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New to Medicare

You're Only New to Medicare Once.

There’s a lot of information online and on social media - but not all of it is accurate or applies to your situation. Instead of trying to piece everything together yourself, let us help you understand how Medicare works before you enroll.

Whether you're turning 65 or leaving employer coverage, Capstone Health can help you make an educated decision with no pressure and no obligation.

Enrollment Timeline

Medicare Enrollment Tool

Not sure when or how to enroll? Answer a few questions to determine your enrollment timeline and which guide fits your situation.

Start the Enrollment Tool →
Personal Help

Ready to Build Your Medicare Plan?

Meet with a local independent Medicare agent who can compare plans based on your doctors, prescriptions, preferred hospitals, and budget.

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Independent Agent - Not a Call Center
Make an Educated Decision
Proactive Annual Reviews

Turning 65 or Coming Off Employer Coverage?

Your Medicare enrollment path depends on more than your age. Whether you are turning 65, still working, leaving employer coverage or already collecting Social Security can affect when you should enroll and which steps you need to complete.

Use the flowchart below for a general overview of the most common enrollment paths. For personalized guidance, interactive tools and detailed enrollment resources, continue to the Medicare Education Center.

Flowchart explaining when to enroll in Medicare when turning 65 or leaving employer coverage

General Medicare enrollment overview: Individual situations can vary based on employer coverage, employer size, disability status, Social Security enrollment and other Medicare eligibility rules.

Medicare Enrollment Videos

Watch the Medicare Enrollment Process

Sometimes it's easier to see the process than read about it. These short videos explain the two most common Medicare enrollment situations and help you understand what to expect before you enroll.

Turning 65 and Not Collecting Social Security

If you're approaching age 65 and are not receiving Social Security benefits, you'll usually need to enroll in Medicare yourself. This video explains when to apply, where to enroll and what to expect.

Leaving Employer Coverage After Age 65

If you've delayed Medicare because you had employer coverage, this video explains your Special Enrollment Period, the forms you may need and how to avoid late enrollment penalties.

New to Medicare Checklist

New to Medicare?

Your Step-by-Step Medicare Timeline

A simple checklist for people getting Medicare before, at, or after age 65. Use this timeline to prepare, compare your options, and avoid common Medicare enrollment mistakes.

Start Needs Assessment Book an Appointment
Creating your planning guide...
20+ YearsMedicare experience
IndependentWe work for you
Local & Family-OwnedServing Florida
No Call CentersSpeak with a real person
6MONTHS
BEFORE 65

6 Months Before 65

Learn and prepare

4MONTHS
BEFORE 65

4 Months Before 65

Prepare for enrollment

3MONTHS
BEFORE 65

3 Months Before 65

Your Medicare Enrollment Window Opens

1MONTH
BEFORE 65

1 Month Before 65

Confirm everything is ready

Helpful Resources

Enrollment PeriodsReview important Medicare timeframes Contact Capstone HealthAsk us about missing cards, dates, or next steps
Have Your Medicare Card ReadyAfter completing the intake form, bring your Medicare card to your appointment or have it nearby for a phone or online meeting.
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AFTER
MEDICARE
STARTS

After Medicare Starts

Stay on track

Ready for Help Comparing Your Medicare Options?

Capstone Health can help review your doctors, prescriptions, budget, and preferences so you understand which Medicare path fits your needs.

First Decision Is Picking the Right Medicare Agent

Illustration showing the revolving door of call center agents, new plans, and captive agents
Choosing the Right Medicare Agent

Choosing the Right Agent Can Matter More Than Choosing the Right Plan

Medicare plans can change every January. A trusted agent shouldn't.
Changing plans annually can sometimes make sense. Changing agents annually rarely does.
The Medicare plan you choose is important—but so is the person helping you choose it. Call centers, captive agents, and independent agents all work differently. Understanding those differences can help you choose someone who will still be there when your needs change.
Call Center High Volume.
High Turnover.
New Relationship Every Year.
Captive Agent One Insurance Company.
Recommendations Limited to Their Products.
Independent Agent Multiple Options.
Personalized Advice.
Long-Term Relationship.
Call Center Medicare Agent

Call Center Agents

Call centers often focus on quick enrollments and high call volume. You may never speak with the same representative twice, making long-term Medicare guidance more difficult.

Captive Medicare Agent

Captive Agents

Captive agents usually represent one insurance company. They can provide good service, but they're limited to recommending plans offered by that carrier.

The Next Decision Is Picking the Right Medicare Coverage

Getting Started

Ready to Take the Next Step?

Whether you're turning 65, retiring, or leaving employer coverage, we're here to help you understand your Medicare options before you enroll.

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Our Team

Meet Our Medicare Team

Learn why people throughout Tampa Bay choose Capstone Health for independent Medicare guidance and year-round support.

Meet Our Team
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Schedule

Book Your Medicare Consultation

Have questions about enrollment, Medicare Supplement plans, or Medicare Advantage? Schedule a no-obligation appointment.

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