Annual Enrollment Period · San Diego
Medicare Annual Enrollment Period Help in San Diego County
I'm Ashley — a licensed, independent Medicare broker serving Chula Vista, South Bay, and all of San Diego County. During the Annual Enrollment Period, I'll help you review your Medicare coverage for 2027 in plain English, at no cost and with zero pressure. And I come to you.
Medicare Annual Enrollment Period: October 15 – December 7, 2026
Any changes you make take effect January 1, 2027.
What You Can Do During Annual Enrollment
The Annual Enrollment Period (AEP) is the once-a-year window when most people can make changes to their Medicare coverage. During AEP you can:
Switch from Original Medicare to a Medicare Advantage plan, or from Medicare Advantage back to Original Medicare
Switch from one Medicare Advantage plan to another
Join, switch, or drop a Medicare Part D prescription drug plan
Any changes take effect January 1, 2027. Even if you decide to keep what you have, it's worth a fresh look — plans can change from year to year.
Why Work With a Local Broker Who Comes to You
Getting out isn't always easy, so I don't ask you to. I meet clients right at home across South Bay and San Diego County. As an independent broker, I'm paid by the insurance carriers — not by you — so reviewing your options is completely free, with no obligation to change anything. My approach is simple: I take the time to understand your needs first, explain things clearly, and never rush you.
Serving South Bay & All of San Diego County
I help seniors across Chula Vista, National City, Imperial Beach, El Cajon, La Mesa, Escondido, and the surrounding communities — and I come to you.
Have both Medicare and Medi-Cal? I focus on helping dual-eligible clients understand their options — learn more here.
About Ashley
Ashley Watson is a licensed, independent Medicare broker (CA License #4052120) who has spent years helping San Diego County seniors make sense of Medicare. She built her practice because she'd seen too many people make confusing, costly enrollment mistakes simply because no one took the time to explain things clearly. Operating as Medicare with Ashley (Watson Insurance), she serves clients across San Diego County — and comes to them.
Frequently Asked Questions
When is the Medicare Annual Enrollment Period in 2026?
The Annual Enrollment Period runs from October 15 through December 7, 2026. Any changes you make during this window take effect January 1, 2027.
What can I change during Annual Enrollment?
During AEP you can switch between Original Medicare and a Medicare Advantage plan, switch from one Medicare Advantage plan to another, or join, switch, or drop a Medicare Part D prescription drug plan.
Does it cost anything to work with a Medicare broker?
No. As an independent broker, I'm paid by the insurance carriers, not by you. Sitting down to review your options is free, and there's no obligation to make any changes.
Do I have to change my Medicare plan during AEP?
No. If your current coverage still fits, you don't have to do anything. But because plans can change each year, it's worth a quick review to be sure it still works for your doctors, medications, and budget.
What areas do you serve?
I serve seniors across Chula Vista, National City, El Cajon, La Mesa, Escondido, and all of San Diego County — and I come to you.
I have both Medicare and Medi-Cal. Can you help?
Yes. Helping dual-eligible clients understand their options is a focus of mine. Reach out and I'll explain what applies to you, at no cost.
What should I have ready for our meeting?
Just a list of your current medications and your preferred doctors. That's usually all I need to help you see whether your coverage still fits.
Watson Insurance (Medicare with Ashley) · Serving San Diego County, California · (619) 947-2325 · ashley@watsoninsurancesd.com
We do not offer every plan available in your area. Currently, we represent 8 organizations which offer 75 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options.
This is a proprietary website and is not associated, endorsed or authorized by the Social Security Administration, the Department of Health and Human Services or the Center for Medicare and Medicaid Services. This site contains decision-support content and information about Medicare, services related to Medicare and services for people with Medicare. If you would like to find more information about the Medicare program please visit the Official U.S. Government Site for People with Medicare at www.medicare.gov.