The ChathamSD is spread over a wide area and requires both float and regular planes to visit.
Here is one option for a route/timeline for visiting the district:
Start in Juneau and leave in the morning for Tenakee. Stay in Tenakee for the morning:
Juneau 8:30a -> Tenakee 9:10a (Alaska Seaplanes)
Then go to Angoon:
Tenakee 1:00p -> Angoon 1:40p (Alaska Seaplanes)
After spending the night and next morning in Angoon, come back to Juneau:
Angoon 1:50p -> Juneau 2:30p (Alaska Seaplanes)
The next morning, fly to Gustavus, spend the day there, and return to Juneau:
Juneau 8:20a -> Gustavus 8:55a (L.A.B.)
Gustavus 3:20p -> Juneau 3:55p (L.A.B.)
Alternately, if you want to overnight in Gustavus:
Juneau 9:00a -> Gustavus 9:30a (Wings)
Gustavus 9:35a - Juneau 10:05a (Wings)
An alternate way of getting to/from Gustavus is with Fjord Flying, aka Chuck: 723.2471.
And lastly, Klukwan is right outside of Haines and has fairly frequent flights. Once you get to Haines you'll need to get a ride or take a cab to Klukwan. To go up and back in one day:
Juneau 7:45a -> Haines 8:15a (Wings)
Haines 2:50p - Juneau 3:20p (Wings)
Comments
In the summer months, Alaska Airlines has daily flights between Juneau and Gustavus (about 11 minutes in the air). Occasionally those flights get cancelled, though, and travelers end up on one of the smaller planes.
Not nearly as fun, though! And wouldn't you still have to show up earlier and then go through all the security hassle...?