Stuart, FL Retirement Advisor — Treasure Coast
Florida Retirement Checklist:
47 Steps Before You Retire
This comprehensive Florida retirement checklist covers every critical action item — from Social Security timing and Medicare enrollment to homestead exemptions and Roth conversion windows — so you can retire with confidence, not guesswork. Whether you’re 18 months out or already considering your transition, these 47 concrete steps will help you avoid costly mistakes and maximize every dollar you’ve saved.
THOMAS DAVIES, CFS · 30+ YEARS EXPERIENCE · FEE-BASED FIDUCIARY · STUART, FLORIDA
Why This Matters
Why Every Pre-Retiree Needs a Florida Retirement Checklist
Retirement in Florida is genuinely different from retirement anywhere else in the country. No state income tax, a robust homestead exemption, hurricane season insurance considerations, a massive Medicare-enrolled population, and a real estate market unlike any other in the Southeast — these variables demand a checklist built specifically for Florida residents, not a generic national template.
At Davies Wealth Management, we’ve guided hundreds of Treasure Coast families through this exact transition. What we’ve learned over 30 years is that the retirees who fare best aren’t necessarily those with the largest portfolios — they’re the ones who made the right decisions in the 18 to 36 months before they retired. Social Security elections, Roth conversion windows, Medicare enrollment deadlines, and beneficiary designations are all largely irreversible once the window closes.
This Florida retirement planning checklist is organized into eight categories. Work through each one sequentially, ideally with a fiduciary advisor who can evaluate how each decision interacts with your specific tax situation, income sources, and family circumstances. Explore our broader Florida Retirement Guide for additional planning resources.
The Cost of Skipping Steps
- ❌ Wrong Social Security timing — up to 32% permanent benefit reduction
- ❌ Missing Medicare enrollment — 10% premium penalty per year for life
- ❌ Skipping Roth conversions — RMDs push you into higher bracket permanently
- ❌ No LTC plan — average Florida nursing home: $100,000+/year
- ❌ No homestead filing — missed property tax savings every year
- ❌ Outdated beneficiaries — assets bypass your will and go to wrong recipients
The 47-Step Checklist
Florida Retirement Checklist: Categories 1–4
The first four categories of your pre-retirement checklist address the financial foundations: income streams, healthcare coverage, tax efficiency, and investment account structure. These decisions are deeply interconnected — your Social Security election affects your Medicare premiums, which affect your tax bracket, which affects your Roth conversion strategy.
Category 1: Income Planning (Steps 1–7)
Social Security timing, pension elections, and bridge income strategies
- Run a Social Security break-even analysis. Delaying Social Security from age 62 to 70 increases your benefit by approximately 77%. Determine the break-even age and whether your health, assets, and spouse’s benefit make delay worthwhile. Review SSA’s official retirement planning tools.
- Evaluate spousal and survivor benefit coordination. The higher earner delaying benefits protects the surviving spouse — this single decision can mean $200,000+ in additional lifetime income for married couples.
- Identify your bridge income strategy. If you retire before 70 but want to delay Social Security, map out exactly which accounts will fund the gap years so you’re not forced to claim early.
- Review all pension elections before you sign. Single-life vs. joint-and-survivor options are irrevocable. Model the break-even for each payout option relative to your spouse’s age and health.
- Calculate your income floor. Add Social Security, pension, and any annuity income together. Your “floor” should ideally cover non-discretionary expenses (housing, food, healthcare) without portfolio withdrawals.
- Build a written income distribution plan for Year 1. Know exactly which account you’ll draw from first and why. Tax-inefficient withdrawal sequencing can cost retirees tens of thousands of dollars over a 30-year retirement.
- Model your portfolio withdrawal rate. A 4% initial withdrawal rate is often cited, but your sustainable rate depends on asset allocation, sequence-of-returns risk, and Social Security start date. Run scenario analyses before finalizing.
Category 2: Medicare & Healthcare (Steps 8–14)
Enrollment windows, Part B premiums, and IRMAA avoidance
- Mark your Medicare Initial Enrollment Period on the calendar. Your 7-month window opens 3 months before your 65th birthday. Missing it triggers permanent Part B late enrollment penalties of 10% per 12-month period. See Medicare’s official enrollment timeline.
- Understand your IRMAA exposure. Medicare Part B and D premiums surcharges (IRMAA) are based on your income from two years prior. In 2024, IRMAA can add $594–$838/month per person. See our Medicare IRMAA Guide for detailed bracket management strategies.
- Choose between Medicare Supplement (Medigap) and Medicare Advantage before 65. In Florida, Medigap guaranteed-issue rights exist only when you first enroll. Waiting and then trying to switch can result in medical underwriting and denial.
- Enroll in Part D drug coverage or confirm creditable coverage. Even if you take no prescriptions today, late enrollment penalties apply and accumulate for life. The penalty is 1% of the national base beneficiary premium for each month you delayed.
- If retiring before 65, plan your bridge healthcare coverage explicitly. COBRA, ACA marketplace plans, and spouse’s employer coverage are your main options. Model the monthly cost — ACA subsidies phase out based on income, so Roth conversions may affect your premium subsidy eligibility.
- Schedule a Medicare IRMAA review with your advisor. If you had a major income event (sale of business, large Roth conversion, property sale) that spiked your MAGI, you can file Form SSA-44 to request a lower IRMAA surcharge using more recent income data.
- Budget for out-of-pocket healthcare costs. Fidelity estimates a 65-year-old couple will spend $315,000 on healthcare in retirement, excluding long-term care. Build this into your retirement income model explicitly — don’t treat healthcare as a residual expense.
Category 3: Tax Planning (Steps 15–22)
Roth conversion windows, estimated payments, and last-working-year strategies
- Identify your Roth conversion window. The years between retirement and age 73 (when RMDs begin) are often your lowest-income years. Converting traditional IRA assets to Roth during this window can dramatically reduce lifetime tax liability.
- Calculate your RMD projection at age 73. Use the IRS Uniform Lifetime Table to estimate what your required minimum distributions will be. If they’ll push you into a higher bracket or trigger IRMAA, accelerating Roth conversions now may be the highest-value financial move available to you.
- Execute last-working-year tax strategies. Maximize 401(k)/403(b) contributions, use any remaining FSA or HSA funds, and consider bunching deductions if you’re near itemization thresholds. Your marginal rate this year may be higher than any year in retirement.
- Set up estimated quarterly tax payments. Without employer withholding, you’re responsible for quarterly payments. Underpayment penalties apply if you owe more than $1,000 at filing. Consult the IRS estimated tax rules for safe harbor thresholds.
- Harvest capital losses and review unrealized gains before year-end. Retiring often coincides with portfolio rebalancing. Tax-loss harvesting in the transition year can offset capital gains from rebalancing or partial Roth conversions.
- Review whether qualified charitable distributions (QCDs) make sense. At age 70½, you can donate up to $105,000 annually directly from your IRA to charity — it counts toward your RMD and reduces your adjusted gross income, which can lower IRMAA and reduce taxation of Social Security benefits.
- Model the impact of Social Security benefit taxation. Up to 85% of Social Security benefits are taxable at the federal level if your “combined income” exceeds certain thresholds. Understand where you’ll fall so you can manage income sources accordingly.
- Engage a CPA who specializes in retirement taxation. Retirement tax planning is significantly more complex than working-years tax preparation. The interaction of RMDs, Social Security, IRMAA, and Roth accounts requires someone who plans, not just prepares.
- Review the tax treatment of inherited IRA accounts you hold. SECURE Act 2.0 changed the rules significantly. Non-spouse beneficiaries must now deplete inherited IRAs within 10 years, which can cause large, bracket-bumping distributions if not managed proactively.
Category 4: Investment Accounts (Steps 23–28)
RMD planning, beneficiary designations, and account consolidation
- Audit and update every beneficiary designation. Beneficiary designations on IRAs, 401(k)s, life insurance, and annuities override your will. An ex-spouse, deceased parent, or missing contingent beneficiary on these accounts can cause assets to pass incorrectly or through probate.
- Consolidate accounts strategically. The average pre-retiree has 4–7 retirement accounts from past employers. Consolidating simplifies RMD calculations, reduces fees, and makes portfolio management more coherent — but always check for any protected pension rights or employer stock before rolling over.
- Shift your investment allocation to match your distribution timeline. A portfolio you’re drawing from in two years should look very different from one you’re not touching for 15 years. Bucket strategies and liability-matching can reduce sequence-of-returns risk in early retirement.
- Review any employer stock concentration in your 401(k). Net Unrealized Appreciation (NUA) rules may allow you to pay capital gains rates — not ordinary income — on highly appreciated employer stock. This can be a significant tax savings, but the window typically only exists at separation from service.
- Establish or review your RMD strategy for age 73+. Decide in advance which accounts you’ll draw RMDs from, whether you’ll reinvest them or spend them, and how they interact with your overall tax bracket management plan.
- Set up systematic withdrawal automation aligned to your income plan. Automating distributions reduces the temptation to time the market or delay withdrawals during downturns — behavioral consistency is one of the most underrated elements of retirement plan success.
The 47-Step Checklist Continued
Florida Retirement Checklist: Categories 5–8
The second half of your retire in Florida checklist addresses the items most people leave too late: estate and legal documents, long-term care planning, Florida-specific tax advantages, and insurance coverage gaps. These aren’t paperwork formalities — each one has real financial and family consequences if neglected.
Category 5: Estate & Legal Documents (Steps 29–34)
Will, durable POA, healthcare surrogate, living will, and trust review
- Execute or update your last will and testament under Florida law. If you moved to Florida from another state, your existing will may be valid but may not reflect Florida-specific considerations like homestead property rules, which override standard inheritance provisions under Florida’s constitution.
- Establish a Durable Power of Attorney (DPOA). Without a DPOA, if you become incapacitated, your family may need a court-ordered guardianship — an expensive, public, and time-consuming process — simply to manage your finances. This document must be drafted while you’re competent.
- Designate a Healthcare Surrogate. Florida’s Healthcare Surrogate Designation names who will make medical decisions if you cannot. Without it, state law creates a decision-making hierarchy that may not reflect your wishes or put the right person in charge.
- Complete a Living Will / Advance Directive. A living will specifies your end-of-life treatment preferences. Florida’s standard form addresses life-prolonging procedures, tube feeding, and anatomical donation — ensure yours is on file with your healthcare providers and accessible to your surrogate.
- Review whether a revocable living trust makes sense. Florida’s
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