100 cities in the Americas, from the easiest first trip to the hardest. The trickiest factor across the region is getting around (average 2.5/5).
| Country | Cities | Average |
|---|---|---|
| 🇨🇦 Canada | 13 | Easy 1.5 |
| 🇺🇸 United States | 34 | Easy 1.6 |
| 🇵🇷 Puerto Rico | 1 | Easy 1.8 |
| 🇦🇷 Argentina | 5 | Moderate 2.4 |
| 🇨🇱 Chile | 4 | Moderate 2.4 |
| 🇺🇾 Uruguay | 1 | Moderate 2.4 |
| 🇨🇷 Costa Rica | 2 | Moderate 2.6 |
| 🇲🇽 Mexico | 14 | Moderate 2.6 |
| 🇵🇦 Panama | 1 | Moderate 2.6 |
| 🇵🇾 Paraguay | 1 | Moderate 2.6 |
| 🇧🇷 Brazil | 6 | Moderate 2.8 |
| 🇩🇴 Dominican Republic | 1 | Moderate 2.8 |
| 🇬🇹 Guatemala | 1 | Moderate 2.8 |
| 🇪🇨 Ecuador | 4 | Hard 2.9 |
| 🇵🇪 Peru | 5 | Hard 3.0 |
| 🇨🇴 Colombia | 5 | Hard 3.2 |
| 🇧🇴 Bolivia | 2 | Very hard 3.5 |
By the five-factor average: Banff (1.4), Quebec City (1.4), Boston (1.4), Calgary (1.4), Chicago (1.4).
Guayaquil (3.6), Uyuni (3.6), Santa Marta (3.4), Cali (3.4), La Paz (3.4). Each city page explains how to handle it.
Across the region, getting around is the hardest (2.5/5). Averages: rip-offs & haggling 2.1, language 2.1, getting around 2.5, payments 1.8, safety 2.5.
Scores run from 1 (easy) to 5 (hard) for rip-offs, language, getting around, payments and safety, based on government travel advisories, Wikivoyage, the EF English index and official transport pages (as of 2026-10-05). Advisories change often — check your government's latest advice before you go. All 502 cities ranked ›