Spring Updates - March 2026

Not to jinx it, but summer is just around the corner. As we gear up for our busy season, here’s an update on the fleet, software, and services we are taking into the 2026 high season.

Airplanes

Our new 206 (57Q) is sitting in a secondary hangar after being towed across the states behind the U-Haul. We’ve made marginal gains in getting it airworthy. With one of Katahdin’s planes needing extensive repairs, installing new magnetos in most of the current fleet, and routine maintenance, our staff has had less time getting 57Q airworthy. We are pushing its introduction into the fleet until the fall.

You’ll see us use DF, our remaining 207, as the fourth plane this summer, accompanying HX, 15X, and KW.

Lastly, we are selling JP. You should buy it, or your friend should buy it. Someone should buy it.

Robin R

The updated water taxi schedule is now live: flypenobscot.com/boat

Last year, we were a bit thin on captains. This year, that’s not the case. Fun fact, even our new dispatcher, Val, has a licence to operate the Robin R. We will be open to more charters this summer to more islands. Hit up dispatch.

Miss Terress

Kevin Waters had a Sea Hawk, the Miss Terress, that he used to transport passengers to the islands after hours or in the fog. It’s largely sat in Journey’s End for the better part of six years after his passing. Since we’ve owned the company, it’s stayed there because we didn’t know what to do with it. Selling it seemed sacrilegious, but it wasn’t big enough for more than a clear day/night with calm seas and on a six-pack license. With the Robin R, it further slid from relevance for the operation.

Terry Waters, god bless her, found Miss Terrisa a new home. We’ve conveyed the boat to Chris, a longtime friend of the Waters, who is taking over the project of rehabbing the boat and keeping it in Penobscot Bay.

Software

We continue to improve the software that we use to run our operations. I get that you can’t tell this, which is a fundamental problem. We continue to ask you, the customer, for things and don't get visibility in return. So, what are we doing with all these new inputs?

Invoicing is now directly built into the system, which is why we may be asking for your credit card information again.

We’ve built in estimated weight and saved passengers for faster reservations and safer operations.

We’ve also improved how we follow flights, giving dispatchers more tools to know where our airplanes are at all times. Will you, the customer, eventually get nice things? Yes. I’ve built enough software to know not to give you a firm date. What you’ll get first is better freight tracking, so you will know if PIA has a package from FedEx or UPS, rather than calling or guessing, and where it currently is. Next will be online booking, so you can book flights without making a phone call. We are targeting the former in May and the latter in June.

Pricing

We’ve started to roll out charter pricing to and from the islands. For 3+ people, it’s actually currently cheaper to charter the plane, and you can add or remove passengers as you see fit. We primarily rolled this out to contractors who would book four passengers and show up with 2, or book 1 passenger and show up with 3. Most of the time, you win and pay $66 a head off of NH or MAT. You can ask the dispatcher for charter pricing now.

Well, what if I charter a flight and then collect 3 others to join me? Aren’t you losing revenue? Honestly, that’s great, love that for you. This is exactly why Venmo exists. We’d very much prefer not to be in the matchmaking business.

We are continuing our enduring march towards dynamic pricing. I still despise the shared flight pricing model, not because I don’t think you should pay less when more people are on the plane, but because you are dependent on others showing up to their flights. And if they don’t, we get raked over the coals for it, like, listen, we brought the plane, we can’t force people to get on it. Again, the goal is not to charge you more. It’s to incentivize you to book earlier and share preexisting flights. We’ve done this from the beginning of time with the mail flight, so it’s a natural extension of existing constructs.

Laundry Service

As a reminder, as you are thinking about your summer rentals, we are offering laundry service. Remember to purchase your reusable bag from the front office the next time you are in!

We’re Coming to You

Lastly, starting in mid-June, we’ll be visiting each island. A third meet-and-greet, a third bribe you with food/beer, and a third to show you the new things we are working on. More to come, but it's kind of the state of the union in real life.

We are looking forward to a busy high season!