There was a time when a weekend away with the guys meant the whole group sharing a roadside hotel room and hitting the dive bars in whatever beach town was closest. Then you get used to the finer things — like a bed to yourself and a bar that can shake a good cocktail — and move beyond those escapes. There’s a new iteration of the guys’ weekend that happens once a thing called maturity strikes, where the destination becomes a luxurious retreat, the dive bars are replaced with Michelin-starred restaurants and the adventures that once involved simply surviving the weekend are replaced with once-and-maybe-never-again experiences. For those, you need planning — making sure to find the perfect spot that’ll keep everyone entertained and comfortable, like the epic guys’ trips we’ve assembled here. Fire up the text streams, gentlemen.

Hotel Distil, Louisville, Ky.; Photo Courtesy of Hotel Distil
Bourbon Country
For the uninitiated, visiting Bourbon Country might sound like a simple road trip hitting two-bit distilleries in podunk America. And while you can still do just that, the stretch of stunning country that rolls along in bluegrass-covered hills between Lexington and Louisville is full of the finer things. That begins with the accommodations for the weekend, the Hotel Distil (marriott.com), on Louisville’s Whiskey Row. The ultra-modern renovated distillery-turned-hotel has good neighbors: Old Forester Distilling Co. (oldforester.com/distillery), a 150-year-old whiskey maker that offers a tour right in downtown’s Whiskey Row; Doc Crow’s barbecue (doccrows.com), a classic Southern barbecue spot and raw bar in a former distillery and one of the finest restaurants in town, Repeal Oak Fired Steakhouse (repeallouisville.com), where a lobster bisque leads into a Japanese A5 Wagyu ribeye. Of course, you’ll be touring distilleries, but to cap the weekend off right, arrange to purchase a barrel from Buffalo Trace (buffalotracedistillery.com). A master distiller will help the guys decide which barrel matches their tastes, assuring each of you will end up with a stash of your own single-barrel bourbon.

Bourbon Street, New Orleans
New Orleans
Perhaps you already had a guys’ trip here years ago, full of forgotten debauchery on Bourbon Street, cheap oysters at Acme and big hurricanes with who-knows-what’s-in-them ingredients. But there’s a New Orleans that caters these days to grown-up bachelor party trips, brimming with adventure, music and comfort. The Crescent City has plenty of top-notch hotels like the Omni Royal and Ritz-Carlton, but Audubon Cottages (auduboncottages.com) offers a respite from the craziness just blocks from it all. After a beignet from Bakery Bar (bakery.bar), a local’s version of Cafe du Monde, head to NOLA Motorsports Park (nolamotor.com), where there’s a 30-acre kart track that’s nearly a mile long. The old classics are always a solid choice here for a meal with the boys (Casamento’s, Commander’s Palace, Mr. B’s Bistro), but for the foodies in the group — and nowadays that’s a given — head to the Bywater neighborhood for the tasting menu and chill wine garden at Saint-Germain (saintgermainnola.com). Afterward, skip Bourbon Street for Frenchman Street and follow the sound of live music to the Spotted Cat (spottedcatmusicclub.com), where you just might see the guys dance for the first time since the last wedding.

Omni Grove Park Inn, Asheville
Asheville
These days it seems there are more Florida license plates in Asheville than there are local ones, so if you haven’t been yet, save the typical stops like the Biltmore tour and hiking Mount Mitchell for a trip with your significant other. Step things up with the guys, starting with a stay at the lavish Omni Grove Park Inn (omnihotels.com), a grand hotel with, thankfully, a bar not far from a pair of two-story lobby fireplaces. With the massive stones used to construct it and a big happy-hour friendly balcony looking out toward Mount Pisgah, the Grove Park Inn feels transported from the Rockies, the kind of mountain escape you’d expect of Presidents Taft, Wilson and Hoover (among the 10 presidents who’ve stayed there). The hotel previously wasn’t known for its dining scene, but the recent arrival of Eldr (eldravl.com) changed that, offering a chef-driven menu and upscale cocktails from a location that’s part of a small village of shops just down the hill from the main lodge. During the day, join the Beer City Brewery Tour (beercitybrewerytoursavl.com), jump on the quirky and comical LaZoom bus (lazoomtours.com) and scale to the top of a series of bald mountain peaks on the Black Balsam Knob trail. End the weekend by heading to Shoji Spa & Retreat (shojispa.com), where the dudes can pop open their best brewery finds around their own open-air hot tub surrounded by nothing but forest.

Kayaking in Alexander Springs, Ocala
Ocala National Forest
The idea of a guys’ trip to a national forest probably evokes thoughts of Colorado or Utah. But Florida has Ocala National Forest (fs.usda.gov), a super-sized Central Park in the upper part of the peninsula, and it’s a playground for the adventurous. Without a luxury hotel anywhere nearby, here you’ll be renting a vacation house (search online rentals for options). Ideally, it’ll come stocked with the toys needed for the weekend, if not, they are also available from rental outfits nearby: four-wheelers, mountain bikes, golf carts, kayaks and maybe a band of horses. There are plenty of places to explore, including four-wheeling trails that can go from sugar sand to thick mud in seconds, mountain bike trails that seem never-ending and hiking that includes a 72-mile stretch of the Florida Trail, the 1,500-mile-long National Scenic trail that continues north to south through the state. After all that adventuring, there are several cold-water springs, including Juniper and Alexander, to wash away the heat. Restaurants aren’t exactly an easy drive from your forest hideaway, so hire Chef Ju’von Personal Chef Services (chefjuvon.com) to whip up a surf and turf feast out by the fire pit.

Horseback riding in Triple Creek Ranch
Triple Creek Ranch
There are dude ranches, where you’ll be rounding up cattle and suffering through pots of beans, and that’s fine and good for a certain kind of traveler — but then there’s the ranch, where you can still live the life of a cowboy without giving up the good life. Triple Creek Ranch (triplecreekranch.com) occupies a staggering 26,000-acre swath of western Montana’s Bitterroot Valley, sandwiched between the towering Rockies and the rolling hills to the east, the calming waters of a rushing river flowing through its center. The adventures here are numerous: mountain biking and horseback riding through native forests; fly fishing for cutthroat and bull trout on the Bitterroot River; scenic drives to catch a glimpse of wild bison or lap in the warm waters of natural springs and, yes, cattle roundups on the ranch working farm. An all-inclusive, Triple Creek serves dishes worthy of its five-star ranking and accommodations include full homes and cabins where all the boys can prepare for those epic cowboy exploits.

Aerial view of the golf course at Streamsong Resort; Photo Courtesy of Streamsong Resort
Streamsong Resort
If you haven’t seen it, at least in photos, it’s hard to describe the surroundings of Streamsong (streamsongresort.com) without platitudes and adjectives that seem like exaggerations. Located in Central Florida, it looks, simply, like a stretch of the Scottish Highlands: rolling hills of green grass, dots of natural sand traps, rough patches of scraggly grass clinging to the tops of the rises and navy-blue pools of water along the fairways. Streamsong brought together two of golf’s best designers, Coore & Crenshaw and Tom Doak, for its three award-winning courses, earning it accolades from all the golf magazines and a following among players who seek out unique places to drive a ball. After 18 holes, Streamsong’s modern resort offers sweeping views of the courses and a Clubhouse Experience package puts all the guys in one spot, with rooms and a soon-to-be-legendary hangout area, replete with pool and poker tables and bar that make it feel like a modern man-cave. Between games, there are restaurants, a spa, fishing and skeet shooting. But the real draw here is golf, headlined by the seventh hole of the Blue course, a 203-yard par three that offers no easy shot, requiring a drive over water to a green surrounded by picturesque dunes. O