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Turning 65Checklist

Turning 65 Checklist

A calm, step-by-step checklist for the months around your 65th birthday. It tells you what to collect, what to look up, and what to decide — without telling you which plan to buy.

Download the PDF (PDF)

Format: PDF. Free to download. No email address, no form, no follow-up unless you ask for one. Last reviewed September 4, 2026. Prepared by Bleu Sky's Insurance Solutions.

Who this is for

  • Anyone approaching age 65
  • People still working past 65 with employer coverage
  • Adult children helping a parent through the transition

What's included

  • What to gather before you start
  • What to check about your current coverage
  • Questions to ask about doctors and prescriptions
  • Decisions to think through
  • Where to confirm official rules and dates

Before you start — gather these

  • Your Social Security or Medicare account login, if you already have one
  • A list of your current doctors, specialists and preferred hospitals
  • A list of your prescriptions, including dose and how often you take them
  • Details of any coverage you have now (employer, retiree, union, VA, TRICARE, Medicaid or Marketplace)
  • Your spouse's or partner's coverage details, if their plan covers you

Review your current situation

  • Confirm whether you or your spouse are still actively working and covered by an employer plan
  • Ask your employer's benefits contact how your plan works once you are eligible for Medicare
  • Note whether you have a Health Savings Account, and ask how enrolling in Medicare affects contributions
  • Check whether any retiree or union coverage requires you to enroll in a specific part of Medicare
  • Write down what you like and dislike about the coverage you have now

Learn the basics

  • Read what Part A and Part B cover, and what they do not
  • Read how Original Medicare with a supplement differs from Medicare Advantage
  • Read how prescription drug coverage (Part D) fits with each choice
  • Learn what “creditable coverage” means for drug coverage you already have
  • Confirm your own enrollment window and any deadlines on Medicare.gov or with 1-800-MEDICARE

Check doctors and prescriptions

  • Ask each doctor's office directly whether they accept the coverage you are considering
  • Check whether your preferred hospital and pharmacy are included
  • Check whether each of your prescriptions is covered, and under what rules
  • Ask about coverage while you travel or spend part of the year in another state

Think through your priorities

Keeping my current doctors matters to me because…
Predictable monthly cost vs. lower cost when I use care — which do I prefer, and why?
Prescriptions I cannot do without
Travel or time spent outside Florida each year
Questions I still want answered

Get help before you decide

  • Write down your questions and bring the list to your appointment
  • Confirm any rule or date with Medicare.gov or 1-800-MEDICARE
  • Talk with a licensed advisor who will explain trade-offs, not just products
  • Keep a copy of whatever you enroll in, and note when you can review it again

This resource is general educational information only. It is not insurance, financial, tax, medical or legal advice, and it does not recommend a specific plan or company. Your own situation may be different — talk with a licensed advisor, and confirm details with the plan or with the official government source before you decide.

Enrollment windows and rules are set by Medicare and can change. Always confirm current rules and dates with Medicare.gov or 1-800-MEDICARE.

We do not offer every available plan in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

Source: Bleu Sky's Insurance Solutions. Last reviewed September 4, 2026.

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Want help applying this to your situation?

A licensed advisor can walk through it with you, at no cost and with no obligation.

Prefer to talk now? Call (813) 360-1884. Consultations are free and carry no obligation.