Medicare Supplement Plans in Hawaii: What to Know for 2027

Thinking about a Medicare Supplement in Hawaii? This 2027 guide lays out the standardized plans (A through N), what each helps pay, and the enrollment rights that matter most — plainly, with no rankings.

Sorting out Medicare in Hawaii? The first thing worth knowing is that plan availability is set at the county level, not statewide — two people an hour apart can have genuinely different options. That's why this guide is organized city by city.

Statewide, about 54% of Hawaii Medicare members are in a Medicare Advantage plan rather than Original Medicare — an official figure that varies widely county to county.

On this page: the companies active in Hawaii, a plain-language explanation of how Medicare fits together, 2027 costs, enrollment timing, free help, and links to every Hawaii city guide. We don't rank or recommend plans.

What Medigap does — and doesn't — cover

Think of Medigap as the layer that sits on top of Original Medicare to absorb the costs it leaves you: the deductibles, the 20% coinsurance, the copays that otherwise have no annual ceiling.

The catch that trips people up is that these plans are federally standardized — a Plan G from one insurer covers exactly what a Plan G from another does. So the letter defines the benefits, and price and service are what separate companies. Medigap doesn't include drug coverage, so most people in Hawaii pair it with a stand-alone Part D plan.

Below we break down what each standardized plan covers and the enrollment rights that matter most in Hawaii. It's a framework, not a ranking — and we don't quote premiums.

The 2027 numbers, from shared to plan-specific

Start with what's fixed for everyone. The standard Part B premium is $202.90 per month in 2026 (2026 amount; 2027 figure will be posted when CMS releases it), and Part A is premium-free for most people who paid Medicare taxes long enough while working.

On the drug side, Part D has real guardrails for 2027: a deductible capped at $700 and, a hard $2,400 ceiling on your out-of-pocket costs for covered prescriptions — the old coverage gap is gone.

Higher earners pay more for Parts B and D through an income-related adjustment called IRMAA, which for 2026 starts above $109,000 in annual income for an individual and is based on your 2024 tax return. Most people fall below that line and pay the standard amounts. The 2027 brackets will be posted when CMS releases them.

Everything past that is plan-specific: the premiums, copays, and coverage details of an individual Advantage or Medigap plan change from plan to plan and year to year. Rather than quote or rank those, we point you to Medicare's Plan Finder and a licensed agent for your exact numbers.

When you can enroll or make changes

Medicare's enrollment windows are federal — the same nationwide — so the timing below applies wherever you live.

Your first window (IEP). When you're new to Medicare, your Initial Enrollment Period is the 7-month window around your 65th birthday month. Signing up on time helps you avoid late penalties that can follow you for years.

Annual Enrollment Period (AEP). Each fall, from October 15 – December 7, anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan. Changes take effect January 1.

Medicare Advantage Open Enrollment. From January 1 – March 31, if you're already in an Advantage plan you get one chance to switch plans or return to Original Medicare.

Special Enrollment Periods can also open after certain life events, like moving or losing other coverage. The interactive calendar further down lays the year out visually.

Getting unbiased help in Hawaii

You never have to make these decisions alone, and you don't have to pay for good help. A few free, trustworthy starting points:

Medicare.gov and 1-800-MEDICARE (TTY 1-877-486-2048) are the official sources for plan details and the Plan Finder. Licensed agents can also compare options with you and handle enrollment.

And to be clear about who we are: MyMedicarePlans.org is a privately owned, independent educational resource. We are not Medicare, not a government agency, and not affiliated with one. We publish plain-language information to help you get oriented — then point you to the official sources and licensed professionals for decisions about specific plans.

Hawaii cities

Pick your city for the county-level picture, the companies active in your area, and local guides: