Medicare Supplement

Medigap in Orlando during the 2027 AEP: what Florida rules actually let you do

ORLANDO, Fla. — As the Annual Enrollment Period opens Oct. 15, 2026 and runs through Dec. 7, one of the most common questions we hear from readers in Central Florida is whether the fall window is also the time to shop a Medicare Supplement — a Medigap policy. The short answer: not really. Medigap runs on its own set of rules, and in Florida those rules can shape what you are able to do after you make an Annual Enrollment Period change.

Here is what the fall window does and does not change for people with Original Medicare and a Medigap policy in Orlando.

Medigap does not have an Annual Enrollment Period

The fall window most people call "AEP" is a Medicare Advantage and Part D window. It is when you can join, switch or drop a Medicare Advantage plan or a stand-alone Part D drug plan for coverage that starts Jan. 1, 2027.

Medigap is different. There is no federal annual window for Medicare Supplement Insurance. You can apply for a Medigap policy in Orlando in January, June or November — the calendar does not decide.

What the calendar does decide is whether an insurer has to take you. That protection comes from your Medigap Open Enrollment Period (a one-time, six-month window that starts when you are 65 or older and enrolled in Part B) or from a federal guaranteed-issue right. Outside those, Florida insurers may ask health questions and can decline, delay or charge more based on your health.

Moving from Medicare Advantage to Original Medicare during AEP

Say you have a Medicare Advantage plan in Orange County — where Orlando sits, and where CMS lists 123 Medicare Advantage plans from 16 carriers for 2026 — and you decide during AEP that you want to go back to Original Medicare and add a Medigap policy for 2027.

Two things need to happen, and they are separate:

1. The AEP change. Between Oct. 15 and Dec. 7, 2026, you disenroll from your Medicare Advantage plan (usually by enrolling in a stand-alone Part D drug plan or by contacting 1-800-MEDICARE). Original Medicare picks up Jan. 1, 2027.

2. The Medigap application. You apply separately to a Medigap insurer. Whether they must accept you depends on whether you have a guaranteed-issue right. If you do not, they can medically underwrite the application.

This is the piece that surprises people. Making an AEP change alone does not guarantee you a Medigap policy.

Guaranteed issue and the "trial right"

Federal law gives certain people a guaranteed-issue right — meaning insurers must sell you a Medigap policy without health screening, within a limited time window and often limited to certain plan letters. Two situations come up often around AEP:

• The Medicare Advantage trial right. If you joined a Medicare Advantage plan when you first became eligible for Medicare, and it has been less than 12 months, you can drop the plan, return to Original Medicare, and buy a Medigap policy with guaranteed issue.
• The "tried MA once" trial right. If you dropped a Medigap policy to try Medicare Advantage for the first time and it has been less than 12 months, you can go back to Original Medicare and, in general, get your old Medigap policy back — or a comparable one — with guaranteed issue.

Other guaranteed-issue situations exist (for example, your plan leaves the service area, or the insurer ends the plan). Florida also has its own rules on top of federal ones, and those get updated. For the current Florida-specific protections, contact the Florida SHINE program (Florida's SHIP) at 1-800-963-5337 or the Florida Office of Insurance Regulation before you cancel anything.

The standardized Medigap letters sold in Florida

Medigap policies are standardized by letter. A Plan G from one company covers the same Medicare-approved services as a Plan G from another; price and customer service are what differ.

For people newly eligible for Medicare today, Florida insurers can sell Plans A, B, D, G, G-HD, K, L, M and N. Plans C and F are only available to people who were eligible for Medicare before Jan. 1, 2020.

The table below lists every insurer approved to sell Medigap in Florida and which letters each one offers. Big national names like AARP - UnitedHealthcare Insurance Company, Humana, Mutual of Omaha (United World Life Insurance Company), Florida Blue and State Farm Mutual Automobile Insurance Company are on it, alongside smaller carriers such as Everence Association Inc., LifeShield National Insurance Company and WoodmenLife. We are not going to name a price — Medigap rates in Florida vary by insurer, age, ZIP code and other factors, and we do not want to steer you.

For current rates, ask Florida SHINE for the state's Medigap rate guide, or use the Medigap policy search at medicare.gov and enter an Orlando ZIP code.

What is actually changing for 2027

Even though Medigap itself does not reset in the fall, a few Medicare numbers do change for 2027 and are worth knowing before you decide between Medicare Advantage and Original Medicare plus Medigap:

• The Part D out-of-pocket cap rises to $2,400 in 2027 (up from $2,100 in 2026).
• The Part D maximum deductible rises to $700 in 2027 (up from $615 in 2026).
• The Part D national base beneficiary premium for 2027 is $41.33 — that is a formula input, not what any specific plan charges.
• The 2027 Part B standard premium and deductible, and the 2027 IRMAA income brackets, have not yet been announced. CMS typically publishes them later in the fall.

On the Medicare Advantage side in Orange County, for plan year 2027 there are 33 plans not returning, 16 new plans and 16 plans with a new name. Your plan's Annual Notice of Change (ANOC), mailed by late September, spells out exactly what is changing on your plan.

If you do nothing during AEP, your current plan renews for 2027 as described in that ANOC — assuming it is still offered.

How to decide, without pressure

A useful order of operations for Orlando readers this fall:

1. Read your ANOC. Note any change to premium, drug list, network or extra benefits. 2. Decide whether Original Medicare with a Medigap policy and a stand-alone Part D plan fits your situation better than a Medicare Advantage plan. 3. If you are considering the switch, check your Medigap eligibility first. Ask the insurer whether you would be underwritten or accepted on a guaranteed-issue basis before you drop your Medicare Advantage plan. 4. If a Medigap policy is confirmed, then complete the AEP change so Original Medicare starts Jan. 1, 2027.

Do it in that order and you will not end up in Original Medicare without a supplement you were counting on.