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One Big Happy Family Adventure

5. Be sure to ask how your resort or cruise line defines "group": "The minimum number of people to qualify for group rates can be as low as eight or ten," says Suzanne Rowan Kelleher,'s family vacations expert. "And never be afraid to negotiate."

6. GateGuru: When you're at the airport with a stroller or a wheelchair in tow, the last thing you want to do is blindly navigate the terminal. This free app shows you the closest ATMs, electronics charging stations, escalators, transit access, and more—not to mention the nearest Starbucks.

7. Plan a game that everyone can play during your trip. Kelleher recommends a destination-themed version of a white elephant exchange: "Everybody finds a cheap souvenir and then swaps. It's a good icebreaker for when you're reconnecting with relatives you haven't seen in a while. The more hilarious the memento, the better."

8. Don't forget to snap one really great group portrait. "Ask whether your resort has a staff photographer," says Kelleher; you might be able to book a session during your stay. Another option she likes is Flytographer, a service that connects travelers with a local photographer in at least 160 destinations around the world.