Turning 65? Start at the First Tee
Turning 65? Start Medicare on the Right Fairway.
Learn what to do before, during, and after your Initial Enrollment Period. Medicare Caddies helps you understand your options, compare Medicare Advantage plans, and enroll online or with help from a licensed insurance agent.
Medicare Caddies is an independent insurance agency and is not affiliated with or endorsed by the U.S. government, the federal Medicare program, or CMS.
Your course map
The Turning 65 timeline
6 months before 65
Scout the course
Confirm your Part A eligibility on ssa.gov, check whether you're getting Social Security (auto-enrollment applies), and pull together a list of your doctors, prescriptions, and preferred pharmacy.
3 months before 65
Initial Enrollment Period opens
Your 7-month IEP begins. Enrolling now means Part A and Part B can start on the first day of your birthday month. This is also the ideal window to compare Medicare Advantage plans in your county.
Birthday month
Coverage can begin
If you signed up early, your Medicare is active. If you're still deciding, you can enroll this month — but coverage will start the month after you sign up.
3 months after 65
Last chance in your IEP
Enrollments this late can delay coverage by up to 3 months and may trigger the Part B late enrollment penalty if you don't have creditable coverage.
After enrollment
Play the round
Set a yearly reminder to review your plan during the Annual Enrollment Period (Oct 15 – Dec 7). Doctors, drugs, and premiums change every year — your plan should keep up.
Pack the bag
Your Turning 65 checklist
Print this or save it — every item on the list is something you'll want handled before your IEP window closes.
- Confirm Part A eligibility
- Decide when to enroll in Part B
- Review employer or retiree coverage
- List your current doctors
- List your current prescriptions
- Compare Medicare Advantage plans in your county
- Choose your preferred pharmacy
- Review dental, vision, and hearing needs
- Enroll when you're ready — online or with an agent
Do the math
Turning 65 calculator
Enter your date of birth to see the exact dates for your Initial Enrollment Period and the earliest day your Medicare coverage can start.
Questions from the tee box
Turning 65 FAQs
▸When should I sign up for Medicare if I'm turning 65?
Your Initial Enrollment Period (IEP) is a 7-month window: the 3 months before your 65th birthday month, the birthday month itself, and the 3 months after. Enrolling in the 3 months before means coverage can start the first day of your birthday month.
▸Do I have to take Medicare at 65 if I have employer coverage?
Not always. If you (or your spouse) work for an employer with 20+ employees and have creditable coverage, you can usually delay Part B without penalty and use a Special Enrollment Period later. Smaller employers, retiree plans, and COBRA follow different rules — confirm before you delay.
▸What is the difference between Original Medicare and Medicare Advantage?
Original Medicare (Parts A and B) is federal coverage you can pair with a standalone Part D drug plan and, optionally, a Medigap policy. Medicare Advantage (Part C) is a private plan that bundles A, B, and usually D — often with dental, vision, and hearing extras — through a network.
▸How much does Medicare cost at 65?
Most people pay $0 for Part A. Part B has a standard monthly premium set each year by CMS, plus IRMAA surcharges for higher incomes. Medicare Advantage premiums vary by plan and county — many carry a $0 monthly premium in addition to Part B.
▸Can I enroll online without talking to an agent?
Yes. Medicare Caddies supports full self-enrollment. You can also request help from a licensed insurance agent at any point — it's your call, no pressure.
Keep learning
Related guides and terms
Sources & references
📚 Where this information comes from
When you're ready, compare plans on your own terms
See Medicare Advantage plans from the insurance companies we represent, or walk the course with a licensed agent whenever you'd like a second set of eyes.
We help compare Medicare Advantage plans from the insurance companies we represent, and we don't offer every plan available in your area.
We're here for more than enrollment.We're here for the entire round.
Most Medicare websites help you choose a plan. Medicare Caddies stays with you after you've enrolled.
Whether you enroll online or with one of our licensed insurance agents, you'll always know who to reach out to when Medicare questions come up. When possible, you'll work with the same Medicare Caddie who already knows your situation — no call center, no starting over, no explaining your story to someone new every time.
- Understanding your plan
- Annual Election Period reviews
- Moving to another state
- Doctor network questions
Medicare Caddies is an independent insurance agency and is not affiliated with or endorsed by the U.S. government, the federal Medicare program, or CMS. Plan availability varies by county.