A surprise birthday party with a half-dozen neighbors hiding in a darkened living room.
An unexpected romantic getaway to the same Italian restaurant you visit every Friday.
And an impromptu family trip to the neighborhood pool.
Sometimes, your plans for a special day or milestone fall a little short. Life is busy and we totally get it — after all, it’s about the people you’re spending time with, not necessarily what you do or where you’re going.
That said, surprise trips can raise the bar for occasions ranging from birthdays to anniversaries, creating lifelong memories where the people are still the main attraction, but the journey and destination are pretty special, too.
But how do you plan surprise trips? When do you take them and where do you go? We have a few ideas to get you started…
Types of surprise trips
Let’s start out with this off-the-wall idea: you don’t need to tie surprise trips to holidays or special occasions. They can happen at random moments, making them true surprises. But because we tend to plan around important days and dates in our lives and those of others, let’s take a look at some of those occasions that are prime for unexpected excursions:
- Surprise birthday trip: Maybe it’s your friend’s big 4-O — and you want to go over the hill with your BFF to Telluride for a dream ski getaway. More power (and powder) to you! Or your daughter just finished her master’s degree in African Studies, and you want to take her to Cape Town as the ultimate graduation present — unannounced, of course. Just remember that the more folks you add to these trips, the more fun they can be, but the harder it is to ace the planning (don’t worry, we have some tips for this down below).
- Surprise romantic getaways: Maybe it’s a second honeymoon, a first babymoon, the backdrop to elope, or a “just because” dream escape. Surprise trips with your significant other have two big advantages: it’s usually just the two of you and you should already know everything from travel partner’s peeves (no middle seat!) to their food allergies. Here’s an idea: Watch Hill, Rhode Island. This idyllic coastal New England town is a romantic’s paradise, featuring white sand beaches and Ocean House, an opulent and inviting Victorian-style hotel with an ancient ski gondola transformed into a fondue pop-up restaurant come winter.1
- Surprise family escapes: This may be the toughest of the surprise trips to organize. That’s because there are so many schedules to navigate and appetites to appease, figurative and literal. So we’ve got a suggestion: a cruise. Because of their all-inclusive nature and something-for-everyone amenities and excursions, unexpected escapes via cruise ship are uniquely suited for families seeking to get away on the sly. We even have a suggestion to make your family boat trip a little extra special: Marvel Day at Sea Disney Cruise. These Bahamas-bound cruises are ideal for kids who are getting a bit too old for Mickey and Minnie (and maybe even parents who still keep up their comic collection). With dates now available for booking in 2020, it’s a great time to review the family calendar to see if you’re free and clear to book. Expect character meet-and-greets with the Avengers, stunt shows-a-plenty, and Marvel-themed movie marathons in addition to all the traditional Disney cruise offerings.2
- Surprise holiday escapes: How about Norway for Christmas? Or Dublin for St. Patrick’s Day? Surprise trips have the rare power to elevate vacations to already amazing destinations with the picture-perfect backdrop. And they can double as gifts, so you can avoid trips to the mall, altogether.
Tips and tricks for surprise trips
Planning a traditional getaway when all the travelers know the itinerary inside out can be tough enough. Couple that with the additional degree of difficulty of having at least one person in your traveling party flying blind is an even harder landing to stick. Here are a few bits of advice to keep the trip on the tracks while keeping the cat in the bag:
- Get a look at their calendars: First, you need to pick a date. So, you’ll need to know what the guest(s) of honor have planned and when. Your homework might include suggesting that everyone in your room start a collective family calendar so you can gain transparency into the best dates for consideration. This could extend to contacting the boss or co-worker of travelers to ensure they don’t have any critical work obligations to attend to. You could always go the “bait-and-switch” route — announcing some ho-hum trip or other diversion that will lock the dates down for everyone, then revealing the true destination at the right moment.
- Don’t lose sight of the little things: Just because you’re orchestrating this awesome trip for others doesn’t mean you can forget that, for example, Uncle Fred suffers from motion sickness, your Best Man can’t swim, and that your daughter is an ovo-lacto vegetarian.
- Get help on the guest list: If you’re planning a larger surprise outing — a birthday for your spouse, for example — resist the urge to build the guest list by your lonesome. Odds are there are dynamics at play you might not be in the loop on. This could include the fact that two of your spouse’s friends you’re thinking could share a cabana haven’t talked since Spring Break ’99. And that your spouse has been reconnecting with a childhood friend you don’t even have on the invitee list. Consult one or two reliable folks who can help dial in the guest list to ensure this is a drama-free escape.
- Don’t use a shared credit card: Sounds like common sense, right? You and your husband share the American Express card, and now he’s frantically texting you about some strange charges to American Airlines and Key West Willie’s Day Trip Fishing. Find a safe and private way of handling prepaid costs. (One other money note: If you’ve got a large traveling party, consider an app built to track and share payments, such as Venmo or Splitwise, for travel expenses ranging from pre-paid tickets to meals.)3
- Throw travelers off the scent: Ok, ok. Maybe it’s the week or even night before it’s go-time. And you can’t delay having guests of the surprise trip pack a bag or two any longer. Tell them to bring something they’ll never use, a red herring, such as mittens when you’re flying to Fiji. This will keep the surprise going a bit longer.4
- Pack peace of mind: We talked about how planning surprise trips can up the ante of stress and anxiety. That’s all the more reason to get travel insurance, which can help troubleshoot snags ranging from cancelled flights to delayed bags (depending on your plan), and provide financial protection for the investment that you’ve made in the big, mysterious getaway. Allianz Global Assistance provides travel insurance plans for trips of all shapes and sizes; take a look.
- Hire a professional: Did you know there are boutique travel agencies that specialize in preparing surprise itineraries so that the destination is a mystery for everyone in the traveling party? Yes, even you, the planner. Connect with companies such as Pack Up & Go and Whisked Away — and they’ll take care of everything.
Everyone wished they had a friend, family member, neighbor or co-worker like you, someone looking to make that special day even more special by coupling it with a dream destination. It’s easy to see why surprise trips can deliver the time of their life, and yours.
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