Medicare Is Confusing. I Make It Simple.
I'm Ashley, a local independent Medicare broker helping San Diego County residents understand their options, compare plans, and choose coverage with confidence — at no cost to you.
Local · Independent · Licensed · No Cost to You

Contracted with Leading Medicare Carriers
How Can I Help?
Wherever you are in the Medicare process, Ashley has helped someone in your exact situation. Tell her where you're starting from.
I'm Turning 65
Learn when to enroll, what Medicare covers, and what decisions you'll need to make before your birthday.
I Want to Review My Plan
Not sure if your current coverage still fits? Ashley can compare your options and help you decide whether a change makes sense.
Medicare Advantage
Learn how Medicare Advantage plans work and whether one might fit your healthcare needs and budget.
Medicare Supplement
Learn how Medigap coverage works alongside Original Medicare and what it actually covers.
Your Local Medicare Broker
Meet Ashley
Ashley Watson became an independent Medicare broker because she watched too many San Diego seniors make costly Medicare mistakes — not from lack of intelligence, but from a lack of someone patient enough to truly explain their options.
As a local San Diego broker, Ashley works one-on-one with each client. She reviews your doctors, your prescriptions, and your budget — then walks you through every option in plain English. No jargon. No rush. No pressure.
Whether you're turning 65, losing employer coverage, or simply want to make sure you're in the right plan, Ashley is here — by phone, video, or in person, 7 days a week, always at no cost to you.

5★
All 5-Star
Google Reviews
Watch & Learn
Welcome to Medicare with Ashley
Meet Ashley and learn how she helps San Diego residents understand their Medicare options with clear, personal guidance at no cost.
Looking for more Medicare guidance? Visit Ashley's YouTube channel →
Why Work With Ashley?
Medicare is complicated. Working with Ashley doesn't have to be.
Independent Broker
Ashley is not tied to any single insurance company. She shops every major carrier to find what's actually best for you.
Represents Multiple Insurance Companies
With contracts across all leading Medicare carriers in San Diego, Ashley can compare dozens of plans side by side.
No-Cost Consultations
Ashley is paid by insurance carriers — never by you. Her time, advice, and enrollment help are always 100% free.
Reviews Your Doctors & Prescriptions
Before recommending any plan, Ashley checks that your current doctors and medications are covered at the best possible cost.
Local San Diego Expert
Ashley lives and works right here in San Diego County. She knows the local plans, local providers, and the people she serves.
Available Year-Round
Need help in March? July? Ashley's office is available 7 days a week, all year — not just during open enrollment.
In-Person Appointments Available
Prefer to meet face to face? Ashley offers in-person appointments in addition to phone and video — whatever is easiest for you.
"If your current plan is already a good fit, Ashley may tell you to keep it."
That's the kind of honest, no-pressure help you'll get. No agenda — just the right answer for your situation.
Client Stories
What San Diego Residents Are Saying
“Ashley made the entire Medicare process so much easier than I expected. She took the time to explain everything and dumbed it down for me haha. She compared my options, checked my doctors and prescriptions, and never made me feel rushed or pressured. I really appreciated having a local Medicare broker in San Diego who came to my house and I could actually call when I had questions. Even after I enrolled, Ashley has continued to be available whenever I need help. I highly recommend Medicare With Ashley to anyone turning 65 or needing help with their Medicare coverage.”
Rosewillie Sullano
San Diego County, CA · Google Review
“Ashley Watson was a lifesaver with Medicare. She broke everything down simply, made sure all my meds were covered, and got me a lower price without making me feel rushed. She really cares about what you need. I can't recommend her enough!”
Omar Silva
San Diego County, CA · Google Review
“Ms. Ashley has been nothing short of a blessing regarding enlightening me on how to maneuver through this medical program. I no longer am a candidate to be billed, especially when I cannot afford it to begin with. If you are reading this, and are affiliated with her organization, please tell them for me: she definitely deserves a raise and/or a promotion.”
Vernon Swain
San Diego County, CA · Google Review
Had a great experience with Ashley? Your review helps other San Diego seniors find trustworthy Medicare help.
Leave a Google ReviewWhat Happens When You Call Ashley?
No scripts. No pressure. Just a real conversation about your Medicare situation.
Tell Me What's Going On
We'll talk about where you are with Medicare and what you're looking for. There's no wrong place to start — Ashley has heard it all.
We'll Compare Your Options
Ashley will help you understand the differences that actually matter for your situation — your doctors, your prescriptions, your budget.
You Decide
Ashley will explain your options clearly and answer your questions. The decision is always yours — she's here to help, not to push.
No pressure. No confusing insurance jargon. Just straightforward Medicare help.
Medicare Plans Ashley Helps With
Ashley explains Medicare Advantage, Medigap plans, Medicare Part D, and more — clearly, so you can choose with confidence.
Have both Medicare and Medi-Cal? Ashley specializes in helping San Diego County residents who qualify for both programs — also called "dual-eligible" clients — understand how the two work together and find the right plan structure.
See how Ashley helps dual-eligible San Diegans →Ashley is deeply knowledgeable about the local and federal programs that help people save money on Medicare — like Extra Help, IRMAA appeals, and California's HICAP resources.
Medicare Part A
Hospital Insurance
Covers inpatient hospital stays, skilled nursing facility care, hospice, and some home health services.
Medicare Part B
Medical Insurance
Covers doctors' visits, outpatient care, preventive services, and medical equipment.
Medicare Advantage
Part C — All-in-One Plans
Combines Part A and B coverage, often with extra benefits like dental, vision, and hearing.
Medicare Part D
Prescription Drug Plans
Helps pay for prescription medications. Essential for managing ongoing medication costs.
Medicare Supplements
Medigap Plans
Fill the gaps in Original Medicare — helping cover copays, coinsurance, and deductibles.
Local Expertise
San Diego Medicare in 2026: What's Changed
Local provider networks and Medicare rules shift every year — Ashley tracks the changes so her San Diego clients don't have to.
Scripps and Medicare Advantage
Scripps Clinic and Scripps Coastal stopped accepting Medicare Advantage plans as of January 1, 2024, and this remains the case in 2026. Patients who want continued access to Scripps doctors typically need Original Medicare, often paired with a Medicare Supplement (Medigap) plan. That said, Scripps hospitals remain in-network with many Advantage plans, and some affiliated groups — such as Golden Physicians Medical Group — still accept certain Advantage plans and can provide access to Scripps Clinic specialists, a nuance that significantly affects plan selection for many San Diego seniors.
UCSD and Medicare Advantage
UCSD Health still participates with several Medicare Advantage plans in San Diego, but access to exclusive UCSD primary care physicians is limited depending on the plan. One option available to San Diego Medicare beneficiaries is UCSD Medical Group access through the SCAN Select plan. Ashley checks current UCSD network participation as part of every consultation for clients who want to keep their UCSD providers.
Sharp HealthCare and Medicare Advantage
Sharp HealthCare — San Diego's largest health system, with eight hospitals and a vast network of affiliated physicians — participates broadly with Medicare Advantage plans in the county. Most major carriers include Sharp providers in-network, but coverage varies by plan and medical group. Choosing a plan that covers your Sharp doctor requires a careful check before you enroll.
How Sharp HealthCare works with Medicare in San Diego →Prescription Drug Cost Cap
Medicare Part D now has an annual out-of-pocket cap of $2,100 on covered prescription drugs for 2026 — a significant protection for seniors managing high drug costs. Once you reach that cap in a calendar year, you pay $0 for covered drugs for the rest of that year.
When You Can Make Changes
The Annual Enrollment Period runs October 15 – December 7 each year, allowing you to switch Medicare Advantage plans, move between Original Medicare and Medicare Advantage, or change your Part D drug plan — with new coverage starting January 1. The Medicare Advantage Open Enrollment Period runs January 1 – March 31 for people already enrolled in a Medicare Advantage plan. Ashley can also check eligibility for Special Enrollment Periods year-round for clients who experience qualifying life events.
Get help during Annual Enrollment →Last updated: July 2026
Service Area
Serving All of San Diego County
Need a Medicare broker in Chula Vista, El Cajon, Escondido, National City, or North County San Diego? Ashley comes to you — by phone, video, or in person, at no charge.
Chula Vista
South Bay
El Cajon
East County
Escondido
North County
Poway
Inland North County
Vista
North County
Oceanside
North Coastal
La Mesa
East San Diego
National City
South Bay
South Bay San Diego
South Bay region
Santee
East County
Imperial Beach
South Bay
Lakeside
East County
Eastlake
East Chula Vista
San Marcos
North County
Mission Valley
Central San Diego
Spring Valley
East County
Lemon Grove
East San Diego
Coronado
Bay Area
San Diego
All neighborhoods
Don't see your city? Call Ashley — if you're in San Diego County, she serves you.
Common Medicare Questions
Plain-English answers to questions Ashley hears every day.
Does it cost anything to work with a Medicare broker?
Nothing at all. My services are completely free to you. I'm paid by insurance companies when I help someone enroll, and the commission is the same regardless of which plan you choose — so my only incentive is finding the plan that actually fits your situation. You never pay more by using a broker than enrolling directly.
Do you represent only one insurance company?
No — I'm an independent broker, which means I'm contracted with multiple insurance carriers, not tied to any single company. I can compare plans from many different insurers side by side and recommend the one that makes the most sense for you. If I only worked with one company, I could only show you their plans. That's not how I work.
Can you review the Medicare plan I already have?
Yes, absolutely. A lot of people I work with already have Medicare coverage but aren't sure if it's still the right fit — especially after a move, a health change, or when their plan changes its benefits at the start of a new year. I'll take a look at what you have and compare it with what else is available. There's no obligation to change anything.
What if my current Medicare plan is already the best choice?
Then I'll tell you to keep it. That happens more often than you might think. My goal isn't to move you to a different plan — it's to make sure you're in the right one. If what you have is already a good fit for your doctors, prescriptions, and budget, I'll say so.
Do you only help people who are turning 65?
Not at all. I help Medicare beneficiaries at every stage — people turning 65, people who lost employer coverage, people who want to review their existing plan, people dealing with a health change, and long-time Medicare members who just want a second opinion. If you have Medicare questions, I'm here.
Can we meet in person if I live in San Diego County?
Yes. I offer in-person appointments throughout San Diego County — at your home, a coffee shop, wherever is easiest for you. I also do phone and video calls, 7 days a week. Whatever is most comfortable for you works for me.
When should I sign up for Medicare?
Your Initial Enrollment Period is a 7-month window: the 3 months before your 65th birthday month, your birthday month, and the 3 months after. If you're still working at 65 with employer coverage from a company with 20+ employees, you may be able to delay without penalty. Missing your window without qualifying coverage can mean lifetime late penalties, so it's worth confirming your situation early.
Get Your Free San Diego Medicare Guide
Not sure where to start? Ashley's free guide walks you through every Medicare option available to San Diego seniors — plain English, no jargon.
- Medicare Advantage vs. Supplement — which is right for you
- How to avoid costly late-enrollment penalties
- What's actually covered (and what isn't)
- San Diego-specific plan options and costs