Bermuda eSIM

Do not assume it does. Bermuda is its own territory in the North Atlantic rather than part of the Caribbean Sea, and it is often not folded into a regional bundle just because the bundle is called Caribbean or North America. The only reliable check is to open the country list attached to the plan and look for Bermuda by name. If it is not spelled out there, choose a plan that names it explicitly instead of hoping the region covers it.

No. Visitors are not permitted to rent cars on the island. What you can hire is a scooter or one of the small two-seat electric vehicles; otherwise you use the buses, the ferries and taxis. In practice that means you will open maps and timetables far more often than on a normal island trip, and it is worth saving the last ferry of the day, because missing it turns into a long taxi ride around the island at a much higher fare.

This is not a city where everything is tapped through an app. Bus and ferry fares are paid with tickets or passes bought at the central terminal in Hamilton, at the ferry docks and from agents around the island. Ask on your first day what the current fare and pass options are and buy ahead, so you are not caught out at the stop. Your data helps far more with reading live departure times and planning connections than with paying.

Most plans here start when the phone first connects to a network at the destination, so you can install in advance at home and switch it on after landing. Each plan page states its own rule.

No. The eSIM is a second line, so you keep your home number for SMS OTP. Turn off roaming data on the home line and set the eSIM as the data line.