Annual Travel Insurance Recommendations?

I investigated a number of the annual policies and while all were much more reasonable in pricing than single trip coverage none of them covered preexisting conditions.

I've been looking at Roam Right. I was going to use for 2020 but trips cancelled before I purchased. They say to purchase within 30 days of final your payment, not when deposit made.

Edited to add on RoamRight: There are levels of coverage and need to (as always) read details, but they include trip cancellation. (Not for covid restrictions....but according to phone conversation with agent if you get medical diagnosed covid while on trip, medical and evac (if needed) is covered. $447....for the age I specified.

More basic policy by Travel Guard,
$259, no age limit, no trip cancellation, but some medical, evac, some travel delay etc.

I'm interested in comments by others on either of these.

Derek, are you looking for comprehensive travel insurance or medical and evac only? If the latter, GeoBlue has annual medical policy and Medjet has annual evacuation policy.

The more I read up on these plans, I am seeing the annual plans cover medical and evacuation for the year but for trip cancellation I would need to purchase a policy for each trip. any thoughts from people who have done this?

I have used GeoBlue for annual medical/evacuation the last few years. It was reasonable but never had to file a claim.

I was using my Costco credit card to cover trip cancellation but they discontinued that in Sept 2019.

I believe Allianz has an animal policy that covers trip cancellation and medical. I think my issue with that policy was the amount of medical coverage wasn’t that high. But it has been a couple years since I’ve looked at it.

Usually if I am doing a trip myself (no cruise or tour) I do t worry about trip cancellation as long as the hotels are refundable. I am more concerned about having medical coverage.

Next year we have multiple tours planned and I haven’t figured out the insurance yet

You can read my detailed write-up on the Nationwide Annual Travel plan that I'm considering for 2022 because I have 2 RS tours scheduled and who knows what other travel I'll plan!

https://community.ricksteves.com/travel-forum/tours/trip-insurance-for-2022-tour

The Nationwide plan does provide options for Trip Cancellation / Trip Interruption coverage.

When you are comparing annual plans, pay close attention to which benefits are aggregate limits for the plan year and which benefits are per person/per trip.

For the plans I compared:
Nationwide's (annual policy) Trip Cancellation/Interruption coverage is an aggregate limit for the plan year. And it appears that you need to decide up front how much coverage you want.

Nationwide's medical coverage, MedEvac and trip/baggage delay limits are per person / per trip.

Naionwide's (annual plan) MedEvac is $250,000 per person / per trip.
TravelGuard's (annual plan) MedEvac is an aggregate $500,000 limit for the plan year, limit of 2 evacuations.

How unlucky am I if I'm evacuated twice in a single year? Yikes. After the first one, would I really be able to go on the 2nd trip?

Most travel / medical policies come with some medical evacuation coverage. As with all policies read the fine print about the med. evac. coverage. Some policies will only pay for evacuation to nearest appropriate medical facility. Others may, or will, return you to your home for further care. There is a company called MedJet that you might want to scope out if you have the time. It us NOT medical or trip cancellation insurance, just evacuation back home. Many different plans. Hope this helps

Be sure to drill down into the policy details for your state. Again, I haven't seen one annual plan that covers preexisting medical conditions (at least for Michigan residents). If you are taking a minor maintenance prescription as I have for many years you have at least one preexisting medical condition. However, I do have PLAN G Medicare which will cover 80% of international medical up to $50,000. Annual policies can be a reasonable gamble for some of us.

GeoBlue Trekker choice plan covers pre-existing according to an email response from them. Check their plan docs in case your state varies.

GeoBlue Trekker only asks that you have primary medical insurance and has a medical limit of $100,000 for those older than 69. I thought it was interesting that you can only purchase it if your trip will begin within 180 days.

Thank you to all who replied.
I looked at the Nationwide Annual policy. good reviews. But it has a 30 day maximum each trip. So that won't work for me but it might work for you..
https://travel.nationwide.com/quote

I am also considering:

Seven Corners Wander Frequent Travel Plus- Annual Travel Insurance
https://www.sevencorners.com/coronavirus/annual-travel-insurance#/quote

and

Arch RoamRight Annual travel policy
https://www.roamright.com

Any recommendations, insight, issues, comments on either of these two travel insurance companies?