Medicare 2026

How the Medicare Timeline Works in Kailua Kona

KAILUA-KONA, Hawaii — Turning 65 on the Big Island comes with a big mailbox moment: your first real Medicare decisions. The good news is that the timeline is set by federal rules, so you don't have to guess when to act. If you plan around your birthday and know what each "part" of Medicare does, the process gets a lot less stressful.

Know your 7-month window

Your Initial Enrollment Period runs for seven months. It starts three months before the month you turn 65, includes your birthday month, and ends three months after. This is the window most people use to sign up for Part A (hospital) and Part B (doctor and outpatient) coverage.

Timing inside that window matters. If you enroll during the three months before your birthday month, your coverage usually starts on the first day of your birthday month. If you wait until your birthday month or after, your start date is pushed back. For most Kailua-Kona residents who don't have other coverage, signing up early in the window is the simplest way to avoid a gap.

The parts, in plain language

Original Medicare has two pieces: Part A (hospital stays, skilled nursing, hospice) and Part B (doctor visits, outpatient care, preventive services). Most people get Part A with no premium because they or a spouse paid Medicare taxes while working. Part B has a monthly premium set each year by the federal government.

From there, you have a choice:

• Original Medicare + Part D (a separate drug plan), often paired with a Medigap (Medicare Supplement) policy that helps with out-of-pocket costs.
• Medicare Advantage (Part C), a private plan that bundles Parts A, B, and usually D together, sometimes with extras.

You can't be enrolled in both a Medicare Advantage plan and a Medigap policy at the same time, so this is a real fork in the road. Take your time with it.

What's new for drug coverage in 2027

If you take prescriptions, the Part D rules have changed a lot in the last two years — mostly in favor of the consumer.

• The annual out-of-pocket cap for covered drugs is $2,100 in 2026. Once you hit it, you pay $0 for covered prescriptions for the rest of the year.
• The maximum Part D deductible is $615 for 2026 (plans can set a lower one).
• The coverage gap ("donut hole") is gone as of 2025. Part D now has three phases instead of four.
• The Medicare Prescription Payment Plan lets you spread your drug costs out in monthly payments through your plan, at no extra charge, if a big bill would be hard to handle all at once.

If you're still working — or your spouse is

Some folks in Kailua-Kona keep working past 65, or are covered by a spouse's job plan. If your employer has 20 or more employees, you may be able to delay Part B without a late penalty and sign up later through a Special Enrollment Period. If the employer is smaller, Medicare often becomes the primary payer at 65, and delaying Part B can cause problems.

Before you assume anything, ask your HR or benefits office in writing how your coverage works with Medicare, and call 1-800-MEDICARE or Hawaii SHIP to confirm.

A quick local snapshot

Kailua-Kona is in Hawaii County, and Medicare plan choices — both Medicare Advantage and stand-alone Part D — are set at the county level. That means a Kona resident and someone in Waimea generally see the same menu of plans, while Oahu residents may see a different one. When you compare options on Medicare.gov's Plan Finder, enter your ZIP code so the results match what's actually available where you live.

Availability and plan details change every year, so even if you helped a parent or friend sign up recently, don't assume the same choices apply to you.

What higher earners should know

Most people pay the standard Part B and Part D premiums. But if your income is above certain limits, you'll pay an extra amount called IRMAA (Income-Related Monthly Adjustment Amount). For 2026, IRMAA surcharges start above $109,000 in income for a single filer (higher for joint filers). Social Security uses your tax return from two years earlier to decide.

If your income has dropped since then — because you retired, for example — you can ask Social Security to reconsider.

Your first steps, in order

1. Mark your 7-month window on a calendar, starting 3 months before your birthday month. 2. Decide about Part B based on any current job-based coverage. 3. Enroll in Part A and Part B through SSA.gov, by calling Social Security, or at a local office (unless you're already getting Social Security, in which case you'll be enrolled automatically). 4. Choose your path: Original Medicare (usually with Part D and often Medigap) or Medicare Advantage. 5. Compare drug plans on Medicare.gov's Plan Finder using your prescriptions and preferred pharmacies.

If you miss your IEP, the next general chance to sign up is the Annual Enrollment Period, Oct. 15 – Dec. 7, or the Medicare Advantage Open Enrollment Period, Jan. 1 – March 31, for people already in an Advantage plan.