Oct 14, 2026 . by June, Big Sur guide
What a first backpacking trip actually feels like, day by day
People ask me what it will be like, and I usually say "great", which is true and useless. So here is the long answer, from a three day trip I led in May with seven people who had never slept outside with a pack on.
The night before
You will pack and repack. You will put in a second fleece and take it out. Someone always texts me at 10pm asking if they really need the rain shell. Yes. Bring the shell.
Day one: the hill
The first two miles are the hardest of the whole trip, and that is not your fault. Your body is figuring out the pack. Your breathing is loud. Around the first switchback, everyone goes quiet and I can hear them deciding whether this was a mistake. Then we stop for a snack in the shade, someone spots the ocean through the trees, and the mood changes. By camp, people are already bragging.
nobody is ever last on purpose
Night one: the noises
The first night is never your best sleep. A deer walks past and sounds like a bear. The wind flaps the tent. Around 2am you realize how many stars there are and stay out longer than you meant to. Bring earplugs. Sleep comes on night two.
Day two: the click
This is the day it clicks. Your legs are sore but they work. You know how the pack goes on. Walking the ridge, nobody checks their phone because there is nothing to check. Lunch takes an hour and a half and no one minds. That evening, the fog comes in under the camp and turns the valley into a white sea. Most trips, someone cries a little. It is fine.
Day three: down, and strange
Going down is easy on the lungs and hard on the knees, so poles help. The last mile feels oddly sad. At the trailhead, car keys and phone buzzing feel loud. Most people eat a burger in total silence.
The week after
You will tell the story too many times. You will look up the next trip at work. That is how most of our second trips get booked, usually within a month.
If that sounds like your kind of tired, the Big Sur coast backpack is where we take most first timers. Bring the shell.