When should I enroll in Medicare?

Your Initial Enrollment Period generally begins 3 months before you turn 65, includes your birthday month, and continues for 3 months after your birthday month. If you are still working and covered by qualifying group health coverage based on current employment, you may qualify for a Special Enrollment Period. Your enrollment timing depends on your circumstances.

What's the difference between Medicare Advantage and Medicare Supplement?

Medicare Advantage (Part C) is an alternative way to receive Medicare benefits through a private Medicare-approved plan and may include prescription drug coverage and additional benefits. Medicare Supplement insurance, also called Medigap, works with Original Medicare to help pay certain Medicare cost-sharing expenses. The two types of coverage work differently and may fit different healthcare and financial needs.

Do I have to pay for Kidwell Insurance Services?

There is no direct fee to clients for our insurance guidance and enrollment assistance. Insurance carriers generally compensate licensed agents when a client enrolls in a plan they represent. Carrier compensation does not increase the plan's premium.

Can I switch Medicare plans?

Depending on your circumstances, you may be able to change Medicare coverage during certain enrollment periods. The Medicare Annual Election Period generally runs from October 15 through December 7 each year. Medicare Advantage enrollees may also have certain opportunities to make changes during the Medicare Advantage Open Enrollment Period from January 1 through March 31. Other Special Enrollment Periods may apply.

What if my doctors are not in the plan's network?

Before enrolling in a Medicare Advantage plan, it is important to verify that your doctors, hospitals, and other healthcare providers participate in the specific plan's network. Network rules vary by plan. Medicare Supplement insurance works with Original Medicare, which generally allows you to see any doctor or hospital that accepts Medicare, subject to Medicare's rules.

Annual Enrollment: October 15 to December 7

Review your plan before the December 7 deadline.

Kidwell Insurance Agency helps Bay Area seniors choose Medicare coverage with a licensed local agent, at no cost to you.

a man sits at a desk reviewing his medicare supplement plan in San Jose, CA

Where are you with Medicare? Choose the one that sounds like you.

A couple sits on a couch talking with an insurance agent about switching medicare advantage plans.

I already have Medicare

Check that your plan still fits your doctors, drugs, and benefits.

Review my plan →

I’m turning 65 soon

Get ready for your enrollment window and avoid costly penalties.

Start here →

a woman and her father sit at a table discussing medicare plan options.

I’m helping a parent or a spouse

Talk it through with a licensed agent. No forms required.

Get help →

Not sure which fits? Call (408) 915-4280 and we will figure it out together.

Licensed in CA

License #6020571

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Our guidance is free. Carriers pay us, not you.

Multiple carriers

Side-by-side comparisons, not one company's plans

Local

Based in Morgan Hill, serving six Bay Area counties

three people discuss the options in Medicare advantage plans.

Medicare guidance built on trust, education, and long-term relationships

We take the time to understand each client's healthcare needs, budget, and concerns so we can recommend coverage with confidence and clarity.

Whether you live in San Jose, Mountain View, Los Gatos, Saratoga, Morgan Hill, or anywhere else in the Bay Area, you get dependable local support at every step.

Three steps from first call to full confidence in your coverage

Step 1

We listen to your health needs, budget, and current doctors. We learn what is most important to you and what type of coverage you might need.

Free Consultation

Step 2

Plan Comparison & Expert Guidance

We partner with many carriers, but we work for you not the insurance companies. We will help you find the plan that is right for you. After researching plans in your area from multiple carriers, we will show you a clear, side-by-side comparison.

Step 3

Enroll With Confidence

We will review what plans cover and what they don’t so you know what is coming and are not surprised. We handle the paperwork with you and stay in your corner long after you are covered.

Every path ends with a real conversation with a local agent.

I'm turning 65 soon

I already have Medicare

I'm helping a parent or spouse

Learn the Basics

Medicare Advantage

Plans from private insurers approved by Medicare, offered as an alternative to Original Medicare.

Read the Advantage guide

Medicare Supplement

Covers costs Original Medicare doesn't, like copays and deductibles. Plans A through N.

Read the Supplement guide

Part D drug plans

Drug costs vary widely between plans. We check your specific medications to keep costs low.

Read the Part D guide

Medicare Questions, Answered

Have a question not listed here? Call (408) 915-4280.

Your Initial Enrollment Period begins 3 months before you turn 65 and extends 3 months after. Enrolling during this window avoids late penalties. If you're still working and covered by an employer plan, you may qualify for a Special Enrollment Period. We can help you determine the right time to enroll.
Medicare Advantage (Part C) replaces Original Medicare through a private insurer and often bundles dental, vision, and prescription coverage. Medicare Supplement (Medigap) works alongside Original Medicare to cover its gaps, like deductibles and coinsurance. Both have pros and cons depending on your health needs and budget — that's exactly what we're here to help you sort out.
No, our guidance is completely free to you. We are licensed independent brokers compensated by the insurance carriers. This compensation does not affect your premium; you pay the same whether you use an agent or apply directly. Our goal is to find the plan that genuinely fits you best.
Yes. Each year during the Annual Election Period (October 15 – December 7), you can switch between Medicare Advantage plans or return to Original Medicare. Some plan changes are also available during the Medicare Advantage Open Enrollment Period (January 1 – March 31). We review your coverage annually to make sure you're still in the best plan for your needs.
Keeping your doctors is a top priority. Before recommending any plan, we verify that your current physicians and preferred hospitals are in-network. If you have a Medicare Supplement plan, you can generally see any doctor who accepts Medicare nationwide, no network restrictions.

Where are you with Medicare?

Or call (408) 915-4280 to talk it through.