About Bayside Health Benefits

Bayside Health Benefits is an independent Medicare agency. We work with 11 financially stable insurance carriers, which allows us to compare a range of options and help clients find coverage that fits their needs. Our role is to provide guidance based on the client’s situation, not to steer them toward one carrier.

That independence is the foundation of every relationship we build here, and it’s why our clients return year after year and why they refer us the people they love.

Before we mention a single plan, we want to understand your world: your doctors and specialists, your prescriptions, your budget, and what matters most to you for the year ahead. The right Medicare plan looks different for every person, and we’re not going to pretend we know yours before you’ve told us.

We lay out the plans that match your situation side by side in an easy-to-understand discussion, with as much time as you need. There’s no rush and no pressure.

Many Medicare Advantage and Prescription Drug Plans change every year. Carriers update their plan structures, networks and pricing. Your health changes too!

We conduct annual reviews with every client and stay reachable when a new prescription, a change in health, or a big life moment makes it time to take another look.

We’re in it for the long haul, as Your Medicare Partner for Life™.

For more than twenty years, we’ve had the privilege of sitting down with Medicare beneficiaries across the State of Florida – the Nature Coast and Central Florida in Spring Hill, Citrus, Pinellas, Pasco, and Polk Counties.

We work with individuals in Assisted Living Facilities (ALF), company-clients of payroll/leasing companies, and individuals across the state. Many of these clients have become family, sticking by our side as we’ve stuck by theirs for their entire Medicare journey.

We know taking the first step can feel uncertain. Here are two ways to begin, entirely on your own terms.

Every Tuesday at 11:30 AM, we host a free Medicare education session open to anyone who wants to understand their options before making a decision. Join one of our Tuesday Webinars.

When you’re ready for a personal conversation, schedule a private appointment with one of our advisors. We’ll walk through your complete situation and talk through what makes sense for you at no cost, and without any pressure.

Call (352) 999-2727 | TTY 711

Our advisors bring together decades of experience, trusted credentials, and a genuine commitment to the people they serve. Click through to learn more about each member of the Bayside Health Benefits Family.

Dayna founded Bayside Health Benefits in 2001 after a career in Human Resources, where she watched people navigate consequential benefit decisions without anyone genuinely in their corner. That experience shaped everything she built here. She holds the Certified Medicare Insurance Planner™ designation, an independent credential focused entirely on beneficiary-first Medicare planning.

Annette spent 35 years as an educator before joining Bayside. She makes the complicated feel manageable, she doesn’t rush, and she won’t move on until you genuinely understand.

What makes Bayside Health Benefits different from other Medicare agencies?

Three things set us apart:
#1. We are fully independent, comparing plans across 11 financially stable carriers with no obligation to any single company.
#2. Our founder holds the Certified Medicare Insurance Planner™ designation, an independent certification focused on beneficiary-first Medicare guidance.
#3. (And our personal favorite) We stay with our clients after enrollment, conducting annual reviews and remaining available when life changes affect their coverage.

Do you offer Medicare guidance in Spanish?

Yes. Annette on our team is fully bilingual in English and Spanish and can provide complete Medicare planning support in either language.

How many insurance carriers does Bayside Health Benefits work with?

We work with 11 financially stable insurance carriers. That independence means we can compare the full range of Medicare plans available in your area and recommend the one that genuinely fits your situation.

How can I get started with Bayside Health Benefits?

Call us at (352) 999-2727 (TTY 711), schedule a free consultation or join one of our free Tuesday webinars at 11:30 AM. Every path is free and carries no obligation to enroll.