Medicare Open Enrollment comes around every fall, and it can be tempting to simply leave your coverage alone—especially if your current plan worked reasonably well this year.
But Medicare plans can change from one year to the next.
Your premiums may change. Your prescriptions may be covered differently. Doctors can move in or out of a plan's network. Copays and deductibles can change. And your own healthcare needs may be different than they were a year ago.
That is why Medicare Open Enrollment can be an important part of your annual retirement and financial planning review.
For 2026, Medicare Open Enrollment runs from October 15 through December 7. Changes made during this period generally take effect January 1, 2027.
Here are some of the most important things to review before deciding whether to keep your current Medicare coverage for another year.
What Can You Change During Medicare Open Enrollment?
During Medicare Open Enrollment, people with Medicare generally have several options.
Depending on your current coverage, you may be able to:
Switch from one Medicare Advantage plan to another
Move from Original Medicare to a Medicare Advantage plan
Move from Medicare Advantage back to Original Medicare
Join, drop, or change a Medicare Part D prescription drug plan
Change Medicare Advantage plans with or without prescription drug coverage
The enrollment period ends December 7, and the plan generally must receive your enrollment request by that date for the change to take effect January 1.
If you are satisfied with your current coverage and the plan continues to be offered, you generally do not have to make a change simply because Open Enrollment has arrived.
But that does not mean you should automatically ignore it.
1. Read Your Annual Notice of Change
One of the first things to review is the information your current Medicare plan sends you explaining what will change for the following year.
Do not assume your 2027 plan will be identical to your 2026 plan.
Look for changes involving:
Monthly premiums
Deductibles
Copays
Coinsurance
Prescription drug coverage
Provider networks
Pharmacy networks
Prior authorization requirements
Supplemental benefits
Maximum out-of-pocket limits
Even a plan that keeps the same name may have different costs or benefits next year.
Medicare recommends beginning to compare your current coverage with upcoming options around October 1, before Open Enrollment officially begins October 15.
2. Are Your Doctors Still in the Network?
If you are enrolled in a Medicare Advantage plan, provider networks can be particularly important.
Ask yourself:
Are the doctors and specialists I actually use still participating in my plan for 2027?
That may include your:
Primary care physician
Cardiologist
Oncologist
Orthopedic physician
Dermatologist
Physical therapist
Preferred hospital
Outpatient facility
Other specialists you regularly see
A plan may look attractive based on premiums and supplemental benefits, but those savings may matter much less if your preferred physicians or hospitals are outside the network.
Do not look only at whether a plan has a "large network."
Look at whether it includes the providers you actually want to use.
3. Review Every Prescription You Take
Prescription drug coverage is another area that deserves an annual review.
Make a current list of your medications, including:
Drug name
Dosage
How frequently you take it
Whether you use a brand-name or generic version
The pharmacy you normally use
Then review how each plan covers those medications.
A prescription that was inexpensive under your current plan in 2026 could move to a different formulary tier or have different cost-sharing in 2027.
You should also look beyond whether a drug is simply "covered."
Ask:
What tier is the medication on?
What is the copay or coinsurance?
Is prior authorization required?
Is step therapy required?
Are there quantity limits?
Is my preferred pharmacy considered preferred or standard?
Would mail-order pricing be different?
Those differences can add up quickly for someone taking several medications throughout the year.
4. Compare the Total Cost — Not Just the Monthly Premium
A $0-premium Medicare Advantage plan can sound extremely attractive.
But a monthly premium is only one component of healthcare costs.
When comparing plans, consider the potential total cost of coverage, including:
Monthly premium
Deductible
Primary care copays
Specialist copays
Hospital costs
Outpatient procedures
Imaging
Prescription drugs
Emergency room visits
Urgent care
Maximum out-of-pocket limits
A plan with a slightly higher monthly premium could potentially be less expensive overall depending on how frequently you use healthcare services.
Likewise, the lowest-premium plan may not necessarily be the most appropriate option for someone with significant or ongoing medical needs.
5. Know Your Maximum Out-of-Pocket Exposure
This number can be easy to overlook.
Medicare Advantage plans generally have limits on the amount you may be required to pay out of pocket for covered Part A and Part B services during the year.
When comparing plans, consider not only what healthcare might cost in a normal year but also what it could cost in a bad year.
Suppose you experience:
A hospitalization
Surgery
Cancer treatment
Extensive physical therapy
Multiple specialist appointments
Another major medical event
Understanding your potential maximum financial exposure can be an important part of retirement planning.
For a retiree living on a relatively fixed income, the difference between plans can affect how much money needs to remain available in emergency reserves.
6. Review Your Prescription Drug Coverage for 2027
Medicare Part D has undergone significant changes in recent years, and the program continues to evolve.
CMS has finalized rules continuing the redesigned Part D structure for 2027 and beyond, including the elimination of the former coverage-gap phase and no enrollee cost sharing for covered Part D drugs once the catastrophic phase is reached.
But the fact that Medicare establishes overall Part D rules does not mean every prescription drug plan is identical.
Individual plans can still differ in areas such as:
Premiums
Deductibles
Formularies
Drug tiers
Pharmacy networks
Copays and coinsurance
Prior authorization requirements
CMS has said final 2027 Medicare Advantage and Part D plan offerings and premium information will be released in September ahead of Open Enrollment.
That makes reviewing your actual plan choices important rather than assuming this year's drug coverage will remain the best option next year.
7. Consider Dental, Vision, Hearing and Other Supplemental Benefits Carefully
Many Medicare Advantage plans advertise supplemental benefits such as:
Dental
Vision
Hearing
Fitness programs
Over-the-counter allowances
Transportation benefits
Meal benefits
Other wellness programs
These benefits can certainly have value.
But they should generally be evaluated alongside the plan's core medical coverage.
For example, a plan offering a generous dental benefit may be appealing—but you should still ask:
Are my physicians in network?
Are my prescriptions covered?
What are the hospital copays?
What is the maximum out-of-pocket limit?
Are referrals required?
What restrictions apply to the supplemental benefit?
The extras can be useful, but they should not necessarily outweigh the parts of the plan that affect your most important healthcare needs.
8. Original Medicare or Medicare Advantage?
Open Enrollment may also be a time to reconsider how you receive your Medicare coverage altogether.
Some people receive benefits through:
Original Medicare, generally consisting of Medicare Part A and Part B, potentially combined with a separate Part D prescription drug plan and possibly Medicare Supplement Insurance, commonly known as Medigap.
Others choose a private Medicare Advantage plan, which generally provides Part A and Part B coverage through the plan and may include prescription drug coverage and additional benefits.
Neither structure is automatically right for everyone.
Things to consider can include:
Provider flexibility
Travel
Premiums
Cost-sharing
Prescription drug needs
Supplemental benefits
Referral requirements
Provider networks
Your expected healthcare utilization
However, there is an important caution if you are considering leaving Medicare Advantage and moving to Original Medicare.
9. Be Careful About Assuming You Can Always Buy a Medigap Policy
Someone moving from Medicare Advantage back to Original Medicare may also want a Medigap policy to help cover certain out-of-pocket costs.
But Medigap rules are different from Medicare Advantage enrollment rules.
There are specific periods and circumstances when an insurer must generally offer you Medigap coverage. Outside certain guaranteed-issue situations, your ability to purchase a policy and the pricing available to you may depend on applicable rules and circumstances.
Medicare specifically warns people considering a switch to Original Medicare that there are limits on when Medigap coverage can be added.
So before dropping a Medicare Advantage plan because you assume you can simply purchase a Medigap policy afterward, understand your options first.
This can be one of the most important parts of making a coverage change.
10. Has Your Health Changed This Year?
Your plan may not have changed much.
But you may have.
Consider whether anything happened in 2026 that could affect the type of coverage you want in 2027.
For example:
Were you diagnosed with a new condition?
Did you begin seeing a new specialist?
Did you start taking an expensive medication?
Are you expecting surgery?
Do you need more dental work?
Are you receiving physical therapy?
Are you traveling more frequently?
Did you move or are you planning to move?
A plan that was an excellent fit two years ago may no longer match your healthcare needs today.
11. Are You Planning to Travel More in Retirement?
Travel can be an overlooked consideration when comparing coverage.
If retirement plans include spending significant time outside the Tampa Bay area—or outside Florida altogether—consider how your coverage works when you are away from home.
Ask questions such as:
Can I see non-emergency doctors outside my local area?
How large is the plan's network?
What happens if I spend several months in another state?
What coverage applies when traveling internationally?
Will my prescriptions be easy to fill while traveling?
Someone who spends most of the year close to home may have very different priorities from a retiree who regularly travels or spends part of the year in another state.
12. Don't Forget About Income-Related Medicare Costs
Medicare planning is not completely separate from tax planning.
Higher-income Medicare beneficiaries may pay additional amounts for Medicare Part B and Part D through the Income-Related Monthly Adjustment Amount, commonly called IRMAA.
Because Medicare premiums can be affected by income reported on prior tax returns, decisions such as:
Roth conversions
Large retirement distributions
Capital gains
Business sales
Investment sales
can potentially interact with future Medicare costs.
This does not mean you should avoid an otherwise beneficial financial decision simply because it could affect Medicare premiums.
It does mean taxes, investments, retirement income and Medicare should ideally be reviewed together.
A Roth conversion, for example, may still make excellent long-term sense even if it temporarily increases Medicare premiums.
The important part is understanding the potential effect before making the decision.
13. Compare Plans Even If You Think You Want to Keep Yours
You do not need to switch plans every year.
Sometimes reviewing your choices will simply confirm that your existing plan still fits your needs.
That is a perfectly reasonable outcome.
The purpose of Open Enrollment is not to make a change just for the sake of making one.
It is to make an informed decision.
Compare:
Your current plan for 2027
versus
Other coverage available to you for 2027.
Then determine whether changing actually improves your situation.
What Happens If You Miss the December 7 Deadline?
For most people, December 7 is the final day of Medicare's annual Open Enrollment period.
Changes made during Open Enrollment generally begin January 1.
There are other Medicare enrollment periods that apply in certain circumstances.
For example, people already enrolled in Medicare Advantage generally have a separate Medicare Advantage Open Enrollment Period from January 1 through March 31, during which they may make certain coverage changes. However, the options during that period are not identical to the fall Open Enrollment period.
Special Enrollment Periods may also apply when certain qualifying events occur.
The simplest approach is usually not to assume you can fix everything later.
If you want to evaluate your options for 2027, try to complete that review before December 7.
A Medicare Review Is Part of Retirement Planning
Healthcare can be one of the largest expenses retirees face.
That means Medicare should not necessarily be treated as a completely separate decision from your financial plan.
Your healthcare coverage can interact with:
Retirement income
Taxes
Roth conversions
Investment withdrawals
Social Security
Cash reserves
Travel plans
Long-term spending needs
A plan that looks inexpensive from an insurance perspective may create different financial risks depending on your health and circumstances.
Likewise, a financial strategy designed to lower lifetime taxes may have temporary Medicare implications that should be considered before implementing it.
Looking at the entire picture can help you make more informed decisions.
Your Medicare Open Enrollment Checklist
Before December 7, consider reviewing:
Your 2027 plan premium
Your deductible
Your doctors and specialists
Your preferred hospitals
Every prescription you currently take
Drug formulary tiers
Pharmacy network
Specialist and hospital copays
Maximum out-of-pocket limit
Dental, vision and hearing benefits
Travel coverage
Expected medical procedures
Changes to your health
Changes to your income
Potential IRMAA considerations
Whether your current coverage still fits your retirement plan
You may ultimately decide to keep exactly what you have.
But you will be making that decision because you reviewed your options—not simply because last year's plan automatically rolled into another year.
Preparing for Medicare Open Enrollment 2026
Medicare Open Enrollment runs from October 15 through December 7, 2026, with elections generally taking effect on January 1, 2027.
That gives Medicare beneficiaries a limited window to review what is changing and decide whether their current coverage continues to meet their needs.
At Generations Tax & Wealth Management, we believe retirement decisions should be considered as part of your entire financial picture. Taxes, investments, retirement income, healthcare expenses and Medicare can all affect one another.
As you prepare for 2027, now is a good time to review not only your Medicare coverage but also how healthcare fits into your broader retirement and financial plan.
If you would like to review your retirement strategy for the year ahead, schedule a conversation with our team today.
This material is intended for general educational purposes only and should not be considered individualized tax, legal, investment, or insurance advice. Medicare rules, plan availability, benefits, costs and individual circumstances can change. Consult Medicare.gov, your plan, and appropriately licensed professionals regarding your specific coverage options.