Hamilton

Hamilton, Bermuda, is one of the most difficult destinations for a backpacker to navigate on a budget. There are virtually no traditional hostels in the city or on the island, meaning the 'cheapest' accommodation often involves guest houses or small Airbnb rentals that far exceed typical budget limits. The vibe is decidedly upscale, and while the pink sand beaches are free, getting to them requires a daily commitment to the public bus or ferry system. For food, your best bet is the 'buffet style' hot bars in local grocery stores like Miles Market or Lindo’s, where you pay by weight, or hitting up the street food vendors during the Harbour Nights if it were peak season. However, in February, street food is scarce. Free activities include walking the Railway Trail or exploring the lush Queen Elizabeth Park. To survive here, you must be disciplined: avoid alcohol at bars where a beer can cost $12, drink tap water (which is safe), and prioritize the free public beaches like Elbow Beach reachable by the pink buses. It’s a beautiful challenge, but one that requires a much higher daily burn than any typical backpacker destination.