Maybe you’re planning a honeymoon for your daughter, or a Golden Anniversary trip for your parents. It’s a beautiful gesture. It’s also a minefield. What you find relaxing (hiking 10 miles) might be their nightmare.
The Discovery Interview
Sit them down. Ask specific questions. Not “Where do you want to go?” but “Do you want to wake up early or sleep in?” “Do you want to see museums or sit by a pool?” “What was the best meal you ever had?”
Listen for their “travel love language.” Some people value luxury hotels; others value unique experiences and don’t care about the room.
The Money Talk
If you are paying, be clear about what is covered. “We are covering flights and hotels; dinners are on you.” If you are just doing the labor of planning but they are paying, get a hard number upfront and stay 10% below it for safety.
Presenting Options, Not Decisions
Don’t book everything without input. Present 3 curated options. “Here are 3 hotels: one is historic, one is modern, one is by the beach. Which vibe do you prefer?” This gives them ownership of the trip.
Use Expedia’s “Trip Boards” feature to save options and share them. They can ‘heart’ the ones they like.
The Digital Handoff
Once booked, organize everything into a clean, printed itinerary AND a digital folder. Include addresses in the local language (for taxi drivers). Buying them a guidebook for the destination is a nice physical touch to get them excited.
The Joy of Gifting Experience
The best part of planning for others is hearing the stories when they return. You facilitate memories that will last a lifetime. That’s a powerful gift.
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