Turning 65 should mean healthcare security, not confusion. Missing a deadline can lead to penalties that stay with you for life. We take the guesswork out of the process—guiding you through your options and ensuring you’re enrolled correctly from the start so your transition into Medicare is seamless and penalty-free.
Why Choose Milestone Family Insurance for Medicare?
Enrollment timing: We help you enroll at the right time so you avoid lifetime penalties.
Plan comparison: We break down Original Medicare and Medicare Advantage side by side, making sure your doctors, hospitals, and needs are covered before you decide.
Prescription savings: We guide you through Part D options and help you take advantage of the new annual cap of $2,000 on prescription drug costs.
Annual review: Medicare plans change every year. We review your coverage annually to be sure your plan still fits your health needs and budget.
Coverage Options
Medicare Part A: Hospital Coverage
What it covers: Hospital stays, skilled nursing, hospice
Cost: Usually $0 (if worked 10+ years) – must enroll
Eligibility: Age 65 or 24mo SSDI
Medicare Part B: Medical Coverage
What it covers: Doctor visits, outpatient care, in-office drugs (chemo, infusions), preventive services
Cost: $202.90/month + 20% coinsurance
Penalty: 10% per year late = Costing you thousands
Medicare Part C: Medicare Advantage
Coverage based on plan formularies (retail/outpatient drugs) – $2,000 annual cap
Note: Part B covers in-office drugs (Part D = pharmacy/retail)
Penalty: 1% per month delayed
Medigap: Fill Medicare Gaps
Covers deductibles, coinsurance – nationwide doctor access
Popular: Plans G, N (
most cost-effective 2026)
Medicare Enrollment Periods
Understanding these periods helps you enroll at the right time, avoid penalties, and make changes to your coverage when eligible.
Late Enrollment Penalties
Missing your initial enrollment window can cost you—sometimes for life. Here’s what you need to know about late enrollment penalties and how to avoid them.
Why Medicare Planning Matters
Tens of thousands lifetime penalty risk from missing enrollment. We ensure:
- Keep your doctors
- Match Part D formulary to your prescriptions
- No Permanent Penalties
- Dental/vision gap coverage
MEDICARE DISCLAIMER: It’s possible that we do not offer every plan in your area. We represent a number of Medicare Advantage organizations throughout the country which offer products 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, or your local State Health Insurance Program (SHIP) to get information on all your options.