Whether you're booking a boys weekend in Wyoming or a winter escape with your sweetheart, you'll need a reliable carry-on for your valuables. So, for journeys near and far, rural and burghal, we turn to the Duluth Pack Classic Rucksack. Handmade in Duluth, Minnesota, it's a handsome, classically tailored backpack that promises to stick with you for the long haul.

The spacious front pouch is tailor-made for your personal items: Even with our smartphone, wallet, and keys inside, we still had plenty of room to spare, and the tight button enclosure meant we never once worried about their safety. A beach towel or a good set of binoculars fit comfortably inside the drawstring-secure main compartment, along with a sweatshirt for cooler evenings. The exterior is fashioned from ruggedized canvas that's available in 15 colors – we claimed one in versatile olive drab green – and premium leather of the highest quality.

We carried ours from Manhattan to the U.S. Virgin Islands, where it safeguarded our reads, water, dried fruit, and towels. It even trekked with us along the craggy coast of St. John, where it proved to be comfortable and sturdy. To top that, in a pretty thick heat, it even kept our water cool.

While the beefy, hand-cut leather straps take a couple months of consistent wear to break in, the bag remains easy on the eyes. After all, it's created to live a long life. So wear it well and then pass it along to your kids. Just don't forget to tell them about the adventures you've been through together. [$140; duluthpack.com]