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The Packing Guide: Autumn Getaways in Style

October 19, 2026

The Packing Guide: Autumn Getaways in Style

In October, a Friday in Milan ends earlier than it did in summer. By four o'clock the light is turning amber over the rooftops. By five, the city is emptying towards the hills.

These are short journeys of two nights, perhaps three. They are also the hardest to pack for. There is no room for the unnecessary, and in a village in the Langhe on a Sunday there is nowhere to buy what you forgot.

This guide follows three of our favourite autumn escapes, and the way we pack for them.

Three autumn escapes from Milan and Modena

Milan to the Langhe, by car. About two hours south-west of Milan, the hills around Alba and Barolo are at their best from October, when the grape harvest ends and the white truffle season begins. The roads climb between vineyards to hilltop villages, and dinner is long. It is the landscape that gave the Langhe Business Bag its name.

Modena to the Apennines, over the Futa. From Modena, the hills begin within the hour. Take the old Strada Statale 65 between Bologna and Florence and you cross the Passo della Futa, part of the Mille Miglia route from 1927 to 1957. In autumn the chestnut woods turn copper and the villages hold their harvest festivals.

Milan to Lake Como, by train. The train from Milano Centrale reaches Varenna in about an hour, and the ferry crosses to Bellagio in a few minutes more. Many lakeside hotels close for winter in early November, so October is the last chance of the year. It is also where our Bellagio Backpack takes its name.

"My favourite autumn weekend is Langhe. You leave Modena after lunch on Friday and you're at dinner by eight." 

Choose the bag by the journey, not the wardrobe

The way you travel decides the bag, and the bag decides everything else.

If you are driving, the bag spends most of its time in the boot and the rest on your shoulder between the car and the door. The Futa Long Handle Weekender suits this. Its long handles go over the shoulder without a separate strap, and its softer body settles into the space around it.

If you are taking the train, choose the structure. The Stelvio Short Handle Weekender keeps its shape on a luggage rack and in a hotel room. Its hand-rolled handles carry a full load comfortably, and a detachable shoulder strap helps on long platforms.

How to pack a weekend bag, step by step

  1. Lay everything out first. Then put a third of it back. For two nights you need fewer clothes than you think, and more room for what you bring home.
  2. Choose one colour palette. Browns, navy, cream and grey all work together in autumn light, so every piece goes with every other.
  3. Wear the heaviest layer. Travel in the coat or the thickest knit so it never takes up space in the bag.
  4. Heavy items at the base. Shoes go in dust bags along the bottom, close to where the handles meet the body. This keeps the weight low and the bag balanced when carried.
  5. Fold knitwear, roll the rest. Knits keep their shape when folded flat. Shirts and T-shirts crease less when rolled.
  6. Small things in one place. Chargers, passports, keys and toiletries go into a single pouch rather than loose in the bag.
  7. Arrival outfit on top. The first thing you take out should be what you will wear to dinner that evening.
  8. Leave room. A weekender packed to bursting strains its seams and zip. Leave space for a bottle of Barolo.

Pack for two temperatures

Autumn in the north is two seasons in one day. Mornings in the valleys can be misty and close to freezing, while the afternoon is warm enough to sit outside.

The answer is layers rather than volume. A fine merino, a shirt that works open or closed and one jacket that suits a walk and dinner will cover most weekends. For the textures that work best in autumn, read our piece on Alcantara and smooth leather.

Keep the journey within reach

The weekender holds the destination. A second, smaller piece holds the journey itself: the book, the scarf for the station, the laptop you hoped not to open.

The Chianti Tote is made for this. It has no fastening, so everything can be reached with one hand. It is slim enough to sit beside you on a train seat, and it takes a 13-inch laptop.

The small things, organised

The Gargano Pouch keeps the small things in one place inside the weekender. Its Schedoni blue Alcantara lining protects glasses and phones from scratches.

On arrival, it changes role. Take out the cables, add the wrist strap and it becomes the clutch you take to dinner. It is the one piece that works on the journey and after it.

When work comes too

Some autumn weekends begin with a Friday meeting. The Langhe Business Bag holds a 14-inch laptop and the working day.

A sleeve on its back slides over a suitcase handle, so it rides on top through stations and airports. When the meeting ends, it goes in the boot with the weekender.

On arrival

Empty the weekender on the first evening and let it breathe in a cool, dry corner, away from the radiator. If the drive brought rain, wipe the leather with a soft, dry cloth and let it dry naturally. Our autumn leather care guide explains more.

Full-grain leather is meant to take on the marks of the journeys it makes. An autumn weekend is a good place to start.

Questions we are often asked

What size weekender bag do I need for a weekend? For two or three nights, one weekender is enough if you pack in layers and keep to one colour palette. If you are flying, choose a size that meets your airline's cabin limit.

Can I take a leather weekender as cabin luggage? Often, yes. Our weekenders are designed for overhead compartments, but limits vary widely between airlines. Check yours before you travel.

Long handles or short handles? Long handles, like the Futa's, go over the shoulder and suit driving and shorter walks. Short handles, like the Stelvio's, give a firmer grip on a heavy bag. A detachable strap adds a shoulder option for longer distances.

Is a leather weekender suitable for autumn rain? Yes. Full-grain leather copes well with light rain. Wipe it dry with a soft cloth, let it dry at room temperature and keep it away from direct heat.

Made for the road ahead.

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