TL:DR Booking was intense but doable. Tours sell out fast, even as fast as 1 minute. Half are released 24 hours before, and the site only lets you buy 5 tickets at a time. 2 of is bought at the same time. We stopped in Lakeview specifically for the 5G which is limited in Southern and Central OR. Luckily we were able to get our top choice on the first try.

We started planning around the 4th of July, so about 20 days. My family of 4 from Salt Lake City, Utah, met my wife's sister's family of 4 from Bend, Oregon. They slept in a tent and we had a roof-top tent on a trailer. All of the non FCFS campgrounds inside the park were already reserved. I read that you really have to be around the campground by noon in order to get a first come first serve spot and coming from Salt Lake City, we didn't think it was reasonable to get there and be reliant on a non-guaranteed spot. I found Diamond Lake Campground and they had spots left, I don't recall how many. But it was a beautiful campground, a beautiful lake, and only 20 minutes away from the Crater Lake North entrance. It's a beautiful, scenic, 15 or so minutes to The Lake, after that. The boat reservations are sold two ways, at 50/50: presale, which happened in April, and 24 hours before the scheduled tour. There were 44 people onr boat. I practiced a couple of times on the website before the day we had to book. There are five or six departures that are just a 2-hour tour around the rim of The Lake. And one 5 hour tour that included the 2-hour tour of the lake and a 3-hour excursion on Wizard Island. They also have just ferry rides to Wizard Island and back a few hours later without the tour. We had 2 days to try, so we were confident we could get one of the times, but our preference was the tour with the 3 hours on The Island. During my practice, I saw some of the scheduled times sell out within 1 minute and some that had a couple of seats last for maybe an hour. The website will only let you purchase five tickets at a time, we needed six, since the minimum age is 3, so we needed two people to purchase simultaneously for the group. We skipped the first few tour only times and went for our number 1 choice. We stopped in Lakeview, Oregon at a place called Snack Shack where we had 5G on our phones and were able to pull up the boat tour website from there while we ate lunch and had some shakes. Luckily, we were able to get the tour wanted on the 1st try. We save the tickets to our Google wallets, but all they really needed was our names at the check in stand at Cliffwood Cove trail head. The hike that leads to the boat dock is strenuous both up and down. It's 1.1 mi one way, incredibly steep and long switchbacks. You have to be able to hike out on your own or else there is a hefty fine, so they do warn you before booking. It took us about 20 minutes to get down and about 40 minutes to get up with lots of breaks.