Last year (2022) I bought an annual Allianz AllTrips Premier policy to cover September trip and June 2023 trip. I am doing the same next year (2024) September trip and June 2025 trip. I chose Allianz because of the good reviews I saw on the forum. Although Allianz includes evacuation, I also buy annual Medjet evac insurance so I can get home if sick or injured. Luckily so far I have not had a claim.
A couple things to keep in mind. The medical is not as much as many individual policies, $50,000 per trip and less on cheaper policies. That works for me because my Medicare supplement has $50,000 lifetime international benefit. Some things, like trip cancellation and interruption are for the term of the policy (one year). So if you choose $5000 benefit and take two trips that $5000 is for both not each.
You cannot buy Alliance AllTrips insurance before two months prior to the date you want to start the policy, unlike an individual policy that you buy soon after you pay your first trip deposit/bill. I sign up for RS tour(s) when they open so a year or more prior to the tour. I buy annual insurance a week before I pay the balance of my RS tour. Between the free cancellation date and final payment date, I self-insurance the deposit. I also buy refundable airline tickets because as I get older things happen and getting a credit may not be workable. Plus I book cancellable hotels so no upfront cost. I book hotels that have a cancel-by date from one day to two weeks prior to stay. Both the refundable plane tickets and cancellable hotels cost more but it is minimal compared to the price of the trip and gives me peace of mind.
As with all insurance policies, read the fine print. Do a side-by-side comparison to analyze which type of travel insurance and what company is best for you.