Retirement is an exciting milestone — but once the celebrations settle, many new retirees realize there’s a lot to organize, especially when it comes to healthcare. Medicare can feel overwhelming at first, and the choices you make in your first few months of retirement can have long-lasting financial and medical impacts.

If you’ve recently retired (or are about to), this guide walks you through a clear, simple Medicare to-do list for your first 90 days, helping you avoid costly mistakes and feel confident about your coverage.

Let’s break it down.

Why the First 90 Days of Retirement Matter for Medicare

Your initial Medicare enrollment window is one of the most important periods in your retirement journey. During this time, you typically have access to plans and options that may not be available later without medical underwriting or penalties.

Missing deadlines or choosing coverage that doesn’t fit your needs can lead to:

  • Lifetime late-enrollment penalties

  • Gaps in healthcare coverage

  • Unexpected out-of-pocket costs

  • Limited plan choices later on

That’s why having a structured plan for your first 90 days is essential.

Days 1–30: Get Organized and Confirm Your Medicare Enrollment

Confirm You’re Enrolled in Medicare Parts A and B

If you were already receiving Social Security benefits, you may have been automatically enrolled. If not, you’ll need to actively enroll.

Start by confirming:

  • Your Medicare Part A (hospital insurance) status

  • Your Medicare Part B (medical insurance) status

  • Your effective start dates

Keep copies of your Medicare card and enrollment confirmations in a safe place.

Review Any Employer Coverage You’re Leaving Behind

If you recently retired from a job that provided health insurance, make sure you understand:

  • When your employer coverage officially ends

  • Whether COBRA is available (and if it makes financial sense)

  • How your previous coverage coordinates with Medicare

This step is critical to avoiding coverage gaps.

Make a List of Your Healthcare Needs

Before choosing any additional Medicare plans, take inventory of:

  • Your doctors and preferred hospitals

  • Prescription medications

  • Ongoing or upcoming procedures

  • Chronic conditions

  • Travel habits

This personal healthcare snapshot will guide smarter Medicare decisions.

Days 31–60: Choose the Right Medicare Coverage

Once you’re enrolled in Parts A and B, it’s time to complete your coverage.

Decide Between Medicare Advantage or Medicare Supplement

Most retirees choose between:

  • Medicare Advantage plans (often bundled with prescription drug coverage)

  • Medicare Supplement plans paired with a standalone prescription drug plan

Each option has different costs, networks, and levels of flexibility. There’s no universal “best” choice — only what’s best for you.

This is where many retirees benefit from working with a licensed Medicare advisor who can compare plans side-by-side and explain everything in plain English.

Enroll in Prescription Drug Coverage

If your chosen plan doesn’t already include drug coverage, you’ll need to enroll in a separate prescription drug plan.

Skipping this step — even if you don’t currently take medications — can result in permanent penalties later.

Confirm Your Doctors Are In-Network

Before finalizing any plan, always verify that your primary care physician, specialists, and preferred hospitals accept your coverage.

This avoids unpleasant surprises at your first appointment.

Days 61–90: Final Checks and Long-Term Planning

Set Up Online Accounts and Automatic Payments

Take time to:

  • Create your Medicare online account

  • Set up premium payments

  • Organize plan documents

  • Save customer service numbers

A little organization now saves frustration later.

Schedule Preventive Appointments

Many preventive services are covered under Medicare. Use this time to book:

  • Annual wellness visits

  • Routine screenings

  • Dental, vision, or hearing exams (depending on your plan)

Staying proactive helps protect both your health and your budget.

Revisit Your Budget

Healthcare is a major expense in retirement. Make sure your budget reflects:

  • Monthly premiums

  • Copays and deductibles

  • Prescription costs

  • Emergency reserves

Understanding your true healthcare expenses early on helps prevent financial stress down the road.

Common Medicare Mistakes New Retirees Make

Even well-prepared retirees can stumble during this transition. Some of the most common mistakes include:

  • Assuming Medicare covers everything

  • Missing enrollment deadlines

  • Choosing plans based only on monthly premiums

  • Forgetting prescription drug coverage

  • Not reviewing plans annually

Working with a professional can help you avoid these pitfalls and stay confident in your choices.

Get Local, Personalized Medicare Guidance

Medicare isn’t one-size-fits-all — especially when your health, finances, and retirement goals are unique.

That’s why many retirees turn to Lehigh Valley Medicare Advisors for personalized, local guidance. A licensed advisor can help you compare plans, understand your options, and make sure everything is set up correctly — at no cost to you.

Final Thoughts

Your first 90 days of retirement set the foundation for your healthcare in the years ahead. By staying organized, meeting deadlines, and choosing coverage that truly fits your needs, you’ll protect both your health and your financial future.

If you’ve recently retired or are preparing to retire soon, now is the perfect time to review your Medicare options and create a plan that gives you peace of mind — so you can focus on enjoying this exciting new chapter. Schedule an Appointment Today!