Keeping it under wraps: how to plan a surprise trip

1. It’s not about you

The best surprise holidays are built around whoever you’re whisking away. They should come first.

What makes her father’s surprise trips so special is how thoughtful they are, says Natasha Yadav. “My dad’s trips are tailored to the person. We’ve done budget and luxe trips; it helps that he has a flair for the dramatic. He’s always thinking, ‘How do I stage this? How do I up the ante?’”

Think of places they’ve always wanted to go, or spots to take their hobby to the next level. Other ideas include favourite movie locations or bucket list experiences.

2. Prepare well

Travel admin is an annoying speed bump, so it’s best to triple-check before you start planning the showstoppers.

“One of the main things to keep in mind when planning a trip is travel restrictions, like visas,” Simran Savlani says. Other considerations include booking airport transfers, hotels, restaurants and tours – and making sure your surprisee is packed for the right kind of weather.

She adds another crucial element, which may sound obvious but might be easily overlooked: “Make sure they are actually free.”

3. Keep it secret

“Don’t let too many people in on the plan, so there’s less chance of someone spilling the beans,” Savlani advises.

Be mindful of communication from your airline, hotels and travel operators, especially if you have joint email or bank accounts.

4. Go with the flow

Things don’t always go according to plan – embrace it, be flexible and don’t stress. In Prem and Kiran Yadav’s case, a surprise skydiving trip to Dubai was derailed by inclement weather. Savlani similarly had to adjust her sister’s trip itinerary after a hungover morning presented obstacles. 

“If something goes wrong, have a plan B,” she notes. “We had a full day of adventures planned for our last day, so we had to pivot.”