Turning 65? Your Complete Florida Medicare Checklist
A step-by-step guide to enrollment timing, coverage decisions, and what to prepare before Medicare begins.
Read the Turning 65 GuideHamilton Insurance Agency
Medicare SolutionsNeed to Enroll?Questions About Medicare?Ask Steve!
Medicare doesn't have to feel overwhelming.
Between Original Medicare, Medicare Supplement (Medigap), Medicare Advantage, and Part D, there's a lot to sort through—but it doesn't have to be confusing. I'm here to make it simple. I'll walk you through your options in plain language, answer your questions honestly, and help you find coverage that fits your health needs, your doctors, your prescriptions, and your budget.
When you're ready, I'll help you enroll in the plan you choose. Let's make this easy.
Compare Original Medicare, Medigap, and Medicare Advantage →
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Medicare Guidance
Compare Your Medicare Options
Understand how Original Medicare, Medicare Advantage, Medigap, and Part D fit together before choosing a coverage path.
Compare Medicare OptionsWhat Does Medicare Really Cost?
Learn how premiums, deductibles, coinsurance, maximum out-of-pocket limits, and IRMAA affect total Medicare costs.
Read the Medicare Costs GuideThe Complete Medicare Part D Guide
Understand formularies, drug tiers, pharmacy networks, deductibles, penalties, and prescription cost limits.
Read the Part D GuideNeed an answer?
Have a Medicare Question?
Search real Medicare questions and clear educational answers in the Steve Answers library.
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See Steve’s Local Event Schedule
Find upcoming Medicare information tables at Walmart, CVS, Walgreens, and other local locations.
View Steve’s ScheduleStart Here
Complete these two steps before comparing Medicare plans.
Turning 65? Your Complete Florida Medicare ChecklistEnrollment timeline • Step-by-step guide→
Compare Your Medicare OptionsOriginal Medicare • Medigap • Medicare Advantage→
Start with the checklist or compare the major Medicare coverage paths.
Ready for a practical plan comparison?
Compare Medicare Plans (opens the external SunFire platform in a new tab)
This secondary link opens a third-party SunFire plan-comparison platform associated with Steve Hamilton. AskSteveMedicare.com does not control SunFire’s privacy or data practices.
We do not offer every plan available in your area. Currently we represent 16 organizations which offer 512 products in Florida. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.
New to Medicare? Start with plain-English answers before you choose a plan.
Visit the Learning CenterWeekly Featured Medicare Question
I may need hip surgery. Is there financial help with my living expenses while I recover?
Medicare and Medicaid primarily cover healthcare and generally do not replace wages or routinely pay personal living expenses. However, Florida and Hernando County residents may qualify for separate programs that help with food, utilities, housing stability, transportation, or other essential needs.
Read Steve’s AnswerPopular Medicare Questions
Start with the question you need answered.
These are the questions people often ask before turning 65, retiring, or reviewing Medicare coverage.
65
Turning 65?
Know your enrollment timeline and avoid costly mistakes.
MAMedicare Advantage or Supplement?
Understand the difference before comparing plans.
RxWhat about prescriptions?
Review Part D, formularies, pharmacies, and drug costs.
ACACan I keep ACA after 65?
Learn what to review before making that decision.
Local guidanceServing clients throughout Florida, with in-person help at local Walmart tables in Hernando and Lake counties.
Independent brokerHelp comparing options from multiple insurance companies.
Education firstClear answers before plan decisions.
No-cost consultationPersonalized Medicare guidance at no cost to you.
Steve's Medicare Tip
A practical thought before you compare plansDo not choose a Medicare plan until you have checked your doctors, prescriptions, preferred pharmacy, and total expected costs—not just the monthly premium.
DoctorsPrescriptionsPharmacyTotal costs
About Steve
Helping Florida seniors understand Medicare—one question at a time.
Steve Hamilton is a Florida licensed insurance professional with Hamilton Insurance Agency. His approach is simple: help people understand Medicare clearly so they can make informed decisions with confidence.
If you are turning 65, retiring, moving to Florida, comparing Medicare Advantage and Supplement options, or reviewing prescription drug coverage, Steve can help you ask the right questions.
Florida Medicare Advantage
16 Carrier Appointments
Medicare Advantage Carriers I’m Appointed With
Steve is appointed with 16 Medicare Advantage carriers serving Florida, giving clients access to a broad range of plan options.
- UnitedHealthcare
- Aetna
- Humana
- CarePlus
- Florida Blue
- Devoted
- HealthSpring (Cigna)
- Wellcare
- Optimum
- Freedom
- Simply
- Ultimate
- Gold Kidney
- Doctors HealthCare Plans
- Health First Health Plans
- BayCare
Also available: PACE (Program of All-Inclusive Care for the Elderly) for those who qualify.
We do not offer every plan available in your area. Currently we represent 16 organizations which offer 512 products in Florida. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.
Contact Steve
Ask your Medicare question.
Call or email Steve for clear Medicare guidance. No pressure. Just answers.
Educational Information
The information on Ask Steve is provided for educational purposes to help you better understand Medicare and your coverage options. Medicare rules, enrollment periods, costs, plan availability, provider networks, and benefits may change over time.
Every person's situation is unique. Your eligibility, enrollment dates, employer coverage, prescription drug needs, healthcare providers, and financial circumstances may affect the Medicare options available to you.
Hamilton Insurance Agency is an independent insurance agency and is not connected with or endorsed by the U.S. government or the federal Medicare program.