Sea Island Resort, Georgia

All work and no play makes Jack a dull boy, so why not give that male exec you know a holiday that’ll really knock his socks off? The “Ultimate Guys’ Golf Experience” from Georgia’s exquisite Sea Island resort should do the trick. Along with an all-inclusive four-night stay at the property’s secluded Lodge at Sea Island, your guy and two friends will enjoy all the perks of a PGA pro, including private golf lessons, custom club fitting, and the real clincher: a round of golf with 2012 Ryder Cup Captain and 20-time PGA Tour winner Davis Love III. $100,000 for a group of three, seaisland.com

Model: Trey Singleton: Campbell Agency; Hair and Make-up: Susie Gray Uphues: Campbell Agency

Get the CAREER-MINDED MAN boardroom-ready with:

Breitling Transocean Unitime Pilot watch $11,200, breitling.com;
Bedali Su Misura navy lightweight wool made-to-measure suit, $3,295, and Bedali Su Misura by Geoff Nicholson tie, $165, bedalisumisura.com;
Pal Zileri blue and white striped shirt, $323, palzileri.com;
Robert Talbott hand rolled silk Carmel pocket square, $75, roberttalbott.com;
Montblanc double-gusset Italian full-grain calfskin briefcase, $1,920, montblanc.com