Hi, I’m Cindy Kowalski
I’m a licensed, independent Medicare advisor serving clients across Florida. I got into this work because I almost made the wrong Medicare decision myself when I turned 65. I spent over a year studying every detail before getting licensed — because I wanted to give people the honest guidance I wished I’d had.
I’m not tied to any carrier. I don’t get paid more to recommend one plan over another. I compare every option available to you in your Florida county and tell you exactly what each one means for your situation.
Why Medicare in Florida Is More Complex Than Most States
Florida has more Medicare beneficiaries than almost any state — over 5.1 million Floridians are enrolled. That scale means more carriers, more plans, and more aggressive marketing than you’ll find anywhere else. What’s available in Sarasota County isn’t what’s available in Duval County. Plan selection in Florida requires knowing your specific ZIP code, not just the state.
Florida has no state income tax, which draws retirees and professionals from across the country. Many arrive mid-year or transition directly from employer coverage — and the coordination between your employer plan end date and your Medicare Part B start date has to be timed precisely to avoid permanent penalties.
Florida is also one of the most heavily marketed Medicare states in the country, with TV ads, mailers, and phone solicitations flooding in every fall. An independent advisor cuts through all of it — comparing every plan available in your ZIP code, not just what’s being advertised.
🌊 Snowbirds & Seasonal Residents: Read This First
If you split time between Florida and another state, your Medicare plan choice matters more than most people realize. HMO plans tie you to a Florida network — which means your doctors up north may not be covered for anything but emergencies. A PPO or Original Medicare with a Supplement plan typically travels with you nationwide. Cindy will walk you through the right approach for your specific situation before you enroll.
611 Plans. One Decision. No Do-Overs Until October.
Florida has more Medicare Advantage plans than nearly any other state. Here’s what the market looks like in 2026:
611 Plans Statewide
More Medicare Advantage plans than 2025 — up from 592. Availability varies significantly by county and ZIP code.
$2.11 Avg. Premium
Average monthly premium dropped from $4.09 in 2025 to $2.11 in 2026 — but the premium is the smallest number to focus on.
67 Counties
Plan availability, networks, and costs vary county by county across Florida. Your ZIP code determines your options — not the statewide average.
⚠️ The Number That Matters Most
The out-of-pocket maximum on Florida plans can reach $6,700–$8,850 per year depending on plan type. That’s what you could owe if you get seriously ill on the wrong plan. Cindy will show you what each plan means specifically for your county, your doctors, and your prescriptions — not just the monthly premium.
Florida’s Birthday Rule — An Advantage Most States Don’t Have
Florida gives Medicare Supplement enrollees a protection that most states don’t offer — and most people turning 65 here don’t know exists.
🎂 Florida’s Birthday Rule
Every year, during the 30-day window around your birthday, you have the right to switch to a different Medicare Supplement (Medigap) plan of equal or lesser value — without medical underwriting.
This means even if your health has changed since you first enrolled, you can shop for a better rate annually — something most states do not allow.
This makes Florida a better long-term environment for Medigap than most states. If you start with a Supplement plan here, you’re not locked in at your initial rate forever — you have an annual window to find a better price on the same coverage.
What This Means When You Turn 65
When you first turn 65, you have a federal 6-month open enrollment window to buy any Medigap plan regardless of health. After that, Florida’s Birthday Rule gives you an annual opportunity to switch to an equal or lesser plan without underwriting. Understanding both windows is essential before you make your first enrollment decision. Cindy will walk you through exactly how this affects your options.
Medicare in Florida Varies by Where You Live
The right plan in Sarasota may be wrong for someone in Jacksonville. Here’s what makes each major Florida area different.
🌴 Sarasota, North Port & Venice
Sarasota County is one of the most retirement-dense counties in Florida, which means strong carrier competition and solid plan options. Sarasota Memorial Health System and HCA Florida Sarasota Doctors Hospital are the dominant systems — verifying your providers are in-network before you enroll is essential. This is Cindy’s home market and she knows the local options in detail.
🎡 The Villages & Central Florida
The Villages spans three counties (Sumter, Lake, and Marion), which creates an unusual situation where two neighbors can have access to entirely different plan lineups. Plan availability is strong here, but the tri-county structure means you need to know which county your primary residence falls in before comparing options.
🌉 Tampa Bay Area
Hillsborough, Pinellas, and Pasco counties each have their own plan availability. The Tampa Bay market is highly competitive with strong options from multiple carriers, but also among the most heavily marketed — mailers and TV ads during AEP can make it hard to separate the good options from the noise. An independent review cuts through the marketing.
🌆 Orlando & Southeast Florida
Orlando is one of the fastest-growing retirement markets in the country, with new retirees arriving from colder states who need to coordinate Medicare with their employer plan exit. South Florida (Miami-Dade, Broward, Palm Beach) has among the highest plan counts in the state — and among the most aggressive carrier marketing. Network verification here is especially critical.
📍 Anywhere in Florida — Cindy Can Help
Whether you’re in a competitive metro or a rural county with limited options, Cindy will compare what’s actually available at your specific ZIP code — not the statewide averages. Call or request a callback and she’ll pull the real numbers for your area.
Your Florida Medicare Enrollment Timeline
You have a 7-month window around your 65th birthday. Miss it — without qualifying employer coverage — and you face a permanent Part B penalty added to your premium every month for the rest of your life.
Your Window Opens
The ideal time to start comparing plans. Cindy can pull every plan available in your Florida ZIP code and walk you through what each one means.
You’re Eligible
Parts A and B activate. If you haven’t enrolled yet, you’re still in the window — but don’t wait. Coverage gaps can create billing complications.
⚠ Window Closes
Miss this and you face a 10% Part B penalty permanently added for every 12-month period you were eligible but didn’t enroll.
📅 Still Working in Florida Past 65? Or Moving to Florida?
If you have creditable employer coverage (20+ employees), you may delay Part B without penalty. If you’re relocating to Florida, your move date triggers a Special Enrollment Period — even if you’re already on Medicare. Getting the timing right when you’re transitioning from employer coverage and moving is a situation where mistakes happen easily. Cindy will tell you exactly where you stand.
Not sure when you should enroll? We’ll look at your specific situation and create a personalized Florida enrollment plan.
The Most Common Medicare Mistakes Floridians Make at 65
Missing the Part B Enrollment Deadline
A 10% penalty permanently added for every 12-month period you were eligible but didn’t enroll. This follows you for life and applies regardless of which plan you eventually choose.
Snowbirds Picking an HMO
If you split time between Florida and another state, an HMO plan covers you for emergencies only outside your service area. Your doctors up north won’t be covered for routine care. This is one of Florida’s most common — and costly — enrollment mistakes.
Not Verifying Your Florida Doctors Are In-Network
Florida has multiple major competing health systems. Your cardiologist at Sarasota Memorial, your oncologist at Moffitt Cancer Center, or your specialist at UF Health may not be in-network on the plan you’re considering.
Not Using Florida’s Birthday Rule
Most Florida residents with Medigap don’t know they can shop for a better rate on their Supplement plan every year during their birthday month — without answering health questions. That’s money left on the table annually.
Choosing Based on $0 Premium
Florida has dozens of $0 premium plans. But a $0 premium plan with an $8,850 out-of-pocket maximum isn’t free. Cindy shows you the full cost picture, not just the monthly number.
Keeping a Plan After Moving Counties
Florida’s retirees move frequently — between metros, to The Villages, or to a new county. Moving triggers a Special Enrollment Period. Your current Advantage or Part D plan may not even be available at your new address.
These mistakes can follow you for decades. Let’s make sure you avoid them.
Request Your Free ReviewWhat a Free Review With Cindy Looks Like
We talk about your situation
Your doctors, your prescriptions, your budget, your retirement plans. 20 minutes by phone. If you’re a snowbird, still working, moving to Florida, or relocating within the state, that changes the conversation — and we’ll address it directly.
I pull every plan available in your ZIP code
Not statewide averages — your specific ZIP code. I filter out plans where your doctors aren’t in-network and show you what each option actually costs based on your medications and usage.
I give you my honest recommendation
Including Original Medicare + Medigap if that’s genuinely better for your situation — especially if you’re a snowbird or travel frequently. I’ll tell you the truth even if it means recommending a plan that pays me less.
I help you enroll — or I don’t
If you decide to move forward, I handle the paperwork. If you want to think it over or get a second opinion, that’s completely fine. No pressure, no follow-up sales calls.
Request Your Free Florida Medicare Review
Leave your name and number — Cindy will call you back personally.
📅 Your 7-month enrollment window has real deadlines. The sooner you start, the better your options — especially with 611 plans to sort through in Florida.
No sales pressure · No cost to you, ever · Independent advice
✓ You’re All Set!
Cindy will call you at the number you provided. Looking forward to speaking with you.
Prefer to call directly? (352) 464-4400