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Medicare Planning

Holistic Medicare Planning Services for Retirement

Healthcare in retirement is one of the most significant financial decisions you’ll make, and one of the most complex. Original Medicare was not designed to cover all your healthcare costs, and the sheer number of plan options, enrollment deadlines, and coverage gaps can leave even the most prepared retirees feeling uncertain about where to turn.

At Evergreen Wealth Advisors, we’re here to help take that uncertainty off your plate. Our licensed Medicare Specialist, Danette Peil, works alongside our wealth management team to guide you through every step of the Medicare process, from understanding when and how to enroll to comparing Medicare plan options that fit both your healthcare needs and your retirement budget.

And because this is part of how we serve our clients, our Medicare guidance comes at no cost to you.

Schedule My No-Cost Medicare Review

What Medicare Doesn’t Cover, and How Medicare Planning Can Help

Original Medicare (Parts A & B) leaves meaningful gaps in coverage, including:

Our Process

Copayments, coinsurance, and deductibles

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Most prescription drug costs

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Dental, vision, and hearing care

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Long-term care and custodial services

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Care received outside the U.S.

Our Medicare Planning Process

Every plan we build is as unique as the person we build it for, so we don’t believe in generic recommendations. As fiduciary financial advisors, we include Medicare planning as part of our holistic financial planning process for clients. By integrating healthcare planning into your broader retirement strategy, we help ensure your Medicare decisions work alongside your retirement income plan, tax strategy, investments, protection planning, and legacy goals to support your long-term financial well-being.

We begin by understanding your unique situation, including your health needs, financial picture, and timeline, so we can help you make more informed decisions about your health coverage and financial future. Together, we will:

  • Identify the right time for you to enroll in Medicare to help avoid potentially costly late penalties
  • Compare Medicare Supplement (Medigap) plans and Medicare Advantage plans across multiple providers
  • Evaluate prescription drug coverage under Medicare Part D to help manage medication costs
  • Explain how each plan type works alongside Original Medicare
  • Help coordinate coverage decisions for both spouses
  • Review your Medicare coverage annually during Open Enrollment as your needs evolve

There are no fees and no obligations. Our goal is simply to help you find the right Medicare coverage for your retirement needs.

Medicare Questions We Help You Answer

Choosing Medicare coverage raises a lot of questions. Here are some of the ones we hear most often and help clients work through every day:

  • When is the right time for me to enroll in Medicare?
  • Will I need to go through underwriting to qualify for a Medicare Supplement plan?
  • What will my Medicare coverage actually cost each month?
  • How could Medicare costs change as I age or if my health needs shift?
  • Can my spouse and I be on the same plan, or do we each need separate coverage?
  • Which Medicare Supplement or Medicare Advantage plan best fits my situation?
  • How does Medicare fit into my retirement income and tax planning strategy?

Ready to Take the Uncertainty Out of Medicare?

Medicare decisions are among the most consequential choices you’ll make as you approach retirement. At Evergreen Wealth Advisors, we’re here to help you make them with confidence.

Reach out to our team today to schedule your no-cost Medicare review.

Schedule Now

Frequently Asked Questions About Medicare Planning for Retirement

When should I start thinking about Medicare?

Ideally, you should begin exploring your Medicare options at least six months before you turn 65. This gives you time to understand your choices, compare Medicare plans, and make sure you’re ready to enroll during your Initial Enrollment Period. If you’re retiring before 65 and losing employer coverage, you may need to consider other options to bridge the gap.


Can you help me compare Medicare Supplement (Medigap) and Medicare Advantage plans?

Yes. We can compare Medicare plans across a wide range of carriers and help you understand the key differences between plan types, including differences in costs, network flexibility, and benefits, so you can make a well-informed decision.


What is the difference between Medicare Part A, Part B, Part C, and Part D?

  • Part A covers inpatient hospital care, skilled nursing facility care, and some home health services. Most people do not pay a premium for Part A.
  • Part B covers outpatient services, doctor visits, preventive care, and medical equipment. Part B requires a monthly premium.
  • Part C (Medicare Advantage) is an alternative to Original Medicare offered through private insurers. These plans typically include Part A, Part B, and often Part D coverage, sometimes with additional benefits like dental or vision.
  • Part D covers prescription drugs and is available as a standalone plan alongside Original Medicare or bundled into a Medicare Advantage plan.


What is a Medicare Supplement (Medigap) plan?

A Medicare Supplement plan, also called Medigap, is private insurance that helps pay for some of the costs Original Medicare doesn’t cover such as copayments, coinsurance, and deductibles. Medigap plans work alongside Original Medicare, not as a replacement, and they do not typically include prescription drug coverage (Part D must be purchased separately).


Can my spouse and I have the same Medicare plan?

Medicare is an individual program. Each person must enroll separately and carry their own coverage. However, we can evaluate options for both of you simultaneously to make sure your coverage is coordinated and cost-effective.


What happens if I miss my Initial Enrollment Period?

If you miss your Initial Enrollment Period without a qualifying Special Enrollment Period (such as losing employer coverage), you may face a late enrollment penalty that permanently increases your Part B premium, and you may have a gap in coverage. We help clients stay ahead of these deadlines to avoid unnecessary costs.


Do I need Medicare if I have employer health insurance at 65?

It depends on the size of your employer. If you work for a company with 20 or more employees, your employer insurance is generally primary and you may be able to delay Medicare enrollment without penalty. If your employer has fewer than 20 employees, Medicare typically becomes primary and delaying enrollment could leave you with coverage gaps. We can help you evaluate your specific situation.


What is the Medicare Open Enrollment Period, and what can I change?

Medicare Open Enrollment runs October 15 - December 7 each year. During this period, you can switch between Original Medicare and Medicare Advantage, change your Medicare Advantage plan, or add, drop, or change your Part D prescription drug plan. Changes take effect January 1 of the following year.


What are the important Medicare deadlines?

Your 65th Birthday Window: When you first become eligible for Medicare at 65, you have a seven-month Initial Enrollment Period: three months before your birthday month, your birthday month itself, and three months after to enroll in Medicare Parts A and B. You also have a separate six-month window starting on the first day of the month you turn 65 to enroll in a Medicare Supplement (Medigap) plan with guaranteed issue rights, meaning no medical underwriting.

October 15 – December 7, Annual Open Enrollment: During this period, you can enroll in or switch Medicare Part D prescription drug coverage, move between Original Medicare and Medicare Advantage, or adjust your existing plan. Changes take effect January 1.

January 1 – March 31, General Enrollment Period: If you missed your Initial Enrollment Period, this is your opportunity to enroll in Medicare Parts A and B. Coverage typically begins the month after enrollment under current Medicare rules. Note that late enrollment may result in higher premiums.

January 1 – March 31, Medicare Advantage Open Enrollment: If you’re already enrolled in a Medicare Advantage plan, you can switch to a different Advantage plan or return to Original Medicare during this period.