Head to head

The Valley (Anguilla) vs San Juan (Puerto Rico).

🇦🇮 Anguilla against 🇵🇷 Puerto Rico, on tax, residence, cost, and the life. Same model, same year, no brochure.

The Valley (Anguilla)San Juan (Puerto Rico)
Effective tax at $300K0%4%
Effective tax at $1M0%4%
Effective tax at $3M0%4%
Kept at $1M$1M$960K
Capital gains0%0%
Cost index (Zurich 100)9575
Safety7/105/10
Schools5/106/10
Sun hours2,9002,900
Supercar street index#97#79
Routes inLump sum residence, Golden visaGolden visa, Founder & talent
Net millionaire inflow 2025 (country, Henley)n/an/a
Flight London99.2
Flight New York4.44.2

Simplified marginal model, indicative 2026 brackets, non-US single filer, no social contributions, deductions, wealth taxes, or treaties.

Verdicts

Who should pick which.

For an executive on salary

The Valley (Anguilla) keeps more of a $1M salary, $40K a year on this model. San Juan (Puerto Rico) answers with schools.

For a founder with an exit

Capital gains land at 0% in both. The order of operations, move then sell or sell then move, decides more than the rate. Neither city taxes wealth as such.

For a family

San Juan (Puerto Rico) leads on schools and a lower cost, The Valley (Anguilla) on safety. Sun hours are level.

The Dossier: The Valley (Anguilla), San Juan (Puerto Rico), and the third you have not considered.Your top 3 modeled on your income, exit, passports, and family. 10 chapters, about 40 pages, as a PDF within 24 hours. $249, refunded within 7 days if it does not change how you think.
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Tax figures use a simplified marginal model with indicative 2026 brackets for a non-US single filer, ignore social contributions, most deductions, wealth taxes, and treaties, and are not advice. Residence rules change often. Verify before acting.