing to share the plane or would like a charter. Charter pricing will usually be cheaper for groups of three or more. We need to ask this question up front because the FAA doesn’t like operators selling charters and adding more passengers to that leg. Charters are priced based on standard tach-hour calculations, which everyone uses from the time the plane takes off until it returns to base. The pricing engine does take into account certain pricing reductions, such as repositioning and hopping. If you select shared, we have replaced the old pricing with a new dynamic pricing. It’s a rules-based engine, and I wanted to take you through all the variables we use.

Time till flight

If you book a flight a week or more out, you are going to get our best pricing. The idea is that the probability of us finding someone else to share that flight with you is high, allowing us to heavily discount from the charter price. As you get closer to the day you want to fly, the likelihood that someone else will want to share your flight decreases, so the price approaches the charter price.

First blocks

We give slight discounts for times that minimize dead time. i.e., if we have a flight landing back at KRKD at 10am, the 10:10am flight time will be slightly lower than the 10:40am time because we don’t have 30 minutes of dead time. We are trying to compact the schedule with this pricing to serve more customers.

Repositioning legs

If you book a time when we are repositioning an airplane to your destination, you’ll get a discount.

Hop legs

Very similar to repositioning legs, but built on the idea of pricing where the plane will be at any given time. If I’m going from Stonington to Rockland and we have a plane on North Haven, it’s cheaper for us to make the quick hop over than to send a plane from Rockland.

Time of day

The majority of our flights are at the beginning or the end of the day. We offer discounts midday to relieve pressure at the start and finish of the day.

I get that there are a lot of variables here, and you will not be able to see the underlying schedule to understand the why of it all. Sadly, with the current FAA regulations, this is the only way we can handle it. Lastly, the current variables that define dynamic pricing are based on extensive research into past traffic to the islands. Pricing is infinitely configurable on our side, so as traffic patterns change, we will adjust pricing accordingly. Likely often in the beginning, as we figure out how this all works.

Fun fact: In 2018, a single-passenger flight to Vinalhaven cost $120.00, the same as it does now. With inflation, that flight would be $162.24 in today's dollars. We know you have many ways to get to the islands. It’s a choice to fly, and we need to price our services as competitively as possible so you make that choice. Even with these pricing changes, it’s never been cheaper to fly.

To make this all work, we need to institute two changes. First, we are moving to non-refundable tickets. This is almost never a problem. 1% of the time, we get no-shows, but they severely mess up the schedule when they do. If we can’t fly, you will have the option to receive a full refund or move to the boat if we make a weather run instead. The dispatchers will be very liberal with weather refunds, as we understand that sometimes you need to choose between an 11am ferry and an iffy 1pm flight. Basically, if we can’t fly for any reason, save pushing the schedule for a medivac, you’ll get a refund.

Second, we are lowering the freight limit from 100 pounds per ticket to 50 pounds per ticket. Again, this affects a small percentage of flyers, but it’s a meaningful change, so I want to explain why. 100 pounds is a ludicrous amount of freight to reserve for every passenger. It’s two VERY large suitcases, heck, Delta would have you sell your firstborn to load that on a plane. It’s a math problem with reservations; if we reserve 100 pounds per passenger, we can fit three passengers per leg, sometimes only two. If we limit it to 50, we can fit up to 4 passengers. 100 artificially raises prices because we are reserving space that may or may not be used.

That being said, we know that sometimes when going out to an island for a week or returning, you have more than 50 lbs, and we want to give you options. First, you can charter and have 800ish pounds of usable weight to play with. Second, the online booking form allows you to specify the extra weight you want to bring on that plane for a fee. Third, and this is the new one, is that you leave it with us or at the airstrip, and we will fly it off/on when we have extra space on a trip for a reduced fee.

This is becoming an issue because we have had to send out secondary planes twice to load additional freight due to discrepancies between what people said they would bring and what they actually brought last week alone. Requesting a freight pickup is a fast follow, so for now, it will be a call to dispatch to notify us. We’ll get to this in freight, but we have a much better tracking system for loose freight.

I encourage you to look at the new online booking. Pick a few origins and destinations and a few different dates.

FAQ:

“I already booked an upcoming flight, will the price change?” No.

“Well, not everyone on the plane will be paying the same price.” Yes, exactly the point. We want to reward people who book early or choose times that work in the existing schedule.

“Same-day flights got more expensive.” Yes, the probability that we will sell additional tickets on that flight is low, so we are pricing it accordingly.

“Can I still call to book a flight?” Yes, dispatch will use the same pricing as online, but will always be able to call.

“My dog died, how dare you still charge me for a flight I can’t take?” I’m sorry about your dog. Dispatch has wide discretion on refunds, and they aren’t jerks.

“Can I book the water taxi online?” Not yet, but within a couple of weeks.

Where is my package?

You might have seen the grounds folks running around with these little scanners, taking pictures of your doorstep or a shed. While we do have some avid birders on the team, they are actually confirming your delivery. We’ve built an offline-first, multi-provider freight-tracking system. When we receive a package, we scan it into our system and track it until it reaches your doorstep or a shed. This works for UPS/FedEx and PIA Air (loose freight).

We have built an online tracking system for you. If PIA has a package, we will be able to tell you where it currently is and, if it was delivered, a picture of where we left it. You can see it here:

flypenobscot.com/freight

No more calling the freight number, or hunting your property, or driving down to the shed on Matinicus just to see if you have a package.

PIA Air

After pricing, loose freight is my least favorite topic. Something gets dropped off at dispatch to head to one of the islands, we should bring it out the next time we head to that island. This seems like a relatively simple task for a logistics company, but sadly, in the peak of summer, it is not. It’s just too busy to be running around looking at every shelf for the potential of a piece of loose freight.

The next time you visit the hangar, ask dispatch to show you their shiny new label printer and scanner. Every piece of freight is now labeled and put into the system alongside FedEx and UPS packages. We know exactly where it is and are no longer reliant on a single person to remember what needs to go out to what island. It’s just a tool, but it should drastically reduce delayed loose freight.

Freight moving forward will be priced in three broad tranches. On the plane with you, priority and whenever. We already talked about it on the plane; priority will be same-day/next-day based on the schedule, and whenever will be our lowest-cost solution. The idea here is to align your needs with the space available on the aircraft so we can properly balance the trade-off between people and freight. More on these solutions in our next update.

We hope to expand this service over the coming months. The north star is priority shipping for perishables or medications. Instead of important packages getting lost in the sea of delivery services, ship it to the hangar, and we’ll put it on the next van/plane out to the island. We aren’t there yet, but we are excited for this future.

Housekeeping

North Haven summer restrictions are in effect as of June 15th. Sortie has these restrictions built in, so you will be unable to book flights if two are already booked for that day.

If you live in North Haven or Vinalhaven, you may have noticed Fly Penobscot stickers on your packages. We have temporarily been asked to help deliver FedEx Ground to the islands. We are working with FedEx to make this a more permanent arrangement. I want to thank the selectboard of North Haven and the town of Vinalhaven for their letters of support on the matter.

• USPS still owes us money, but it’s trending in the right direction.
• Customer favorites, DeAndre, Mason, and Genevieve, are coming back again this summer.
• Intern Tom joined us. He lives on Vinalhaven. Say hi.
• Buy one of our airplanes
• New 206 comes online in the fall.

Meet and Greets

We are coming to the islands over the next two Sundays to chat. We want to hear your ideas on how we can improve our services, and we are happy to deep dive into any of the topics in this post.

• Islesboro: 6/14 from 1-3pm at the Islesboro Community Center
• North Haven: 6/14 from 4-6pm at North Haven Brewing Company
• Vinalhaven: 6/21 from 1-3pm at the American Legion
• Matinicus: 6/21 from 4-6pm at the PIA Wharf

I’ll be there along with a handful of PIA representatives. Come say hi.

The Team

Lastly, I want to give a shout-out to the crew at PIA. I’m not going to pretend it’s been a smooth transition from the time we took over in November 2023 to now. I will tell you that, heading into this summer, we are the best prepared in my time here.

Lonny, Zak, Liam, and Holden have been consistently keeping planes safe and ready to fly. The pilots Stan, OG Steve, Olivia, Bennett, Cut Steve, Carson, and Hamish have all been with us for a while and care deeply about the island residents. The dispatchers, Susan, Val, and Robert, all have a strong command of the systems in place and are pleasantly keeping the pilots safe. Bo and the ground crew had their freight load doubled by FedEx and didn’t bat an eye. Cindy, Wink, Preston, Jadon, Ant, Walter, Rob, Holly, and Lauren (who we just hired to deliver FedEx on Vinalhaven) have worked long hours recently and have done it all with a smile.

Our boat captain quit two weeks before the season started, but you would never know it. We spent last summer building a bench, and Steve and Chris took over the trips seamlessly. Intern Tom showed up thinking he was getting an office job, but instead, we’ve had to fly him out to Vinalhaven to load his Subaru full to the gills and deliver packages. He’s rolling with it. Through all the chaos of USPS and general winter woes, the back office of Matt, Chelsea, and Alane has kept this place afloat.

Also, the team of Sortie developers, Dan, Pedro, Lakshmi, Collin, Charlie, and Eva. You’ll never meet them, but the first time you track a package or book a flight, you’ll appreciate this crew. Will we have some hiccups with the new systems? Yes, but there are a bunch of developers on standby to make it right.

And lastly, my lovely wife, who has dealt with the stresses of running a small airline with grace.

We have a great team to crush this summer. We hope you get a chance to fly with us.

Onwards.

• Sean