If you’re already planning multiple cruises in a year, an annual travel insurance policy is usually the better move. It’s simpler, often cheaper than buying three separate cruise line policies, and the coverage is more consistent across all trips.
Cruise line insurance is convenient, but it’s usually limited and geared toward protecting the cruise company first. Annual policies from third party insurers tend to have better trip interruption, delay, and medical coverage, plus clearer rules.
Since you already have medical transport covered, you can focus the policy on interruption, cancellation, and delays, which might bring the cost down. Just make sure the annual plan covers cruise specific issues like missed ports and itinerary changes.
A lot of frequent cruisers go the annual route once they pass one or two trips a year.