The best time to initially enroll in Medicare is during the initial enrollment period.

During the initial enrollment period, you are allowed to bypass the questions regarding medical history. The initial enrollment period is a seven-month period. It starts three months prior to your 65th birthday month, the month of your birthday and three months after your 65th birthday month.

You are able to enroll in Medicare Part A (hospital insurance) and Part B (medical insurance — doctors office visits and other non-hospital care) via the website link above.

Part A is free if you have worked 10 years (40 quarters) contributing to the Social Security system. Medicare Part B is not free. In 2021, Part B premiums for middle incomes cost $148.50 per month. Medicare Parts A and B pay 80 percent of your care costs.

Once you have successfully enrolled in Medicare Parts A and B, it is time to take a look at filling in the Medicare gaps — the other 20 percent of a bill. You can view available Medicare supplemental plans at

Plan G is the richest plan new enrollees can join. It has a $203 part B deductible in 2021. The most competitive companies for age 65 are $85 to $110 per month, depending on your gender.

Before applying for a specific plan, make sure your doctor accepts the insurance company and policy. To apply for a Medicare supplemental policy, you will need your Medicare number and the effective date of your Medicare Part A and B plans. The Part A date is the first day of your 65th birthday month.

Medicare Part D (drug plan): Once you’ve settled your primary Medicare needs, it’s time to choose a prescription card if necessary for any maintenance medications or future prescription needs. To choose a prescription plan that best fits your needs, go to and click “Continue without logging in” if you haven’t yet set up a account.

Select Drug Plan (Part D) and enter your zip code to continue to available plans. Follow the prompts about pharmacy preference, etc., until you get to the “Add Your Prescription Drugs” page. Enter any prescriptions you take for an accurate estimate of your out-of-pocket expense per year with each drug plan.

You’ve seen Joe Namath’s TV ad for free and inexpensive Medicare Advantage plans. He makes it sound better than sliced bread. Joe is totally focused on price but gives few details.

Medicare Advantage plans are 100 percent insurer based (no Medicare), are generally cheaper (0 to $50 per month). They are cheaper for a reason. You get less. Medicare Advantage plans have limited PPO networks for doctors and hospitals, much higher ($3,000-$8,000) out-of-pocket maximums (versus $203 in 2021 for a Plan G Medicare supplement), usually co-pays every office visit and a single ”cookie cutter” prescription card that may not fit your prescription needs.

There is no right or wrong. Traditional Medicare vs. Medicare Advantage are just two different approaches. See

What you need is objective information to compare traditional Medicare supplements with Medicare Advantage Plans. Our recommendation: Work with an unbiased agent who is licensed in both Medicare supplement and Medicare Advantage plans with all the major companies. You will receive objective and an unbiased education to make a prudent decision each year.

Open enrollment in year two and onward is Nov. 15 to Dec. 7 for a Jan. 1 renewal. Next time we will focus on how to enroll if you stay on your employer’s group medical after age 65 and renewing Medicare Supplement and Medicare Advantage plans in year two and beyond.

Bob Land is president of Landmark Financial Services.