The mail started six months ago — postcards, "final notices" that aren't from anyone official, and dinner-seminar invitations. Ignore all of it. There are exactly four dates that matter when you turn 65, one decision that's hard to undo, and one deadline that never comes back. Here's the whole thing, month by month, for 2026.
Required disclosures: Smooth Health Solutions is not connected with or endorsed by the United States government or the federal Medicare program. We do not offer every plan available in your area. Currently we represent 0–78 organizations which offer 0–2,613 products in your area. The exact number of organizations and products depends on your ZIP code, county, and plan year. Please contact Medicare.gov, 1‑800‑MEDICARE, or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options. This page is educational — it explains enrollment timing, not any specific plan.
Your Initial Enrollment Period (IEP) is seven months long: the three months before your birthday month, your birthday month, and the three months after. Everything below hangs off that window.
Two questions set your whole path: Will you still have employer coverage at 65? and Are you already drawing Social Security? If you're drawing Social Security, Parts A and B enroll automatically — your card just shows up. If you're still working, the 20-employee rule (below) decides whether delaying Part B is safe or a costly mistake. Sort this out now, calmly, before the window opens.
Not on Social Security yet? Apply at ssa.gov/medicare (about 15 minutes online), by phone at 1‑800‑772‑1213, or at a Palm Beach County Social Security office (find yours with the office locator). Enrolling in these three months means coverage starts the first day of your birthday month — no gap. This is also the right time to start comparing the two paths, unrushed.
Parts A and B are active (if you enrolled in time). Now the real decision: Medicare Advantage or Original Medicare + Medigap — and either way, drug coverage, because skipping Part D without other creditable drug coverage builds a lifelong penalty. In 2026, Part B runs $202.90/month with a $283 deductible; Part D out-of-pocket drug costs are capped at $2,100 for the year.
Your Medigap open enrollment period: six months from your Part B start date to buy any Medigap plan sold in Florida — Plan G, Plan N, any of them — with zero health questions. After this window, Florida carriers can generally underwrite: decline you or charge more based on health. If you want the go-anywhere setup (it works at every major Palm Beach County hospital), this is when it's cheapest and easiest to get. It does not reset.
October 15 – December 7 is the Annual Enrollment Period. If you chose an Advantage or Part D plan, read the Annual Notice of Change letter that arrives each September — premiums, drug lists, and networks move every year, and South Florida's plan lineup shifts more than most.
This is the most expensive wrong guess in Medicare, so here it is plainly:
Employer has 20+ employees: your group plan stays primary. If the coverage is creditable, you can usually delay Part B (and often Part D) without penalty, then enroll penalty-free through a Special Enrollment Period when employment or the coverage ends. Many people in this position enroll in premium-free Part A only — though if you contribute to an HSA, even Part A needs thought first.
Employer has fewer than 20 employees: Medicare becomes primary at 65 whether you enroll or not — meaning your group plan can refuse to pay what Medicare would have covered. Delaying Part B here can leave you effectively uninsured while paying premiums. Most people in this situation need to enroll on time.
Retiring before 65? That's an ACA question, not a Medicare one — a marketplace plan with subsidies bridges the gap, and the subsidy calculator shows what that costs at your income.
Bring your birthday, your work situation, your doctors, and your prescriptions. I'll map every deadline to your calendar and compare both paths against what's actually filed in Palm Beach County — educational first, no pressure ever.
No cost. No obligation to enroll. We do not offer every plan available in your area.
SHINE (Serving Health Insurance Needs of Elders) is Florida's free, unbiased State Health Insurance Assistance Program, delivered locally through the Area Agency on Aging of Palm Beach/Treasure Coast — trained volunteer counselors, no sales, reachable through floridashine.org or 1‑800‑963‑5337. Licensed agents like me are also free to work with — carriers pay the commission, not you. Plenty of my clients use both: SHINE for unbiased education, an agent for the plan-by-plan legwork and someone to call when something breaks in February.
And a mailbox rule for the months ahead: Medicare will never call or visit you to sell anything. Anything urgent-looking that isn't from Medicare.gov, Social Security, or your own plan is marketing — including the ones stamped "important plan information."
Seven months: the three months before your birthday month, your birthday month, and the three after. Turning 65 in June 2026? Your window runs March 1 through September 30, 2026 — and enrolling March–May starts coverage June 1 with no gap. (One quirk: a birthday on the 1st of a month shifts everything a month earlier.)
Without a Special Enrollment Period, you wait for the General Enrollment Period (January–March) and may owe a lifelong Part B late penalty — 10% per 12 months you were late — plus a Part D penalty that also never goes away. The penalty calculator shows what a delay would cost you, for life.
More than almost anything else. Original Medicare + Medigap travels with you — it works in both states, no networks. Most Medicare Advantage plans are county-based networks, which can make six months up north complicated. If you split the year, read the snowbird section of Medicare in Florida before choosing a path.
Original Medicare largely doesn't. Many Advantage plans include some dental/vision/hearing benefits (read the details — allowances vary widely), and standalone ancillary policies fill the gap for Medigap households. The ancillary coverage guide explains the options honestly.
Three lists: every doctor you'd hate to lose, every prescription with dosage, and the hospital you'd want in a bad year (here's how Palm Beach County hospitals fit in). With those three lists, any honest comparison — agent, SHINE, or Medicare.gov — gets 10× more useful.
The decisions that come right after the timeline:
Important: Smooth Health Solutions is not connected with or endorsed by the United States government or the federal Medicare program. We do not offer every plan available in your area. Currently we represent 0–78 organizations which offer 0–2,613 products in your area. The exact number of organizations and products depends on your ZIP code, county, and plan year. Please contact Medicare.gov, 1‑800‑MEDICARE (1‑800‑633‑4227; TTY 1‑877‑486‑2048), or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options. This page is for general education, reflects 2026 amounts published by CMS, and is not a complete description of benefits or a recommendation of any specific plan. Enrollment cannot be guaranteed until an application is accepted by the applicable insurance company or program.