Destination is key
Your rendezvous point sets the tone. If your group prefers a degree of independence, opt for a walkable city like San Francisco, New York, Chicago or Portland, where you can all follow your separate muses once the planned outings are done for the day. Pick a centrally located spot for lodging with coffee shops and restaurants in reach so people don't have to rely on the group (or the group's planner) to make every move.
If your crew is tight-knit with unified interests, you can pick a more secluded locale. “Italy is one of the top choices for group trips lately,” says Michelle Rago, a destination event planner. “It really has it all, from relaxed beaches to thriving cities, not to mention hundreds of years of history, great food and good service.” She notes that Spain and Portugal are also currently in high demand.
For cross-generational trips, Rago also recommends guest ranches in Montana or Colorado, where families stay close together, but have the freedom pursue activities such as horseback riding, kayaking or trout fishing. And while the turquoise shores of a Caribbean resort spell “vacation” for many, Rago cautions that unless small kids are involved, there are fewer things to do.
The ultimate challenge, however, is planning a road trip. A few summers ago, parenting blogger Yashy Murphy drove from Dublin to the shores of southwestern Ireland with her husband, a toddler, her in-laws and two aunts. "Some people liked to sleep in, while others were early risers, so I made sure to plan morning activities and come back in time for lunch to meet the rest of the group," she recalls. Ireland was an excellent choice, because of the relatively short distances between stops, and the diversity of beautiful landscapes and historic sights.