To help you navigate these options and find the best plan for your needs, we’ve teamed up with Chapter to provide personalized, 1-1 guidance.


Signing up for Medicare is a significant milestone that requires careful planning and understanding of your options. Whether you're approaching your 65th birthday or considering delaying enrollment due to continued employment, knowing the key steps is essential to ensure you get the coverage that best meets your healthcare needs. From researching costs and coverage options to gathering necessary documents and making important decisions about Medicare Advantage, Part D, and Medigap, following a timeline for enrollment can make the process smoother and help you avoid any gaps in coverage.


Click here to download a printable checklist.


Steps for Signing Up for Medicare: Medicare Enrollment Checklist


6-12 months before turning 65:

  • Familiarize yourself with the different parts of Medicare (Part A, B, C, D)
  • Research costs associated with Medicare
  • Determine if you'll qualify for premium-free Part A
  • Explore financial assistance options, if needed (e.g., Medicaid, Medicare Savings Programs (MSP), Extra Help)

3-6 months before turning 65:

  • Decide when you want to enroll during the Initial Enrollment Period or delay if still working
  • Check if your doctors accept Medicare
  • Research Medicare Advantage and Part D prescription drug plans in your area
  • Consider meeting with a licensed Medicare agent for guidance

1-3 months before turning 65:

  • Gather necessary documents (e.g., Social Security card, birth certificate, proof of citizenship)
  • Decide between Original Medicare or Medicare Advantage
  • Choose and enroll in a Part D drug plan if needed
  • Select a Medicare Supplement (Medigap) plan if desired

During your Initial Enrollment Period:

  • Enroll in Medicare Part A and Part B through Social Security
  • Sign up for Medicare Advantage and/or Part D if you've chosen those options
  • Schedule your "Welcome to Medicare" preventive visit

After enrolling:

  • Look for your Medicare card in the mail (usually arrives within 30 days)
  • Set up your online Medicare account at Medicare.gov
  • Review your coverage and costs annually during Open Enrollment (Oct 15 - Dec 7)


To help you navigate these options and find the best plan for your needs, we’ve teamed up with Chapter to provide personalized, 1-1 guidance.


Whether you choose Original Medicare, Medicare Advantage, or add prescription drug and Medigap coverage, following a clear timeline ensures that you get the coverage you need without any delays or gaps.

Remember, once enrolled, it’s important to review your coverage annually to make sure it continues to meet your needs.