Medicare, Made Clear — Before the Deadlines Decide for You.
The average Tampa-area beneficiary chooses from 133 plan options (CMS, 2026). We turn that noise into a side-by-side decision built on your doctors, your prescriptions and your budget — with every deadline mapped.
What are my two paths onto Medicare?
Path one: Original Medicare + a Supplement (Medigap) + Part D. You keep federal Medicare as your primary coverage, add a Supplement to fill its cost gaps (like the $1,736 Part A hospital deductible, per CMS.gov), and add a standalone drug plan. Any doctor who accepts Medicare, anywhere in the country, no referrals.
Path two: Medicare Advantage (Part C). A private plan replaces how you receive your benefits — usually bundling drug coverage and extras like dental or vision, often at $0 or low monthly plan premium, in exchange for provider networks and plan rules. A $0 premium is never "free coverage": you still pay your Part B premium and the plan's cost-sharing when you use care.
Which path is right for me?
Honest answer: it depends on variables only you have — your doctors, your prescription list, how much you travel, and how you'd rather pay (steady premiums vs. pay-as-you-go). Our job is to run both paths against your real inputs. In 2026 the math changed again: the $2,100 Part D out-of-pocket cap (CMS.gov) means drug-heavy households should re-run comparisons they last did years ago.
What deadlines do I need to know?
Your Initial Enrollment Period is the 7-month window around your 65th birthday. The Annual Enrollment Period (October 15 – December 7) is when existing beneficiaries can change plans. Miss your window without creditable coverage and the Part B late-enrollment penalty adds 10% per full 12-month delay — for life (Medicare.gov). Full details in our enrollment periods guide, or estimate your own exposure with the penalty calculator.
How does a SkyWell Medicare review work?
Three steps. 1) Listen: your doctors, drug list, budget and travel. 2) Compare: we screen the plans available in your county — all 133 options in Hillsborough for 2026 — down to the few that genuinely fit. 3) Decide together: you see the side-by-side, you pick, we handle the enrollment paperwork and stay your point of contact all year, including your annual re-review.
Medicare Planning FAQ
Should I choose Medicare Advantage or a Medicare Supplement?
It depends on how you weigh premiums against flexibility. Advantage plans often have $0 or low monthly premiums but use networks and prior authorization; Supplements cost more monthly but let you see any provider who accepts Medicare with predictable out-of-pocket costs. We compare both against your doctors, drugs and travel patterns.
What does Medicare cost in 2026?
The standard Part B premium is $202.90/month with a $283 deductible; the Part A hospital deductible is $1,736 per benefit period; Part D out-of-pocket drug costs are capped at $2,100 for the year (source: CMS.gov).
How many plans should I actually compare?
In Hillsborough County there are 133 MA and Part D options for 2026 (CMS CY2026 Landscape). We narrow that to the 2–3 that genuinely fit your doctors, prescriptions and budget — then show you why.
Do I pay more using an agent?
No. Premiums are identical whether you enroll through an agent or directly with the carrier. Our compensation comes from the carriers we represent.
What if I'm still working at 65?
You may be able to delay Part B without penalty if you have creditable employer coverage. Getting this call wrong triggers a lifelong penalty of 10% per full 12-month delay — it's the single most important timing question we answer.
Turning 65 in the next year?
That's the perfect time to talk — free consultation, no pressure.