Editor’s note: Meetings & Incentives Worldwide received the Gala Award for Best Multiple-Day Event Program for a Corporation or Association.
Picture this: your attendees are departing in the early morning hours after what you’ve carefully orchestrated to be the trip of a lifetime, and suddenly, Mt. Etna erupts in the distance. Not dangerously, but spectacularly—nature’s own fireworks display against the dark Sicilian sky, visible from the hotel as a stunning finale to an already unforgettable experience. For Meetings & Incentives Worldwide and their client AF Group, this serendipitous moment was the exclamation point on a program that attendees would later describe as “the best incentive trip they’ve ever been on.”
The AF Group Sicily Incentive Trip, which earned Meetings & Incentives Worldwide the 2026 Gala Award for Best Multiple-Day Event Program for a Corporation or Association, rewarded top-performing independent insurance agents with an experience in Taormina that went far beyond the typical incentive program. Hosted at the San Domenico Palace, Taormina, A Four Seasons Hotel, the program brought attendees from across the United States to this ancient Sicilian town for a highly personalized journey that prioritized authentic connections—both among attendees and with the destination itself.
What made this program truly exceptional wasn’t just the stunning location or luxury accommodations, but rather the philosophy that guided every decision: unreasonable hospitality. Instead of treating all attendees identically, the team at Meetings & Incentives Worldwide created 100% personalized experiences tailored to individual preferences, interests, and even offhand comments made during the trip. This wasn’t about generic welcome gifts or one-size-fits-all excursions. This was about truly seeing each attendee as an individual and crafting moments that would resonate on a deeply personal level.
The personalization began before attendees even arrived. During registration, the team asked about motion sickness tendencies, and those who answered ‘yes’ received customized motion sickness kits to help navigate Sicily’s winding roads. Attendees selected from a menu of small-group activities based on their interests, and each choice came with thoughtfully curated gifts. Those who took a cooking class with a Michelin-star chef received an autographed cookbook and a bottle of the olive oil used during the class. Wine tour participants found bottles waiting in their rooms—red or white, specifically chosen based on preferences gathered during registration. Attendees who explored a local artist’s studio discovered original artwork waiting for them back at the hotel.
But the real magic happened onsite, where the team spontaneously gifted attendees based on what they learned during the trip. When a couple mentioned they loved the pasta-making class so much they planned to recreate it for their grandkids, the team visited a local market and purchased the exact flour and tools used during the class. An attendee who casually mentioned she’d always dreamed of owning a beige Vespa with tan leather seats received a toy Vespa painted in those exact colors. During the cooking class, when one attendee admired the knife the chef used to prepare fish, the team discreetly learned which knife it was, drove to a specialty store in a nearby town, and purchased it for him.
These weren’t expensive gestures for the sake of extravagance; rather, they were meaningful touches that demonstrated genuine attention and care. One attendee who played tambourine spontaneously joined the live band during the Celebration Evening. The next day, the team bought her a tambourine and left it in her room with a note: “Whenever you play, we hope you remember your time in Sicily.” Another attendee mentioned in passing that she collected ashtrays from famous hotels and restaurants. The team persuaded the iconic Bam Bar in Taormina to sell them one of their (unused) ashtrays just for her—items not typically available for purchase.
This level of personalization extended to the program’s structure itself. Rather than following a rigid schedule, attendees enjoyed significant flexibility to craft their own experiences. The innovative “Taste of Taormina” experience exemplified this approach beautifully. Instead of a traditional group excursion with a set itinerary, attendees received vouchers to local hidden gems for authentic Sicilian bites—cannoli, arancini, and more—along with vouchers for a local ceramic shop. They could explore in whatever order they chose, join optional walking tours by signing up through the event mobile app, or simply wander the ancient cobblestone streets at their own pace. The day concluded with everyone reconvening at “La Dolce Vita” Happy Hour, where the team had bought out the patio of a restaurant in the town square.
The small-group activities throughout the program offered remarkable variety while maintaining that crucial element of customization. Attendees could choose from cooking classes in “Grandma’s kitchen” with a local Italian Nonna in her 18th-century home, a Godfather tour that included a meet-and-greet with actress Simonetta Stefanelli who played Apollonia in the films, or various Mt. Etna experiences ranging from hiking and horseback riding to Jeep tours and e-mountain biking. Each activity was enhanced beyond what would typically be available to the public, creating truly one-of-a-kind experiences that attendees couldn’t replicate even if they returned to Sicily on their own.
The program’s Celebration Evening showcased how thoughtful design can engage all the senses to create lasting memories. Held at La Canonica degli Archi, a former palace built in the 1700s that now serves as a private residence and gallery, the evening began with attendees walking through a candlelit garden to a wall lined with champagne glasses. Each glass contained a gemstone—most were cubic zirconia, but three lucky attendees discovered real diamonds. Certified gemologists flown in from France verified the stones onsite, adding an element of excitement and anticipation to the arrival experience.
Throughout the evening, opera singers serenaded attendees between dinner courses, starting with classical opera, moving to 70s hits, and ending with contemporary orchestral pop. The dinner courses themselves were named after parts of an opera—Overture, Aria, Intermezzo, and Finale—rather than the traditional Italian course names. After dinner, two distinct afterparty zones allowed attendees to continue celebrating in ways that suited their preferences: a dance floor with a live band for those wanting high energy, and a cigar lounge with a bourbon bar for those seeking a more relaxed atmosphere.
Of course, creating such a personalized and ambitious program didn’t come without significant challenges. The team faced what they dubbed “The White Lotus Effect” when, just two months after signing their hotel contract in August 2022, HBO premiered season two of The White Lotus—set at the exact hotel they’d just booked. The show’s popularity among jetsetters and influencers caused costs across Taormina to skyrocket seemingly overnight. While room rates were locked in, everything else—from food and beverage to spa services, excursions to entertainment—increased exponentially.
Rather than compromising on quality, the team got creative with budget management. The Taste of Taormina experience, for instance, the cost per person for the food vouchers was considerably less when compared to a group lunch buffet at the hotel. Similarly, by buying excursion gifts locally in small quantities and offering vouchers to local shops, the team not only saved money but also infused funds directly into the local economy and provided more authentic experiences. These strategic decisions ultimately saved the team considerably while actually enhancing the attendee experience—a remarkable achievement that demonstrates the power of creative problem-solving.
The challenges extended beyond budget considerations. On the day attendees were scheduled to fly to Europe, tornadoes and severe thunderstorms hit more than 15 states across the United States. The air travel team worked overtime to rebook delayed and cancelled flights, ultimately exchanging 66 tickets—more than a third of all attendees. The rebooking led to additional layovers, and luggage was lost across Europe in Amsterdam, London, Rome, and beyond. The team tracked lost luggage for four days, sending staff to the airport daily to collect incoming bags. They even flew one attendee back to Rome with an Italian-speaking escort to successfully retrieve his luggage. In the meantime, team members shopped locally for attendees’ must-have items, like leaving a new bottle of hairspray in one attendee’s room after overhearing her concern about her lost luggage.
Unexpected road closures due to construction in Taormina created longer transfer times than anticipated, but the team turned this potential negative into an opportunity. They strategically assigned attendees to specific 10-person vans based on business connections and regional sales interests, transforming extended travel time into valuable networking opportunities. The small size of Taormina’s restaurants presented another logistical puzzle—historically, this program had featured dine-arounds with multiple seatings at four or five restaurants, but the intimate nature of Sicilian restaurants meant they could only accommodate eight to 10 people per reservation. This required coordinating nine different restaurants each night of the dine-arounds, with staff members walking groups from the hotel to ensure successful seating and then returning to handle payment.
The complexity of executing the Celebration Evening required a multiple-hours-long pre-conference with 19 people to bring the venue up to the required quality standards. This included changing food and beverage offerings with the caterer, utilizing different spaces in better condition, adding décor to hide imperfections, moving existing furniture, making landscape improvements, and completely redesigning room layouts. The venue was hosting its first event of the season, which added to the challenge but also meant the team could shape the space exactly as needed.
What truly set this program apart was how it balanced structure with flexibility, luxury with authenticity, and group experiences with individual attention. The program mobile app, powered by SpotMe, utilized a new feature that allowed attendees to sign up for optional activities on the day of rather than requiring advance registration. This gave attendees flexibility to join art tours of the hotel, guided walking tours of Taormina, or hikes at a nearby national park based on their interests and availability right up to the last moment. The app also featured a “pay it forward” wall where attendees could share their favorite discoveries—from entrée recommendations to the best gelato they’d ever tasted—creating connections and enhancing everyone’s experience.
Upon arrival, attendees were welcomed with a surprise Zen Lounge featuring complimentary offerings from the hotel spa—neck, shoulder, and scalp massages; facial pressure point massages; manicure stations; Tibetan singing bowls; and more. This thoughtful touch helped attendees rejuvenate after nearly a full day of travel and set the tone for the care and attention they would receive throughout the program.
The Farewell Reception featured another unique experiential gifting opportunity. A local artist painted live, creating three different paintings, and attendees chose their favorite painting along with a custom frame. The artist then created original paintings to order, which were shipped in bulk to the United States for framing before being delivered to each attendee. Every single person received an original, hand-painted work of art as a lasting memento of their time in Sicily.
The results speak volumes about the program’s success. Multiple attendees declared it the best incentive trip they’d ever attended, with one noting, “I have had the good fortune of attending a number of carrier incentive trips and this rated at the very top. What a great mix of sophistication, relaxed environment, scenery, food, and activities.” Another added, “Best carrier trip that I’ve ever been on in over 25 years traveling with carriers.”
Perhaps most telling was the feedback about the team itself. One attendee shared, “I can’t say enough positive things about the amazing event staff. From the time we arrived, until the morning we departed, they made absolutely sure everything ran seamlessly. They went above and beyond to make us feel comfortable. Their attention to detail was incredible—they truly thought of everything! The professionalism and genuine hospitality really stood out, and it was obvious they were passionate about creating a memorable experience for us.”
As attendees departed that early morning with Mt. Etna erupting in the distance—nature’s own spectacular sendoff—they carried with them not just memories of a beautiful destination, but deeply personal experiences that made them feel truly seen and valued. And for the event planning community, this award-winning program serves as a powerful reminder that the most memorable experiences come not from following a formula, but from genuinely caring about the people you’re serving and being willing to go above and beyond—or as they called it, practicing unreasonable hospitality—to create moments that matter.
Congratulations to Meetings & Incentives Worldwide and all of this year’s recipients, who were honored during Cater+Event 2026 this past March in Los Angeles. Keep an eye on our website as we profile all of this year’s award recipients.
Click through the slideshow for a look at this award-winning event.
