Destination Unknown

Is surprise travel right for you?

I'm a control freak, both at home and abroad. I like curating my family's experiences—making sure we have delicious meals, hosting get togethers over the holidays, and planning our vacations.

Yet, paradoxically, I am sick of making decisions. It's hard to juggle everyone's preferences, and at least one person is usually unhappy with the result. It's easier to go with the tried and true: summer rentals in Montauk, winter breaks in Florida or Vermont.

This dilemma is exactly what draws family planners to surprise vacations, according to Lillian Rafson, founder and CEO of Pack Up + Go. “You choose the parameters: plane or car trip, outdoors or city-focused, budget (from $500 per night for road trips and $900 per person for air travel), must-have activities, and so on,” she explains. “We do the planning and booking, including accommodations, dinner reservations, preplanned activities, and curated recommendations based on your interests.”

The only caveat: you don’t know where you’re going until the last minute. “Believe it or not, the surprise element can lower your stress level,” Rafson says. “Instead of one person being responsible for everything, you’re having an adventure together.”

Pack Up + Go specializes in U.S. destinations, and has sent 40,000 clients to more than 300 locations nationwide. “We offer 24/7 customer support and full refunds up until your date of departure. We’ll also cover the costs for glitches like canceled flights and restaurant closings,” Rafson says.

A trend that's picking up steam

The idea of launching yourself into the unknown will become even more appealing in 2024. Travel giant Booking.com surveyed more than 27,000 travelers in 33 countries and discovered that more than half planned to take a mystery trip. Across the board, the survey noted, "We'll see a noticeable shift from planning to spontaneity. A majority (55%) of travelers surveyed prefer to embark on their journeys without set plans, while two thirds (69%) opt for loose itineraries, allowing them to adapt as they go."

Let the adventure happen

Steven Harris has taken three mystery trips with a travel agent specializing in international vacations, including 10 days in Peru and five in the Caribbean. ?“At first, I wanted to discover a new place that I hadn’t explored,” he says. “My most recent trip was to surprise my boyfriend, who hadn’t traveled much, by going somewhere international.

“In both cases, the surprise factor took the planning and decision making out of my hands. Since I like to plan every detail, this forced me to just let the adventure happen.”

Harris set parameters for each experience. “I’m a foodie, so for the longer trip I asked for a variety of culinary experiences, from street food to Michelin starred. I love history, culture, animals, and nature.?Absolutely no kayaking.?Not just a beach vacation.?And I wanted luxury hotels.” He adds, “For the shorter trip, a beach vacation was okay. The place also needed to be LGBTQ+ friendly.”?

His experience was somewhat mixed. “The first trip was to Peru. It checked all the boxes and was one of the most incredible experiences I’ve ever had. The most recent trip was to Cura?ao. They booked us on an ATV adventure, which was outside our comfort zone, but it turned out to be a lot of fun. A bigger problem was that the resort they’d chosen was not at the level we expected.?The company took care of it, but it was disappointing.”

In spite of the hiccups, Harris is very open to the concept of surprise travel. "I understand my must-haves better, so I can be clear and specific about what works for me going forward.”

Top tips

Rafson agrees that detailed communication is key. “The more we know about your interests and travel style, the better the trip is going to be.” She recommends that everyone who will be participating fill out the pre-trip survey together.

It's also important to choose the right travel planner—someone you can trust to honor your preferences and ask the right questions when needed. In addition to Pack Up + Go, The Vacation Hunt has trips ranging from three to 14 days and incorporating all-inclusive, international, and Caribbean options. The UK-based, internationally focused Journee is highly rated by TripAdvisor and incorporates a detailed planning survey that covers all my bases.

At the high end, luxury travel agent Black Tomato offers “Get Lost” adventures averaging $15,000 per person, and including tailor-made expeditions?to wilderness destinations?like Mongolia or the Arctic. Travelers are outfitted with all the gear they need and given a satellite phone for emergencies. The journey ends with a five-star retreat—although I would probably skip directly to that.

The Great Travel Experiment is a monthly newsletter, free to LinkedIn members, that explores new ways to see the world: from wellness journeys to sustainable retreats, heritage tours, language immersion, digital nomading, volunteer vacations, retirement research, and more. For more information, contact @deborahgaines on LinkedIn or [email protected].