Turning 65 Soon? Your Complete Medicare Transition Timeline for Virginia Beach Residents
- Claire Jaramillo
- Sep 3
- 5 min read
Turning 65 Soon? Your Complete Medicare Transition Timeline for Virginia Beach Residents
Congratulations! Turning 65 is a major milestone that comes with an important healthcare transition – moving from your current insurance to Medicare. While this transition might feel overwhelming, having a clear timeline and understanding what to do when will make the process smooth and stress-free.
After helping hundreds of Virginia Beach residents navigate their Medicare transition over the past 10+ years, I've developed a timeline that ensures you get the coverage you need without gaps, penalties, or last-minute panic.
Let me walk you through exactly what you need to do and when, so you can transition to Medicare with confidence.

9 Months Before Your 65th Birthday: Assess Your Current Situation
What to Do:
● Review your current health insurance coverage and costs
● Make a list of your current doctors and verify they accept Medicare
● List all medications you take and their current costs
● Consider your healthcare needs and preferences
● Evaluate your budget for Medicare-related expenses
Why This Matters: Understanding your current situation helps you choose Medicare options that maintain continuity of care and fit your budget.
Virginia Beach Consideration: Our area has excellent healthcare systems like Sentara and Bon Secours. Verify that your preferred facilities and doctors work with Medicare.
6 Months Before Your 65th Birthday: Understand Your Timeline-
Time to call Retha Rish Insurance Agency for a Medicare 101.
What to Do:
● Determine your Initial Enrollment Period (7 months: 3 months before your 65th birthday, your birthday month, and 3 months after)
● Understand how your current employer coverage affects Medicare timing
● Learn about Special Enrollment Periods if you're still working
● Research Medicare Supplement guaranteed issue rights
Why This Matters: Your enrollment timing affects your rights to Medicare Supplement insurance and can impact penalties and coverage gaps.
Important Note: If you're still working with employer coverage, you may be able to delay Medicare Part B without penalties, but this decision requires careful consideration.
4 Months Before Your 65th Birthday: Start Serious Planning
What to Do:
● Begin comparing specific Medicare plan options available in Virginia Beach
● Research Medicare Supplement insurance companies and their rates
● Compare Medicare Advantage plans if you're considering that option
● Understand how Medicare coordinates with any other insurance you might have
Why This Matters: This gives you time to thoroughly research options without feeling pressured to make quick decisions.
Local Focus: Hampton Roads has specific plan options and provider networks that might be different from other areas. Make sure you're looking at plans actually available in our region.
3 Months Before Your 65th Birthday: Make Your Decisions
What to Do:
● Choose between Original Medicare with supplements or Medicare Advantage, if you don't understand call your local broker
● Select specific plans based on your healthcare needs and budget
● Gather all necessary paperwork for enrollment in part A&B- and enroll to get your Medicare card.
● Schedule appointments to get enrolled in either Medicare Supplement and part D or Medicare Advantage, if working with a broker
● Notify your current insurance about your upcoming Medicare transition
Why This Matters: Making decisions 3 months early ensures you can enroll during the optimal time in your Initial Enrollment Period and gives you time to fix any issues that arise.
Decision Framework:
● If you want maximum doctor choice: Original Medicare + Medicare Supplement
● If you want lower premiums and don't mind networks: Medicare Advantage
● If you travel frequently: Original Medicare + supplements work nationwide
1-2 Months Before Your 65th Birthday: Complete Your Enrollment
What to Do:
● Enroll in Medicare Part A and Part B (if you're not delaying Part B)
● Enroll in your chosen Medicare Supplement plan during your guaranteed issue period
● Enroll in a Part D prescription drug plan
● OR enroll in your chosen Medicare Advantage plan
● Confirm all enrollments were processed correctly
Why This Matters: Enrolling 1-2 months before your birthday ensures coverage starts on time and gives you opportunity to fix any enrollment issues.
Critical Timing: Your Medicare Supplement Initial open enrollment period starts when you enroll in Part B, not when you turn 65. Don't miss this window!
Your 65th Birthday Month: Finalize the Transition
What to Do:
● Confirm your Medicare coverage is active
● Receive your Medicare cards and new insurance cards
● Update all healthcare providers with your new insurance information
● Schedule any needed appointments with new doctors if you had to change
● Cancel or modify your previous health insurance as appropriate
Why This Matters: Ensuring smooth activation prevents coverage gaps and billing issues.
1-3 Months After Your 65th Birthday: Settle Into Your New Coverage
What to Do:
● Use your new Medicare coverage and understand how it works
● Keep all documentation and understand your benefits
● Address any issues or questions that arise
● Schedule your annual wellness visit (covered 100% by Medicare)
● Set calendar reminders for future Medicare Open Enrollment periods
Why This Matters: The first few months help you understand how your new coverage works and identify any adjustments needed for next year.
Special Considerations for Virginia Beach Residents
If You're Still Working: Many Virginia Beach residents work past 65. If you have employer coverage, you may be able to delay Medicare Part B without penalties, but this requires meeting specific criteria. Call your Broker to discuss this.
If You Have Retiree Health Benefits: Some employers offer retiree health benefits that work with Medicare. Understanding how these coordinate is crucial for maximizing your coverage.
If You Spend Time in Other States: Many Hampton Roads residents are snowbirds or have vacation homes. Medicare Supplement plans work nationwide, while Medicare Advantage plans have geographic limitations.
Common Timeline Mistakes to Avoid
Starting Too Late: Beginning your Medicare research just weeks before turning 65 leads to rushed decisions and potential mistakes.
Missing the Open Enrollment Period: You have only 6 months from when you enroll in Part B to get Medicare Supplement insurance without health questions.
Not Coordinating with Current Coverage: Failing to properly time the end of your current coverage with the start of Medicare can create gaps.
Ignoring Prescription Drug Coverage: Even if you don't take medications now, you need creditable prescription drug coverage to avoid future penalties.
How I Help Virginia Beach Residents with Their Medicare Transition
As your local Medicare broker, I provide timeline-specific guidance: 6-9 Months Out: Detailed analysis of your specific situation and needs 3-4 Months Out: Specific plan recommendations and enrollment planning 1-2 Months Out: Enrollment assistance and paperwork help After 65: Ongoing support and annual reviews
I understand the local healthcare landscape in Virginia Beach, Norfolk, and Chesapeake, and I'll ensure your Medicare transition maintains access to the doctors and hospitals you prefer.
Your Medicare Transition Doesn't Have to Be Stressful
With proper planning and the right timeline, transitioning to Medicare can be smooth and successful. The key is starting early, understanding your options, and getting help from local experts who know the Hampton Roads healthcare market.
Call Retha Rish Insurance Agency at 757-692-8388 or email rrish@asb.insure to begin planning your Medicare transition.
Don't wait until the last minute to plan for one of the most important healthcare decisions of your life. Start your Medicare transition planning today, and ensure you get the coverage you need from day one.





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