We are booked on a Road Scholar trip in late May 2020 that cruises up the Inside Passage and ends with two-and-a-half days in Sitka. While there, the tour will take us on a walking tour of the town; on a whale/wildlife cruise; and to the Sound Science Center, Totem Park, Sitka Historical Society Museum, Russian Bishop's house, St. Michael's Orthodox Cathedral, and Alaska Raptor Center. We also have one free afternoon and one free evening there while with the group. On the free afternoon, we could go to the Sheldon Jackson Museum, go back to the National Historical Park, or just take a hike. We will be right "downtown" and will not have a car. This is my question: Should we book another day or two on our own in Sitka after the tour, or will we have exhausted the possibilities for that town?
The Sitka Tribe of Alaska operates a bus system that will take you pretty much anywhere you want to go in the area. An all day ticket costs about $5 per person. http://ridesitka.com/
During our own visit we used it as a hop-on, hop-off, bus to explore all of the various routes. One place that might be of particular interest to you is Old Sitka Historic Park - the location of the original Russian settlement of New Archangel which was abandoned in favor of the present site where Sitka now stands in around 1804 ... after the local indians rose up and massacred the Russian colonists.
There's a pretty forest walk nearby which crosses a stream that was loaded with Pink Salmon spawning when we were there ... also in late May I think.
You can see the headress worn by the chief who organized and led the attack (and other artifacts) in the excellent Sitka Museum.
Sitka is one of the prettiest little towns in Alaska ... which is saying a lot. I don't think you'll regret any extra time you devote to a visit. One caution: since it's a popular stop for cruise ships the little town can fill up when they're in port. If you head out for some independent exploration you'll leave all that behind.
And bring your waterproofs - it does rain quite a bit.
The Shcldon Jackson Museum is very good and easily reached from downtown or from the Totem Park. You could see it during part of your free afternoon. That's the only place of interest in "urban" Sitka that your tour doesn't cover, as far as I know.
If you book another day or two in Sitka, you might want to spend it outside the town, hiking or another wildlife cruise or something like that. Another option, which I haven't visited, is the Fortress of the Bear, a "safe haven for orphaned bears" a few miles outside Sitka. From the website it looks like a zoo, where you can get within 25 feet of brown bears (similar to grizzlies) in a 3/4 acre habitat. It's closed this coming winter for construction but likely open by May, when the ships start arriving.
Sitka is quite a small island and the tour you've described covers the main points.
Unless you can identify specific additional places you want to see or specific additional hikes you want to do, I wouldn't recommend additional time there.
We ended up with an unexpected and unexpectedly interesting visit to the local hospital there, but I don't imagine that would be on anyone's intentional itinerary!
Sitka is one of the best small towns in Alaska....maybe anywhere, based on our of course unbiased opinion after 44 years in Alaska. Your tour seems to cover the main spots. But there is more to do & see depending on your interests.
* The buses can cover scenic areas to the north & south of town.
* If it is open on schedule, catch a performance in the Harrigan Centennial Hall near the library - the backdrop for the stage is an ocean view.
* Stop in the Old Harbor Bookstore downtown. And check out the baked goods in the Back Door Bakery attached.
* If you are birders and the weather cooperates, visit by boat the St. Lazaria National Wildlife Refuge.
* Stop in at the Sitka Pioneer Home to check out the Art Deco interior.
* Walk or bus a bit north of downtown to the Thomsen Harbor - a mix of yachts, cruising boats, commercial fishing boats and sport fishing charters. Usually lots of eagles nearby seeking scraps from the fish cleaning tables.
* Wander thru the shops downtown - a lot of "just stuff" but some of the finest local and Alaskan museum quality arts & crafts available.
* And of course, the sea food is fresh.
Sitka is charming. What other islands will you be going to? The Alaska ferry system is amazing and you may find that one of the other stops on the ferry system will also give you some "experiences". Good adventures await.
The State was threatening to close the Museum, sell or transfer the collection in the Sheldon Jackson Museum. Does anyone have an update?
From its website, the Sheldon Jackson seems to be operating now. I didn't see any references to it closing. But it is part of the Alaska State Museum system (the bigger one in Juneau is very good if the OP will be there), and the state has been having a fiscal crisis, so closures might be possible in the future.