San Juan, Puerto Rico, USA

San Juan rocks if you want familiar U.S. systems, English-speaking hospitals, and walkable beachfront neighborhoods—but if you use a walker or wheelchair, those pretty cobblestones and crumbling sidewalks will make you want to scream or throw rocks. Pick your neighborhood carefully. San Juan gives you compact tourist zones where hotels, pharmacies, and restaurants cluster together—Old San Juan, Condado, Miramar, Isla Verde. You won't need a car if you stay in the right spot. As a U.S. territory, you get U.S. medical standards, U.S. dollars, and English widely spoken in tourism and healthcare. That's a huge stress reducer for older Americans. Daily costs run lower than big mainland cities, but beachfront neighborhoods and imported goods will hit your wallet. If you're on a fixed income, pay attention to where you're staying and what you're buying. Getting around The Tren Urbano (metro) runs 10.7 miles and connects with buses and the Cataño ferry. It's been offering free rides while they update ticketing. Sounds great, except: Stations aren't always near hotels Buses are inconsistent for accessibility and schedules You'll probably end up using taxis, Uber, or hotel shuttles like everyone else Wheelchair-accessible taxis exist but arrange them through your hotel in advance—don't assume you'll find one on the street. If you need elevators: Modern hotels and malls in Condado, Miramar, and Isla Verde are built to U.S. standards. Skip the charming walk-ups in Old San Juan.