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Chaperone Health Insurance Plus

2027 Medicare Open Enrollment Checklist for Florida

Reviewed October 2026 · Covers the 2027 plan year

Medicare open enrollment for 2027 coverage is open now, from October 15 to December 7, 2026. It’s the one time each year when most people can look at their Medicare Advantage or Part D plan with fresh eyes and decide whether it still fits. Plans can change their costs, drug lists, and networks every year, so the plan that worked well for you in 2026 may not work the same way in 2027, even if you change nothing.

I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, based in Fort Lauderdale. I’ve spent 14 years in insurance and the last 8 focused on Medicare, and every fall I go through this same checklist with my clients. Below is the checklist I use, step by step, in plain language. If you’d like to go through it together, book a free plan review and I’ll get back to you personally within 24 to 48 hours.

✓ No cost. No obligation to enroll.

December Calendar

I’LL EVEN CALL YOUR DOCTOR

Get a Free Quote From a Medicare Broker During the Medicare Open Enrollment Period

The Medicare open enrollment period goes by quickly, so before you decide whether to keep or change your plan, I check:

  • Your 2027 Annual Notice of Change, line by line
  • Your doctors and hospitals against each plan’s network, including HCA Florida, Memorial, and Baptist Health
  • Your full-year cost for your current plan and each alternative, not only the premium

If anything is unclear, I call your doctor’s office to confirm it. Your quote is free, with no obligation to enroll. Get your free quote and I’ll do the research for you.

Hear how I help you choose a plan with confidence.

MORE THAN A FREE QUOTE

Why Choose Me for Medicare Open Enrollment

When you’re choosing who to review your plan with this fall, here’s what to look for, and what you can expect from me.

I Read the Fine Print With You: I go through your 2027 Annual Notice of Change line by line and point out the changes that actually affect you, such as a drug moving to a higher tier or a specialist leaving the network.

Your Doctors, Hospitals, and Prescriptions Checked First: Before I recommend any plan, I check your doctors, hospitals, and every prescription against its network and drug list, including your pharmacy. If something is unclear, I’ll call your doctor’s office myself.

Every Question Answered, at Your Pace: Open enrollment runs only seven weeks, and most people spend less than an hour reviewing their plan. I take as long as you need, explain each piece in plain language, and answer every question until it makes sense. There’s no pressure and no obligation to enroll.

The Plan That Costs Less for You: The lowest premium isn’t always the lowest cost. I calculate your full-year cost for your current plan and every alternative, including copays, drug costs, and your out-of-pocket maximum, before you decide whether to switch.

My Help Costs You Nothing Extra: Insurers pay my commission, and plan premiums are generally the same whether you enroll through me or directly, so you get personal guidance and ongoing support at no additional charge.

Both Paths, Side by Side: If you’re thinking about leaving Medicare Advantage for Original Medicare, or the other way around, I lay out both paths and explain what you’d gain and give up, including whether a Medigap plan would be available to you.

I Handle the Paperwork: If you choose a plan, I complete the application with you, confirm your enrollment window, and follow it through to approval, so the process is as simple as a conversation.

Licensed and Verified: I’m licensed in 33 states, I complete AHIP’s annual Medicare certification, and I’m certified for the 2027 plan year. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.

I Stay Your Agent After You Enroll: Work with me directly, in person, by phone, on Zoom, or at your home in Broward, Miami-Dade, or Palm Beach, and I reply within 24 to 48 hours. I review your coverage every Annual Enrollment Period and help with claims and billing in between.

You can read all 25 reasons we should work together on my Why Choose Me page.

When Is Medicare Open Enrollment? The 2027 Medicare Open Enrollment Dates

Medicare’s fall open enrollment, also called the Medicare Annual Enrollment Period, runs from October 15 to December 7 every year. For the 2027 plan year, that means October 15 to December 7, 2026. Any change you make takes effect January 1, 2027. Your plan must receive your enrollment request by December 7, so it’s best not to wait until the last day.

Here are the other dates worth knowing for this cycle:

By September 30, 2026: your Medicare Advantage or Part D plan should have sent your Annual Notice of Change (ANOC) for 2027, by mail or by email if you chose electronic delivery. It lists what’s changing in your plan for next year.

October 15, 2026: the 2027 Annual Enrollment Period opens. Medicare’s Plan Finder on Medicare.gov shows 2027 plans, and you can enroll in a 2027 plan any time through December 7.

December 7, 2026: the last day to join, switch, or drop a plan for 2027. If you do nothing, you generally stay in your current plan for 2027 with its new costs and benefits, as long as the plan is still offered in your area.

January 1, 2027: new coverage starts. Bring your new member card to your first appointment and your first pharmacy visit of the year.

Some people also have a Special Enrollment Period that lets them change plans at other times, for example after moving, losing other coverage, or qualifying for Extra Help or Medicaid. If one of those applies to you, I’ll help you confirm your window.

What You Can Change During the Medicare Annual Enrollment Period

During open enrollment, Medicare lets you make several kinds of changes, depending on the coverage you have now. You can switch from one Medicare Advantage plan to another, with or without drug coverage. You can leave Original Medicare and join a Medicare Advantage plan, or leave a Medicare Advantage plan and return to Original Medicare. If you have Original Medicare, you can join, switch, or drop a standalone Part D drug plan.

If you make more than one plan choice during the Medicare annual enrollment window, the last one you make by December 7 is generally the one that counts. Joining a new Medicare Advantage or Part D plan usually ends your old plan automatically when the new one starts, so you won’t need to cancel your old plan yourself in most cases. If you’re leaving a Medicare Advantage plan for Original Medicare, think through your drug coverage at the same time, because you’d need a separate Part D plan to keep it.

Medicare Advantage plans are offered by private insurance companies approved by Medicare. They’re a different way to receive your Part A and Part B benefits, not a supplement to Original Medicare. I keep the two paths separate when I compare them, because the rules and long-term costs are different.

Your 2027 Medicare Open Enrollment Checklist, Step by Step

This Medicare checklist follows the order I use with clients. Each step builds on the one before it, so it’s worth going in order.

Step 1: Read Your 2026 Plan’s Annual Notice of Change. Your ANOC compares your plan’s 2026 benefits and costs with its 2027 benefits and costs. Look at the premium, the deductible, your copays for doctor visits and hospital stays, the out-of-pocket maximum, the drug list, and the provider and pharmacy networks. If your notice says your plan is leaving your area or won’t renew for 2027, that changes your options and your timing. My guide to what your 2027 Medicare ANOC or non-renewal notice means walks through how to read it, and my guide to 2027 Medicare Advantage changes in South Florida covers what’s changing across the region.

Step 2: Check Your Doctors and Hospitals. Make a list of every doctor you see, including specialists, plus the hospitals, labs, and imaging centers you use. Then check each one against the 2027 network of every plan you’re considering, by the exact plan name, since one company can offer several plans with different networks. In South Florida, many people want to stay with a particular health system, such as HCA Florida, Memorial Healthcare System, or Baptist Health, so I check those relationships carefully. Provider directories aren’t always up to date, so when something is unclear, I call the doctor’s office to confirm.

Step 3: Check Your Prescriptions and Pharmacy. Write down every medication you take, with the dose and how often you fill it. For each plan, check whether each drug is covered, which tier it’s on, and whether it comes with rules like prior authorization, step therapy, or quantity limits. Then check your pharmacy. Many plans charge less at preferred pharmacies, and a pharmacy that was preferred in 2026 may not be preferred in 2027. My Medicare Part D page explains how drug coverage works in more detail.

Step 4: Add Up Your Total Yearly Cost. The premium is only one piece of what you pay. Add the premium to your deductible, your expected copays and coinsurance for the care you usually get, and your estimated drug costs for the full year. Then look at the plan’s out-of-pocket maximum, which is the most you’d pay for covered medical services in 2027 if you had a hard health year. For drug coverage, Medicare’s limits for 2027 are a deductible of no more than $700 and an out-of-pocket cap of $2,400 for covered Part D drugs. Comparing full-year cost, based on your own doctors and prescriptions, is the most reliable way to compare plans.

Step 5: Look at Extra Benefits Realistically. Many Medicare Advantage plans include benefits Original Medicare doesn’t cover, such as dental, vision, hearing, fitness, or an over-the-counter allowance. These can change from year to year, and some plans are scaling them back for 2027. Check how much the benefit actually covers, whether there’s an annual limit, and whether you have to use specific dentists or eye doctors. A benefit you won’t use shouldn’t outweigh your doctors and prescriptions.

Step 6: Think About Travel and Time Out of Area. If you spend part of the year outside Florida, or travel often to see family, check how each plan handles care away from home. Medicare Advantage plans cover emergency and urgent care anywhere in the U.S., but routine care outside the plan’s service area is often limited, especially with HMOs. Some PPO plans cover out-of-network care at a higher cost. If you’re away from your plan’s service area for more than six months in a row, your plan may disenroll you. Original Medicare works with any provider in the country that accepts Medicare, which is one reason some frequent travelers prefer it.

Step 7: See Whether You May Qualify for Extra Help. Extra Help is a Medicare program that may lower your Part D premium, deductible, and drug costs if your income and resources are limited. You automatically qualify if you have Medicaid, a Medicare Savings Program, or Supplemental Security Income. Otherwise, you can apply through Social Security. If you qualify, you also get more chances to change your drug coverage during the year. My Extra Help and Special Situations page has more detail.

Step 8: Compare Your Options and Decide by December 7. Once you know what matters most, compare your current 2027 plan with the alternatives that fit. Medicare’s Plan Finder on Medicare.gov lets you compare plans side by side, and I’m glad to go through it with you or double-check what you find. If you decide to change, enroll before December 7, 2026, then watch for your new member card and welcome packet before January 1, 2027.

Medigap Isn’t Tied to Medicare Open Enrollment

Medicare Supplement (Medigap) plans follow different rules. They work alongside Original Medicare to help pay costs it leaves behind, like deductibles and coinsurance, and they’re sold all year. They aren’t part of the October 15 to December 7 window. The Annual Enrollment Period covers Medicare Advantage and Part D plans only.

Your best chance to buy a Medigap plan is your one-time Medigap Open Enrollment Period, a six-month window that starts the month you’re 65 or older and enrolled in Part B. During that window, insurance companies must sell you any Medigap policy they offer, without medical underwriting. Outside it, Florida insurers can generally review your health history and may charge more or deny coverage, unless you have a guaranteed issue right, such as when a Medicare Advantage plan leaves your area.

That matters if you’re thinking about leaving a Medicare Advantage plan for Original Medicare this fall. You can make that move during open enrollment, but a Medigap plan isn’t guaranteed to be available to you, so it’s worth checking before you leave your current plan. My guide to switching from Medicare Advantage to Medigap without underwriting explains when guaranteed issue rights apply.

Before You Change Plans: What to Weigh

A new plan can be the right move, but every change comes with trade-offs. A plan with a lower premium may have a narrower network or higher copays. A plan with richer extra benefits may not include your specialist or your pharmacy. Leaving a Medicare Advantage plan for Original Medicare can open up any provider that accepts Medicare, but it may mean higher monthly costs and, outside your Medigap open enrollment period, a health review for a Medigap plan.

Staying put is a choice too, and often a good one. If your 2027 ANOC shows few changes and your doctors and drugs are still covered at a cost that works for you, keeping your plan may be the simplest answer. Either way, I’ll lay out what you’d keep, what you’d gain, and what you’d give up, so you can decide with the full picture.

MORE WAYS I CAN HELP

Find the Right Coverage for Every Stage of Life

Most households need more than one kind of coverage, and what you need changes as life does. Keep reading for the details on this page, or see all the coverage I help with and my guides to each type of insurance:

Frequently Asked Questions About Medicare Open Enrollment

When Is Medicare Open Enrollment for 2027?

Medicare open enrollment for 2027 coverage runs from October 15 to December 7, 2026, and any changes you make start January 1, 2027. This is different from the ACA Marketplace open enrollment for people under 65, which has its own dates.

When Does Medicare Open Enrollment End?

It ends December 7, 2026. Your plan must receive your enrollment request by that date. After December 7, most people can only change plans if they have a Special Enrollment Period, such as after a move or if they qualify for Extra Help.

What Happens if I Don’t Do Anything During Open Enrollment?

If your plan is continuing in 2027, you generally stay in it automatically, with whatever changes are listed in your ANOC. If your plan is leaving your area, your non-renewal notice explains your options and deadlines, and you’ll want to choose new coverage so you aren’t left without drug coverage.

What Is the Medicare Advantage Open Enrollment Period?

The Medicare Advantage Open Enrollment Period runs from January 1 to March 31 each year. It applies only to people who are already in a Medicare Advantage plan on January 1, and it allows one change: switching to a different Medicare Advantage plan, or leaving Medicare Advantage for Original Medicare, with the option to join a standalone Part D plan. It’s separate from the fall Annual Enrollment Period, and it isn’t available to people in Original Medicare.

Can I Use Medicare Plan Finder on My Own?

Yes. Medicare Plan Finder on Medicare.gov lets you enter your drugs and pharmacy and compare 2027 plans in your area. Many of my clients use it before or after we meet. What I add is a second set of eyes: I confirm networks with doctors’ offices, check drug restrictions, and stay available after you enroll.

Can I Help a Parent Review Their Plan During Open Enrollment?

Yes. With your parent’s permission, I’m glad to include you in the plan review, by phone, on Zoom, or at their home in Broward, Miami-Dade, or Palm Beach. It helps to have their current member card, their ANOC, and a list of their doctors and medications ready.

Do You Offer Every Medicare Plan in My Area?

No. We do not offer every plan available in your area. Currently we represent 8 organizations which offer 65 products in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY users should call 1-877-486-2048), 24 hours a day, 7 days a week, to get information on all of your options. In Florida, you can also get free, unbiased Medicare counseling through the state’s SHIP program, called SHINE.

You can find more plain-language guides in my Medicare Knowledge Center.

Book a Free Plan Review

Pick a time for a free 15-minute call by phone or video, and we’ll go through your 2027 open enrollment checklist together before December 7. Bring your ANOC, your member card, and your list of doctors and medications. My help never costs you anything extra.

Call or text: (954) 410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309

Meet by: phone, video, at my office, or at home in Broward, Miami-Dade and Palm Beach.

Roxroy Ashley - Licensed Insurance Agent

How we'll work together

Five steps, no pressure, and I stay with you after you enroll.

 

1

We talk about you

By phone, Zoom or face to face. Your health, your budget, your doctors.

2

I check the details

Doctors, hospitals, prescriptions and pharmacy, checked against each plan.

3

We compare real costs

A full-year estimate for each option, explained in plain language.

4

You decide, I enroll you

No pressure. If you choose a plan, I handle the application with you.

5

We review every year

Plans and networks change. I check yours each year and help with claims in between.