That being said, I would never plan such a trip for people whose preferences and peccadilloes I didn’t know so well; the potential for catastrophic error is too high. Pulling off a surprise vacay successfully requires a different mind-set, extreme detail management and a fair amount of stealth. To help you navigate the unique challenges of organizing such a trip, I gleaned tips from a trio of experienced travel professionals and paired them with insights I’ve gained along the way.
Remember: My family is in the dark about our sunny getaway, so please don’t mention this article to them. Thanks for your help!
Cover your tracks. Keeping secrets in the digital age can be incredibly difficult, but it’s possible with some spycraft-level effort. Use an email address to which only you have access to receive all confirmations and correspondence. Don’t request text alerts for flights or other bookings, because they may pop up at inopportune moments. Never add your family’s frequent-flier mile numbers to a reservation, because they may receive an alert with the itinerary. (Just don’t forget to add them once everyone is in on the surprise.) If possible, put all trip charges on a personal credit card. However, if you only have joint accounts, ask your partner to avoid looking at the relevant statements. Finally, when browsing for bookings or researching your destination, “search on your phone instead of a computer, and close all your tabs afterwards,” advises Jen Campbell Boles, founder of Explore More Family Travel, a family-focused travel agency.
Consider everyone’s obligations. Although a vacation is intended to be a welcome break from normal routines and obligations, those can’t be ignored. Before you make any nonrefundable reservations, ensure that your partner can get time off from their job and that there aren’t any too-costly penalties for pulling a child out of a sport, summer camp or school. There is nothing worse than a vacation during which one of the parents is stressing about a big work project or deadline, or a child is moping because they aren’t competing in a championship game or are missing time with the BFF they only see at camp.
Find co-conspirators. To pull off a surprise this big, you’re going to need help. Relatives and your partner’s dearest friends are your best bets — if they can keep a secret. They can provide intel you lack and ask your partner the questions you don’t want to ask, so you don’t pique their suspicions. If you feel comfortable approaching your partner’s boss, and you believe they can help ease stress around work commitments, bring them onboard, too. Finally, if the whole idea of putting together a vacation is freaking you out for whatever reason, consider engaging the services of a professional trip planner.
Pick their perfect destination. “Ask yourself, ‘Where do they want to go?’ ” says Guido Adelfio, president of Bethesda Travel Center, which creates custom vacations. “Bucket-list spots always go over well.” Think about what your partner and children like to do, their energy levels and their comfort zones. For a trip like this to deliver the intended wow factor, it must be designed with their tastes in mind. Now is not the time to go somewhere you’ve been aching to visit.
Craft a balanced itinerary with a few blowouts. Creating a schedule that pleases everyone is a herculean feat. Exponentially up your chances of success by including one element every day for each person to enjoy, even if on some days that moment is a small one. Always leave extra time between activities, so you don’t get stressed if you’re running late. Leave a few big chunks open on your calendar, so you can simply chillax or do something unexpected on the fly. Take your vacation to the next-next level by including a few splurge-y, splashy moments. “Think about buying concert tickets or tickets to a sporting event. Get a nice restaurant reservation. Go drive a Ferrari,” Adelfio recommends. “Do something with a little panache.”
Steer clear of danger. This is not the trip to push someone out of their challenge zone and into their panic zone. “I wouldn’t include any activity with an element of danger that you’re uncertain how they’ll respond to it,” advises Rob Taylor, founder of the LGBTQ family travel blog 2TravelDads. “It could lead to anxiety, them not being able to process it or feeling obligated to participate because it was a surprise, even though they don’t want to. For example, if you surprised me with a day of rock climbing or rappelling, I would literally break down in front of you.”
Gather paperwork and pack properly. Do not screw this step up, or your entire trip will be in jeopardy. If you’re going out of the country, double-check that everyone’s passports are up to date, keeping in mind that some countries will deny a visitor entry if their passport is valid for less than six months. Check whether there are any regulations regarding coronavirus safety and vaccinations. Speaking of the latter, ensure that everyone has any vaccinations required at the destination. Don’t forget to pack everyone’s medications, and bring along any necessary medical documentation. Last but not least, you must make sure they bring the right wardrobe, so they can comfortably enjoy all the activities you have planned.
Making your grand reveal. I advise letting partners and family members know in advance that you’re going somewhere, so they’re prepared to be gone. However, how much you tell them and when depends on your style and what you believe will achieve the biggest bang for your efforts. Adelfio suggests telling them at a momentous occasion, such as a birthday party or family event. You could also have your traveling companions open clues to help them figure out the destination, which Campbell Boles recommends. Another idea is to have everyone pack two bags — one with beach gear and one with wintry clothing, for example — and then tell them which to bring just before you depart for the airport. Or you can reveal the trip in stages, creating fun revelations throughout the vacation.
When Taylor and his husband want to surprise their two sons, they share selective slivers of information. “We’ll say we are going to California or Georgia, but we’ll leave it there,” he says. “Or we’ll say, ‘Here are some things you should be packing.’ That leaves it a little mysterious but sets an expectation about what’s ahead.”
Temper your expectations. Be honest with yourself about why you’re planning the trip. Otherwise, you could be in for a surprise of your own. “You don’t know how people will respond to a surprise that clearly took a lot of your time, effort and money to plan,” Taylor says. If your big “ta-da!” doesn’t get the reception you’d hoped for, at least you’ll have the consolation of knowing your motives were pure. Take in any negative feedback gracefully, keep it in mind for future travels and do your best to ensure that everyone gets the most out of the trip they’re on.
Potential travelers should take local and national public health directives regarding the pandemic into consideration before planning any trips. Travel health notice information can be found on the Centers for Disease Control and Prevention’s interactive map showing travel recommendations by destination and the CDC’s travel health notice webpage.