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Pick your persona. Get a path.

Every golfer plays a different course. Every Medicare beneficiary has a different starting point. These paths curate exactly the guides, terms, questions, and calculators for where you are today.

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Turning 65

Your first tee-off. Learn how Medicare works, when to enroll, and how to pick the coverage path that fits your life.

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Already on Medicare

Already teed off? This path helps you review, refine, and switch plans at the right time.

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Veteran

How Medicare fits with VA and TRICARE benefits, and when adding coverage actually helps.

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Still Working Past 65

Weigh delaying Medicare against enrolling on time when employer coverage is still in play.

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Helping a Parent

You're the caddie for a parent. Here's the path through Medicare from a caregiver's perspective.

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Retiring Soon

Retire on your terms. Time your Medicare enrollment to avoid gaps and penalties.

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Low Income / Extra Help

Programs that reduce Medicare costs — Extra Help, MSPs, and dual-eligible Special Needs Plans.

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Moving on Medicare

A move can open a Special Enrollment Period. Here's what changes and when.

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Disabled Under 65

Medicare eligibility for people under 65 on SSDI, ESRD, or ALS, and the plan choices that come with it.

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Medicare Caddies

Independent Medicare education & plan comparison.

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Speak with a Licensed Caddie(210) 903-5069

🏌️ Your Caddie for the Long Game — whether you enroll online or with a licensed agent, you'll have a dedicated Medicare Caddie available year-round for questions, reviews, and life changes. Learn more.

Medicare Caddies is an independent insurance agency. We are not affiliated with, endorsed by, or connected to the U.S. government, the federal Medicare program, or the Centers for Medicare & Medicaid Services (CMS). We help compare Medicare Advantage plans from the insurance companies we represent, and we don't offer every plan available in your area.