Turning 65 on the Connecticut shoreline. A plain-English Medicare guide for 2026.

If you're turning 65 in the next twelve months, three things are about to start happening at once: a flood of mail from carriers you've never heard of, well-meaning advice from friends who picked their plan in five minutes and don't remember why, and a quietly ticking clock with real penalties attached. This is the plain-English version of what to do, in what order, with the bits that matter most highlighted.

I've been writing Medicare on the Connecticut shoreline for twenty-five years. Most of what people get wrong about Medicare is wrong because it was explained to them in a hurry, by someone with a script, on a thirty-second phone call. Slow down for ten minutes and the whole thing makes sense.

The four parts of Medicare — what each one does

Medicare is one program with four lettered parts. Two are run by the federal government (A and B); two are run by private insurers under federal rules (C and D). The names sound like they're in random order, and that's because they were added to the program at different times by different acts of Congress.

• Hospital coverage (Part A). Inpatient hospital stays, skilled nursing after a hospital stay, hospice, and some home health. Free for most people who paid Medicare taxes for 10+ years.
• Doctor visits and outpatient (Part B). Doctor visits, outpatient procedures, lab work, durable medical equipment, preventive care. Costs about $185/month in 2026 for most people, more if your modified adjusted gross income is over $106,000 single or $212,000 jointly (the IRMAA surcharge).
• Medicare Advantage (Part C). Private bundled plans that take over the role of Hospital and Doctor coverage, usually include Prescription drug coverage, and often add extras like dental, vision, hearing, and gym memberships. You're still in Medicare; you've just delegated administration of it to a private carrier in exchange for the network rules and copay structure of that carrier's plan.
• Prescription drug coverage (Part D). Bought either as a standalone plan to pair with Original Medicare, or bundled inside a Medicare Advantage plan.

You'll also hear about Medicare Supplement (Medigap) plans — private policies that fill the holes in Original Medicare (the 20% Doctor-coverage coinsurance, the Hospital deductible, etc.). Medigap is not a separate part of Medicare; it pairs with Hospital and Doctor coverage (Parts A and B) as an alternative to going the Advantage route.

The timeline: what to do, when

The single most important thing to know is the seven-month Initial Enrollment Period (IEP). It runs from three months before the month you turn 65 through three months after.

• Six to nine months before your 65th birthday: Start the conversation. Inventory which doctors you want to keep, what prescriptions you take, and whether you'll travel.
• Three months before your 65th birthday: Your IEP opens. Enroll in Doctor coverage (Part B) during this window and your coverage starts the first day of your birthday month.
• The month you turn 65: Your Doctor coverage (Part B) starts (assuming you signed up).
• Three months after your 65th birthday: Your IEP closes. Miss it and you may pay a permanent late-enrollment penalty for the rest of your life on Doctor coverage (10% per year delayed for Part B) and Prescription drug coverage (1% of the national base premium per month delayed for Part D).

If you're already collecting Social Security or Railroad Retirement benefits, the federal government will sign you up for Hospital and Doctor coverage (Parts A and B) automatically and mail you a card. If you're not, you have to actively enroll — either online at SSA.gov, by phone, or in person at a Social Security office.

What to do if you're still working at 65

Two questions decide it: how big is your employer, and how good is your current plan?

• Employer with 20+ employees: Your employer plan is generally primary, Medicare is secondary. You can usually delay Doctor coverage (Part B) without penalty as long as you have continuous credible coverage. When you eventually retire, you'll get an 8-month Special Enrollment Period (SEP) to sign up for Doctor coverage (Part B) without penalty.
• Employer with fewer than 20 employees: Medicare is generally primary, the employer plan is secondary. You typically need to enroll in Doctor coverage (Part B) at 65, even if you keep working. This is a place a lot of people get burned.
• You have an HSA-qualified high-deductible plan: Enrolling in any part of Medicare disqualifies you from contributing to your HSA. Plan accordingly — you may want to stop HSA contributions before enrolling.

Original Medicare vs. Advantage: the actual choice

Once you have Hospital and Doctor coverage (Parts A and B), the next decision is whether to pair them with a Medicare Supplement (Medigap) plus a standalone Prescription drug plan (Part D), or to roll the whole thing into a Medicare Advantage plan that bundles Hospital, Doctor, and Prescription drug coverage, plus extras, under one private carrier.

The honest tradeoffs:

• Original Medicare + Medigap + Prescription drug plan (Part D) means higher monthly premiums (roughly $150–$300 for a Plan G Medigap policy in Connecticut, plus $40–$60 for a Prescription drug plan (Part D)) but the broadest possible network (any provider that accepts Medicare, anywhere in the country) and very low out-of-pocket costs once you've met the small Plan G deductible. Predictable. Best for people who travel, have specialists they want to keep, or have a low tolerance for surprise bills.
• Medicare Advantage means lower monthly premiums (often $0 in Connecticut), bundled drug coverage, and frequently extras like dental, vision, hearing, and a gym membership — but you're locked into a network, you pay copays at the point of service, and out-of-pocket costs can hit several thousand dollars in a bad year (capped by an annual maximum that varies by plan). Best for healthy people who don't travel much, who are price-sensitive on premiums, and who want the bundled extras.

Neither is universally better. The right answer depends on the specifics of your health, your network, your prescriptions, and your tolerance for variability. There's a longer comparison here.

Don't skip the prescription part (Part D)

Even if you currently take no prescriptions. The late-enrollment penalty is roughly 1% of the national base beneficiary premium for every month you delay, added permanently to whatever prescription drug plan you eventually pick. The dollar amount is small — a few dollars a month, lifetime — but it grows for every month you wait, and the math gets ugly the longer you put it off.

The exception: if you have credible prescription drug coverage from another source (an active employer plan, the VA, certain union retiree plans), you don't accrue the penalty during that period. Get the credible-coverage letter in writing and keep it.

If you're also on Medicaid

If you're 65 (or about to be) and already on HUSKY (Connecticut's Medicaid), the Medicare conversation is the most consequential one you'll have. There are specific Medicare plan types — Dual-Eligible Special Needs Plans (D-SNPs) — designed for people on both programs, which, for those who qualify, can include $0 copays, broader benefits, and care management built in. The plan choice matters more here than almost anywhere else in Medicare. Read about how the two programs work together.

Where I fit in

I'm an agent — multi-carrier, certified annually with each. I don't charge you for the consultation. The carriers pay a small commission if and when you enroll through me, the same commission whether you enroll through me or through a 1-800 number. So my job is genuinely to figure out what fits your life, not to push a particular plan.

If you're three to nine months out from your 65th birthday, the right time to start the conversation is now — before the mailings, before the deadlines, while there's still room to think.

Sources and further reading

• Medicare.gov — the federal Medicare program's consumer site
• SSA.gov — for Doctor coverage (Part B) enrollment
• State of Connecticut CHOICES program — free, unbiased Medicare counseling for CT residents
• Medicare & You handbook — the federal annual reference, mailed to every beneficiary in September

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