4 Ways to Bring the Surprise Travel Trend to Meetings

Skift Take

The trend for mystery trips is on the rise — but your destination doesn’t have to be a secret to be a surprise. We reveal how event planners can inject the unexpected into their next off-site meeting by seeking out classic activities with a dash of quirkiness, creativity, and place.

This content was created collaboratively by the Arizona Office of Tourism and Skift’s branded content studio, SkiftX.

Who doesn’t like surprises? According to’s latest survey of over 27,000 travelers across 33 countries worldwide, so-called “surprise vacations” are quickly gaining in popularity — with over half (52 percent) of respondents saying they’re eager to sign up for a trip where they don’t know the destination until arrival.

While this level of surprise may not be practical for most business meetings and events, off-site activities offer multiple opportunities to satisfy this new craving for the unexpected. By taking traditional activities such as wine tasting, nature immersion, and golfing and giving them a novel twist, meeting planners can bring a new dimension to tried-and-tested classics.

To help you inject an element of surprise into your next off-site agenda, Skift Meetings partnered with the Arizona Office of Tourism to uncover unique takes on some of the most popular group leisure activities.

1. Work for Your Wine in the New Wave of Wine Tastings

Wine tastings are a perennially popular activity to help attendees get a taste for the region – as well as speed along team bonding! However, a new crop of adventurous wine experiences are liberating wine tasting from the bar and bringing it to life among Arizona’s vines and valleys.

The state has three major wine-growing regions: Sonoita-Elgin, Willcox, and the Verde Valley, and over 100 wineries statewide. Innovative winemakers are dreaming up more active ways for visitors to imbibe the local flavors, whether they’re a self-proclaimed oenophile or thirsty beginner.

The seasonal grape harvest gives visitors a chance to roll up their sleeves (and pant legs) by participating in traditional grape-stomping sessions. In July Sonoita Vineyards in southern Arizona hosts an annual HarvestFest, where alongside the usual culprits – wine tastings, food and wine pairing, vineyard tours, live music – you can also squash out your stress in a grape-stomping competition. In September, it’s a similar story at the aptly named Great Crush Festival at Arizona Hops and Vines, where adults can stomp the sweet stuff while the kids are distracted by a petting zoo and homemade sodas at the “Sober Shack”.

For those who want to stomp on a grander scale – and work off your wine tasting – the mountains and grasslands around Keeling-Schaefer Vineyards in Willcox are prime hiking territory. The area is close to Chiricahua National Monument, known as The Land of Standing-Up Rocks, and former home of the Chiricahua Apache, and is also a top attraction for birders twitching to catch a glimpse of a rare species.

If you want to amp up the adventure, Sedona Adventure Tours offer a “Water to Wine” tour that jets off with a one-hour kayaking trip down the Verde River to Oak Creek, taking in cottonwood trees, great blue herons, mule deer, beavers and bald eagles along the way. Paddlers are rewarded by crossing the finish line at Alcantara Vineyards, where they can tuck into cheese, antipasto, and a cool sip of local wine.

Those who want to experience the thrill of the wilderness but might not be able to set out on foot or by kayak can enjoy a more accessible adventure aboard the Verde Canyon Railroad. Passengers have been clinking a glass aboard the train since 1990, and in 2002 the “Grape Train Escape” was born, serving international wines in a nod to the old-school glamor of train travel.

Verde Canyon Railroad
Verde Canyon Railroad

2. Swap Beerfest for Wine Festivals With a Twist

While toasting a warm tankard of beer in a tent might be a summer rite of passage, Arizona’s new wave of wineries is heralding an altogether more sophisticated festival year-round. For example, you can sample both regional and international wines at festivals including Uncorked Wine Festival in April and The Arizona Wine Festival in January, where 21 of Arizona’s best wineries join forces with artisan food, vintage treasure and fine art sellers.

There are also several wine festivals that might surprise travelers by leaning into the local culture and geography. In Downtown Phoenix, the self-guided Urban Wine Walk in April lets visitors take in the city streets at their own pace – which might get a little slower, or wobblier, as they pick up a wine sample and complimentary snack at each participating bar and restaurant. In August, the Annual Mountain Artists Guild Fine Art & Wine Festival in Prescott blends the art of wine with a taste of art, showcasing outstanding fine art vendors, artist demonstrations, and interactive art activities.

And in April, the Annual Blessing of the Sonoita Vineyards Festival takes in everything you’d expect of a vineyard tour like wine tasting and pairings, alongside something you definitely wouldn’t: a procession behind Father Greg, who’s been giving the vineyard its annual blessing for years.

3. Channel Your Inner Cowboy Off the Beaten Track

It’s almost a given that any off-site meeting will include spending some time in the surrounding natural environment. But in Arizona, the landscape of Sonoran desert, breezy pine forest, and rustling grassland was meant to be explored one way: on horseback.

Guests at the Tanque Verde Ranch in Tucson, one of Condé Nast Traveler’s top 10 Southwest resorts for 2023, can saddle up for a mounted scavenger hunt, as well as participate in fishing, hiking, or mountain biking. And at Tombstone Monument Ranch, you can travel (horse)back in time – the ranch is modeled after an 1880s Old West town, allowing visitors to pretend they’re a character in their favorite Western with horseback riding, archery, and shooting practice, as well as tours of Tombstone, Bisbee, the Dragoon Mountains, and Chiricahua National Monument. In Wickenburg, the historic Kay El Bar Guest Ranch, up to 28 guests can hunker down in its original 1918 adobe structures or strike out for the horizon on horseback— and at the nearby Flying E Ranch, visitors can try their hand at being a ranch hand with team cattle penning.

Arizona is blazing the trail for accessible adventure at the Stagecoach Trails Guest Ranch in Yucca, possibly the world’s only fully handicapped-accessible guest ranch, where disabled riders can be mounted for trail and arena riding. With over 360,000 acres of accessible federal land and cowboy singers and storytellers in the evening, it’s a magical way to include those who might not usually expect to have such an intimate experience.

Arizona snowball

4. Take a Fresh Swing at Classic Sports

For travelers seeking a surprising switch up, when they’re done with the desert sun they can head to Arizona Snowball, the state’s largest ski resort. Thanks to the region’s biodiversity, they can enjoy skiing or snowboarding in the morning and be golfing by the afternoon.

While golfing might be seen as a more sedate sport, there’s still plenty of scope to add a touch of the unexpected at one of Arizona’s many world-class golf courses. Take Tubac Golf Resort + Spa: set on the historical Otero Ranch, first established in 1789 and the site of the largest cattle ranch in Arizona’s history, the resort bears many marks of its storied Spanish-colonial past, such as adobe walls, rustic wood beams, and vibrant Spanish tiles. Guests can even hike part of the Juan Bautista de Anza National Historic Trail that connects to the property and was used by colonists in 1775 making the trek from Mexico to San Francisco.

And while you might imagine endless sands, as Hank Swiggett, Tubac’s general manager, points out: “Although Tubac is in a desert, many are surprised to learn the resort is centered in a biodiverse hotspot, of which there are only 11 in the world.” This means it’s a verdant landscape with cool ponds, tall cottonwood trees, and over 265 species of rare birds that can’t be found anywhere else in the United States.

To learn more about all of the hidden surprises that Arizona has to offer your next meeting or event, visit

This content was created collaboratively by the Arizona Office of Tourism and Skift’s branded content studio, SkiftX.