Medicare guidance that starts with your situation.
Instead of dropping you into a plan list, Insure Orlando helps you understand where you are, what matters next, and what should be verified before you compare coverage.
Enrollment windows are fixed. Missing the right one can cause coverage gaps or, in some situations, ongoing late-enrollment penalties.
Where are you in your Medicare journey?
Four different experiences because the right questions differ depending on where you are today.
Statewide guidance with a disciplined process.
The site is designed to educate first and make the handoff to plan comparison intentional, not confusing.
20+ years of experience
Two decades of Medicare experience applied to real enrollment, transition and annual-review situations.
Serving all of Florida
Licensed Florida agents with an in-person office at One Senior Place — not a national call center.
Multiple coverage paths
We work with multiple Medicare carriers and coverage options, so the roadmaps explain the decision framework before any recommendation.
Ongoing support mindset
The goal is not simply enrollment; it is helping clients understand what should be reviewed over time.
Learn without leaving the journey behind.
Short answers live inside the roadmaps. These official Medicare resources are available when you want the deeper source material.
When can I sign up for Medicare?
Official Medicare guidance on Initial, Special and General Enrollment Periods.
Working past 65How Medicare works with job-based coverage
Official guidance on delaying enrollment, employer coverage and HSA considerations.
Coverage choicesOriginal Medicare vs. Medicare Advantage
See how the two main ways of getting Medicare coverage differ.
MedigapMedicare Supplement basics
Learn how Medigap works alongside Original Medicare.
PrescriptionsMedicare drug coverage
Understand Part D, formularies, pharmacies and drug-plan basics.
Prefer to talk it through with a person?
Our team of licensed Florida agents can help review the questions your roadmap surfaces — whether you're in Orlando or anywhere else in the state. We also meet clients in person at One Senior Place. The site is designed to make that conversation more productive, not replace it.
We do not offer every plan available in your area. Currently we represent 11 organizations which offer 77 products in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY: 1-877-486-2048), 24 hours a day, 7 days a week, to get information on all of your options.
Meet us in person at One Senior Place.
We meet clients at One Senior Place in Altamonte Springs — a trusted Central Florida resource hub for seniors and their families. Drop in, or call ahead to book a time.
Insure Orlando at One Senior Place
715 Douglas Avenue
Altamonte Springs, FL 32714
Ready to compare Medicare plans?
We make the handoff explicit before you leave Insure Orlando, so you know why you're entering a separate comparison and enrollment platform.
Did your Medicare plan change for 2027?
If you received a letter saying your Medicare Advantage or Part D plan won't be available next year — or your plan is changing benefits, networks, or premiums — this section walks through what it means and what to do next.
Choose what best describes your situation.
Not sure what applies to you?
Start with the 2027 Coverage Checkup. It walks through your plan changes, providers, and prescriptions in about 5 minutes.
My Medicare Advantage plan is ending. What now?
If you received a letter saying your Medicare Advantage plan won't be available in 2027, you're not alone. Carriers across Florida have reduced their service areas, and many members are affected. The letter looks scary, but your coverage isn't disappearing — you just have to make a choice before a specific deadline.
The earlier you act, the more options you have. Your Special Enrollment Period has a hard end date.
Why did my plan leave?
There are three common reasons a Medicare Advantage plan stops serving your area:
- Carrier exit. The insurance company decided to stop offering plans in your county or ZIP code.
- Service Area Reduction (SAR). The plan still exists, but it's no longer available where you live.
- Contract termination. CMS ended the plan's contract, usually for performance or compliance reasons.
In all three cases, you qualify for a Special Enrollment Period (SEP) that gives you extra time to pick new coverage.
Your Special Enrollment Period
If your plan ends on December 31, your SEP starts December 8 and runs through the last day of February. During this window, you can:
- Join a different Medicare Advantage plan
- Return to Original Medicare (Part A and Part B)
- Add a standalone Part D drug plan if you go back to Original Medicare
What happens if you do nothing
You're automatically returned to Original Medicare. You'll have Part A and Part B, but no prescription drug coverage and no extra benefits like dental, vision, or hearing. To get drug coverage, you'd need to enroll in a standalone Part D plan.
What to check before you choose
- Find your letter. It will tell you the exact date your coverage ends.
- Mark your calendar. Note the start of your SEP and the Medigap deadline (63 days after coverage ends).
- Check your doctors. If you want a new Medicare Advantage plan, confirm your providers are in-network.
- Check your prescriptions. Make sure any new plan covers your medications at a reasonable cost.
- Decide: Medicare Advantage or Original Medicare + Medigap. This is the big choice. We can walk you through both.
No. You never lose Original Medicare (Part A and Part B). You only lose the private Medicare Advantage plan that was managing your benefits.
Want help reviewing your options?
We're licensed Florida agents. We can walk through your letter, check your doctors and prescriptions, and help you understand your SEP and Medigap rights — no obligation.
Call 407-487-2540 Email UsWhat happens if I don't pick a new Medicare plan?
If your Medicare Advantage plan is leaving and you do nothing, you don't lose Medicare — but you do lose the extra coverage your plan was providing. Here's the honest picture.
You're automatically returned to Original Medicare
If your Medicare Advantage plan ends and you don't choose a replacement, you're automatically enrolled back into Original Medicare. That means:
- Part A stays. Hospital coverage continues as long as you're eligible.
- Part B stays. Doctor and outpatient coverage continues — you keep paying the premium.
- Part D does not. If your Medicare Advantage plan included drug coverage, you lose it. You'd need a standalone Part D plan.
- Extra benefits end. Dental, vision, hearing, fitness, and other supplemental benefits disappear.
Original Medicare does not cover most outpatient prescription drugs. Without a Part D plan, you'd pay full retail price for medications.
What it actually costs you
The big change is in how you pay for care:
- Hospital stays: You pay a deductible per benefit period, then daily coinsurance for extended stays.
- Doctor visits: Original Medicare generally pays 80% of covered services; you pay the other 20% with no cap.
- Prescriptions: You pay full price unless you enroll in Part D.
For a generally healthy person with low prescriptions, this can be manageable. For someone with chronic conditions or expensive medications, the costs add up fast.
The window is not open forever
You get a Special Enrollment Period because your plan is leaving. If your plan ends on December 31:
- Your SEP starts December 8
- Your SEP ends on the last day of February
If you miss that window, you can only enroll in a new plan during the Annual Enrollment Period (Oct 15 – Dec 7) the following year — meaning a coverage gap for most of the year.
That's a valid choice. But if you go that route, you should look at a Medigap plan to cap your out-of-pocket costs. You only have a short window to buy one without health underwriting.
Want to review what's next?
We can walk through what your current coverage actually does, what changes if you do nothing, and what options you have — no obligation.
Call 407-487-2540 Start 2027 CheckupCan I get Medigap if my Medicare Advantage plan ends?
Yes — and this is the part most people miss. If you return to Original Medicare when your plan ends, you get a guaranteed-issue right to buy a Medigap policy with no health questions. But the window is short, and if you miss it, you may never qualify again.
What Medigap does
Medigap (Medicare Supplement) is a private insurance policy that works alongside Original Medicare. It helps pay the costs Original Medicare doesn't cover — like deductibles, coinsurance, and hospital costs.
The main benefit: no provider networks. You can see any doctor or hospital that accepts Medicare, nationwide.
What "guaranteed issue" means
Under federal law, you have a guaranteed-issue right to buy certain Medigap policies when your Medicare Advantage plan leaves your area. That means:
- The insurance company cannot deny you coverage because of your health
- They cannot charge you more because of pre-existing conditions
- They cannot make you wait for coverage to start (for most conditions)
Outside this window, insurance companies can review your health history, deny coverage, or charge higher premiums. For someone with any medical history, this window is the one that matters most.
The window: 60 days before, 63 days after
You can apply for Medigap as early as 60 days before your Medicare Advantage coverage ends, and no later than 63 days after it ends.
Example: If your plan ends December 31, your Medigap guaranteed-issue window runs November 1 through March 4. After March 4, you lose the guaranteed-issue right.
Do not wait until the last week. Processing delays can cost you the window entirely.
What you need to do
- Confirm your plan is leaving. Check the letter from your carrier for the exact end date.
- Decide if you want Original Medicare + Medigap. This is a real choice — Medigap premiums are typically higher than Medicare Advantage premiums, but they cap your costs and let you keep any doctor.
- Apply during the window. Submit the application to the Medigap carrier of your choice before the 63-day deadline.
- Enroll in Part D separately. Medigap doesn't cover prescriptions. You'll need a standalone Part D plan.
Frequently asked questions
Can I get Medigap if I have health problems?
Yes — during the guaranteed-issue window. The insurance company cannot deny you or charge more based on your health history.
Which Medigap plan should I pick?
Plans are standardized by letter (A, B, C, D, F, G, K, L, M, N). Plan G is currently the most popular for new enrollees. Plan F is closed to anyone who became eligible for Medicare after January 1, 2020.
What if I miss the window?
You can still apply for Medigap, but insurance companies can review your health and deny you or charge more. For some people with serious health conditions, that means Medigap may not be available at all outside the guaranteed-issue window.
How much does Medigap cost?
It varies by plan letter, carrier, age, and location. In Florida, Plan G typically runs $120–$250 per month for someone turning 65, depending on the carrier and your ZIP code.
Want help with the Medigap window?
We can confirm your deadline, compare Medigap carriers, and walk through the application with you — no obligation.
Call 407-487-2540 Email UsTurning 65? Your roadmap starts here.
Answer a few focused questions and build a personalized Medicare roadmap around your timing, current coverage, doctors, prescriptions and priorities.
Turning 65 Medicare Roadmap
Six focused checkpoints. Each answer becomes part of your live roadmap.
Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period or you are in your Initial Enrollment Period.
Still working past 65? Build the right Medicare transition.
Your job coverage, employer size, HSA, prescription coverage and retirement timing can all affect when Medicare should enter the picture.
Working Past 65 Medicare Roadmap
Six checkpoints. Your answers become a live Medicare transition plan.
Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period or you are in your Initial Enrollment Period.
Make sure your Medicare coverage still fits for 2027.
Plans, prescriptions, providers and your own priorities can change. This guided checkup helps you identify what deserves a closer look.
Your 2027 Medicare Coverage Checkup
We build your review as you answer. Nothing here assumes you should switch plans.
Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period or you are in your Initial Enrollment Period. Your 2027 Annual Notice of Change arrives by September 30; Annual Enrollment ends December 7.
Medicare answers, without the pressure.
Choose the question on your mind. We'll give you the short answer first, let you go deeper if you want, and show you the next step only when it makes sense.
Your Medicare Answer Path
Short answer first. More detail only when you want it.
Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period or you are in your Initial Enrollment Period.
You're continuing from Insure Orlando to PlanEnroll.
PlanEnroll is a separate Medicare comparison and enrollment platform used by Insure Orlando when you're ready to review plan options.
PlanEnroll is a separate company/platform from Insure Orlando. Plan-specific information should be verified for the applicable plan year and service area before enrollment. We do not offer every plan available in your area. Currently we represent 11 organizations which offer 77 products in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY: 1-877-486-2048), 24 hours a day, 7 days a week, to get information on all of your options.