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You will need birthdates and social security numbers for each person in your household, a list of current prescriptions, and a list of doctors you would like covered. You will need an estimate of what your household income will be for the year you are enrolling, this includes your spouse's income if you are married, and the source of the income. You will be asked for some personal information, such as address, phone number, and date of birth. 

Often when you are enrolling in an individual or family plan it is because there has been a major change to employment in your household, and therefore your income. Don't worry, you can update your income throughout the year if you find your estimate to be incorrect. You can use this link to see what should be counted as income:  What’s included as income | HealthCare.gov 

You can login to your account (or create a new one) at Healthcare.gov and print or download a copy of the tax form by following instructions from this page:  How to Use Form 1095-A, Health Insurance Marketplace® Statement | HealthCare.gov  You can also call the Marketplace call center at 1-800-318-2596 and ask them to send you another copy. 

You will need your Medicare card or Medicare number and Part A & B start dates, a list of current prescriptions, and a list of doctors you would like covered. If you prefer to setup automatic payments you should bring your checkbook or the credit or debit card you would like to use for payment as well. You will be asked for some personal information, such as address, phone number, and date of birth. 

If you begin taking Social Security more than four months before you turn 65 your Medicare card will be mailed to you automatically. If not, you will get a Medicare card after enrolling in Medicare. This is done through the Social Security Administration by phone or online. Follow this link to the Social Security website for more information on how to enroll in Medicare:  Sign up for Medicare | SSA 

If you were automatically enrolled in Medicare and received a card there are instructions on how to decline coverage on the back of the card. Follow the instructions or call the number listed if you need help. 

Your initial enrollment period (IEP) begins three months before the month of your 65th birthday, unless your birthday is on the first, then your IEP begins four months before the month of your birthday. It's best to start the enrollment process as early as possible in case there are delays in processing. If you are covered by an employer or union plan, you may be able to delay enrollment without penalty. Speak to your benefits administrator to see how this will affect you. Follow this link to the Social Security website for more information on when to enroll in Medicare: When to sign up for Medicare | SSA 

 It’s important to sign up for Medicare coverage during your Initial Enrollment Period, unless you have other coverage that’s similar in value to Medicare (like from an employer). If you don’t, you may have to pay an extra amount, called a late enrollment penalty. Follow this link to the Medicare website for more information on late enrollment penalties:  Avoid late enrollment penalties | Medicare 

Yes, you are able to stay on a group plan or union plan without penalty as long as the plan is considered creditable coverage. Ask the plan administrator whether the plan in question meets the standards to qualify as creditable coverage.