Paradies tree

8 Tips for Gifting a Surprise Vacation

As we head into peak gift-giving season, there’s a certain type of present that relies on the ultimate in planning: A surprise vacation. For a travel lover, is there any greater gift than a new adventure? We vote no — but you have to be able to pull it off without a hitch. (Hint: Make sure your recipient’s passport is valid!) In the spirit of wanderlust, follow these tips to help you give the perfect surprise vacation.

Know Your Travel Companion!

Before you even start planning a surprise vacation, make sure you really understand your companion’s preferences and wishes when it comes to travel. Think it through: Would they rather hike a mountain or explore a city museum? Are they beach bums or luxury resort lovers? Do they crave adventure, relaxation, or cultural immersion? Your surprise destination should align with their travel desires.

Timing is Everything

The timing of your trip has to align with your recipient’s schedule. If you can sneak a peek at their calendar, do it. Check for any prior commitments, holidays, or work obligations. Whisking them away for a mid-week adventure can be a delightful break—but not if it coincides with a huge work deadline. Do your best to make sure they’ll be able to relax and enjoy. 

Enlist Help

Planning a surprise vacation is no small feat, so it’s not a bad idea to get some assistance. Consult with close friends, family members, or even travel experts who can both keep the secret and contribute to the grand reveal. 

Drop Hints

Your travel lover probably has a bucket list. If you can manage subtlety, try (carefully!) dropping hints or starting conversations about destinations they’ve always dreamt of visiting. Listen attentively and take mental notes, because you might end up getting valuable insights into their jetsetting aspirations.

Surprise within a Surprise

Why reveal the destination immediately? It might take some extra work, but an extra special reveal might include multiple layers of surprise. Perhaps start with a themed gift box filled with items that hint at the destination – such as travel guides, local delicacies, or souvenirs. Add clues until you get to the grand reveal of the travel itinerary.

Pack Their Bags

If you can do it without provoking suspicion, take the stress out of travel prep by packing their bags in secret. Choose clothing, shoes, and accessories that suit the climate and activities of the destination. Don’t forget to include a well-thought-out packing list and any travel essentials they might need.

Go the Extra Mile

For an unforgettable surprise, consider upgrading your travel experience. Arrange for a private chauffeur, book a historic villa, or reserve a table at a Michelin-starred restaurant. Hire a private chef, or find an unusual or exclusive experience to book. The extra details can make all the difference in creating an memorable vacation experience.

Make it a Surprise for You, Too

Here’s a different twist on the surprise trip: Make it news to both of you! There are several travel agencies that specialize in crafting surprise adventures for you. Book one, and open it together so you both get the thrill of finding out your destination. Try a surprise trip creator like Pack Up & Go, which plans trips based on your preferences and budget, then sends you an envelope with the big reveal. Other options include the flat-budget mystery vacations from The Vacation Hunt and the more luxe bespoke vacations from Black Tomato.

Share Story

Related Articles