Medicare made clear · Every island in Hawaii
Turning 65, retiring from the state or the county, or wondering whether your plan still covers the specialist you fly to Oahu for? Sit down with a credentialed independent agent who will walk you through Medicare Advantage, Medigap and Part D in plain English — patiently, and at no cost to you.
No cost, no obligation, no pressure.
Tell us a little about you and Darin will reach out. Prefer to talk now? Call (702) 706-6564.
Hawaii is different
Hawaii has two health plans that most of the state already belongs to, an ocean between most residents and the nearest specialist, and one of the highest Medicare Advantage enrollment rates in the country. Start with what is actually for sale on your island.
Most of Hawaii gets care through Kaiser Permanente’s own clinics and Moanalua Medical Center, or through HMSA’s network of Queen’s, Hawaii Pacific Health and independent doctors. Medigap does not pay inside Kaiser; keeping Kaiser on Medicare means Kaiser Senior Advantage. Which system you use decides the shortlist before price does.
How Advantage works in HawaiiAdvantage plans are sold by county, and Kaiser Senior Advantage’s service area is Honolulu County, most of Hawaii Island and the island of Maui. On Kauai, Molokai and Lanai the choice is shorter, and specialty care is often a flight away. A Medigap policy works at any Medicare provider on any island or the mainland.
Neighbor islands & traveling for careState and county retirees on EUTF must take Part B and get the premium reimbursed. Oahu’s military retirees reach 65 with TRICARE For Life waiting, and veterans who use the Matsunaga VA or the Akaka clinic still need Part B on time. Each is a different calculation.
Veterans & MedicareMedicare in 2026, at a glance
Premiums and deductibles change every year. Here are the current 2026 Original Medicare figures — we refresh them annually so you are never reading last year’s numbers.
Source: Centers for Medicare & Medicaid Services, 2026 Medicare Parts A & B Premiums and Deductibles (released November 14, 2025) and 2026 Part D parameters. Higher earners may pay an income-related surcharge (IRMAA) — see our 2026 costs & IRMAA page.
Where to start
There is no single “best” plan — only the one that fits your doctors, your prescriptions, your island and your travel. Here is the plain-English version of your choices.
All-in-one Part C plans, often $0 premium, that use a local network — in Hawaii that usually means choosing between Kaiser, HMSA and a few national carriers, island by island.
How Advantage worksMedigap pairs with Original Medicare and lets you see any provider that accepts Medicare — Queen’s, Straub, Hilo Benioff, or a specialist on the mainland.
How Medigap worksStandalone drug coverage chosen around your medications and pharmacy. 2026 out-of-pocket cap: $2,100.
How Part D worksAdvantage plans built for a chronic condition, for nursing-facility care, or for people with both Medicare and Med-QUEST.
About SNPsYour situation matters
The rules change a lot depending on what else you have and where you get your care. These are the situations Hawaii residents ask us about most.
Which plans follow you to Queen’s or Straub from Hilo, Lihue or Kaunakakai, what HMSA’s interisland travel benefit actually covers, and when a Medigap policy is the safer bet.
Neighbor island MedicareRetiring from the state, the DOE, UH or a county? EUTF requires Part B, reimburses the premium, and has a 60-day proof deadline that catches people. What to do and when.
Turning 65 & EUTFTRICARE For Life, Tripler, the Matsunaga VA, the Akaka clinic in Kapolei — and why Part B timing still matters.
Veterans & MedicareQUEST Integration, the Medicare Savings Programs that pay your Part B premium, and Dual Special Needs Plans that coordinate both.
Dual-eligible helpFree guide
A clear, step-by-step walk-through of your enrollment windows, the Hawaii-specific choices in front of you — Kaiser or HMSA, EUTF, neighbor island care — and the deadlines that carry a lifelong penalty if you miss them. No sign-up required.
Read the Turning 65 guide Get the free 295-page bookWho you’ll be working with
Gerontologist · Registered Social Security Analyst® · U.S. Air Force Veteran
Darin Weidauer (HI License #18580338) is an independent Medicare insurance agent, credentialed gerontologist, and Registered Social Security Analyst® who helps Hawaii retirees and people approaching 65 make sense of their options — clearly, patiently, and with no cost to them. A 22-year U.S. Air Force veteran who retired as an officer, Darin holds five master’s degrees, including an MBA and a Master’s in Dispute Resolution from Pepperdine and a Master’s in Long-Term Care from USC, and became a credentialed gerontologist in 2014 — studying the human side of aging, not just the paperwork.
A former Professor of Aerospace Studies at Loyola Marymount University who has lectured at more than 50 colleges and universities, Darin now channels that teaching instinct into plain-English Medicare education through one-on-one reviews, no-cost workshops, and his book Retire With Confidence. More about Darin →
Serving communities across Hawaii
We work with people on every island by phone and video. Find Medicare guidance for your town:
Or explore Medicare by region — the parts of the state we all know by name:
Near a base? We help military retirees and veterans coordinate TRICARE, VA care and Medicare:
Questions Hawaii residents ask
There is no cost to you. Independent Medicare agents are paid by the insurance carriers when you enroll, so our help comparing plans, answering questions, and reviewing your coverage each year is free. Your plan premium is the same whether you enroll with our help or on your own.
Yes, through Kaiser Permanente Senior Advantage, Kaiser’s own Medicare Advantage plan. Kaiser is an integrated system, so a Medigap policy does not pay for care inside it; if you want to keep your Kaiser doctors, Senior Advantage is the way. Its service area is Honolulu County, most of Hawaii County and the island of Maui, so we check that your island and your ZIP code are inside it.
Original Medicare with a Medigap policy covers any provider that accepts Medicare, on any island or the mainland, with no referral or travel rule. HMSA’s neighbor island Akamai Advantage plans include help with interisland travel when HMSA refers you to a specialist on another island; Kaiser refers within its own system. We read the plan’s travel rules with you before you enroll.
Most people first enroll during their Initial Enrollment Period, the seven months around their 65th birthday. After that, the Annual Election Period runs October 15 to December 7 each year, and the Medicare Advantage Open Enrollment Period runs January 1 to March 31. Moving to another island, losing a plan, or qualifying for Med-QUEST opens a Special Enrollment Period.
EUTF retiree medical plans require you to enroll in Medicare Part B when you become eligible and to send EUTF proof within 60 days, or the retiree plan is cancelled. EUTF then reimburses eligible retirees for the Part B premium. We walk through the timing so nothing lapses.
No — and we will always be upfront about that. We represent a number of insurance organizations and products in Hawaii, not all of them. The easiest next step is to call us at (702) 706-6564 and we will walk through what fits you. To compare every option on your own, Medicare.gov, 1-800-MEDICARE, and Hawaii SHIP (1-888-875-9229) have the complete list.
Ready when you are
A short, friendly conversation — no pressure, no cost. We’ll look at your doctors, your prescriptions, your island and your travel together.
Written and reviewed by Darin Weidauer — licensed insurance agent (NPN 18580338, HI License #18580338), Gerontologist (USC Leonard Davis School of Gerontology), MBA, Registered Social Security Analyst, and 22-year U.S. Air Force veteran.Last reviewed September 13, 2026. Plan availability, benefits and costs change every plan year — verify current details at Medicare.gov, 1-800-MEDICARE, or Hawaii SHIP at 1-888-875-9229.