In 2026, the "easiest" Caribbean country for residency or citizenship depends on whether you seek speed or low cost. Dominica is often cited as the most affordable and straightforward for single applicants, with a highly streamlined Citizenship by Investment (CBI) process that requires no residency or visitation. For those prioritizing speed, St. Kitts and Nevis offers one of the fastest processing times in the region, sometimes granting approval in as little as four to six months. If you are looking for a residency that doesn't necessarily lead to immediate citizenship, the Cayman Islands and The Bahamas offer "Residency for Persons of Independent Means," though these require much higher financial thresholds. For most digital nomads or retirees, Antigua and Barbuda is a top choice due to its flexible "Nomad Digital Residence" visa, which allows you to live and work remotely on the islands for up to two years with minimal red tape, provided you meet the annual income requirements.