Hi, I’m Cindy Kowalski
I’m a licensed, independent Medicare advisor serving clients across Sarasota County and Southwest 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 Sarasota County and tell you exactly what each one means for your doctors, your medications, and your budget.
Why Medicare in Sarasota Requires Extra Attention
Sarasota is one of the most popular retirement destinations in the country — which means the Medicare market here is unusually complex. More carriers compete here than in most counties, which is good news for your options, but makes the decision harder.
Many people moving to Sarasota from other states are surprised to find their previous plan doesn’t transfer. When you relocate, you qualify for a Special Enrollment Period — but it comes with a deadline, and missing it means penalties or gaps in coverage.
Because Sarasota attracts active retirees, the choice between an HMO (which keeps you in-network) and a PPO (which lets you see any doctor) matters more here than almost anywhere else — especially if you split time between Florida and another state.
🌴 The Midwest → Florida Pipeline
Many Sarasota retirees are moving from Indiana, Illinois, and Ohio. If you’re relocating from one of those states, Cindy is licensed in your home state too. She can help you transition your coverage across state lines without gaps or penalties.
43 Plans. One Decision. No Do-Overs Until October.
Once you enroll, you’re locked in until the Annual Enrollment Period. Here’s what the Sarasota market looks like in 2026:
43 Total Plans
Medicare Advantage plans available in Sarasota County in 2026 — more than most Florida counties.
29 at $0 Premium
Plans with no monthly premium — but $0 premium doesn’t mean $0 cost. Out-of-pocket maximums vary widely.
23 PPO Plans
Critical if you travel, snowbird, or see out-of-area specialists. HMOs won’t cover you outside the network.
⚠️ The Number That Matters Most
The average out-of-pocket maximum across Sarasota plans is $5,727 per year. That’s how much you could pay if you get seriously ill. Some plans cap it lower — some cap it higher. Cindy will show you exactly what each plan means for your situation.
Medicare in Sarasota County 2026 — What You Need to Know
43 plans. One decision. In this short video, Cindy walks you through exactly what the Sarasota Medicare market looks like in 2026 — and what to watch out for.
Questions after watching? (352) 464-4400 — free, no obligation.
Your Medicare Enrollment Timeline
You have a 7-month window around your 65th birthday. Miss it and you face permanent Part B penalties — added to your premium every month for the rest of your life.
Your Window Opens
The ideal time to start. You have time to research, compare plans, and make a thoughtful decision. This is when Cindy recommends calling.
You’re Eligible
Parts A and B activate. If you haven’t enrolled yet, you’re still in the window — but the clock is ticking.
⚠ Window Closes
Miss this and you face a 10% Part B penalty added permanently for every 12-month period you were eligible but didn’t enroll.
📅 Still Working Past 65?
If you have creditable employer coverage (20+ employees), you may delay enrollment without penalties. If your employer has fewer than 20 employees, different rules apply. Cindy will help you figure out exactly what applies to your situation.
Not sure when you should enroll? Let’s create your personalized timeline.
The Most Common Medicare Mistakes People Make at 65
Missing the Part B Enrollment Deadline
A 10% premium penalty added permanently for every 12-month period you were eligible but didn’t enroll. This follows you forever.
Choosing a Plan Based on $0 Premium
A $0 premium plan with a $5,700 out-of-pocket maximum isn’t free. The premium is just one number. Cindy shows you the full cost picture.
Picking an HMO as a Snowbird
HMO plans only cover emergency care outside the service area. If you split time between Florida and another state, you likely need a PPO.
Not Checking If Your Doctors Accept the Plan
Provider networks change every year. Your primary care doctor or specialist may not be in-network — and your plan won’t alert you.
Ignoring Future Underwriting Rules
Choose Advantage now, develop health issues later, and you may not qualify for a Supplement plan when you want to switch. Your first decision matters most.
Not Reviewing Drug Coverage
A medication that costs you little today may cost hundreds next year. Drug formularies change annually and plans won’t notify you proactively.
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 medications, your budget, your lifestyle. 20 minutes, no pressure. If you split time between Florida and another state, that matters for your plan type.
I compare every plan available to you
All 43 plans in Sarasota County, filtered to what actually fits your situation. Not just the ones that pay the highest commission — all of them.
I give you my honest recommendation
Including Original Medicare + Medigap if that’s genuinely better for you. 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 decide to wait or go elsewhere, that’s fine. No pressure, no follow-up sales calls.
Request Your Free Sarasota 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.
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