How to Take a Group to Cuba

Local partners and thorough planning helped Streamlinevents pull off a successful incentive trip to the "Pearl of the Antilles" -- despite fundamental challenges.


Cuba is a mystery to most Americans. As the rest of the world opened up with the help of affordable air travel, the Internet and social media, it remained hopelessly closed thanks to a decades-long trade embargo. When former President Barack Obama lifted the embargo in 2015, however, the latch finally lifted on Cuba's iron gate. Now, travelers are flocking to the island nation from the United States in search of brand-new people, places and experiences.
Among the most enthusiastic visitors are incentive travelers, who are attracted to Cuba for its convenient location, warm weather and bygone culture.
Unfortunately, many of the things that make Cuba so appealing also make it a challenging destination in which to execute a successful incentive program, says Annette Chinn, president and CEO of Streamlinevents, which plans more than 600 meetings, incentives and events every year for corporate clients such as Salesforce, Kaiser Permanente and Allstate. Last May, she organized a three-night, four-day incentive trip to the island for Rubrik, a leader in cloud data-management software.
"Rubrik wanted something edgy, exciting and unique for its inaugural incentive trip," notes Chinn, who organized the program for the company's top 50 global salespeople and their guests. "As a leading tech innovator, the company was looking for a destination holding the promise of elegance and the challenge of the unknown. With Cuba recently opened to U.S. travelers, our goal was to deliver a five-star experience in an unfamiliar and adventurous setting."
The event, which achieved 98 percent participation, is a blueprint for incentive planners taking their first group to Cuba.
The first obstacle that incentive planners must overcome is the question of what is and isn't legal about traveling to Cuba, arising when, after President Obama eased travel restrictions for Americans in 2015, President Donald Trump tightened them again in 2017.
"Visiting the 'Pearl of the Antilles' can be confusing for American travelers in light of the tighter restriction issued last year," Chinn says. "Since the Trump administration restricted travel to Cuba in November 2017, many people think visiting the island is illegal again for U.S. citizens. But that's not true. The regulations have become stricter, but it's still possible for Americans to visit individually or as a group."
According to Chinn, the Obama administration allowed travel to Cuba by issuing "people-to-people" licenses whereby U.S. citizens could visit the island to interact and engage with its people, the premise of which was education. The Trump administration eliminated people-to-people licenses and instead now issues a general license that affords travelers the same opportunities using different nomenclature.
"Although people-to-people licenses were eliminated, Americans can still visit Cuba under the 'educational/people-to-people' category or under the 'support for the Cuban people' category," Chinn says. "In practical terms for the MICE market, you need a reasonable schedule of planned activities that support the Cuban people, which is pretty simple. Most MICE programs show support in Cuba by purchasing meals at local paladares - private enterprise restaurants - and possibly by attending a private musical concert, renting classic American cars that are owned and operated by locals, perhaps taking a cooking class, hiring local guides and experts on various subject matters -- the list is endless."
Given the confusion around regulations, planners must be prepared to answer questions and put their clients at ease. "When we reassure clients that we know how to bring American incentive groups to Cuba, interest spikes," Chinn says. "We let them know we handle all the logistics to make traveling there easy."
If step one is reassuring clients that incentive travel to Cuba is legal, step two is planning a program that makes your trip legal by providing "support for the Cuban people."
"This may sound complicated. However, nearly everything a MICE planner might want to do for their clients in any other area of the world - meals, tours, guides, the arts, hotels, gratuities, a little salsa? - can be done in Cuba, and nearly every venue will qualify for a 'support for the Cuban people' general license," says Chinn, whose program featured daily cultural exchanges that satisfied U.S. regulations. Highlights, for instance, included:
• Cigar making. Streamlinevents treated participants to a presentation on the making of the world-famous Cuban cigar, the Habano. "The presentation was by two renowned and award-winning cigar sommeliers," says Chinn. "It was a wonderful day. Attendees traveled to the sommeliers' restaurant just outside of Havana in a picturesque fishing village not far from Ernest Hemingway's home in San Francisco de Paula, where he wrote The Old Man and the Sea. At the restaurant, attendees enjoyed a tasty lunch of fried plantains and Ajiaco, a traditional Cuban pork stew. The high point of the excursion was the presentation on the art of cigar making, where attendees discovered why Cuban cigars are considered the best in the world. They learned how to roll the cigars and pair them with three other local treasures: rum, coffee and chocolate."
• Art galleries. Incentive participants got a taste of local life in neighborhoods surrounding Old Havana via the area's art galleries and public art displays. "We visited Fusterlandia, a masterpiece of public art by Cuban artist José Fuster. Seeing streets lined with mosaic tiles of every color was a feast for the eyes," Chinn says. "Fusterlandia is an ongoing neighborhood art project that began roughly 20 years ago. Today, it covers several suburban blocks with whimsical and stylized art. You're stepping into another world here. It's like being inside a kaleidoscope surrounded by imaginative folk-art themes."
• Paladares. The family-run restaurants in private homes known as paladares are a mainstay of Cuban culture. "I highly recommend dining at paladares, one of the best ways to enjoy authentic Cuban cuisine," says Chinn. "These restaurants are contributing to a more competitive and vibrant food scene in Cuba. They are a new wave of eateries in settings like converted parts of private homes and historic mansions. In many ways, paladares operate like traditional restaurants, yet they provide great insight into life in Cuba today."
• Walking tours. A traditional favorite for tourists in Cuba is a walking tour of Old Havana with an expert local guide. "The tour took attendees down sunny cobblestone streets, where Havana's beautiful 16th-century Spanish colonial architecture is on full display," notes Chinn. "Our guide focused on the city's history, culture and people. Attendees took in galleries, shops and public art displays. They also saw the places that have made Old Havana a World Heritage Site. Among the sights: beautiful squares, Central Park and the gorgeous art-deco Bacardi Building."
For Chinn, the highlight of the entire trip was an awards gala that took place on the group's final night in Cuba, at the Gran Teatro de La Habana Opera House, which opened in 1838 and is now home to the Ballet Nacional de Cuba.
"Gran Teatro is an icon of Old Havana and renowned for its magnificent neo-baroque architecture," Chinn says. "On the third floor, we discovered a beautiful open space that had been used for large receptions in the past. Grand windows serve up breathtaking views of Central Park and the Capitol Building. Gran Teatro captured the spirit of our event. As soon as we saw the space, we knew it would set the stage for a magical evening that would live on in the memories of attendees."

Securing the venue wasn't easy, however. "Even a full buyout offer couldn't secure Gran Teatro for the final night of our trip. Taking a stance of 'I'm the client with money to influence decisions' doesn't work," Chinn says. "The truth is, relationships are all-important in Cuba. And fortunately we had a great partner in the Cuban DMC, who played a key role in our negotiations. It was also good fortune that a member of our team, Josh Adams, spoke fluent Spanish. He explained the mutual advantage of holding the event there. His point was this: Gran Teatro would provide a wonderful platform to demonstrate the value of culture to the Cuban people -- a great thing to show Americans on their first visit to the island."
Says Adams, "The learning here is the importance of showing respect for other cultures. As event planners, our job is to be sensitive to the culture of the destinations where we work. This eases our path. People are more receptive to working with you if they feel you value their way of life and get the nuances. They're happy to show the pride they have in their country. This helps us all find that balance that allows the local culture to shine."

Yet another key lesson was learned while planning transportation to Gran Teatro: Streamlinevents wanted to transport its group to the gala in a caravan of 50 classic cars for which Havana is famous.


"We envisioned a grand departure, with 50 shiny cars rolling into the plaza in front of our hotel. But after repeated requests, we learned only five cars at a time could pull up to the entrance," Chinn says. "So we planned a staggered departure, disappointed this would lack the 'Wow!' we wanted. But on the night of the dinner, the hotel surprised us. All 50 vehicles flooded into the plaza in a spectacular display of brightly colored cars. We told attendees to pick the car that best spoke to them for a drive to the dinner in a 'mystery venue.' Then, we all streamed out of the plaza in a classic car parade for a 45-minute evening drive along malecon and past Old Havana landmarks only to end up back at Gran Teatro, just a block from our hotel. The lesson here? Be flexible and embrace the magic of Cuba. Oh, and always be ready with a backup plan."
Just a few years ago, one of the biggest challenges for incentive groups in Cuba was the lack of luxury hotels. Slowly but surely, however, new properties are coming online to satisfy demand.
"We stayed at the five-star Gran Hotel Manzana Kempinski La Habana, which opened last year as the brand's first luxury hotel in Cuba," reports Chinn, who says the hotel is ideal for groups of 100 to 150 guests.
Groups that aren't challenged by the lack of luxury hotels are sure to be challenged by procurement policies. "The country has a regulation of one bottle of water per person, per day, procured only at the local market. The one-bottle-one-person-per-day regulation also applies to wine," Chinn says. "Our solution? The team worked with the local DMC agency to procure and store beverages for all guests on a three-day, four-night visit -- one bottle at a time. During the trip, we stored water in the team's sleeping rooms to ensure everyone stayed hydrated."
Gifts also pose a unique challenge. "Cuba's import restrictions meant the team couldn't bring all the gifts we wanted into the country," Chinn continues. "To support small Cuban businesses, we sourced handcrafted gifts by local artisans. Our team went on a 'treasure hunt' through Old Havana to find unique items. Some artisans didn't have the quantities on hand that we needed, so they handcrafted gifts just for our guests and delivered them to us at the hotel. For example, one item was jewelry by a woman who invited us to her home and helped us custom-design bracelets for all the women on the trip. We also visited a local perfumery and selected a gender-neutral scent made in Havana. Fragrances came in beautiful vintage bottles hand-sealed with wax for safe travel."
Such nuances required Streamlinevents to begin planning its event earlier than normal. "Our planning began a year in advance, with a scouting trip to find partnerships, lodging and activities," Chinn says. "Because Cuba is a new incentive market for the U.S., we needed to immerse ourselves in the activities, processes and infrastructure we know so well in our regular operations. We especially wanted to start forming the crucial partner network we needed to create a top-tier event in Cuba on a viable timeline."
Because Streamlinevents allowed ample time for accruing knowledge and building relationships, the event exceeded expectations both for the client and its attendees.
Concludes Chinn, "Cuba is a fascinating and welcoming destination. While doing business there is different than in the U.S., the island offers a first-class travel experience as well as adventure and mystique. We look forward to doing many more trips there in the future."