Difficulty: Moderately Easy
Step1
Check out destinations that offer a variety of options and activities within a short walking or driving distance. For example, if one traveler likes the nightlife and another likes to unwind on remote bike trails, choose a location with proximity to both.
Step2
Set sail on a cruise, especially if you are traveling with people of different ages and physical abilities. Most ships have children's programs, card and game rooms that appeal to less mobile and/or older travelers, stage shows for the whole gang, and all types of food at all hours of the day. See 413 Plan a Cruise.
Step3
Look into a packaged vacation such as those offered by Club Med (clubmed.com). These are perfect for large, multigenerational family gatherings because everyone gets to do exactly as they please. Hole up with a book on the beach or play tennis dawn to dusk. Dive, sail, swim, golf or do nothing at all. Everything-- booze, towels, entertainment and food--is included.
Step4
Try to schedule at least one time or meal each day during which you can all gather and catch up. Maybe you've done something the rest of the group might be interested in after all.