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Medicare Planning in Orange County, NY

Make Confident Decisions About Your Healthcare Coverage.

Medicare is a critical piece of your retirement picture—but the rules, deadlines, and options can feel confusing. At Cammareri Wealth Management Group, we help individuals and couples in Orange County, NY and beyond understand how Medicare works, what choices are available, and how those decisions fit into the rest of their financial and retirement plan.

Medicare Planning, Made Clear

Know What You Need, When You Need It, and Why It Matters

Medicare isn’t one-size-fits-all. There are different parts, enrollment windows, and coverage tradeoffs that can affect both your healthcare and your budget for years to come. Our role is to turn the jargon into plain language and help you choose a path that supports your health needs and financial goals.


Grounded in our five core commitments—communication, consolidation, customized strategies, comprehensive planning, and long-term commitment—we walk through your options step by step. We help you understand how Medicare interacts with employer coverage, retirement income, and potential long-term care needs, so your decisions feel organized instead of rushed. While we don’t work for Medicare or any government agency, we help you make sense of your choices and prepare for conversations with licensed insurance professionals where needed.


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Four Key Dimensions of Smart Medicare Planning

Medicare planning isn’t just about picking a plan—it’s about fitting coverage into your larger retirement picture. We focus on four key dimensions:

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Clarifying Your Healthcare Needs and Priorities

We start by talking through your current health, doctors, prescriptions, and preferences around networks and flexibility. We also discuss your budget and how much predictability you want in premiums vs. out-of-pocket expenses. This clarity helps guide which types of coverage may be the best fit.

Understanding Your Medicare Options and Timelines

Next, we walk through how Medicare works in plain language: Parts A and B, Medicare Advantage, Medigap (supplement) plans, and prescription drug coverage. We highlight important enrollment periods and potential penalties so you know what needs to be done—and by when—to avoid gaps or unnecessary costs.

Integrating Medicare With Your Retirement and Estate Plan

Medicare is just one part of your financial picture. We connect your coverage choices with your retirement income, long-term care planning, and legacy goals. This comprehensive approach helps you think beyond just premiums and deductibles and see how healthcare fits into your broader plan.

Coordinating Medicare With Employer or Retiree Coverage

If you or your spouse are still working or have retiree coverage, things can get complicated fast. We help you understand how Medicare interacts with employer plans, COBRA, and retiree benefits, and what might change when one of you stops working. The goal is to avoid overlapping coverage or unintended gaps.

Key Areas We Help You Think Through

Choosing When to Enroll in Medicare

We help you decide when it makes sense to enroll in Medicare based on your age, employment status, and existing coverage. Together, we look at how timing affects premiums, penalties, and coordination with other insurance.

Comparing Medicare Options in Plain Language

Original Medicare, Medicare Advantage, Medigap, prescription coverage—it can all blur together. We outline the key differences in simple terms, so you understand the tradeoffs around cost, flexibility, and provider access before you select a path with a licensed insurance professional.

Coordinating Medicare With a Spouse’s Coverage

If you’re married, decisions made by one spouse can affect the other. We help you look at the full household picture—ages, work status, coverage options—so your Medicare choices support both of you, not just one person at a time.

Planning for Healthcare Costs in Retirement

Premiums, deductibles, copays, and uncovered expenses all need a place in your retirement budget. We help you estimate healthcare costs, factor them into your income plan, and think through how to manage unexpected medical expenses without derailing your long-term goals.

Connecting Medicare to Long-Term Care and Legacy Goals

Medicare doesn’t cover everything, especially when it comes to long-term care. We help you understand where Medicare stops, how other strategies may fill the gap, and what that means for your spouse and legacy goals if one of you needs extended care.