That being said, I would never plan a trip like this for people whose preferences and minutiae I don’t know very well; the potential for catastrophic failure is too high. Successfully hosting a surprise vacation requires a different mindset, extreme detail management, and a good dose of stealth. To help you navigate the unique challenges of organizing a trip like this, I’ve collected tips from a trio of seasoned travel professionals and paired them with insights I’ve learned 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 is possible with some spy-level effort. Use an email address that only you have access to receive all confirmations and correspondence. Don’t request text notifications for flights or other bookings, as these may come at inopportune times. Never add your family’s frequent flyer mileage numbers to a reservation as they may receive an itinerary notification. (Just don’t forget to add them once everyone is amazed by the surprise.) If possible, charge all travel expenses to a personal credit card. However, if you only have joint accounts, ask your partner not to look at the related bank statements. Finally, if you’re looking for bookings or researching your travel destination, “search on your phone instead of a computer and then close all your tabs,” advises Jen Campbell Boles, founder of Explore More Family Travel, a family-focused travel agency.
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Consider everyone’s duties. While a vacation is meant to be a welcome break from normal routines and commitments, these cannot be ignored. Before making any non-refundable reservations, make sure your partner can take time off work and that there aren’t too expensive penalties for pulling a child out of a sport, summer camp, or school. There’s nothing worse than a vacation where a parent is frustrated about a big work project or deadline, or a child is moping about not being able to attend a league game or missing out on time with their best friend they only see at camp.
Find co-conspirators. To conjure up such a big surprise, you need help. Relatives and your partner’s best friends are your best bets – if they can keep a secret. You can provide information you’re missing and ask your partner the questions you don’t want to ask so you don’t arouse their suspicions. If you’re comfortable reaching out to your partner’s boss and you think they can help you relieve stress related to work commitments, get them on board as well. Finally, if for some reason the whole idea of putting together a vacation freaks you out, you should enlist the services of a professional travel planner.
Choose your perfect destination. “Ask yourself, ‘Where are they going?’ says Guido Adelfio, President of Bethesda Travel Center, which creates bespoke trips. “Bucketlist spots always hit home.” Think about what your partner and kids enjoy doing, how much energy they have, and their comfort zones. For a trip like this to deliver the intended wow factor, it needs to be designed with taste in mind. Now is not the time to go to a place you’ve been wanting to visit for a long time.
Create a balanced itinerary with a few glitches. Creating a schedule that everyone likes is a Herculean feat. Increase your chances of success exponentially by including an element each day that each person can enjoy, even if some days that moment is just a small moment. Always allow extra time between activities so you don’t get stressed if you’re late. Leave a few big pieces on your calendar so you can just relax or spontaneously do something unexpected. Take your vacation to the next level by throwing in some luscious, splashy moments. “Thinking about buying concert tickets or tickets to a sporting event. Get a nice restaurant reservation. Drive a Ferrari,” recommends Adelfio. “Do something with a little panache.”
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Avoid danger. This isn’t the trip to push someone out of their challenge zone into their panic zone. “I wouldn’t include activities with an element of danger that you’re not sure how they’re going to react to,” advises Rob Taylor, founder of LGBTQ family travel blog 2TravelDads. “It can lead to anxiety, they can’t process it or they feel obligated to go in because it was a surprise even though they don’t want to. For example, if you surprised me with a day of climbing or abseiling, I would literally collapse in front of you.”
Gather paperwork and pack properly. Don’t mess up this step or your entire journey will be in jeopardy. When leaving the country, double check that everyone’s passports are up to date and remember that some countries will refuse entry to visitors if their passport is less than six months valid. Check if there are regulations on coronavirus safety and vaccination. Speaking of the latter, make sure you have all the vaccinations required at your destination. Don’t forget to pack any medication and bring any necessary medical records with you. Last but not least, you need to make sure they bring the right wardrobe so they can comfortably enjoy any activities you plan to do.
Make your big reveal. I advise telling partners and family members in advance that you are going somewhere so they are prepared to leave. However, how much you tell them and when will depend on your style and what you think will make the biggest bang for your efforts. Adelfio suggests telling them on a momentous occasion like a birthday party or family gathering. You can also provide clues to your travel companions to help them figure out the destination, which Campbell Boles recommends. Another idea is for everyone to pack two bags — say, one with beach gear and one with winter clothes — and then tell them which ones to bring just before they leave for the airport. Or you can unveil the journey in stages, creating fun revelations throughout the vacation.
When Taylor and his husband want to surprise their two sons, they exchange specific information. “We’re going to say we’re going to California or Georgia, but we’ll leave it at that,” he says. “Or we’ll say, ‘Here are some things to pack.’ That makes it a bit mysterious but gives some anticipation of what lies ahead.”
Lower your expectations. Be honest with yourself about why you are planning the trip. Otherwise, you might be in for a surprise yourself. “You don’t know how people are going to react to a surprise that clearly took a lot of time, effort and money to plan,” says Taylor. If your big “ta-da!” doesn’t get the reception you hoped for, but at least you’ll have the comfort of knowing your motives were pure. Take any negative feedback gracefully, keep it in mind for future trips and do your best to ensure everyone gets the most out of the journey they are on.
Martell is a writer from Silver Spring, Md. His website is nevinmartell.com. Keep finding him Twitter and Instagram: @nevinmartell.
Prospective travelers should consider local and national health guidelines regarding the pandemic before planning a trip. For travel health advice information, see the Centers for Disease Control and Prevention interactive map of travel advice by destination and the CDC’s travel health advice website.