It’s almost inevitable. You’re sitting around your friend’s living room or grabbing a beer and burger and someone will mention a burning desire to get away from it all. They want to head to the mountains, the beach, a historic city—anywhere that gives them the chance to share a new adventure with old friends. In its best moments, traveling with friends means common interests, big laughs, and new stories to add to the rotation.
Some groups make it a tradition to rent the same lake house or beach bungalow every year. If you’re looking for something new, here are 15 ideas for great cities, countries, islands, and resorts to explore with your best buddies.
Montreal
Europe is too far to travel for a long weekend, but Montreal offers that charming European vibe—and it’s a quick plane ride away. Brush off your high school French and check into the new boutique Hotel William Gray tucked into Old Montreal, the city’s charming historic district, which is now filled with sleek shops and inviting restaurants. Eat your way through Mile End and Plateau, pick up a bagel at Saint-Viateur, check out nightlife hot spots, and stroll through Jean-Talon, one of Montreal’s oldest public markets. Montreal is gearing up to celebrate its 375th anniversary with a year’s worth of events planned to mark the occasion meaning it’s a great time to visit.
Destination Kohler, Wisconsin
Set in the village of Kohler, Wisconsin—two-and-a-half hours north of Chicago and one-hour north of Milwaukee—Destination Kohler is made up of several lodges and clubs with chic accommodations, sophisticated dining options, activities for all interests, and a world-class spa (after all, this is where the Kohler bathroom fixture empire started). Visit in winter to challenge your friends to learn the art of Bavarian curling or go on a pheasant hunt, while summer activities include golfing at the PGA-approved courses, horseback riding, fishing, or trap shooting. There’s so much to do at Destination Kohler that you may just forget to leave at the end of the trip.
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