Enrollment tips
Medicare enrollment tips for Naples: how to use October 15 to December 7 well
October 2, 2026 · 6 min read
The Annual Enrollment Period runs from October 15 to December 7 every year. That is eight weeks to review your Medicare coverage, change plans, or decide to stay exactly where you are, with any change taking effect January 1.
Most people can do this well in under an hour if they work from a list. Here is the list I walk Naples clients through, in order.
1. Start with the letter that already arrived
Your plan mails an Annual Notice of Change each September. It is not junk mail. It shows your new premium, your new drug costs, and anything leaving the plan for January 1. Read that first, before any brochure or advertisement.
2. Write down your prescriptions and what you pay
Include the dose, not just the drug name. A plan that covered something last year can move it to a different tier, which changes what you pay at the counter without anything changing about the drug itself.
3. Check your doctors and your pharmacy, one at a time
Provider networks change every year, and pharmacies are often split into preferred and standard tiers. Confirm each doctor you see and the specific pharmacy counter you use, not just the brand name.
4. Compare the whole year, not the monthly premium
Add up the premium, the deductible, your regular prescription costs and the visits you expect. The plan with the lowest premium is often not the plan with the lowest yearly cost.
5. Ask about prior authorization and step therapy
If you take something long term, ask whether the plan needs approval before it pays, or requires you to try a different drug first. These rules are the most common January surprise.
6. Think about travel and the snowbird question
Medicare Advantage plans generally cover emergencies anywhere, but routine care happens inside the plan's service area. If you spend part of the year in another state, check how that works before you choose.
7. Be careful with calls you did not ask for
Medicare rules do not allow unsolicited calls about Medicare Advantage or drug plans. If someone pressures you on the phone, hang up, and call back on a number you looked up yourself.
8. Keep proof of what you chose
Save your enrollment confirmation, your new plan card, and a note of the date you enrolled. It makes any correction much easier later.
9. Ask for free help if you want a second opinion
Florida's SHINE program and 1-800-MEDICARE both answer questions at no cost, and Medicare.gov lets you compare every plan in your zip code. A licensed agent can help as well, also at no cost to you.
The deadline that matters
December 7 is the last day to make a change for January 1. If you miss it and you are in a Medicare Advantage plan, the Medicare Advantage Open Enrollment Period from January 1 to March 31 allows one change. If you are on Original Medicare with a stand-alone drug plan, your next window is the following fall.
If you would rather sort through this with someone who does it every day, bring your list to a free 30 minute review. We check your doctors, your prescriptions and your costs together, and you decide what to do with the answer.
Want this checked against your own plan?
Bring your doctors and your prescription list to a free 30 minute review with Ella Young, a licensed agent with SelectQuote in Naples.
This article is general information, not a plan recommendation. Plan benefits, networks and costs are set by the insurance carriers and can change every January 1. Ella Young Insurance is a licensed insurance agency working with SelectQuote and is not connected with or endorsed by the U.S. government or the federal Medicare program. We do not offer every plan available in your area. Please contact Medicare.gov, 1-800-MEDICARE, or Florida's SHINE program to see all of your options.
