RetirementIntermediate5 min read

Healthcare in retirement: Medicare and beyond

The parts, the enrollment windows, and the thing people forget about retiring before 65.

Healthcare is the most underestimated retirement expense. Even with Medicare, the average retired couple spends an estimated $300,000+ on healthcare over retirement — premiums, deductibles, prescription drugs, and out-of-pocket costs. Planning for it is not optional.

Medicare's parts, plainly

  • Part A — hospital insurance. Most people pay nothing for this because payroll taxes funded it during their working years.
  • Part B — medical insurance (doctors, outpatient, preventive). Standard 2025 premium around $175/month, more for high earners.
  • Part C — Medicare Advantage. A private-sector bundle that replaces A and B with different tradeoffs. Often includes extras like dental and vision.
  • Part D — prescription drug coverage. Standalone plan you buy in addition to original Medicare.
  • Medigap (supplemental) — covers costs original Medicare doesn't, like deductibles and coinsurance. Not compatible with Medicare Advantage.
The IRMAA surcharge
If your income exceeds certain thresholds, you pay higher Part B and Part D premiums. This is based on your tax return from 2 years ago. For some retirees, especially those with big Roth conversions, this can add $2,000–5,000/year in premiums. It's worth modeling before doing any tax-adjacent move in retirement.

The pre-65 problem

If you want to retire before 65, you need to bridge health coverage until Medicare kicks in. Options: ACA marketplace (subsidies scale with income, so retirees with low taxable income can qualify for generous subsidies), COBRA from your former employer (expensive but immediate), or spouse's employer plan. This bridge can cost $10,000+/year per person — factor it into your retirement number.

Long-term care

Neither Medicare nor most health insurance covers long-term care (nursing home, in-home care for chronic conditions). 70% of people over 65 will eventually need some form of long-term care. Options: self-insure from your retirement savings (requires a much larger portfolio), long-term care insurance (expensive but increasingly offered as hybrid life/LTC policies), or rely on Medicaid (only after spending down most of your assets). No option is good, but ignoring the question is worst.

Enrollment windows: the deadlines with teeth

Medicare enrollment is not automatic for most people, and missing the window carries permanent penalties. Your Initial Enrollment Period is seven months long: the three months before your 65th birthday month, the month itself, and the three months after. Skip Part B without qualifying coverage and the late penalty is 10% of the premium per full year missed — forever. Skip Part D and it's about 1% per month missed, also permanent. The exception: if you (or your spouse) are still working with employer coverage from a 20+ employee company, you can delay penalty-free and use a Special Enrollment Period when the job ends.

COBRA does not count
The classic trap: retiring at 64, taking 18 months of COBRA, and assuming it protects you past 65. COBRA is not 'active employer coverage' in Medicare's eyes. If you're on COBRA at 65 and skip Part B enrollment, you get the lifetime penalty AND a gap where COBRA pays secondary to Medicare you don't have — meaning claims can be denied almost entirely. Enroll in Part B at 65 regardless of COBRA.

What retirement healthcare actually costs per month

Coverage pieceTypical monthly costNotes
Part A (hospital)$0Premium-free with 10+ years of work history
Part B (medical)~$185Higher with IRMAA surcharges at higher incomes
Part D (drugs)$0-$50Varies by plan; out-of-pocket drug costs now capped at $2,000/yr
Medigap Plan G$120-$250Varies by state, age, and insurer
Medicare Advantageoften $0 premiumInstead of B-supplement route; costs come as copays and networks
Dental/vision/hearing$30-$60Original Medicare covers almost none of it
Typical monthly costs per person at 65 (2025-26 estimates)

Add it up and a typical couple on original Medicare with Medigap and drug coverage spends roughly $700-$1,000 a month on premiums alone (estimate) — before deductibles, dental work, or hearing aids. That's the number to put in the retirement budget, not zero. The often-quoted $300,000+ lifetime figure is just this monthly reality compounded over 25 years.

Medicare Advantage vs. Medigap: the fork in the road

At 65 you effectively choose between two systems. Medicare Advantage plans advertise $0 premiums and extras like dental, but they use networks, require prior authorizations, and can cost thousands in copays in a bad health year. Original Medicare plus Medigap costs more every month but lets you see nearly any doctor in the country with minimal paperwork. Here's the asymmetry people learn too late: you can always move from Medigap to Advantage, but moving the other way after your first year usually requires passing medical underwriting — develop a chronic condition on Advantage and you may never be able to buy Medigap at a reasonable price. The cheap-looking choice at a healthy 65 can be the expensive one at a sick 78.

Two healthy 65-year-olds, ten years later
Rita picks a $0-premium Advantage plan; Sam pays $165/month for Plan G. For ten healthy years Rita saves roughly $20,000 in premiums. At 75, both develop conditions needing specialists and regular imaging. Sam sees any specialist he wants; his out-of-pocket is a few hundred dollars a year. Rita navigates prior authorizations and in-network limits, hits her plan's $5,500 annual out-of-pocket maximum two years running, and can't switch to Medigap because underwriting declines her. Neither choice was wrong — but only one of them was reversible (estimates; plans vary by county).

Common Medicare mistakes

  • Missing the Part B window while on COBRA or retiree coverage that doesn't qualify — the most expensive paperwork error in retirement.
  • Ignoring the annual Open Enrollment (Oct 15 - Dec 7). Part D and Advantage plans change formularies yearly; the plan that was cheapest for your medications two years ago often isn't now.
  • Triggering IRMAA accidentally with a big Roth conversion or home-sale gain at 63+ — premiums are based on your tax return from two years prior.
  • Contributing to an HSA after Medicare enrollment begins (not allowed; Part A can even backdate six months — stop HSA contributions in advance).
  • Assuming Medicare covers long-term care, dental, hearing aids, or care abroad. It covers none of them.

The bottom line: healthcare is a five-figure annual line item in most retirement budgets, and Medicare is a system of deadlines and one-way doors more than a benefit that simply arrives. Enroll on time, choose the Advantage-vs-Medigap fork with your 80-year-old self in mind, rerun your drug plan every fall, and budget honestly. Done right, it's a manageable bill; done by default, it's the biggest avoidable expense of later life.

Check your understanding

1 of 3
You retire at 64, take 18 months of COBRA, and are still on COBRA at 65 — so you skip enrolling in Medicare Part B. What happens?

Not quite — try again.

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