Turning 65 in San Diego? Here's Your Medicare Checklist

Turning 65 is one of the most important milestones in your healthcare journey — and one of the most confusing. Medicare has deadlines, penalties, and rules that catch a lot of people off guard. This checklist will walk you through exactly what to do, and when, so you don't miss anything important.

When Does My Medicare Coverage Actually Start?

Your Medicare eligibility begins on the first day of the month you turn 65. But your enrollment window — called the Initial Enrollment Period (IEP) — is actually a 7-month window:

• 3 months before your birthday month
• Your birthday month
• 3 months after your birthday month

The earlier you enroll within this window, the sooner your coverage starts. If you wait until the last 3 months, your coverage may be delayed by 1–3 months.

The Medicare Turning-65 Checklist

3 Months Before Your Birthday Month

• ☑ Sign up for Medicare Part A (hospital coverage) — usually free if you paid Medicare taxes for 10+ years
• ☑ Sign up for Medicare Part B (medical coverage) — $185/month standard premium in 2025
• ☑ Decide: Medicare Advantage OR Original Medicare + Supplement?
• ☑ Compare Part D prescription drug plans based on your current medications
• ☑ Talk to a local Medicare broker in San Diego to review your options at no cost

Your Birthday Month

• ☑ Confirm your Medicare card has arrived (or check your Medicare.gov account)
• ☑ Verify your chosen plan begins on time
• ☑ Notify your doctor's offices of your new coverage

After Enrollment

• ☑ Update your pharmacy with your Part D plan information
• ☑ Review your Medicare Summary Notices (MSNs) for billing accuracy
• ☑ Schedule an Annual Wellness Visit — it's covered 100% by Medicare

What If I'm Still Working at 65?

This is one of the most common situations Ashley helps with in San Diego. If you're still working and covered by an employer plan with 20 or more employees, you may be able to delay Part B enrollment without penalty. But the rules are specific — and getting it wrong can result in a permanent late enrollment penalty. It's worth a quick call to confirm your situation.

What Are the Medicare Late Enrollment Penalties?

Part B penalty: Your Part B premium increases by 10% for every 12-month period you were eligible but didn't enroll — and this penalty is permanent. On a $185/month premium, that adds up fast over a 20-year retirement.

Part D penalty: 1% of the national base premium for every month you went without creditable drug coverage. Also permanent.

The good news: if you take the right steps at the right time, these penalties are completely avoidable.

What Medicare Options Are Available in San Diego?

San Diego County has some of the most competitive Medicare plan options in California. You'll have access to multiple Medicare Advantage plans from carriers like Humana, Aetna, Blue Shield, and others — many with $0 premiums and included dental and vision. If you prefer more flexibility, a Medicare Supplement (Medigap) plan paired with Original Medicare lets you see any Medicare-accepting provider in the country.

Frequently Asked Questions

Do I need to sign up for Medicare if I have coverage through my spouse's employer?

It depends on the size of your spouse's employer. If their company has 20 or more employees, you can usually delay Medicare without penalty. Smaller employers may make Medicare primary, meaning you should enroll on time.

Can I get help at no cost?

Yes. Ashley Watson is a licensed, independent Medicare broker in San Diego who provides free consultations to anyone approaching Medicare. She's not tied to any carrier, so her only job is finding the right plan for you.

How long does enrollment take?

Signing up for Parts A and B through the Social Security Administration takes about 30 minutes online. Choosing and enrolling in a Medicare Advantage or Supplement plan typically takes one meeting with Ashley — usually under an hour.

Get Help From a San Diego Medicare Expert — Free

If you're turning 65 in San Diego and want to make sure you're doing this right, schedule a free consultation with Ashley Watson. She'll walk through your exact situation, explain every option, and help you enroll with confidence. You can also reach her directly at (619) 947-2325.