Health Insurance for Early Retirement in Florida
Quick answer: You have four ways to cover the gap between your last day of work and Medicare at 65: COBRA from your old employer, a plan you buy yourself, your spouse’s work plan, or an arrangement through your own business. COBRA is usually the most expensive. What you pay for your own plan depends on your income, and in retirement you have more control over that than you did while working.
People plan their retirement savings down to the decimal and then treat health insurance as something to sort out later.
It is usually the second biggest cost of those years. It is also the one you have the most control over, which is why it deserves more than a shrug.
What are my options before 65?
| Option | How long | Roughly what it costs |
|---|---|---|
| COBRA | 18 months | The full price of your old work plan. Usually the priciest. |
| Buy your own plan | Until Medicare | Depends heavily on your income. Can be the cheapest. |
| Your spouse’s work plan | While they work | Often cheapest. Often forgotten. |
| Through your own business | While it runs | Efficient, because you pay premiums before tax. |
Is COBRA worth it?
COBRA lets you keep the exact plan you had. Same doctors, same card, nothing changes.
Except the price. At work your employer paid most of it. Now you pay all of it, plus a small admin fee. A plan that cost you $450 a month can arrive at $1,900.
COBRA genuinely is the right call sometimes:
- You are in the middle of treatment and changing doctors would be a mess.
- You have already paid your deductible this year.
- You retire in autumn and only need to reach 1 January.
- Your income is well over the cut-off, so no discount is coming anyway.
Otherwise, COBRA is what happens when nobody makes a decision. It is the option that requires no thought, which is exactly why so many people end up on it.
You get 60 days to choose COBRA, and it backdates to the day your old cover ended. So you can shop around first and still fall back on it. Losing your job cover also gives you 60 days to buy your own plan.
Why your own plan might be cheaper than you think
Here is what early retirees miss. The discount you get is based on your income, and in retirement you often choose your income.
While working, your income was your salary. Now it is whatever you decide to take out, and from which account.
For 2027 the help stops above $63,840 on your own or $86,560 as a couple. Under that line the discount can be worth thousands. Over it, nothing.
What counts as income when you are retired?
Not what you spend. What shows up on your tax return.
Take $80,000 out of your brokerage account and the government does not count $80,000. It counts your profit on the shares you sold. Sell shares you paid $30,000 for and that is $50,000 of income.
Counts: money out of a traditional IRA or 401(k), Roth conversions, profit on investments you sell, dividends, interest, rent, pensions, part-time work.
Does not count: money out of a Roth you already paid tax on, getting your original investment back, HSA money spent on medical bills.
Do not leave yourself with a gap
Losing work cover gives you 60 days to buy your own plan. Miss it and you wait until November.
Two practical things. New plans start on the 1st of a month, so retiring on the 10th without planning leaves three weeks uncovered. And make sure the new plan is actually live before the old one stops. An email saying “application received” is not cover.
Does the date you retire matter?
More than people expect.
- Retire in autumn and most of that year’s salary is already earned, so no discount that year. Retire in January and you get a full low-income year.
- Retire after you have paid your deductible and COBRA to 31 December can make sense, then switch on 1 January.
- Retiring at 63 or 64? Watch your income, because what you earn at 63 sets your Medicare price at 65.
- Time it with your spouse. Six extra months on their work plan is sometimes worth more than six months of salary.
Where to start
More than a year out? Work out roughly what your income will be and which accounts you will draw from. That one number drives most of the cost.
Within a few months? Get prices for every option before you commit to anything. COBRA’s 60-day rule exists so you can shop first. Compare the whole year, not the monthly figure, and check your doctors are on whatever you are considering.
Frequently asked questions
Is COBRA or my own plan cheaper after retiring early?
Usually your own plan, because COBRA means paying the full price of your old work plan with no help from your employer. COBRA can win if your income is above the cut-off so no discount is available anyway.
How long does COBRA last?
Normally 18 months, and up to 36 months in some situations like divorce. It is not long enough on its own to get you from an early retirement in your fifties to Medicare at 65.
What counts as income when I am retired?
Money out of a traditional IRA or 401(k), Roth conversions, profit on investments you sell, dividends, interest, rent, pensions and part-time work. Money out of a Roth you already paid tax on does not count, and neither does getting your original investment back.
Can I get health insurance if I retire at 60 in Florida?
Yes. Nobody can turn you down or charge you more for existing health problems. Losing your work cover gives you 60 days to buy a plan. Whether you get help paying depends on your income that year.
What if there is a gap between my old and new plan?
You are uninsured and you pay for anything that happens. New plans start on the 1st of a month, so retiring mid-month can leave you exposed for weeks. COBRA can be backdated within 60 days to plug a short gap.
Does retiring early change what Medicare costs me later?
It can. Medicare charges higher earners more, based on your tax return from two years earlier. So your income at 63 sets your Medicare price at 65. Big Roth conversions just before Medicare are worth discussing with your accountant.
Talk it through with someone local
Planman Insurance is an independent agency in Delray Beach. We compare options across carriers, explain the trade-offs in plain language, and there is no cost to talk.
This article is general information, not tax or legal advice. Figures are current as of 4 August 2026 and change annually. Confirm your own numbers with a licensed agent and your tax professional before acting.