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Chaperone Health Insurance Plus

Signing Up for Medicare at 65 or Retirement: Medicare Enrollment Near You in Fort Lauderdale, Florida

Turning 65 and retiring are two of the biggest coverage changes you’ll make, and they come with deadlines and penalties that are easy to miss. I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, based in Fort Lauderdale. I’ve spent 14 years in insurance and the last 8 focused on Medicare, and I specialize in helping people who are turning 65, leaving employer coverage, or retiring before Medicare starts.

Signing up for Medicare is only the first step. I’ll help you time your enrollment around your birthday, your retirement date, and any employer coverage you have now, then compare your Medicare options against your doctors, your prescriptions, and your full-year cost. If you’d like help with Medicare enrollment, book a free plan review and I’ll get back to you personally within 24 to 48 hours.

✓ No cost. No obligation to enroll.

Turning 65 or Retiring

I’LL EVEN CALL YOUR DOCTOR

Get a Free Medicare Quote From an Agent Who Does the Research for You

Your next plan depends on the path you choose, so before your deadlines arrive, I check:

  • Your doctors and hospitals against each plan’s network, including HCA Florida, Memorial, and Baptist Health
  • Your prescriptions and pharmacy against each drug list
  • Your full-year cost, not only the premium

 

If you’re retiring before 65, I compare Marketplace plans with keeping your employer plan through COBRA the same way. If a detail is unclear, I call your doctor’s office myself. Your quote is free, with no obligation to enroll. Get your free quote and I’ll do the research for you.

Hear how I help you choose a plan with confidence.

Is It Mandatory to Sign Up for Medicare at Age 65?

It depends on your situation, which is why so many people ask. If you’re already receiving Social Security or Railroad Retirement Board benefits at least four months before you turn 65, you’ll usually be enrolled in Part A and Part B automatically, and your Medicare card arrives in the mail before your birthday month. If you aren’t receiving those benefits yet, you’ll need to sign up yourself, usually through Social Security.

Whether you should sign up right away depends mostly on your other coverage. If you don’t have health coverage from your own or your spouse’s current job, enrolling during your Initial Enrollment Period is usually the safest choice, since waiting can lead to gaps and late-enrollment penalties. If you or your spouse are still working and covered by that employer’s plan, you may be able to delay Part B without a penalty. The rules depend on the size of the employer and the type of coverage, so I’ll go through your specifics with you before you decide anything.

MORE THAN A FREE QUOTE

Why Work With Me on Your Turning 65 Medicare Decisions

When you’re comparing Medicare agents for the first time, here’s what to look for, and what you can expect from me.

Your Doctors, Hospitals, and Prescriptions Checked First: Before I recommend any plan, I check your doctors, hospitals, and every prescription against its network and drug list, including your pharmacy. If something is unclear, I’ll call your doctor’s office myself.

Every Question Answered, at Your Pace: Medicare is new to you, and there’s a lot of it. I take as long as you need, explain each piece in plain language, and answer every question until it makes sense. There’s no pressure and no obligation to enroll.

The Plan That Costs Less for You: The lowest premium isn’t always the lowest cost. I calculate your full-year cost for every plan, including copays, drug costs, and your out-of-pocket maximum, based on your health needs, before you choose.

My Help Costs You Nothing Extra: Insurers pay my commission, and plan premiums are generally the same whether you enroll through me or directly, so you get personal guidance and ongoing support at no additional charge.

Both Paths, Side by Side: Medicare Advantage, Medigap, and Part D each work differently, and the choice you make at 65 can affect your options later. I lay out every path that fits your situation and explain what you’d gain and give up with each.

Your Deadlines Handled: Your Initial Enrollment Period is seven months long, and missing it can mean lifetime penalties. I map out your dates, including when to leave employer coverage if you’re still working, complete the application with you, and follow it through to approval.

Licensed and Verified: I’m licensed in 33 states, I complete AHIP’s annual Medicare certification, and I’m certified for the 2027 plan year. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.

I Stay Your Agent After You Enroll: Work with me directly, in person, by phone, on Zoom, or at your home in Broward, Miami-Dade, or Palm Beach, and I reply within 24 to 48 hours. I review your coverage every Annual Enrollment Period and help with claims and billing in between.

You can read all 25 reasons we should work together on my Why Choose Me page.

 

When to Sign Up for Medicare Before Turning 65

Your Initial Enrollment Period is a seven-month window around your 65th birthday: the three months before your birthday month, your birthday month itself, and the three months after. Signing up during the first three months is usually best, because your coverage can then start on the first day of your birthday month. If you sign up during your birthday month or later, coverage starts the first day of the month after you sign up. If your birthday falls on the first of the month, your window and your start date each move up one month.

I suggest starting the conversation about six months before your birthday. That gives us time to confirm your eligibility, review any employer or retiree coverage you have, check your doctors and prescriptions, and look at your options before the deadlines arrive. Medicare isn’t only for people turning 65, either. People under 65 who qualify because of a disability or certain medical conditions have their own enrollment timeline, and I help them plan it too.

When to Sign Up for Medicare if Still Working

If you’re still working at 65, your employer’s size matters. When your employer has 20 or more employees, the group health plan usually pays first and Medicare pays second, and many people in that situation delay Part B until they retire. When your employer has fewer than 20 employees, Medicare usually pays first, so delaying Part B could leave you with large bills your employer plan won’t cover. Many people with job-based coverage still sign up for Part A at 65, since most people don’t pay a monthly premium for it.

When your job or your job-based coverage ends, whichever comes first, you generally have an eight-month Special Enrollment Period to sign up for Part B without a late-enrollment penalty. You also generally have two full months after the month your employer coverage ends to join a Medicare Advantage or Part D plan. COBRA and retiree health coverage don’t count as coverage from current employment for Part B timing, which trips up a lot of people. Your drug coverage also needs to be creditable, meaning it’s expected to pay at least as much as standard Medicare drug coverage, to avoid a Part D penalty later. Your employer’s plan sends a notice each year that tells you whether it is.

If you contribute to a Health Savings Account (HSA), timing matters there too. You can’t contribute once you’re enrolled in any part of Medicare, and when you sign up after 65, Part A coverage can be backdated up to six months (but not before the month you turned 65). I can’t give tax advice, so I’ll point out where this applies and suggest you confirm the details with your tax professional.

What Happens if You Don't Sign Up for Medicare at 65

If you miss your Initial Enrollment Period and don’t have coverage from current employment, a few things can happen. You may have to wait for the General Enrollment Period, which runs from January 1 to March 31 each year, with coverage starting the month after you sign up. That can leave you without coverage for months.

You may also pay a late-enrollment penalty. The Part B penalty is generally 10% of the standard premium for each full 12-month period you could have had Part B but didn’t, and it usually lasts as long as you have Part B. The Part D penalty applies if you go 63 days or more in a row without Part D or other creditable drug coverage after your Initial Enrollment Period ends, and it generally lasts as long as you have Part D coverage.

Timing also affects Medigap. Your Medigap Open Enrollment Period is the six months that start the month you’re 65 or older and enrolled in Part B. During that window, you can buy any Medigap policy sold in your state, regardless of your health. After it ends, you may be asked health questions and could be turned down or charged more, except in certain situations where you have a guaranteed right to buy a policy. I’ll make sure you know when your window opens.

Health Insurance After Retirement Before Medicare

Retiring early is exciting, but it can leave a gap between your last day of job-based coverage and your 65th birthday. Losing job-based coverage generally qualifies you for a Special Enrollment Period, usually 60 days, to enroll in an ACA Marketplace plan. Depending on your household income, you may qualify for financial help that lowers your monthly premium, and since retirement often changes your income, I’ll help you estimate it carefully. COBRA is another option. You usually pay the full cost of the plan plus up to a 2% administrative fee, and dropping COBRA voluntarily generally doesn’t open a Special Enrollment Period, so it’s worth comparing both before you choose.

Retirement also affects your spouse. Medicare covers individuals, not families, so if you move to Medicare and your spouse is younger than 65, they’ll need their own coverage. Because I help about 148 individuals and families with ACA/Marketplace coverage each year (based on my own client records), in addition to my Medicare clients, I can plan both sides of your household’s transition at the same time. That way, you keep one trusted agent before and after 65.

Choosing Your Coverage After You Enroll in Medicare at 65

Once Parts A and B are in place, most people choose between two main paths. One is Original Medicare paired with a Medicare Supplement (Medigap) plan and a separate Part D prescription drug plan. The other is a Medicare Advantage (Part C) plan, offered by private insurance companies approved by Medicare. Medicare Advantage is a different way to receive your Part A and Part B benefits, not a supplement or an add-on. The rules, networks, and long-term costs of each path differ substantially, so I walk every client through both before we narrow anything down. You can read more about each path on my Medicare page.

If your former employer offers retiree coverage, I’ll help you understand how it works with Medicare before you change anything, since dropping retiree coverage may mean you can’t get it back later.

MORE WAYS I CAN HELP

Find the Right Coverage for Every Stage of Life

Most households need more than one kind of coverage, and what you need changes as life does. Keep reading for the details on this page, or see all the coverage I help with and my guides to each type of insurance:

Is Getting Help With Medicare Enrollment Right for You?

Working with an independent agent can be a good fit if you’re turning 65 in the next several months, still working and unsure whether to delay Part B, retiring before 65 and need coverage until Medicare starts, or planning coverage for a spouse on a different timeline. It can also help if you take several prescriptions, see specialists, or want to keep a particular doctor or hospital. If you’ve already done your own research, I’m glad to double-check your plan. My help comes at no extra cost to you, and there’s no obligation to enroll. I’m also upfront about how I’m paid: sales agents may be compensated based on a consumer’s enrollment in an insurance plan.

We can meet by phone, on Zoom, at my office in Fort Lauderdale, or at your home anywhere in Broward, Miami-Dade, and Palm Beach counties. If you live in another state where I’m licensed, we can work together by phone or Zoom.

Frequently Asked Questions About Turning 65 and Retiring

How Much Does Medicare Cost at Age 65, and Is Medicare Free at Age 65?

My help comes at no extra cost to you. Plan premiums are generally the same whether you enroll through me or directly with the insurance company. Medicare itself isn’t free, though. Most people don’t pay a monthly premium for Part A if they or their spouse worked and paid Medicare taxes for about 10 years, and people who didn’t may be able to buy it. Part B has a standard monthly premium set each year, and people with higher incomes pay more. Part B also has a yearly deductible, and after that you generally pay 20% of the Medicare-approved amount for most services.

Whatever you add on top, whether that’s a Medigap plan, a Part D plan, or a Medicare Advantage plan, has its own premium and cost sharing. That’s why I give you a full-year estimate for each option that includes the premium, deductible, copays, expected drug costs, and the out-of-pocket maximum where the plan has one. All quotes are estimates and aren’t final until you’re enrolled. If your income and resources are limited, you may qualify for Extra Help or a Medicare Savings Program, and I’ll help you find out whether you do.

Do You Have to Sign Up for Medicare at 65 if You’re Still Working?

Not always. If you have health coverage through your own or your spouse’s current job at an employer with 20 or more employees, you can usually delay Part B without a penalty and sign up later during a Special Enrollment Period. With a smaller employer, Medicare usually pays first, so delaying Part B can be costly. If you already receive Social Security benefits, you’ll be enrolled automatically, and you can choose to turn down Part B if your job-based coverage qualifies. I’ll help you check how your employer plan works with Medicare before you decide.

Who Is Not Eligible for Medicare at Age 65?

To qualify at 65, you generally need to be a U.S. citizen, or a lawful permanent resident who has lived in the U.S. for at least five years in a row. People who don’t meet those requirements generally aren’t eligible. A short work history doesn’t necessarily keep you out of Medicare: if you or your spouse didn’t pay Medicare taxes long enough, you may still be able to buy Part A and enroll in Part B. If you’re not sure where you stand, I’ll help you figure out your next steps, including other coverage options if Medicare isn’t available to you yet.

Can I Have Both Employer Insurance and Medicare?

Yes. Many people keep job-based coverage and have Medicare at the same time. The two work together through coordination of benefits, meaning one pays first and the other pays second. Which one pays first usually depends on whether the coverage comes from current employment and on the employer’s size. Having both makes sense in some situations and adds cost without much benefit in others, so I’ll look at your employer plan’s costs and coverage next to your Medicare options.

Is There a Penalty for Not Signing Up for Medicare When I Turn 65?

There can be. If you don’t sign up for Part B when you’re first eligible and don’t have coverage based on current employment, you may pay a Part B late-enrollment penalty that usually lasts as long as you have Part B. If you go 63 days or more in a row without Part D or other creditable drug coverage after your Initial Enrollment Period, you may pay a Part D penalty as well. Coverage from current employment, and drug coverage your plan confirms is creditable, can protect you from these penalties. I’ll help you confirm yours before you delay anything.

What’s the First Step in Signing Up for Medicare at 65?

If you’re not enrolled automatically, you sign up for Part A and Part B through Social Security, online at ssa.gov, by phone, or at a local office. Aim to apply during the three months before your birthday month so your coverage can start on time. Before you apply, it helps to know whether you’ll keep any employer coverage, since that affects whether you need Part B right away. Think of it as a turning 65 Medicare checklist: confirm your eligibility, decide on your Part B timing, then choose how you’ll fill in the rest of your coverage. I offer help with Medicare enrollment in Fort Lauderdale and across South Florida, and I’ll walk through each step with you.

My Husband Is Retiring and I Need Health Insurance. What Are My Options?

If your spouse is retiring and you’ve been on their employer plan, you’ll need your own coverage when that plan ends. If you’re 65 or older, you can generally sign up for Medicare during a Special Enrollment Period, since your coverage was based on your spouse’s current employment. If you’re under 65, losing that coverage generally qualifies you for a Special Enrollment Period to enroll in a Marketplace plan, and you may qualify for financial help depending on your household income. COBRA may also be available. I’ll compare these options side by side so you’re not left with a gap.

Do You Offer Every Medicare Plan in My Area?

No. Being independent means I compare plans from multiple carriers, but I don’t offer every plan. We do not offer every plan available in your area. Currently we represent 8 organizations which offer 65 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options. 1-800-MEDICARE is available 24 hours a day, 7 days a week, and TTY users should call 1-877-486-2048. In Florida, you can also get unbiased Medicare counseling through the state’s SHIP program, called SHINE.

Can You Help With Medicare at 65 if I Live Outside South Florida?

Yes, if you live in one of the 33 states where I’m licensed. Most of my clients are in South Florida, where we can meet at my office in Fort Lauderdale or at your home in Broward, Miami-Dade, or Palm Beach counties. Clients in other states work with me by phone or Zoom. Either way, I reply within 24 to 48 hours.

Roxroy Ashley - Licensed Insurance Agent

How we'll work together

Five steps, no pressure, and I stay with you after you enroll.

 

1

We talk about you

By phone, Zoom or face to face. Your health, your budget, your doctors.

2

I check the details

Doctors, hospitals, prescriptions and pharmacy, checked against each plan.

3

We compare real costs

A full-year estimate for each option, explained in plain language.

4

You decide, I enroll you

No pressure. If you choose a plan, I handle the application with you.

5

We review every year

Plans and networks change. I check yours each year and help with claims in between.

Book a Free Plan Review

Pick a time for a free 15-minute call by phone or video. I’ll check whether your doctors are covered, and my help never costs you anything extra.

Call or text: (954) 410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309

Meet by: phone, video, at my office, or at home in Broward, Miami-Dade and Palm Beach.