1. Bear Creek Weekender

Price: $498.00 at freepeople.com
A simple, weathered bag, casual and timeless. This bag is made of soft, durable oiled leather with antique brass grommets for “feet” and a detachable shoulder strap “belt.” It zips close at the top for security, and has plenty of room for everything you need for two overnights on the train to Istanbul. Or Toronto. Or London.

2. Canyonlands Weekender

Price: $598.00 at freepeople.com
If there’s a more gorgeous weekender out there, I’ve yet to see it. What could be more beautiful than a tan leather bag with twin front pockets adorned with rich crocodile on the flaps and weathered brass buckles and hardware? But this bag isn’t just pretty, it’s roomy, generously proportioned for all of your get-away necessities.

3. Madera Weekender

Price: $488.00 at freepeople.com
A marvelous weekender for a very good cause, a portion of the proceeds from the sale of this bag goes Azahar, an organization that promotes peace through yoga and the arts. The bag itself is hand-made of vintage, repurposed cotton, so no two are identical, but all are gorgeous.

4. Rosemallow Weekender

Price: $428.00 at freepeople.com
This lush vintage-inspired bag is ideal for a romantic weekend, or a quick trip somewhere exotic. It features an intricate print with a soft ultra-suede lining, leather handles, and a detachable leather shoulder strap. Choose from a brown and pink print, or black and blue.

5. Moto Traveler Bag

Price: $968.00 at freepeople.com
This ultra-worn looking leather bag is buttery soft, magnificently aged, almost antiqued, made by Giorgio Brato. It’s roomy, slouchy, casual, ideal for a weekend away. Carry it cross-body as a messenger bag, too, when the rendezvous is over.

6. Rugged Aviator Bag

Price: $298.00 at freepeople.com
This rugged vintage duffel bag is made of durable cotton canvas, perfect for his things or yours, with two top handles and an adjustable, detachable shoulder strap for easy carrying. It’s made on Stockholm by GANT and measures 11” wide by 17" across by 18" tall.

7. Leopardito Bag

Price: $428.00 at freepeople.com
Made in India of soft goat suede by Old Gringo, this bag is wonderful. I love the very subtle leopard print, and the very structured design. Use it to carry the essentials of a weekend trip, or as a work or school bag.

With so many gorgeous weekend bags, I’m tempted to buy more than one… however will I choose? I adore the Canyonlands, but the Aviator is really cool, too… which one do you like best, and why? Or have you spied another weekender somewhere else that you’re currently coveting? Please let me know!