Arcangelo D’Apolito is a Partner in Winckworth Sherwood’s Private Wealth, Trusts & Tax team, advising UK-based and international entrepreneurs, investors, senior executives, trustees and family offices on complex UK and international tax matters, with a particular focus on cross-border private wealth, private capital and succession structuring.

His practice spans international tax planning, estate and succession planning, trust and holding structures, international mobility, investment structuring and tax risk management. He regularly advises individuals and families whose wealth is concentrated in real estate, operating businesses and private investments, often across multiple jurisdictions.

Dual-qualified in England and Italy, Arcangelo is recognised for advising internationally mobile individuals, business owners and family offices with UK, Italian and wider European connections. He frequently coordinates multi-jurisdictional projects involving overseas lawyers, tax advisers, trustees and other professional advisers, acting as a trusted lead adviser and single point of contact to deliver integrated, commercially focused solutions.

Alongside his advisory practice, Arcangelo has extensive experience in tax investigations and dispute resolution. He advises clients on voluntary disclosures, negotiated settlements and high-value disputes involving offshore structures, historic planning arrangements and succession issues. His advisory and contentious experience enables him to help clients structure wealth efficiently while managing long-term tax risk and preserving planning objectives.

Clients value Arcangelo’s ability to combine technical excellence with pragmatic commercial judgement. He is often retained as a trusted adviser to individuals, families and family offices over many years, helping them navigate complex international issues and coordinating their wider network of advisers.

Before joining Winckworth Sherwood, Arcangelo held senior positions at PwC and KPMG in London and was a Tax Partner at leading Italian law firm Macchi di Cellere Gangemi. He has more than 20 years’ experience advising clients on UK, Italian and international tax matters.

Arcangelo is a member of the Society of Trust and Estate Practitioners (STEP), the International Bar Association and the Institute of Chartered Accountants in England and Wales. He regularly speaks at international conferences and contributes to publications on private wealth and international tax matters.

Recent experience

• Advising a UK resident UHNW investment professional and his family on a multi-jurisdictional wealth structuring project involving income tax, capital gains tax and inheritance tax planning.
• Advising internationally mobile business owners and senior executives on establishing and unwinding cross-border structures in connection with relocation to and from the UK.
• Assisting multiple senior executives in resolving disputes arising from failed tax avoidance arrangements, securing settlements involving claims exceeding £10 million.
• Advising an Italian UHNW family on the acquisition, ownership and succession planning of a significant Central London real estate portfolio.
• Advising private equity-backed businesses and their senior management teams on executive remuneration, incentive arrangements and retention structures.

Spoken Languages

Italian, English, German