5 Medicare Mistakes Florida Retirees Make Every Year

Florida retirees lose money and coverage every year by making the same Medicare mistakes. A licensed Medicare advisor explains what to watch for in 2026.

Author: Lynsey Brennan, Licensed Medicare Advisor | FL License #G007269 | Published September 12, 2026 Reading time: 6 min read

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Quick Answer

Florida retirees most often get tripped up by missing enrollment deadlines, assuming their current plan still fits their needs, and overlooking drug coverage details that can lead to unexpected costs. Catching these mistakes early — ideally before October 15, when Annual Enrollment opens — can make a real difference in what you pay and how your care works in 2026.

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Key Takeaways

• Missing your Initial Enrollment Period can trigger a Part B late enrollment penalty that lasts for life.
• Florida's Medicare Advantage enrollment rate is 56.1% (CMS Medicare Monthly Enrollment, 2024) — meaning the majority of Florida seniors are in Advantage plans, which aren't right for everyone.
• The 2026 Medicare Advantage in-network out-of-pocket maximum can be as high as $9,350 (CMS, 2025) — a number most people don't know until they need care.
• The 2026 standard Part B premium is $202.90/month, and your income may push that higher through IRMAA surcharges (CMS, November 2025).
• Reviewing your plan every fall during Annual Enrollment takes about an hour and can help you avoid paying for coverage that no longer fits.

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Table of Contents

1. Missing Enrollment Deadlines — and Paying for It for Years 2. Choosing a Plan Based on the Premium Alone 3. Ignoring Drug Coverage Until You Need It 4. Skipping the Annual Plan Review 5. Not Accounting for IRMAA Surcharges After a Life Change 6. Assuming Medicare Advantage and Medigap Are Interchangeable

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Missing Enrollment Deadlines — and Paying for It for Years {#missing-enrollment-deadlines}

This is the mistake I see most often — and it's the one with the longest-lasting consequences.

When you turn 65, you have a 7-month Initial Enrollment Period (IEP) to sign up for Medicare Part B. If you miss it without having qualifying employer coverage, the penalty is a 10% premium increase for every 12-month period you delayed. That penalty is permanent — it follows you for life.

In 2026, the standard Part B premium is $202.90/month (CMS, November 2025). A two-year delay could mean your baseline premium is already $40-plus higher than your neighbor's — every single month, for as long as you have Medicare.

Florida has a large population of people who retire before 65 and drop employer coverage without realizing their Medicare clock has started. If you're in that group, review your enrollment windows carefully before you make any coverage changes.

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Choosing a Plan Based on the Premium Alone {#choosing-a-plan-on-premium-alone}

A $0 monthly premium sounds great. But a Medicare Advantage plan with no monthly cost can still expose you to up to $9,350 in out-of-pocket costs for in-network care in 2026 — and that cap only applies to in-network services (CMS, 2025). Out-of-network costs on PPO plans may be higher, with no cap at all.

That doesn't mean Medicare Advantage is a bad choice. For healthy retirees who rarely use specialists, a lower-premium plan may work out well. But if you have ongoing health conditions, see multiple doctors, or travel frequently, a Medicare Supplement (Medigap) plan — which typically has a higher monthly premium — may cost less overall because it limits what you pay when you actually use care.

This is a genuine trade-off, not a trick. The right answer depends on your specific health needs and finances.

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Ignoring Drug Coverage Until You Need It {#ignoring-drug-coverage}

Part D is one of the most misunderstood pieces of Medicare — and skipping it has consequences.

If you go without creditable drug coverage for 63 or more consecutive days after your IEP, you'll pay a late enrollment penalty on top of your Part D premium for as long as you have that coverage. The penalty adds up fast.

Even if you don't take many prescriptions right now, enrolling in a low-cost Part D plan protects you from that future penalty. And if you do take medications, the 2026 Part D out-of-pocket maximum for covered drugs is $2,100 (CMS CY 2026 Part D benefit parameters) — a significant improvement that makes drug coverage more valuable than it used to be.

Insulin is capped at $35/month under Medicare Part D, regardless of which plan you're on. That's one concrete cost you can count on. For everything else, use the plan comparison tool to check whether your specific drugs are covered before you commit.

Our Part D drug coverage guide walks through how formularies work and what to look for when comparing plans.

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Skipping the Annual Plan Review {#skipping-the-annual-plan-review}

Plans change every year. Premiums shift. Formularies drop drugs. Networks lose doctors. What worked in 2025 may not work as well in 2026.

Annual Enrollment runs October 15 through December 7 each year. During this window, you can switch Medicare Advantage plans, switch from Advantage to Original Medicare, or change your Part D plan. Most people let it pass without a second look.

With over 56% of Florida Medicare beneficiaries enrolled in Medicare Advantage plans (CMS Medicare Monthly Enrollment, 2024), that's a lot of people whose plans may have quietly changed in ways that cost them money.

Check your Annual Notice of Change (ANOC) letter when it arrives in September. Compare it against what you paid and used this year. If something looks different, it probably is.

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Not Accounting for IRMAA Surcharges After a Life Change {#not-accounting-for-irmaa}

IRMAA — the Income-Related Monthly Adjustment Amount — adds a surcharge on top of your Part B and Part D premiums if your income from two years ago exceeds certain thresholds. In 2026, those surcharges are based on your 2024 income.

This catches people off guard after a retirement year that included a home sale, 401(k) withdrawal, or other one-time income event. Your premium could jump significantly for a year.

What most people don't know: you can appeal an IRMAA surcharge if your income has since dropped due to a qualifying life event — like retirement itself. This involves filing Form SSA-44 with Social Security. It's worth doing.

Check 2026 Medicare costs for the current IRMAA brackets. A licensed Medicare advisor can help you figure out whether an appeal makes sense in your situation.

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Assuming Medicare Advantage and Medigap Are Interchangeable {#assuming-advantage-and-medigap-are-interchangeable}

They're not — and this confusion leads to some of the biggest coverage gaps I see.

Medicare Advantage replaces Original Medicare entirely. You get Medicare benefits through a private insurer, usually with network restrictions, prior authorization requirements, and lower premiums. Medigap (Medicare Supplement) works alongside Original Medicare to cover costs like deductibles and coinsurance — with no networks and no referral requirements, in most cases.

Switching between them isn't always easy. If you move from Medicare Advantage back to Original Medicare and want to add a Medigap plan, you may face medical underwriting in Florida — meaning insurers can review your health history and may charge more or decline coverage.

Understanding the differences before you choose matters. Our Medicare Advantage vs. Supplement comparison breaks this down in plain terms, and our Medicare Advantage guide goes deeper on how those plans actually work.

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Frequently Asked Questions

Q: When is the Medicare Annual Enrollment Period in 2026? A: Annual Enrollment runs October 15 through December 7 each year, including 2026. Changes you make during this period take effect January 1 of the following year.

Q: What is the Part B penalty for late enrollment? A: The penalty is 10% of the standard Part B premium for each full 12-month period you went without Part B and weren't covered by qualifying employer insurance. In 2026, the standard Part B premium is $202.90/month (CMS, November 2025), so the math adds up quickly — and the penalty is permanent.

Q: Can I switch from Medicare Advantage to a Medigap plan in Florida? A: Yes, but timing matters. Outside of your Initial Enrollment Period or other special windows, Florida insurers may require medical underwriting for Medigap, which means they can consider your health history. There are exceptions — speaking with a licensed Medicare advisor before switching is a good idea.

Q: What does the $2,100 Part D out-of-pocket cap mean for me? A: Starting in 2026, once you've spent $2,100 out of pocket on covered Part D drugs in a calendar year, you pay $0 for covered drugs for the rest of the year (CMS CY 2026 Part D benefit parameters). This is a significant change from previous years and makes drug coverage more protective for people with high medication costs.

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The Bottom Line

Medicare isn't simple — but most of the mistakes Florida retirees make are avoidable with the right information at the right time. Whether you're turning 65 soon, already enrolled, or just wondering whether your current plan still makes sense, a second opinion from someone who knows the details can be worth your time.

Schedule your free Medicare review with me directly. I'll look at your actual situation — your doctors, your drugs, your budget — and give you a straight answer.

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Sources

• CMS Medicare Monthly Enrollment, 2024 — Florida Medicare Advantage enrollment rate (56.1%)
• CMS, 2024 — National Medicare Advantage enrollment (~54%)
• CMS, November 2025 — 2026 Part B premium ($202.90/month) and Part B deductible ($283)
• CMS CY 2026 Part D Benefit Parameters — 2026 Part D out-of-pocket threshold ($2,100); insulin cap ($35/month)
• CMS, 2025 — 2026 Medicare Advantage in-network out-of-pocket maximum ($9,350)
• Social Security Administration — Form SSA-44, IRMAA Life-Changing Event Appeal
• Medicare.gov — Enrollment periods, late enrollment penalties, Annual Enrollment Period dates

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This article is for educational purposes and is not affiliated with or endorsed by the federal Medicare program or any government agency. HealthPlan Connect is a private, licensed Medicare advisory service. FL License #G007269.