Do you want to insure the cost of your trip, flights and hotels you already paid for, or do you want medical insurance, which is what most want.
Insurance is based on risk, meaning your age, the country/region you are going, and past medical issues.
So, most good travel insurance you can cover part or all of your travel expenses if you pre paid for them, just keep in mind the higher the amount you wish to insure, the higher the cost.
For Medical, which is most important IMO, you want Primary Insurance to cover a hospital stay/surgery etc, and you also was secondary insurance, if the country you reside covers your primary in a another country, rare but possible.
The other insurance you want with Medical, is Evacuation Insurance, this is what will be most beneficial should they need to transfer you to a good hospital in another country, region or all the way back home, as its a private medical jet with a DR and a nurse. $250K Minimum.
So, I use Squaremouth, a website broker for travel Insurance, you can list all the countries you plan to visit, the dates, and then pay with coverages.
I usually insure my air flights, say $1500.00 USD, then get Primary Insurance, usually $250K or more, and Evacuation Insurance $500K, once home, my insurance covers my medical.
For my age in the 50's, and wife in the 40's, ist usually about $100 each for 30 days...good peace of mind.
It also comes standard with Trip Interuption, Lost Baggage, Flight Delays/cancellation. Keep in mind all that these are paid via claim after the fact, you submit to be reimbursed.
The Medical is same type claims, if small, if major issue, hospitalization etc. the insurance takes over payment with the institution are are being treated at, and coordinates all medical treatment transfers etc.