Confused About Medicare?
Your trusted Medicare broker in San Diego — taking the time to actually explain your options, clearly and without pressure.
Whether you're turning 65 in San Diego, need Medicare enrollment help, or want to compare plans, Ashley guides you through Medicare Advantage, Medicare Supplements, Part D, and more. Always free. Always honest. No pressure.
Contracted with Leading Medicare Carriers
Meet Ashley Watson
A Medicare Broker Who Actually Cares
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
Hear From Ashley Directly
Ashley regularly shares Medicare tips and answers common questions on her YouTube channel. Watch a video, then schedule a free call when you're ready.
Want a specific video here? 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.
Client Stories
What San Diego Residents Are Saying
"I was completely overwhelmed by Medicare when I turned 65. Ashley walked me through everything step by step, and I never felt rushed or pressured. I finally feel confident about my coverage — something I couldn't say before working with her."
Margaret T.
La Jolla, CA
"We needed two separate plans that worked with our different doctors. Ashley found options that saved us over $200 a month combined."
Robert & Carol H.
Chula Vista, CA
"After moving to San Diego, I needed to change my Medicare plan. Ashley made the whole transition painless. She followed up three times just to make sure everything went smoothly."
Dorothy L.
Escondido, CA
"Ashley actually told me my current plan was fine and didn't need to change. That kind of honesty is rare. I trust her completely."
Frank M.
National City, CA
"I called three different agents before finding Ashley. She was the only one who took time to actually explain what I was signing up for. Couldn't recommend her more."
Barbara S.
Oceanside, CA
"We were so stressed about the open enrollment deadline. Ashley called us back within the hour and handled everything. Absolute lifesaver."
James & Linda P.
El Cajon, CA
Had a great experience with Ashley? Your review helps other San Diego seniors find trustworthy Medicare help.
Leave a Google ReviewMedicare 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. However, some affiliated medical groups — such as Mercy Physicians Medical Group — still accept certain Advantage plans and can admit to Scripps hospitals, 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.
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.
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
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.
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.
What's the difference between Medicare Advantage and a Medicare Supplement?
Medicare Advantage (Part C) plans are offered by private insurers, often with $0 premiums, and usually include drug coverage and extras like dental and vision — but you typically use a network of doctors. Medicare Supplement (Medigap) plans work alongside Original Medicare, let you see any doctor nationwide who accepts Medicare, and have predictable costs, but come with a monthly premium and require a separate Part D drug plan. The right choice depends on your doctors, prescriptions, budget, and travel habits.
How much does it cost to work with a Medicare broker?
Nothing. My services are 100% free to you. I'm paid by the insurance companies when I help you enroll, and the commission is the same regardless of which plan you choose — so my only incentive is finding the plan that actually fits you. You never pay more by using a broker than enrolling directly.
What is the Medicare Annual Enrollment Period?
The Annual Enrollment Period (AEP) runs October 15 through December 7 every year. During this window you can switch Medicare Advantage plans, move between Original Medicare and Medicare Advantage, or change Part D drug plans, with new coverage starting January 1. Plans change their benefits, networks, and drug lists every year, so an annual review is worth doing even if you're happy with your current plan.
Do Medicare Advantage plans in San Diego really cost $0?
Many San Diego County Medicare Advantage plans have a $0 monthly premium, but $0 premium doesn't mean $0 cost. You still pay your Part B premium, plus copays and coinsurance when you use care. The best plan for you depends on your doctors, your prescriptions, and how you use healthcare — which is exactly what I help you compare.
Can I keep my doctor if I change Medicare plans?
It depends on the plan type. With Original Medicare plus a Supplement, you can see any doctor in the U.S. who accepts Medicare. With Medicare Advantage, your doctors need to be in the plan's network. Before recommending any plan, I check that your doctors, hospitals, and prescriptions are covered — that's step one of every consultation.
Which areas of San Diego do you serve?
I work with Medicare beneficiaries throughout San Diego County, including San Diego, Chula Vista, El Cajon, Escondido, La Mesa, and National City. Consultations are free and can be done by phone, video, or in person.
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
Send Me the Free Guide
Ashley will send it to you personally — no spam, ever.