Preparing for Medicare: What to Know Before You Turn 65

Published June 9, 2026

At a Glance

• Timing is everything. Your Initial Enrollment Period is just seven months around your 65th birthday. Miss it and Part B and Part D surcharges follow you for life.
• Higher earners, plan ahead. IRMAA surcharges are based on income from two years prior — so decisions before 65 (Roth conversions, capital gains timing) shape what you’ll pay.
• Medigap vs. Medicare Advantage. For affluent retirees the choice usually turns on access and flexibility over premium — the post lays the trade-offs side by side.

Most people spend decades saving, investing, and planning for retirement. Yet one of the most consequential financial decisions of those years has almost nothing to do with your portfolio. It comes down to a government program, a single birthday, and a deadline you do not want to miss.

The program is Medicare, and the window to enroll opens around your 65th birthday. Signing up on time lets you make full use of the coverage you’ve already paid for — and preserves your flexibility as healthcare becomes a larger line item later in retirement. Here’s what’s worth understanding before that birthday arrives.

The enrollment window — and why timing matters

Medicare was created in 1965 to give older Americans access to affordable healthcare. It isn’t free, but if you or your spouse paid payroll taxes for at least 10 years, you’ve already funded a meaningful share of it — a good reason to claim your benefits as soon as you’re eligible.

Your Initial Enrollment Period runs for seven months: the three months before the month you turn 65, your birthday month, and the three months after. Miss it, and you can face delayed coverage and permanently higher premiums — surcharges designed to discourage people from waiting until they’re sick to sign up. You enroll through the Social Security Administration’s website.

One important exception: if you’re still covered by a current employer’s group health plan (yours or a spouse’s), you may be able to delay enrollment without penalty. Whether that applies depends on the size of the employer and the specifics of the plan, so it’s worth confirming rather than assuming.

The four parts, briefly

Part A — hospital coverage. Covers inpatient hospital stays, skilled nursing care, hospice, and some home healthcare. For most people there’s no monthly premium, because you prepaid it through payroll taxes. You’ll still owe deductibles — $1,736 in 2026 for the first 60 days of a hospital stay, with meaningful copays beyond that. If you’ve paid in over your career, there’s no penalty for delaying Part A — and no real reason to.

Part B — outpatient coverage. Covers doctor visits, the ER, preventive care, lab work, and medical equipment. The standard 2026 premium is $202.90 per month (higher for upper-income households — more on that below), with a $283 annual deductible and a 20% coinsurance on most services. Missing your Initial Enrollment Period adds a permanent 10% surcharge for every full 12 months you delayed.

Part C — Medicare Advantage. Optional plans from private insurers that bundle Parts A and B, often with Part D, and frequently add dental, vision, and hearing. They typically replace Part B’s open-ended 20% coinsurance with fixed copays and a capped annual out-of-pocket maximum. You still pay your Part B premium, plus any additional plan premium — though some Advantage plans charge none.

Part D — prescription drug coverage. Sold through private insurers; the average 2026 premium is about $34.50 per month, with an annual deductible up to $615 depending on the plan. If you already have creditable drug coverage (through a current employer, say), you can delay without penalty. Otherwise, waiting adds a permanent 1% surcharge for every month you go without it.

Medigap: filling the gaps

Medigap policies are supplemental private coverage that pick up out-of-pocket costs left by Parts A and B. They carry higher premiums — sometimes several hundred dollars a month — but they smooth out the unpredictable copays and coinsurance that can otherwise add up.

The timing here is its own trap. Your six-month Medigap enrollment window opens the first month you’re both 65 and enrolled in Part B. Enroll during that window and you cannot be turned down or surcharged for preexisting conditions. Wait, and that protection may disappear. Note, too, that you can have Medigap or Medicare Advantage — not both.

Medigap vs. Medicare Advantage: which fits an affluent retiree?

For families with substantial assets, this choice usually turns on access and flexibility, not the monthly premium. Here’s how the two approaches compare on the factors that tend to matter most at higher levels of wealth:

Feature	Medigap (Original Medicare + Supplement)	Medicare Advantage (Part C)
Provider access	Unrestricted. See any doctor or specialist nationwide that accepts Medicare — no networks.	Network-based. Limited to local or regional HMO/PPO networks; a preferred specialist may be out of network.
Care approvals	Minimal. Original Medicare rarely requires prior authorization, so physicians drive care decisions.	More gatekeeping. Prior authorization is common and can delay specialist care.
Global coverage	Usually included. Most Medigap plans cover foreign-travel emergencies up to plan limits.	Emergency-only. Typically thin abroad — a gap for frequent international travelers or multi-property owners.
Cost structure	Predictable. Higher monthly premium, low cost at the point of care (Plan G still leaves the 2026 Part B deductible of $283).	Variable. Lower premium, but copays accrue up to an annual out-of-pocket maximum.
Concierge medicine	Compatible. Pairs cleanly with concierge or private-physician memberships.	Often friction. Managed-care network rules can conflict with concierge practices.

Comparison reflects how Original Medicare with Medigap and Medicare Advantage generally work; specifics vary by plan. Sources: Medicare.gov; KFF.

For those who prize unrestricted access to specialists and minimal administrative friction — and who can comfortably carry a higher premium — Medigap (often Plan G) tends to be the better fit. Families who prefer a lower premium and don’t mind network rules may still do well with Medicare Advantage. The right answer depends on your health, how much you travel, and how you like to receive care, and it’s worth weighing alongside the rest of your plan.

A note for higher-income households

For many of the families we work with, the standard premiums are only the starting point. Higher-income retirees pay an Income-Related Monthly Adjustment Amount — IRMAA — on top of their Part B and Part D premiums. The surcharge is tiered, and it can add hundreds of dollars a month per spouse at the upper brackets.

The detail that surprises people most: IRMAA looks back two years. Your 2026 premiums are based on the income you reported for 2024. That lag is exactly why the years leading up to 65 matter so much. Decisions about Roth conversions, when to realize capital gains, and how to time large or charitable distributions can ripple into what you pay for Medicare later. It’s one more reason a thoughtful approach to spending and withdrawals pays off, and a conversation worth having well before your enrollment year.

The takeaway

Medicare has a lot of moving parts, and the penalties for getting the timing wrong follow you for life. The good news is that the decisions are manageable with a little preparation. With some advance planning, many retirees can keep their healthcare costs in check even as their medical needs grow — and avoid the avoidable surcharges along the way.

This is one piece of a larger retirement picture that also includes how your accounts are organized and whether your core legal documents are current. If you’re approaching 65 — or helping a parent who is — we’re glad to walk through how Medicare fits into your plan and to coordinate the timing with the rest of your financial life.