Massimo Caldara

Practice Areas

Massimo Caldara is Managing Partner of Caldara & Associati. With over 25 years of professional experience, he has developed extensive expertise in both domestic and international tax matters, with a strong focus on advising high and ultra high net worth individuals. His practice includes wealth and estate planning, corporate reorganizations, and cross-border relocations of residence.

He also assists private clients with the legal and tax implications of holding financial and non-financial assets abroad, including foreign asset reporting obligations and international asset structuring.

His advisory work often involves complex asset classes such as crypto-assets and art, and he regularly advises professional athletes and individuals in the sports industry on cross-border tax planning and asset protection. In addition, he advises financial intermediaries and fiduciary entities on tax-efficient solutions in international contexts.

Career

Massimo Caldara holds a degree in Economics and Business from the University of Milan and a Master’s in Corporate Tax Law from Bocconi University.

Before founding his own firm, he gained significant experience at leading international law and tax firms and was later a partner at a leading tax boutique in Milan.

He is a regular speaker at seminars and conferences on domestic and international tax and wealth planning matters.

Professional Memberships

Massimo Caldara is a member of the Wealth Planning Commission of the Milan Bar of Chartered Accountants and is actively involved in professional associations such as IFA Italy and STEP Italy. He is also a member of the International Tax Specialist Group (ITSG).

He is registered with the Milan Bar of Chartered Accountants and the Italian Register of Statutory Auditors.

Publications

Massimo Caldara is a frequent contributor to We‑Wealth, where he has authored numerous articles on tax law and wealth planning, including:

“Tasse ridotte per chi si trasferisce in Italia: novità sulle agevolazioni” – analisi delle opportunità fiscali per chi decide di trasferire la propria residenza in Italia

“Adozione maggiorenne: vantaggi nella pianificazione successoria” – esplorazione delle implicazioni patrimoniali nell’adozione da parte di adulti"

“Trust o fondazione: quale scegliere per il passaggio generazionale?” – confronto tra trust e fondazioni come strumenti di successione

“Residenza fiscale e domicilio in Italia: guida ai nuovi criteri” – guida pratica sui recenti cambiamenti nella normativa fiscale italiana

“Donazione ed eredità: novità fiscali nel trasferimento di ricchezza” – panoramica sugli ultimi aggiornamenti normativi relativi a donazioni ed eredità

“Residenza fiscale delle società: attenzione alla sostanza economica” – approfondimento sul concetto di “substance” per la residenza fiscale societaria

“Oro e altri metalli preziosi: tasse più pesanti con la legge di Bilancio” – impatto delle nuove disposizioni fiscali sugli investimenti in metalli preziosi

“Bitcoin e criptovalute: novità rilevanti sul trattamento fiscale” – panoramica delle principali novità normative su criptovalute

“Convivenza di fatto: riflessioni su patrimonio e impatto fiscale” – riflessioni sul trattamento fiscale delle coppie di fatto

“Visti di ingresso: adempimenti e tempistiche per cittadini Ue ed Extra‑Ue” – guida chiara sulle procedure fiscali e burocratiche per visti d’ingresso

“Trasferimenti da e verso l’estero: entry tax ed exit tax?” – approfondimento sulle imposte di ingresso e uscita in contesti cross‑border

Languages Spoken

Massimo Caldara speaks English, Spanish and Italian.