October 22, 2025

Adventure Destinations League

Navigating Travel Wonders

Cuba’s Comeback and Caribbean Growth Drive Sunwing’s Winter Travel Strategy

Cuba’s Comeback and Caribbean Growth Drive Sunwing’s Winter Travel Strategy

TravelPulse Staff

With early bookings outpacing last year and expanded options across the Caribbean and Latin America, Sunwing Vacations Group says it is entering the winter season with strong momentum.

Sunwing Vacations Group hosted 160 leaders from across its brands last week for its third annual Amplify leadership event, sponsored by NexusTours. 

The gathering focused on business updates, destination performance, and preparations for the winter travel season.

With demand shifting from transborder travel to Latin American and Caribbean destinations, Sunwing Vacations Group says it is ready to meet the growing interest.

“We are excited to see the momentum for the 2025-2026 winter season,” said Andrew Dawson, president of Sunwing Vacations Group.

“Advance bookings are running ahead of last winter and we are excited to see so many vacationers taking advantage of the great Early Booking Bonus offers. We are especially thrilled to be expanding our reach with new destinations like Samana (Dominican Republic), Managua (Nicaragua) and San Andres (Colombia) for Sunwing Vacations and direct to Havana (Cuba) for WestJet Vacations.”

Updates and Highlights

Among the event’s highlights were business updates from John Weatherill, WestJet Group EVP and CCO, who reinforced the airline’s commitment to supporting the tour operator’s growth.

Samantha Taylor, WestJet Group EVP and CEO, shared details on continued investments in guest experience, including the expansion of in-flight Wi-Fi.

NexusTours also outlined enhancements to its operations, including new branded catamarans, additional transfer vehicles, and the launch of its Travel Agent Portal, now available to all travel advisors booking through Sunwing Vacations Group brands.

The event recognized several brand milestones:

  • Vacation Express reported a record year with notable growth in Jamaica.
  • WestJet Vacations expanded its offerings in Latin American and Caribbean destinations.
  • WestJet Vacations Quebec achieved strong year-over-year growth.
  • Luxe Destination Weddings was recognized as a top performer, driving volume across sister brands.

GlobalMedic’s Rahul Singh also presented on the organization’s ongoing partnership with Sunwing Vacations and future volunteer opportunities.

Cuba’s Comeback

Dawson noted renewed enthusiasm for Cuba among Canadian travellers.

“Cuba is absolutely thriving again,” he said. 

“We’re seeing Canadian travellers rediscover what makes this destination so special. The combination of authentic culture, beautiful beaches, great value and improved guest experiences is creating incredible momentum. Canadians are finding they can enjoy an amazing vacation experience without breaking the bank.”

Taylor highlighted recent milestones in WestJet’s guest experience investments. 

“We’re excited that Sunwing guests are now travelling onboard WestJet flights and experiencing the enhanced service,” she said. 

“We recently celebrated a major milestone of 100 of WestJet’s 737 aircraft now offering WestJet Wi-Fi, presented by TELUS. This transforms the way guests can stay connected, stream content and browse seamlessly throughout the flight.”

Travel Advisors at the Centre

The group emphasized the continued importance of travel advisors heading into the busy winter season.

“We’re seeing momentous growth from travel advisors this winter,” said Steph Ng, WestJet Group VP of Marketing. 

“That’s why we continue to recognize our advisor community in this year’s winter campaign – they’re the driving force behind connecting Canadians to their dream vacations and we’re committed to supporting their success.”


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