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Free educational guide

Healthcare Costs in Retirement: Planning Before and After Medicare

A general framework for thinking through health coverage and costs across retirement, from leaving work through Medicare and beyond.

Who it helps

People planning to retire before Medicare eligibility, or already on Medicare and wanting a fuller picture of ongoing health-related costs.

Why it's worth an hour

Healthcare spans several different systems across retirement — employer coverage, marketplace plans, Medicare, and out-of-pocket costs — and the transitions between them are where gaps and surprises tend to happen.

What's inside
  • How to plan for the coverage gap before Medicare eligibility
  • What to weigh when considering marketplace coverage
  • How HSA rules interact with Medicare enrollment
  • Where dental, vision, and hearing coverage typically fit
  • How to think about prescription costs over time
  • What to consider for travel and out-of-state coverage
  • How to build healthcare into a retirement budget
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Educational information only. No cost and no obligation. We never ask for account balances or account numbers, and we never sell your details.

Written and reviewed by Joe DontiUpdated September 10, 2026Related service: Medicare Planning
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  1. 1

    Plan for the gap between leaving work and Medicare eligibility

    Retiring before reaching Medicare eligibility creates a coverage gap that needs its own plan, whether through COBRA, a spouse's employer plan, retiree coverage, or a marketplace plan. This gap can last several years and is worth costing out in detail before you set a retirement date, not after.

    Questions to answer
    • · How many years, if any, is our gap before Medicare eligibility?
    • · What coverage options are realistically available to us during that gap?
    • · What would each option cost per month, in full?
  2. 2

    Weigh marketplace coverage on its own terms

    Health insurance marketplace plans can bridge the gap before Medicare, with premiums that may be affected by household income for that year. Because marketplace considerations depend on income, timing a retirement date or other income events around this can matter. Review current options directly through the marketplace rather than assuming last year's plan and price still apply.

    Questions to answer
    • · What marketplace plans are available in our area for the gap years?
    • · How would our income during those years affect marketplace costs?
    • · How does marketplace coverage compare to COBRA or retiree coverage?

5 more sections in the full guide.

Add your name and email above to read the rest on this page and print a copy. We only need two fields — never account balances or account numbers.

  • Understand how HSA rules interact with Medicare enrollment
  • Know where dental, vision, and hearing coverage typically fit
  • Think about prescription costs over the full retirement, not just this year
  • Plan for travel and out-of-state or seasonal coverage
  • Build healthcare into a full retirement budget line
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Official sources

Rules change. Confirm anything that affects a decision against the current official source.

Where this fits in our work

This guide accompanies our medicare planning work. Joe Donti meets with Arizona households by appointment — in the Scottsdale office, by phone, or on Zoom.

This guide is general education and is not individualized investment, tax, legal, Medicare, or insurance advice, and it is not a recommendation to buy or sell any product or security. Investing involves risk, including possible loss of principal. Insurance and annuity guarantees depend on the claims-paying ability of the issuing carrier. Rules and figures change — confirm current details with the official sources above and with your own tax, legal, or insurance professional.