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The Best Weekend Bags for an Impromptu Road Trip

Bennett Winch Suede Weekender

Ever wanted to throw caution to the wind, hop in your car and just… drive? You’re not alone. There’s nothing like an unplanned weekend getaway, taking in scenic roads and breathtaking vistas, whether it’s an iconic driving route or something much more off the beaten path. Packing for it though might be easier said than done. You need something more than your usual rucksack and much less than a proper suitcase. You instead need a weekend bag, with enough room for a couple of changes of clothes and your travel necessities. It’s up to you whether that includes a portable watch winder or not. Either way, here are the bags that will have you pulling up to your new home for the weekend in style, car notwithstanding.

Sunspel Weekend Bag, £475

Sunspel Weekend Bag
Sunspel Weekend Bag

A weekend bag is an essential and few brands do essentials quite as well as Sunspel. Their fuss-free Weekend Bag is made, like their t-shirts, from cotton – specifically bonded Italian organic cotton canvas, with cotton twill handles and leather trims. The result is a breezy, lightweight yet rugged bag that you can have on standby for whenever you get itchy feet. It doesn’t matter when, where or driving what, navy goes with everything.

Available at Sunspel.

Antler Urban Light Overnight, £125

Antler Urban Light Overnight

If you plan on travelling with the barest essentials, then this is the bag for you. The compact Urban Light Overnight from specialist Antler is deceptively roomy for its footprint, with plenty of convenient hidden pockets for valuables. And while it’s specifically designed to fit under an airline seat, that just means it’ll do even better in the unfortunately small boot of your little country runaround – doubly so if it’s in a matching Antler (or British Racing) green.

Available at Antler.

Harber London Leather Weekender Bag, £999

Harber London Leather Weekender Bag

Designed in London, made in Spain, Harber’s weekender is relaxed and comfortable in a combination of vegan tan leather and German microsuede. A little more low-key than some on this list, it’s a bag designed around comfort first and foremost thanks to lovely handles and an extra carry-on strap, with plenty of pockets inside to keep everything organised. Heading somewhere remote and expecting a walk at the end of the drive? This is the bag for you.

Available at Harber London.

Carl Friedrik Granville Weekender, £745

Carl Friedrik Granville Weekender
Carl Friedrik Granville Weekender

A classic weekend bag if ever there was one, Carl Friedrik’s Granville pairs a large interior capacity of 33 litres with a tapered silhouette that stops it feeling blocky. Not that it’s in much danger there; the beautiful full-grain leather – here in chestnut brown – is deliciously supple. With a semi-aniline coating, the Granville is more hardwearing than it looks, just in case you’re a little too eager to hop out after a long drive. And if you find yourself overpacking, it fits perfectly on top of a suitcase, too.

Available at Carl Friedrik.

Hugo Boss Suede Holdall, £1,295

Hugo Boss Suede Holdall

Forget hefty leather numbers as supple as a wingback armchair and say hello to sumptuously soft suede. With its modern beige colouring, this leather-trimmed number from Hugo Boss matches your neutral weekend ensemble and with plenty of space inside, is as cool, calm and collected as you are. And even if that’s just not you, it’s a great-looking bag, constructed with the expertise of one of fashion’s sharpest labels.

Available at Hugo Boss.

Bennett Winch Suede Weekender, £1,875

Bennett Winch Suede Weekender
Bennett Winch Suede Weekender

Bennett Winch made their name on their original weekend bag, so they know a thing or two about the humble two-day stopover essential. A substantial 42-litre capacity with separate compartments for shoes and a laptop, it’s OCD-level organisation at its finest. This version comes in a visually decadent tobacco brown suede, albeit one that’s much more hardwearing than you’d expect. For one, it’s fully waterproof, so even if you forget to look at the weather forecast before you leave, at least your clothes will stay dry.

Available at Bennett Winch.

Connolly Red Sports Grip Bag, £1,700

Connolly Red Sports Grip Bag
Connolly Red Sports Grip Bag

If your idea of the perfect weekend away is convoying across the Cotswolds in a classic car rally, then this is the bag for you. The red leather is as bright as any racing livery, helped along by the oversized badges that wouldn’t look out of place co-piloting the Mille Miglia and motoring-inspired touches like the car bonnet strap roller buckles. With a generous capacity and solid construction, it has enough room to hold everything bar your post-drive gala dinner jacket.

Available at Connolly.

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About the author

Sam Kessler

Legend has it that Sam’s first word was ‘escapement’ and, while he might have started that legend himself, he’s been in the watch world long enough that it makes little difference. As the editor of Oracle Time, he’s our leading man for all things horological – even if he does love yellow dials to a worrying degree. Owns a Pogue; doesn’t own an Oyster Perpetual. Yet.