Ashford Insurance

Get Your Ready for Medicare Checklist

Medicare Made Easy

Get Your Ready for Medicare Checklist

Download: Get Your Ready for Medicare Checklist Here:

What to do to get prepared for Medicare

Medicare can be complex, but our checklist has everything you need to get ready to enroll. You can download the PDF here: ashfordinsurancegroup.com/medicare-checklist

6 Months Before You Turn 65 

  • Understand your enrollment options
    • Enroll on time to avoid penalties and delays in coverage, depending on when is best for you.
    • If you want to enroll in your Initial Enrollment Period, set a reminder for yourself for 3-months before your 65th birthday.

4 Months Before You Turn 65:

  • Make a list of health care benefits you want such as vision, dental or prescription drugs. 
  • Compare plans for coverage packages 
  • Confirm that your current Doctor and/or specialists accept Medicare or Medicare Advantage plans 
  • Calculate costs per month/year for:
    • Premiums
    • Deductibles
    • Co-pays
    • Coinsurance
  • Make sure to ask these important questions:
    • Will I have to choose hospitals and healthcare providers from a network?
    • Are my drugs on the plan’s drug list (or formulary)?
    • Will my doctors accept the coverage?
    • If not, are there doctors near me who will?
    • Does the plan include the pharmacies I currently use?
    • Will I need referrals to visit specialists?
    • Can I get my prescriptions through the mail?
    • Will the plan cover me if I get sick while traveling in another state?
    • Does the plan have a good quality rating?
    • What will my prescription drugs cost?
  • Make your decision.
  • Note: If you’re already receiving Social Security benefits, you’ll be automatically enrolled in Parts A and B. Start looking for your Medicare card to arrive in the mail.

3 Months Before You Turn 65:

  • Enroll in Original Medicare (Parts A and B) during your Initial Enrollment Period. Learn how to enroll. 
  • Enroll in a Medicare Supplement Plan (Medigap) OR a Medicare Advantage (MA) Plan. You only need one of these options. Do NOT enroll in both a Supplement and a MA plan.
    • Contact an Ashford Insurance agent to enroll in a Supplement or MA plan. 
  • Enroll in a Part D Prescription Drug Plan. 
    • If you are enrolled in a MA plan that includes prescription drug coverage, do NOT enroll in a Part D Plan. 
  • Confirm receipt of Medicare card(s). 
  • Learn how to use your Medicare.


Next, learn: How Medicare Works