Editor’s note: While Havana remains a fascinating option, some of the offerings of this specific trip may no longer be available due to recent travel restrictions.

Do people often ask you, “What are the hot, new incentive destinations?”

If you answered yes, you’re not alone. This is one of the most frequently asked questions for incentive travel professionals. And it’s a question I seldom answer.

Why? Because successful incentive trips aren’t about following the up-and-coming destinations and latest trends. Winners can visit these places without our help. The important thing is what you do when you get to the destination.

Extraordinary incentive programs provide unique experiences guests couldn’t possibly create on their own.

Let me give you an example …

Cultural Immersion: Havana

Cuba holds an allure for American travelers as a destination that’s nearby yet out of reach, due to more than five decades of travel restrictions.

Streamlinevents managed an incentive trip there last year. As a tech innovator, our client Rubrik wanted a trip combining safety and comfort with the challenge of the unknown. Havana fit the bill as a city rich in history and culture with new experiences for winners.

We stayed at the Gran Hotel Manzana Kempinski in the heart of Old Havana with a rooftop event terrace overlooking the city.

On the final night of the trip, we held the awards gala at Gran Teatro de La Habana Opera House, home to the Ballet Nacional de Cuba. Gran Teatro is an icon of Old Havana, famous for its neo-baroque architecture.

Exquisite event space on the third floor captured the spirit of our trip. However, the space was off-limits to foreigners. Even a full buyout offer couldn’t secure it.

Fortunately, our DMC, Vaya Soujourns, helped us navigate the complexities of doing business in Cuba. The company has taken groups there for decades. Their insider’s view proved invaluable in our talks with Gran Teatro.

In the end, we secured the venue. This set the stage for an evening attendees will never forget.

Josh Adams, streamlinevents’ Industry Relations Strategist explains, “As incentive planners, we must be cultural ambassadors who embrace the magic of each destination where we work. People are happy to share their pride in country when they know you respect their way of life. Understanding the nuances helps us find that balance that lets the local culture shine.”

Vintage Cars

Getting to Gran Teatro was also memorable. We organized transportation via the vintage cars for which Havana is known. However, local restrictions limited only five cars at a time to pull up to the hotel.

But Hotel Kempinski made special arrangements. On the night of the gala, guests were wowed when all 50 cars to drive into the hotel plaza in a spectacular show of bright-colored cars.

Wanting to surprise winners, we kept the gala venue’s identity top-secret. The classic car parade took them on a 45-minute drive past Old Havana landmarks and back to Gran Teatro, just a block from our hotel.

The lesson here is this: Incentive trips don’t have to be about high-end hotels and celebrity chefs. Guests want enriching cultural experiences. When they enjoy new adventures in a safe, secure setting, they welcome the opportunity to visit places that have previously gone unexplored.

The Havana trip exceeded all expectations because it provided incredible people-to-people experiences, leaving guests with lifetime memories.

Classic Destinations and Lesser-Known Gems

How else can you create unforgettable experiences?

Go beyond the obvious choices. Pair classic destinations with lesser-known spots for innovative itineraries. For example:

  • Paris/Bordeaux – See masterpieces at the Louvre and Musée d’Orsay. Then board a high-speed train to Bordeaux. Savor this city’s food and wine heritage via foodie experiences unavailable to the general public and tours of legendary wine-producing estates. Enjoy tastings of wine made with grapes from the vineyards you’ve just strolled.
  • Sydney/Melbourne – Add Australia’s sports and cultural capital to your itinerary. Melbourne is a vibrant city of wall-to-wall street art and multicultural cuisine. Just outside the city are white-sand beaches and lush rainforests. Kangaroo and koala spotting, anyone?
  • Buenos Aires/Mendoza – Explore buzzing Buenos Aires. Then head to Mendoza in the foothills of the Andes Mountains. Take in this cosmopolitan city known for its wineries. Then try your hand at cattle roping during a day at a working ranch.

The point is, go beyond conventional choices. Leverage your expertise, curiosity and buying power to create unique experiences winners would miss if planned on their own.

It’s never a good idea to accept off-the-rack itineraries. Successful programs demand planners curate locally inspired, one-of-a-kind experiences. When you personalize every detail and give compelling options, you create programs that amaze and inspire.

Incentive trips aren’t just a thank you for past success. They’re motivators for repeat performance and long-term loyalty. This calls for programs as extraordinary as the winners we celebrate.

Annette Chinn is founder and CEO, streamlinevents, a full-service meetings and events management company based in the San Francisco Bay Area. She brings to her role 25 years of experience in corporate meetings, events and incentive travel.