Early Retirement Health Insurance Checklist for Florida (Ages 55-64)

By Licensed Florida Health Insurance Agents Updated April 2026

Retiring before 65 is a dream for many Floridians — and health insurance is the single biggest obstacle standing between that dream and reality. Without the right plan, healthcare costs during the bridge years from early retirement to Medicare can consume a staggering portion of your savings. With the right plan, it becomes a manageable expense.

This checklist walks you through every step, from the moment you start considering early retirement through the day you transition to Medicare. Print it out, share it with your financial advisor, and check off each item as you go.

Phase 1: Pre-Retirement Planning (6-12 Months Before You Retire)

Checklist Item 1: Know Your Exact Employer Coverage End Date

Contact your HR department and get written confirmation of the exact date your employer health insurance ends. Common scenarios:

Last day of the month you leave: If you retire on March 15, coverage ends March 31. This is the most common arrangement.
Your last day of employment: If you retire on March 15, coverage ends March 15. Less common but some employers do this.
End of the following month: Some generous employers extend coverage one month past your departure. Rare but worth asking about.

Knowing this date precisely is critical because it determines when your Special Enrollment Period begins and when you need new coverage to start.

Checklist Item 2: Request Your COBRA Information

Ask HR for the following COBRA details in advance:

Monthly COBRA premium for your current plan (this is the full premium — employer + employee portion — plus up to a 2% administrative fee)
Coverage options available under COBRA (sometimes you can choose a different plan tier)
COBRA election deadline (60 days from coverage end or COBRA notice, whichever is later)

You likely will not choose COBRA, but you need the numbers for comparison. COBRA for a couple ages 55-64 typically runs $1,800-$2,800/month. That is $21,600-$33,600 per year.

Checklist Item 3: Inventory Your Healthcare Needs

Create a complete list of:

All current prescription medications (drug name, dosage, frequency)
Your primary care physician and their practice/group
All specialists you see regularly
Any ongoing treatments or upcoming planned procedures
Preferred hospitals and imaging centers
Current medical equipment or supplies (CPAP, insulin pump, etc.)

This list is essential for comparing marketplace plans. A plan that does not cover your medications or include your doctors is not truly cheaper — it is just shifting costs to you in a less visible way.

Checklist Item 4: Schedule Pending Medical Care

While you still have employer coverage with its typically lower deductibles and copays:

Complete any deferred medical procedures
Get dental work done (especially if your employer plan has dental)
Schedule annual physicals and screenings
Fill 90-day prescription supplies before your coverage ends
Get updated prescriptions from your doctors
Complete vision exams and get updated eyewear prescriptions

Checklist Item 5: Project Your Retirement Income

Work with your financial advisor to project your modified adjusted gross income (MAGI) for the year you retire and each subsequent year. Include:

Pension income (if applicable)
Social Security (if you plan to claim before 65)
Traditional IRA/401(k) withdrawals
Roth conversions (count as income)
Capital gains from investment sales
Dividend and interest income
Rental property income
Part-time or consulting work income

Your projected MAGI determines your ACA subsidy. The difference between a $50,000 MAGI and a $100,000 MAGI could mean $12,000+ per year in premium savings for a couple.

Checklist Item 6: Optimize Your Income Strategy for Subsidies

Based on your income projection, explore strategies to lower MAGI:

Delay Social Security. Benefits you do not take do not count as income. Delaying also increases your eventual monthly benefit by approximately 8% per year from age 62 to 70.
Draw from Roth accounts. Roth IRA and Roth 401(k) withdrawals do not count as MAGI. If you have Roth savings, using these during the bridge period keeps income low.
Minimize traditional account withdrawals. Every dollar you pull from a traditional IRA or 401(k) counts as income. Withdraw only what you need.
Plan Roth conversions carefully. Roth conversions are smart for long-term tax planning but increase your MAGI in the conversion year. Balance conversion amounts against subsidy impact.
Time capital gains. If you need to rebalance your portfolio or sell assets, plan the timing to avoid large income spikes in any single year.

Checklist Item 7: Research Marketplace Plans in Your County

Before you retire, preview the marketplace plans available in your Florida county:

Visit Healthcare.gov and browse plans (you can preview without applying)
Note which carriers are available in your area
Check if your doctors are in-network for each carrier
Verify your medications are on each plan's formulary
Compare premiums at different income levels to understand the subsidy structure

Checklist Item 8: Choose Your Retirement Date Strategically

If you have flexibility on timing:

Best timing: Retire in January or early in the year. This means most of the calendar year will have lower retirement income instead of your full salary, resulting in a lower MAGI and higher subsidies for that year.
Avoid: Retiring in November or December. Ten to eleven months of full salary will push your annual income too high for significant subsidies in the retirement year.
Alternative: If you must retire late in the year, consider timing it for just after January 1 of the following year instead.

Phase 2: The Transition (0-60 Days After Retirement)

Checklist Item 9: Confirm Your Coverage End Date

On your last day, verify with HR exactly when your health coverage ends. Get it in writing (email is fine). You need this date for your marketplace application.

Checklist Item 10: Do NOT Automatically Elect COBRA

You will receive a COBRA election notice from your employer or their COBRA administrator. Key facts:

You have 60 days to elect COBRA from the date of the notice or the date you lose coverage, whichever is later.
COBRA is retroactive. If you elect within 60 days, coverage goes back to the day your employer plan ended, with no gap.
This gives you a safety net: if something happens medically during the transition period, you can elect COBRA retroactively to cover it.
Do NOT elect COBRA preemptively unless you specifically need to maintain your current plan for a medical reason (like an ongoing treatment series with a specific provider).

Checklist Item 11: Apply for Marketplace Coverage Immediately

You have a 60-day Special Enrollment Period (SEP) triggered by loss of employer coverage. Do not wait until the last day.

Go to Healthcare.gov or call the marketplace at 1-800-318-2596.
Have ready: Social Security numbers for both spouses, projected annual income, your coverage end date, and information about any other coverage available (including COBRA).
Choose a start date for your new plan. Marketplace plans can start as early as the first of the month following your application.
Select your plan based on the research you did in Phase 1.

Checklist Item 12: Compare COBRA vs. Marketplace One Final Time

Before committing to a marketplace plan, do a final side-by-side comparison:

Monthly premium: COBRA premium vs. marketplace premium after subsidy
Network: Can you keep your doctors on the marketplace plan? If not, how important is that?
Deductible reset: If you have already met your deductible on your employer plan and COBRA continues that plan, your deductible remains met through the end of the plan year. Switching to a marketplace plan means starting a new deductible from zero.
Ongoing treatment: If you are in the middle of a treatment series (chemotherapy, physical therapy, etc.), continuity of care may favor COBRA for the short term.

Checklist Item 13: Set Up Dental and Vision Coverage

Most ACA marketplace plans do not include adult dental and vision coverage. If you had these through your employer, you will need separate plans:

Standalone dental plans are available on and off the marketplace, typically $30-$60/month per person.
Vision plans cost $10-$20/month per person.
Some carriers (like Florida Blue) offer bundled dental and vision products you can add to your health plan.

Checklist Item 14: Address Prescription Drug Continuity

Verify all current medications are on your new plan's formulary before enrolling.
If a medication is not on formulary, ask your doctor about therapeutic alternatives that are covered.
Request prior authorizations from your new plan before your old coverage ends, if possible.
Use a pharmacy discount card (like GoodRx) as a backup during any transition gaps.

Phase 3: Annual Maintenance (Each Year Until Medicare)

Checklist Item 15: Re-Evaluate Your Plan During Open Enrollment Every Year

Open enrollment runs from November 1 through January 15 each year. Every year you should:

Log into your Healthcare.gov account and review available plans for the new year.
Check for new carriers entering your market or existing carriers changing networks.
Update your income estimate for the coming year.
Compare at least 3-4 plans across different carriers and metal tiers.
Verify your doctors and medications are still covered by your chosen plan.

Plans change every year. A plan that was the best value this year may not be next year. Never auto-renew without checking.

Checklist Item 16: Update Your Income Estimate as Needed

If your income changes during the year (you start part-time work, sell investments, or begin receiving a pension), update your estimate on Healthcare.gov. This adjusts your monthly subsidy so you do not face a large reconciliation at tax time.

Checklist Item 17: Maximize HSA Contributions (If Eligible)

If you are on an HSA-eligible high-deductible plan:

Contribute the maximum: $8,550 for family coverage in 2026, plus $1,000 catch-up if age 55+.
Use the HSA strategically: pay current medical expenses out of pocket if you can, and let the HSA grow tax-free for future use.
Remember: you must stop HSA contributions when you enroll in Medicare.

Checklist Item 18: Monitor Your MAGI Throughout the Year

Keep a running estimate of your annual MAGI. If you are approaching a subsidy cliff or CSR threshold, you may want to adjust your income strategy mid-year. For example:

Delay selling appreciated assets to the following year
Reduce traditional IRA withdrawals and supplement with Roth withdrawals
Defer part-time income if possible

Checklist Item 19: Keep All Health Insurance Documentation

Maintain organized records of:

Form 1095-A (Health Insurance Marketplace Statement) — you need this for your tax return
Premium payment records
Explanation of Benefits (EOBs) from your insurance carrier
All medical receipts if you have an HSA
COBRA election notice and any related correspondence

Phase 4: Medicare Transition (The Year You Turn 64-65)

Checklist Item 20: Understand Your Medicare Timeline

Your Initial Enrollment Period (IEP) for Medicare is a 7-month window:

Begins 3 months before the month you turn 65
Includes the month you turn 65
Ends 3 months after the month you turn 65

For the earliest coverage start date, enroll during the 3 months before your birthday month.

Checklist Item 21: Enroll in Medicare Part A and Part B

Part A (Hospital Insurance): Premium-free for most people (if you or your spouse paid Medicare taxes for 40+ quarters). Enroll even if you do not think you need it — there is no cost and late enrollment penalties apply.
Part B (Medical Insurance): Standard premium is approximately $185/month in 2026, with income-related surcharges (IRMAA) for higher earners. IRMAA is based on your MAGI from two years prior.
Enroll at SSA.gov or at your local Social Security office.

Checklist Item 22: Choose Your Medicare Supplement Strategy

You have two main paths:

Medicare Supplement (Medigap) + Part D: Original Medicare with a Medigap plan covers virtually all your medical costs with any doctor who accepts Medicare. Add a standalone Part D plan for prescriptions. This is the most flexible option.
Medicare Advantage (Part C): An all-in-one plan from a private carrier that replaces Original Medicare. Often includes drug coverage, dental, and vision. Lower monthly cost but typically requires using in-network providers.

Checklist Item 23: Coordinate Your Marketplace-to-Medicare Transition

Your marketplace plan should end the day before your Medicare coverage begins.
Contact the marketplace to terminate your plan as of your Medicare start date. Do not just stop paying — formally end the plan to avoid being charged.
If your spouse is younger than 65, they continue on the marketplace plan. Update the household information to reflect one person.
Recalculate the younger spouse's subsidy based on the updated household coverage situation.

Checklist Item 24: Stop HSA Contributions

You must stop contributing to your HSA the month your Medicare coverage begins (or up to 6 months before if you enroll in Part A retroactively). You can still use existing HSA funds tax-free for medical expenses, including Medicare premiums.

Critical Mistakes to Avoid

Mistake 1: Assuming You Cannot Afford Coverage

Many early retirees look at unsubsidized premiums ($1,500-$2,500/month for a couple) and panic. With proper income management, subsidized marketplace premiums for the same couple can be $200-$600/month. Do not make retirement decisions based on sticker-price premiums.

Mistake 2: Retiring Without a Coverage Plan

Some people retire impulsively — a bad day at work, a buyout offer — without first mapping out their health insurance strategy. This often leads to expensive COBRA elections or gaps in coverage. Plan before you resign.

Mistake 3: Missing Enrollment Deadlines

You have 60 days from losing employer coverage to enroll in a marketplace plan. Miss this window and you wait until the next open enrollment period, which could leave you uninsured for months. Mark the deadline on your calendar immediately.

Mistake 4: Ignoring the Income-Subsidy Connection

A $30,000 Roth conversion might make tax sense in isolation but could cost you $5,000 in lost health insurance subsidies. Every financial decision during the bridge years should be evaluated for its impact on ACA subsidies.

Mistake 5: Not Enrolling in Medicare on Time

If you miss your Medicare Initial Enrollment Period, you face a permanent late enrollment penalty on Part B premiums (10% for each full 12-month period you were eligible but not enrolled). This penalty lasts for as long as you have Part B — potentially decades.

Mistake 6: Choosing a Plan Based Only on Premium

The cheapest monthly premium is not always the cheapest plan. A $200/month Bronze plan with a $9,200 deductible will cost you far more than a $450/month Gold plan with a $2,000 deductible if you need surgery or ongoing treatment. Consider your likely total costs, not just the monthly bill.

Your Next Step

If you are planning early retirement in Florida, health insurance planning should start at least 6-12 months before your target date. At Find My Health Coverage, we specialize in helping Florida residents navigate this exact transition. We will walk through this checklist with you, compare your specific plan options, and help you enroll in the coverage that best protects your health and your savings.

Our services are free — we are compensated by the insurance carriers. Contact us to schedule your pre-retirement health insurance consultation.