Anthony Orphanos

With over 18 years of experience in financial planning, estate management, and investment advisory services, I founded Vineyard Wealth Group to help families, individuals, and non-profits navigate their financial journeys with confidence. My approach combines personalized planning, trusted advice, and innovative strategies tailored to each client’s unique goals and values, with a particular emphasis on Social Security analysis and decision-making as a cornerstone of financial success. Prior to starting Vineyard Wealth Group, I spent nearly 14 years at Charles Schwab, managing a $15 billion complex with over 30 employees, and served as a Senior Financial Advisor at Martha's Vineyard Investment Advisors. These experiences honed my ability to deliver comprehensive and collaborative wealth management solutions. As a CERTIFIED FINANCIAL PLANNER® professional, I bring advanced expertise in asset management, estate planning, tax strategies, and Social Security planning, along with credentials as an Accredited Asset Management Specialist® and Chartered Mutual Fund Counselor®. My Six Sigma Black Belt certification further reflects my commitment to efficiency and excellence in service delivery. Beyond the numbers, I’m deeply invested in my community. I serve on the board of the Martha’s Vineyard YMCA, actively support local initiatives, and completed the 2023 Boston Marathon, raising over $8,000 for the Doug Flutie Jr. Autism Foundation. Let’s connect and explore how I can help you achieve financial clarity, optimize your Social Security decisions, and enjoy lasting peace of mind.

James Simpkins is a Wealth Management Advisor at Merrill Lynch Wealth Management. With 20 years of experience on the floor of the New York Stock Exchange and a decade at Merrill, he utilizes his extensive industry background to help clients navigate financial markets and pursue their long-term goals. His areas of expertise include legacy planning, liquidity management, retirement income, portfolio management, and values-based investing, among others. James works closely with clients to develop personalized financial strategies based on their individual objectives, risk tolerance, and liquidity needs. James holds a Bachelor's Degree from Colgate University and maintains professional designations including CERTIFIED FINANCIAL PLANNER (CFP) and Personal Investment Advisor (PIA). Beyond his professional work, he is involved with the Marthas Vineyard Boys and Girls Club and enjoys golfing, skiing, and spending time with his family.

Robert Areano is a Wealth Management Advisor with Merrill Lynch Wealth Management. He holds the professional designation of Personal Investment Advisor (PIA). Robert earned an Associate's Degree from Massachusetts Bay College. His expertise focuses on wealth management and investment advisory services within the financial sector.