How to Sign Up for Medicare in 2026 : Step-by-Step Guide for First-Timers Turning 65
If you’re turning 65 in 2026, and you’ve never had Medicare before, the process can feel confusing, especially with all the mailers, phone calls, and ads that start showing up.
This article, “How to Sign Up for Medicare in 2026,” is a step-by-step guide to help you understand exactly what to do (and when to do it) as you approach Medicare eligibility, written in plain English for people who are new to Medicare. If you live in Pasco, Hillsborough, Pinellas, Hernando, Citrus, or any of our other counties surrounding Tampa Bay, the process is the same.
If I miss anything, email us at support@myphss.com, and we’ll help you get a clear answer.
Table of Contents
Step 1: Know your “7-month Medicare signup window”
For most people turning 65, your first chance to enroll is called your Initial Enrollment Period (IEP).
It lasts 7 months:
3 months before the month you turn 65
Your birthday month
3 months after the month you turn 65
Important detail: If your birthday is on the first day of the month, your 7-month window starts one month earlier than usual.
Why this matters
If you miss your IEP and you don’t qualify for a Special Enrollment Period, you may have delays and late enrollment penalties for Part A (if you have to pay for it) and Part B.
Step 2: Decide if you’ll be automatically enrolled or if you must sign up
Here’s the simple rule:
You may be automatically enrolled at 65 if:
You are already getting Social Security benefits (or Railroad Retirement) far enough in advance, Medicare notes that automatic enrollment typically applies if you start receiving Social Security at least 4 months before you turn 65.
You must actively sign up if:
You are not receiving Social Security yet and want Medicare to start at 65. In that case, you sign up through Social Security.
Step 3: Choose whether you need Part B right away (this is where people mess up)
Medicare has “Parts,” but you only need to remember this:
Part A = hospital coverage
Part B = outpatient/doctor coverage
Most people need both to avoid coverage gaps.
If you’re NOT working (or you don’t have active employer coverage)
You usually enroll in Part A and Part B during your Initial Enrollment Period.
If you ARE still working and have employer coverage
You might be able to delay Part B without penalty, but only if your coverage is from a group health plan based on current employment (yours or a spouse’s). Medicare & You explains you can enroll in Part B later during a Special Enrollment Period tied to active employment and employer coverage.
Critical warning: Medicare & You is very clear that COBRA, retiree coverage, VA coverage, and individual Marketplace coverage do not count as “current employment” coverage for that Special Enrollment Period.
This is one of the biggest reasons people get stuck with penalties and gaps.
Step 4: Sign up for Medicare (the actual signup step)
In most cases, you sign up through Social Security, not Medicare.
The easiest way (online)
Social Security allows you to enroll online for:
Part A and Part B, or
Part A only (if delaying Part B for employer coverage)
Other ways
You can also call Social Security to enroll; SSA provides the main phone number and enrollment guidance.
Step 5: Know when your Medicare coverage will start
Timing matters. Medicare & You explains the start dates depending on when you enroll during your Initial Enrollment Period:
If you enroll in the first 3 months of your IEP, coverage generally starts the first day of your birthday month (or the prior month if your birthday is on the 1st).
If you enroll during your birthday month or the last 3 months of the IEP, your coverage starts the first day of the month after you sign up.
Step 6: Decide how you want your Medicare coverage “built” (two common paths)
Once you have Part A and Part B, you typically choose one of these paths:
Option A: Original Medicare + Part D + (optional) Medigap
Original Medicare (Part A and B)
Add a Part D drug plan (optional but common)
Add a Medicare Supplement (Medigap) if you want help with out-of-pocket costs
Option B: Medicare Advantage (Part C)
A Medicare Advantage plan usually bundles:
Part A + Part B coverage through a private plan
Often includes Part D drug coverage
You can only join these plans during certain enrollment periods, including your Initial Enrollment Period when you’re new to Medicare.
Local note: In the Tampa Bay area, plan networks and hospital systems can vary a lot by county and ZIP code. That’s why we always check doctors, prescriptions, and preferred hospitals before you enroll.
Step 7: Create a “Medicare folder” before you pick a plan (simple checklist)
Before you choose any plan, gather these:
A list of your medications (name + dosage)
Your doctors and specialists
Your preferred hospitals/medical groups
Your Florida zip code(s) (even within Tampa Bay, ZIP code can change plan availability)
Your expected retirement/working status for 2026
This one step prevents the most common mistake: picking a plan that looks good on price but doesn’t cover the doctors you actually use.
Step 8: Watch out for Medicare scams and pressure sales
If someone calls you out of the blue and tries to “verify your Medicare number,” “activate your benefits,” or rush you into a plan, slow down.
When in doubt, use official sources and written notices. Medicare-related fraud ramps up every year around enrollment seasons, so it’s worth being cautious.
Download "Medicare and You 2026 Handbook".
Every year, Medicare releases a new edition of the Medicare & You Handbook.” This is basically your Medicare Bible, and you should familiarize yourself with it. You can click the image to download a PDF version. If you need any other version, you can see all your options by clicking here.
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