Private health insurance for Naples and Collier County

Naples is full of people who answer to themselves: business owners, consultants, and people who retired early. I'm a licensed health insurance agent, and I help them find coverage that fits, whether that's until Medicare or for as long as they work for themselves.

Sterling Watnem in a navy suit, smiling outdoors
A wooden pier stretching into calm Gulf water at dusk

In Naples, working for yourself is normal

Self-employment is more common in Naples than almost anywhere else in Florida. In the city, about 28% of working residents are self-employed, and about half of all households earn $150,000 or more, based on Census Bureau estimates. Across Collier County, about 18% of workers are self-employed.

If that sounds like you, nobody hands you a benefits packet. And at higher incomes, the Marketplace usually charges full price. For 2027 coverage, tax credits stop at $63,840 for a single person and $86,560 for a couple. Above those numbers, a private plan is worth comparing.

Who I help in Collier County

  • Self-employed and business owners

    Nobody hands you a benefits packet. I compare private and Marketplace plans for consultants, owners, and teams of about 5 or 6.

  • Retired before 65

    Medicare starts at 65. If you stepped away from work early, I compare COBRA, a Marketplace plan, and a private plan for the years in between.

  • Splitting the year up north

    A local network may not do much for you in Michigan or New Jersey in July. Ask me about nationwide PPO options.

  • Paying for a concierge doctor

    That fee covers access to your doctor, not a hospital stay, surgery, imaging, or a specialist. I'll find a plan that works around the doctor you already like.

Your local hospitals

Most Collier County hospital care runs through NCH, with NCH Baker Hospital downtown and NCH North Hospital, or through Physicians Regional's Pine Ridge and Collier Boulevard campuses. On every plan we compare, I check which of these, and which of your doctors, are in network.

Getting started is simple

  1. See your prices first

    Use my estimator for a quick look at private and Marketplace prices.

  2. Choose a call time

    When you're ready, pick a 30-minute time slot.

  3. Compare on a shared screen

    We'll go over your choices together, plan by plan.

  4. Count on me after enrollment

    I don't disappear after you sign up. Questions come to me instead of an insurance company hold line.

Good to know

The estimate is a starting point, not a final price, and private plans can decline an application based on your health answers.

What Naples clients ask me

  • I'm retiring before 65. Which kind of plan makes sense?

    If you're healthy, a private plan can be a strong fit for those bridge years. If you're managing a condition or take costly medications, a Marketplace plan may be the safer choice. I'll tell you honestly which way I'd lean and why.

  • Can I apply for a private plan outside open enrollment?

    Marketplace plans are generally limited to open enrollment, which runs November 1, 2026 to January 15, 2027 for 2027 coverage, unless you have a qualifying life event. Private plans follow their own rules, so it's worth a call even in the middle of the year.

  • I own a business with a few employees. Can you help with that too?

    Yes. I help owners with small teams, usually around 5 or 6 people, compare practical coverage, and I explain everything in plain language.

  • Do you help people outside the city of Naples?

    Yes. I work with people all over Collier County, including North Naples, Pelican Bay, Golden Gate, Marco Island, and Ave Maria. I help people in nearby Bonita Springs and Estero too.

See what coverage could cost you

It takes 4 quick questions to see both a private and a Marketplace estimate. You don't need to give me your email.

A phone in Sterling's hand showing an incoming call from a client