AKStafford

The cruise line's do a great job of cruising through Southeast Alaska. But I am not fan of their land tours through Southcentral Alaska. This opinion is based on two years as a tour bus driver for those tours. I think a better option is renting a vehicle and putting together your own great trip. With your large group, that may be more challenging... Of the two choices you listed, I would go with option 1. Option 2 uses McKinley Princess Lodge which is just a passenger warehouse in the middle of no where.

Use the transit bus: https://www.nps.gov/dena/planyourvisit/shuttles.htm

Alaska has been fighting for an exception for years with no luck.

I recommend DIY over the cruise line tours. I drove tour bus for the cruise lines for a couple of years and my opinion is based on that. It's getting pretty late to get a good deal on a rental car for 2024. And you'll have to pay the one-way drop off fee. 4 day for Fairbanks to Seward is tight. It all depends on what you want to see and do. I'd also suggest some research at the TripAdvisor forum for Alaska travel to get more ideas for the land portion of your trip: https://www.tripadvisor.com/ShowForum-g28923-i349-Alaska.html

Juneau is in a temperate rain forest. It is what it is. The key to Alaska weather: hope for the best, plan for the worse and have fun no matter what. And any weather forecast more than 36 hours out is just a guess.

What sort of weather are you worried about?

I think you are overestimating the number of towns that are in Southeast Alaska....

I've always called that location City Market...https://www.newsagaya.com/markets/city-market/

I'd contact the AvisAlaska office in Kodiak: https://www.avisalaska.com/locations/kodiak/ Taking a taxi to the airport should be pretty simple though.

Rent a car and drive out to Fossil Beach: https://maps.app.goo.gl/FuShnYkgVqubV7X79

Icy Strait Point is located at Hoonah: http://visithoonah.com/ And have you looked here: https://icystraitpoint.com/ ?

You could take a cab or an Uber to City Market, which would be the closest grocery store, the evening before. It's address is 900 West 13th Avenue

I drove tour bus for two years for those cruisetours. I would not recommend them. You'd be better off renting a car and putting together your own great trip. The TripAdvisor forums can be a great help: https://www.tripadvisor.com/ShowForum-g28923-i349-Alaska.html

Have you looked at booking a private transfer: https://www.bactrans.com/

June, July or August. Definitely not April or October.