Getting started
Turning 65 in Palm Beach County
Maybe you've lived in Boynton Beach for decades, or you moved down from New Jersey last year and changed your address to Jupiter. Either way, your 65th birthday starts a clock. Medicare gives you seven months to enroll: the three months before your birthday month, that month, and the three after.
Enroll in the first three months and coverage starts the first day of your birthday month. Wait longer and the start date slides back. It pays to start planning around 64 and a half.
- A seven-month sign-up window built around your birthday
- Separate rules if you're still on a job-based plan
- Six months to buy Medigap with no health questions
- Free help from a team that knows the county
Your dates
Turning 65 enrollment calculator
Find your Medicare enrollment window
Enter your date of birth to see your Initial Enrollment Period, the best month to apply, the earliest date coverage can start, and what to check if you still work. Our team can then go over the dates with you.
Your Medicare enrollment timeline
- Initial Enrollment Period
- Month to apply
- Coverage could begin
- You turn 65
Check your employer coverage first
Still working, or covered by a spouse's employer plan? If that employer has 20 or more employees, you can usually delay Part B without a penalty. Under 20 employees, Medicare typically pays first at 65, and waiting can leave you underinsured. An HSA contribution changes the math again. Check with HR before you decide, or ask a licensed agent to walk through it with you.
Next step:
This is an estimate based on standard Medicare rules and your date of birth. It is not an official determination. Confirm your dates with Social Security or Medicare.gov.
Timeline
What to do, month by month
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1
Six to three months before your birthday
Decide whether to take Part B now or wait because of coverage from a current job. Start a list of your doctors and prescriptions, including any you see in another state.
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2
Three months before
If you aren't enrolled automatically, apply for Part A and Part B with Social Security. If you already collect benefits, your card comes on its own.
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3
Two months before
Pick a route: Original Medicare with Medigap and Part D, or a Medicare Advantage plan. Check which plans include your doctors and hospital here in the county.
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4
One month before
Send in your applications so the cards arrive before coverage begins. Confirm your old coverage doesn't end before the new coverage starts.
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5
After your birthday
Your six-month Medigap window opens when Part B begins. For those months, your health can't affect your price or whether a company accepts you.
Still working?
Job coverage changes your dates
If you or your spouse still work and the employer has 20 or more workers, you can usually delay Part B without a penalty and keep the job plan. Most people still take Part A, since it's usually premium-free. The exception is anyone putting money into an HSA, because enrolling in any part of Medicare ends HSA contributions.
When the job ends, you have eight months to enroll in Part B. COBRA and retiree coverage don't stretch that window, no matter what the paperwork suggests. This is one of the costliest Medicare mistakes people make. Check the numbers with the Part B penalty calculator.
Small employers follow different rules
If your employer has fewer than 20 workers, Medicare usually pays first once you're 65. Delaying Part B could leave you with bills the job plan won't cover. Check with HR before you decide.
Choosing
Two routes to pick from
- Original Medicare with Medigap and Part D: any doctor in the U.S. who takes Medicare, a higher premium, few bills
- Medicare Advantage: a lower premium, a local network, copays as you go, and often dental and vision
- Either way, the Part B premium is still yours to pay
- A licensed agent can price both routes for you at no cost
Read more about Medigap, Medicare Advantage and Part D drug plans, or start with the Medicare checklist. If your first window passes, you can still make changes during Annual Open Enrollment, October 15 to December 7 each year.
Close to home
Turning 65 around Palm Beach County
We help new enrollees from Tequesta and Jupiter down through Lake Worth Beach, Wellington and Boca Raton. Your doctors shape the decision. The county's hospitals are spread across several systems, from Jupiter Medical Center and Palm Beach Gardens Medical Center in the north to Delray Medical Center and Boca Raton Regional Hospital in the south, and an Advantage network may not include all of them. If you plan to spend part of each year in another state, factor that in before you pick a route. If you use the Thomas H. Corey VA Medical Center, think through how VA care and Medicare fit together. Find your town on our service areas page. For free, unbiased counseling, call SHINE (Serving Health Insurance Needs of Elders), Florida's free Medicare counseling program, at 1-800-963-5337.
Have us check your enrollment timeline
We'll confirm your dates, see whether your job coverage lets you wait on Part B, and price both routes. It's free, and you don't have to enroll.
What to expect
Free review- A licensed agent calls you back during business hours, Mon-Fri, 9:30am-6:30pm ET
- Your doctors and prescriptions get checked before any plan is suggested
- No fee for our help, and your premium is the same either way
- No obligation to enroll, and no pressure if you'd rather stay put
Reviewed by the licensed insurance agents at Palm Beach Senior Insurance. Last reviewed: October 2026. Office hours: Mon-Fri, 9:30am-6:30pm ET.
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A licensed agent will call you during business hours, Mon-Fri, 9:30am-6:30pm ET. If you'd rather not wait, call 561-000-0000 now.
Common questions
Turning 65 questions in Palm Beach County
How long is my Initial Enrollment Period?
Will I be signed up for Medicare automatically?
Can I delay Part B while I'm still working?
What does Part B cost in 2026?
I just moved to Florida. Does that change anything?
When can I get Medigap without health questions?
Where can I get free Medicare counseling in Florida?
Turning 65 this year?
We'll confirm your dates, look up your doctors and price both routes. Free, with no obligation to enroll.