There’s nothing quite like surprising the people you love with a getaway they didn’t see coming. The idea of crafting the perfect trip—one they’ll remember for years—sounds like a dream, right? But I get it, planning a surprise holiday can feel a little overwhelming. From finding the right destination to keeping it all under wraps, it’s a lot. But, here’s the thing: it’s all worth it when you see their faces light up and know you’ve given them a memory they’ll cherish forever.
Back in 2023, I did this very thing for my family! (Well, my boys, anyway. The hubs was in on it.) I had such a blast crafting a unique reveal for them as part of their Easter basket, by way of a scavenger hunt. It was absolutely worth it to see their faces light up with a trip to Las Vegas!
We lived in Las Vegas for several years, and my eldest son was born there. He’d never been back since we left when he was two, and my youngest had never been.
So, whether you’re planning something special for your partner or pulling off a fun family adventure, I’ve got some tips to help you create the ultimate experience—without losing your sanity.
Step 1: Pick Your Dates, and Be Sneaky About It
The first (and honestly, most important) step to planning a surprise trip is getting the dates locked in. Whether it’s for a milestone birthday, a wedding anniversary trip, or just because you need to hit pause and reconnect, having the dates set early gives you the breathing room to plan everything else. If your partner or family member has a busy work schedule, now’s the time to get creative. If they’re employed, a quick chat with their boss to arrange the days off is key—but make sure they can keep it quiet. Nothing ruins a surprise faster than a well-meaning colleague asking, “So, where are you going on your vacation?”
For our trip, summer was the obvious choice for school, but there were still summer sports and work to navigate. We ended up with early August, which I have to say is not highly recommended for a trip to the desert!
Step 2: Budget Wisely Without Cutting the Fun
Let’s be honest: family adventures and romantic getaways can add up, especially if you’re aiming to make them unforgettable. But that doesn’t mean you have to go broke doing it. Once you’ve picked the dates, figure out how much you want to spend for your holiday budget. You can create magic on any budget; it just requires a bit of planning. For a family trip, maybe it’s a few days at a nearby lake or a scenic road trip. If it’s just you and your significant other, a weekend in a cute Airbnb or a quick getaway to a charming city might be all you need to feel like you’ve escaped. Prioritize experiences over splurging on luxury, unless you’ve been eyeing a particular splurge for a special occasion.
Step 3: Pick a Destination That Makes Memories
Here’s the fun part—choosing where to go. But remember, the destination isn’t just about what’s fun or trendy; it’s about what will create lasting memories for your family or partner. If your dream destination is to go to London for the day, then great, but their dream destination may be Paris. Is there a place that holds sentimental value? Maybe it’s a destination they’ve always talked about but never visited. Whether you’re thinking of a family-friendly theme park, a cozy cabin in the mountains, or a vibrant city with endless activities, pick something that you know will be meaningful to them. After all, it’s not just about getting away—it’s about making moments you’ll laugh about and reminisce over for years to come.
I’m personally a big London fan, as evidenced by things like my Union Jack table – I’m a total Anglophile! If you ever decide to visit, be sure to book with Radical Storage for your luggage during your day trips.
Step 4: Take Charge—You’re the Vacation Mastermind
This is your show, so own it! As the trip’s planner, you’re in control of the itinerary, the surprise elements, and the overall vibe. If it’s a family trip, balance the activities so everyone’s interests are covered—from kid-friendly adventures to some grown-up time for you and your partner. For a romantic getaway, think about the little details that will make your partner smile. Keeping things quiet and handling all the logistics ahead of time makes the surprise even sweeter. Just make sure no one lets it slip (looking at you, kids).
Step 5: Choose the Right Place to Stay (It Matters!)
When it comes to accommodations, you don’t have to choose between budget and comfort—you can have both. Look for places that fit the personality of the person or people you’re surprising. If it’s a family trip, maybe go for a rental with enough space for everyone to spread out and relax. A place with a backyard for the kids to run around in is a win! For a romantic weekend, a boutique hotel with cozy charm or a rustic cabin in the woods can set the perfect mood. Take time to find a spot that feels special but still fits your budget. If you’re choosing somewhere to go where they absolutely love the luxury hotels, then see what deals you can get on luxury escapes.
Step 6: Book Flights (or Hit the Road) Early
If flights are part of the plan, the earlier you book, the better. Keep an eye on deals and don’t be afraid to use flight comparison websites to score the best price. If you’re planning a family road trip, map out your route and plan fun stops along the way to break up the drive. Snacks, a killer playlist, and maybe a surprise pit stop (hello, ice cream!) can make the journey just as fun as the destination. Don’t underestimate the magic of a spontaneous road trip either—sometimes, the most unforgettable moments happen when you least expect them.
Step 7: The Little Extras (Because Memories Are in the Details)
The best memories come from those little extras that make the trip feel unique. Think about your family’s or partner’s favorite activities and plan something special around them. Is your partner a wine lover? Set up a wine tasting experience. Are the kids into dinosaurs? Add a stop at a quirky roadside attraction. If the person that you’re gifting over holiday to would love a wine tour or a food tour or a walking tour, then get that booked in so that you can show them that you know them very well. A surprise within a surprise holiday is like the icing on the cake of birthdays. These small details show that you know what makes them tick, and they’ll remember those moments long after the trip is over.
(My aunts are HUGE fans of walking tours – I think they’ve walked over most of Europe!)
Step 8: The Big Reveal (Get Creative)
Now that you’ve planned the trip, it’s time for the big reveal! How you reveal the surprise is almost as important as the trip itself. You could wrap up some travel-related clues (think a map, a mini suitcase, or a pair of sunglasses), or you could turn it into a fun scavenger hunt around the house. The key is to make it fun, memorable, and personal to the person or people you’re surprising. And when the reveal happens? Keep it between you and your loved ones—no need to blast it on social media. Those moments are priceless.
Want to plan your own surprise, but keep it budget-friendly?
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