Almost nobody's first solo trip goes badly for logistical reasons. It goes badly because of a Tuesday evening in a town where you know nobody and the restaurant has given you a table for one by the door.
That specific discomfort passes, usually around day three. Knowing that in advance helps more than any packing list.
Choose the destination for ease, not ambition
For a first trip, pick somewhere with good public transport, a common travel language, and enough other travellers that solo arrival is unremarkable. Portugal, Japan, Scotland, Vietnam, Slovenia and New Zealand all work. Somewhere requiring a hire car, three connections and a phrasebook does not.
The first 48 hours
Book the first two nights before you leave, and pick accommodation with a common space — a guesthouse or small hotel with a shared kitchen or terrace. Arriving into somewhere you have already chosen removes the worst decision fatigue of the trip.
Plan one anchor activity for the first full day. A walking tour, a cooking class, a long hike. It gives the day a shape and, incidentally, produces most of the people you will end up eating with.
Eating alone
The genuine trick: eat at counters. Ramen bars, tapas counters, market stalls, breakfast bars. Sitting at a counter with other solo diners is completely normal everywhere in the world; a two-hour dinner alone at a table for four is where the self-consciousness lives.
Bring a book, not a phone. It signals contentment rather than waiting.
Meeting people without forcing it
Activities beat bars. Anything with a shared task — a class, a group walk, a language exchange, a hostel kitchen — produces conversation without either party having to start one from nothing.
Accept that some of these people are for that afternoon only. That is the arrangement, and it is a good one.
The part nobody mentions
You will be bored at some point, and boredom alone feels different from boredom with company. It is not a sign the trip is failing. Some of the best hours of solo travel are the aimless ones: a bench, a coffee, a market, no plan at all.
For a gentle first destination, see three Lisbon walks or two weeks in Japan on a real budget.