Retirement Planning for Tampa & Hillsborough County
Retirement Planning in Tampa, Florida
Planning to retire in Tampa, or already retired in the Tampa Bay area? We help you build a clear plan for income, taxes, Social Security, Medicare and insurance, so you know exactly how long your savings will last.
- A monthly retirement paycheck you can plan around
- Medicare and life insurance chosen to fit your whole plan
- Storm and insurance costs built into your Tampa budget
Every session is free. Meet face to face in Tampa or by video. No obligation. Prefer to talk now? Call (407) 974-7100
Retiring in Tampa Bay
What Makes Retirement Planning in Tampa Different
Retirement planning in Tampa starts with a Florida advantage: no state income tax on Social Security, pensions or 401(k) and IRA withdrawals. The bigger planning issue is insurance. After Hurricanes Helene and Milton hit the Tampa Bay area in 2024, homeowners and flood insurance became one of the largest budget lines for Hillsborough County retirees, so we build it into your income plan from day one.
Tampa also has some of the best healthcare in the Southeast, including Tampa General Hospital, Moffitt Cancer Center, AdventHealth Tampa and St. Joseph's Hospital. That means more Medicare choices, and the right one depends on the doctors and hospitals you want to keep.
How We Help Tampa Retirees
Retirement Planning & Insurance Services in Tampa
Because one planner coordinates everything, your Medicare and life insurance are chosen to fit your income, tax and legacy plan, not sold on their own. Start with a free quote or a free guide.
Retirement Income Planning
Turn your savings, pensions and Social Security into a dependable monthly paycheck that lasts.
Annuities
Guaranteed income and protection from market losses, when an annuity genuinely fits your plan. We compare rates and fees honestly.
Tax-Efficient Strategies
Roth conversions, RMD planning and smart withdrawal order to reduce taxes over your lifetime.
Social Security Optimization
Choose when and how to claim, including spousal and survivor strategies, to maximize lifetime benefits.
Healthcare & Long-Term Care
Build Medicare premiums, out-of-pocket costs and long-term care into your plan before a crisis forces the decision.
Estate & Legacy Coordination
Beneficiary reviews and working alongside your attorney and CPA so your wishes are carried out.
Medicare Insurance · Free Quote
Compare Medicare Plans in Tampa
Hillsborough County has dozens of Medicare Supplement, Medicare Advantage and Part D options. We compare them side by side around the Tampa doctors and hospitals you want to keep.
- Medigap Plan G, Plan N and High-Deductible G rates
- Check your doctors at TGH, Moffitt, AdventHealth and BayCare
- No cost to you and no pressure to enroll
Life Insurance · Free Quote
Compare Life Insurance Quotes
Protect your spouse, pay off the mortgage, cover final expenses or leave a tax-free legacy. We shop multiple top-rated companies so you get the right coverage at the right price.
- Term, whole life, IUL and universal life compared
- Final expense coverage for ages 50 to 85
- Lock in your rate before your next birthday
Free Retirement Guides
Free Guides for Tampa Pre-Retirees & Retirees
Plain-English guides written by Roger. Pick one, fill in the short form, and your free PDF is on its way. Read it on your phone or print it for the kitchen table.
The Tax-Smart Retirement Income Guide
Turn your savings into a paycheck that lasts, and keep more of it away from the IRS.
Get the Free Guide
9 Retirement Blunders to Avoid
The costly mistakes retirees make most often, the questions that prevent them, and a 10-point checklist.
Get the Free Guide
7 Retirement Tax Mistakes That Could Cost You Thousands
The avoidable tax errors that quietly shrink retirement income, and what to do about each one.
Get the Free Guide
The 2026 Florida Retirement Checklist
40 steps in five phases, including the residency and Homestead steps Florida retirees often miss.
Get the Free Checklist
The 2026 Truth About Annuities
How annuities can grow your savings with protection from market losses, and why income is optional.
Get the Free Guide
Annuity Do's and Don'ts
6 do's, 6 don'ts and 8 questions to ask before you move a single dollar into an annuity.
Get the Free GuideFree Tools
Run Your Own Numbers in a Few Minutes
Tampa Bay Storm & Insurance Planning
Hurricane and Flood Costs in a Tampa Retirement Plan
For most Tampa Bay retirees, insurance and storm costs are a bigger planning issue than taxes. Here is how we build them into your retirement income plan.
Flood Is a Separate Policy
A standard homeowners policy does not cover flooding. Flood coverage is a separate policy, and federal flood policies usually have a 30-day waiting period, so buy it before storm season, not when a storm is in the forecast.
Get the Florida ChecklistKnow Your Hurricane Deductible
Florida hurricane deductibles are often 2%, 5% or 10% of your dwelling coverage. On a $400,000 home, a 5% deductible is $20,000 out of pocket before insurance pays.
See Florida retirement costsA Storm Cash Reserve
We set aside cash for deductibles, evacuation and repairs, so a storm never forces you to sell investments after a market drop or take a large taxable IRA withdrawal.
Book a free planning sessionCheck Your Evacuation Zone
Hillsborough County uses evacuation zones A through E. Your zone affects flood risk, insurance cost and how often you may need to leave, so check it before you buy a home.
Read: Affordable places to retirePlan for Rising Premiums
Florida homeowners premiums have risen sharply in recent years. We budget for future increases, not just this year's bill, so your income plan still works in year ten.
Review my budgetProtect the Surviving Spouse
When one spouse passes, a Social Security check stops but the insurance bills do not. Life insurance and the right income plan can keep the Tampa home affordable for the survivor.
Get a Free Life Insurance QuoteWe work with retirees across Tampa Bay, including South Tampa, Brandon, Riverview, Sun City Center, Apollo Beach, Wesley Chapel, St. Petersburg and Clearwater, in person or by video.
Tampa Retirement Checklist
What Tampa Retirees Should Plan For
A few Tampa-specific items belong in every retirement plan we build for Hillsborough County residents.
Homestead Exemption
If you own your home, file with the Hillsborough County Property Appraiser by March 1 to cap future increases in your assessed value.
Get the Florida ChecklistHomeowners and Flood Insurance
Coastal and low-lying areas can pay far more for coverage. Price insurance on the exact address before you buy.
See Florida retirement costsA Storm Cash Reserve
Keep 12 to 24 months of expenses in safe, liquid accounts so a storm or a market drop does not derail your income.
Get the Income GuideMedicare Choices
Hillsborough County has many Medicare Advantage and Supplement options. Start with the doctors and hospitals you want to keep.
Get a Free Medicare QuoteProtect Your Spouse
When one spouse passes, a Social Security check stops and taxes can jump. Life insurance can fill that gap and protect the house.
Get a Free Life Insurance QuoteSocial Security Timing
When you claim can change your lifetime benefits by tens of thousands of dollars, especially for married couples.
Book a free claiming reviewMoving to Tampa? Get the Free 2026 Florida Retirement Checklist
40 steps covering Florida domicile, Homestead, insurance and documents, so your former state cannot keep taxing your retirement income.
Our Process
How Working With Us Works
Four simple steps to a retirement plan you understand and trust.
Discover
Share your goals, income sources and biggest questions in a free Retirement Clarity Session.
Analyze
We review your savings, pensions, Social Security, taxes, insurance and healthcare costs.
Plan
We build a written retirement income plan and walk you through it in plain English.
Adjust
We review your plan regularly as tax laws, Medicare rules and your life change.
Your Retirement Planner in Tampa
Meet Face to Face in Tampa
I'm Roger Fishel, an independent retirement planner with more than 20 years of experience. Most people come to me with accounts, policies and advice that were never designed to work together. My job is to be the one person who coordinates all of it, your income, taxes, Social Security, Medicare, insurance and estate plan, so every decision supports the others.
I meet with Tampa clients face to face all the time, so we can sit down together and go through your plan in person. If video is easier, your spouse or adult children can join from wherever they are.
Relocating to Tampa from the Northeast or Midwest? We can start planning before you move.
Frequently Asked Questions
Tampa Retirement Planning FAQs
Straight answers to the questions we hear most from Tampa Bay pre-retirees and retirees.
Do you work with retirees in Tampa?
Yes. Roger meets face to face with pre-retirees and retirees throughout Tampa and Hillsborough County all the time, and video or phone meetings are available too.
How much do I need to retire in Tampa?
It depends on your housing, insurance and healthcare costs. Many Tampa retirees spend more on homeowners and flood insurance than retirees in inland Florida cities, so we build your budget around your actual costs, not national averages. Our free Retirement Income Guide is a good place to start.
How do hurricanes and flood insurance affect retirement planning in Tampa?
They are often the biggest budget question for Tampa Bay retirees. We plan for homeowners and flood premiums that keep rising, a hurricane deductible that can be 2% to 10% of your dwelling coverage, and a cash reserve so a storm never forces you to sell investments at a bad time. See storm and insurance planning.
Can you quote Medicare plans for Tampa and Hillsborough County?
Yes. We compare Medicare Supplement, Medicare Advantage and Part D plans available in your ZIP code, at no cost to you, and choose coverage that fits your doctors, budget and overall retirement plan. Get a free Medicare quote.
Do you offer life insurance quotes in Florida?
Yes. We compare term, whole life, indexed universal life and final expense coverage from multiple top-rated companies, and size it to fit your income, tax and legacy plan. Get a free life insurance quote in about two minutes.
Does Florida tax retirement income?
No. Florida has no state income tax, so Social Security, pensions and retirement account withdrawals are not taxed by the state. Federal income tax still applies.
I am moving to Tampa from another state. When should I start planning?
Before you move. Starting early lets us plan the sale of your current home, Florida insurance costs, your Homestead Exemption and Florida domicile. Grab the free 2026 Florida Retirement Checklist.
What do your meetings cost?
Every session is free, with no obligation. Your Retirement Clarity Session is a conversation about your goals and questions, not a sales pitch.
Plan. Protect. Prosper.
Get Clarity About Your Tampa Retirement
Schedule a free Retirement Clarity Session, or start with a free quote. Either way, you will leave with clear next steps, even if you never work with us.
Not ready to talk yet? Get the free Retirement Income Guide or call (407) 974-7100.
