You and the same four guys have booked a golf trip every year for a decade, and the rotation is starting to feel predictable - new course, same weekend. The annual golf trip doesn't need to die, but it makes a better floor than a ceiling. These five getaways each hand the group a fresh reason to travel, and every one still leaves room to get a round in for the guys who get twitchy without a club in their hands.

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Written by: James Hills

Last Updated: 03 June 2026

A guys trip to the Maltese islands almost always points at Valletta - the walled capital, the Grand Harbour, the cruise ships. Gozo is the other move. It's the second-largest island in the Maltese archipelago, a 25-minute ferry from Malta's northern tip, and it trades Valletta's history-and-crowds energy for diving, wine, and a slower pace for the kind of trip you take to switch off.

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Written by: James Hills

Last Updated: 02 June 2026

Chicago is one of my favorite cities to visit, and as someone who lived there for nearly a decade, it's a city I'm proud to share with friends whenever they ask where to go. This is the city of big shoulders - a town where nobody's afraid to grab a beef sandwich dripping with juice, scream for their sports teams, and look at the world a little differently. Bring the guys and Chicago will keep all of you busy for a long weekend without ever feeling like a tourist trap.

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Written by: James Hills

Last Updated: 01 June 2026

Morocco belongs on the short list for a guys trip, even if it never crosses most groups' minds. As one of the most stable and accessible countries in Africa, it hands a group something Vegas or Cabo can't ... at least not with any sort of actual authenticity ... camel treks across the Sahara, switchback mountain roads, ancient walled cities, and Atlantic surf, all in one trip. Sure, you can find that other places, but they are imitations designed to evoke the mystique and glamor, but this is the real deal. Here's how to plan a Morocco mancation, from getting there to where to point everyone once you land.

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Written by: James Hills

Last Updated: 31 May 2026

San Francisco rewards a guys weekend with more range than you get from most American cities - four professional sports teams within an hour of downtown, Napa and Sonoma wine country an hour north, Alcatraz in the bay, the original cable car system still running, and a counterculture history that defined the modern city. It's a 7-by-7-mile peninsula packed with more activity, history, and weirdness than cities five times its size, and for California guys trips it's the anchor city to pick over LA or San Diego when the group wants substance over weather.

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Written by: James Hills

Last Updated: 29 May 2026