Turning 65 in New York?
Here’s Everything You Need to Know About Medicare

If you’re turning 65 soon, Medicare is probably one of the biggest decisions on your mind, and rightfully so. The choices you make during your first enrollment window can affect your coverage and costs for years to come.

As an independent Medicare broker serving Queens, Long Island, Nassau County, Suffolk County, the Bronx, Westchester, Rockland County, Richmond County, Kings County, and all of New York City, I created this guide to answer the three questions I hear most from New Yorkers approaching 65:

1. When do I need to enroll in Medicare?
2. What are my plan options and what are the differences?
3. Do I need to enroll in Medicare if I’m still working?

Let’s walk through each one.

When Do I Need to Enroll in Medicare?

The most important enrollment window for most New Yorkers turning 65 is called the Initial Enrollment Period (IEP). This is a 7-month window that works as follows:

Important: Enrolling in the first 3 months of your IEP before your birthday month gives you the earliest possible coverage start date. Waiting until your birthday month or after delays your coverage.

For a complete walkthrough on how to enroll, see our step-by-step guide to applying for Medicare

For a complete breakdown of every 2026 Medicare premium, deductible, and out-of-pocket cost, see our Medicare Costs 2026 guide

What Happens If You Miss Your IEP?

Missing your Initial Enrollment Period without a valid exception can result in permanent late enrollment penalties:

• Part B penalty: 10% added to your premium for every 12-month period you were eligible but didn’t enroll — for life
• Part D penalty: 1% of the national base beneficiary premium for every month you went without creditable drug coverage for life

These penalties add up quickly. A New Yorker who delays Part B enrollment by 2 years could pay 20% more on their Part B premium every month for the rest of their life.

What Are My Medicare Plan Options — and What Are the Differences?

Once you have Medicare Part A and Part B (Original Medicare), you have two main paths to choose from. This is the decision that confuses most New Yorkers turning 65, so let’s break it down clearly.

Path 1: Medicare Advantage (Part C)

Medicare Advantage is an all-in-one alternative to Original Medicare offered by private insurance companies approved by Medicare. Instead of using Original Medicare directly, you get your benefits through the plan.

Best for: New Yorkers who want low premiums, extra benefits like dental and vision, and are comfortable using a network of doctors.

Path 2: Medicare Supplement (Medigap) + Part D

Medicare Supplement plans, also called Medigap, work alongside Original Medicare to cover costs that Medicare doesn’t pay, such as deductibles, copays, and coinsurance. You keep Original Medicare and add a Medigap policy on top of it.

Best for: New Yorkers who want freedom to see any doctor, travel frequently, or want highly predictable out-of-pocket costs.

Medicare Advantage vs. Medicare Supplement — Side by Side

Do I Need to Enroll in Medicare If I’m Still Working?

This is one of the most common questions I receive — and the answer depends on the size of your employer.

If Your Employer Has 20 or More Employees

Your employer’s group health plan is considered your primary insurance. In this case:

• You can delay Part B enrollment without penalty
• You’ll receive a Special Enrollment Period (SEP) when you eventually leave your job or lose your employer coverage
• You have 8 months from when your employer coverage ends to enroll in Part B penalty-free
• Most people in this situation still enroll in Part A at 65 since it’s free and provides a secondary layer of coverage

If Your Employer Has Fewer Than 20 Employees

This is where New Yorkers get surprised. With a small employer:

• Medicare becomes your primary insurance at 65 — even if you’re still working
• If you don’t enroll in Part B, your employer plan may pay as if Medicare were primary, leaving large gaps in coverage
• You should enroll in both Part A and Part B at 65, regardless of your employment status

What About COBRA?

COBRA coverage does not count as employer-sponsored insurance for Medicare purposes. If you’re on COBRA when you turn 65, you should enroll in Medicare during your Initial Enrollment Period. Delaying Medicare enrollment while on COBRA can result in permanent late enrollment penalties.

Serving New Yorkers Turning 65 Across the Metro Area

Craig Smith Insurance Group provides free, independent Medicare guidance to seniors across the New York metro area including:

Queens • Long Island • Nassau County • Suffolk County • the Bronx • Westchester County • Rockland County • Richmond County (Staten Island) • Kings County (Brooklyn) • and all of New York City

As an independent broker, I represent multiple insurance carriers — not just one. That means I compare plans across every major carrier available in your ZIP code and recommend what’s best for your situation, not what pays the highest commission.

We do not offer every plan available 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. Craig Smith Insurance Group is not affiliated with or endorsed by Medicare or any government agency.