Classic Vacations‘ winter 2026 holiday trends report shows luxury clients spending the holidays somewhere warm, in accommodations big enough to bring the family together, with those who want a specific villa or suite booking months in advance.
Classic Vacations: What’s Trending
The Caribbean, Mexico and Hawaii account for 94 percent of the company’s 2026 festive bookings, with the Caribbean alone holding 42 percent. The Dominican Republic, Cancun and Maui lead bookings within their regions. Europe remains the choice for clients who want a traditional December, with Italy, France and England drawing travelers to Christmas markets and local customs.
Most of these trips are about time together. Multigenerational families, many traveling during school breaks, want private villas, spacious accommodations and resort amenities that work for every age, and some are choosing a resort or villa so the property takes over the hosting. Couples and smaller families are starting their own traditions away from home, with some couples choosing a shared trip over holiday gifts, while birthdays and anniversaries give other travelers a reason to go.
That priority points to where clients spend. Fuel surcharges are a consideration, but Classic’s team has not seen them significantly change clients’ plans, and clients are still paying more for premium airfare, private transfers, yacht charters, guided excursions and personalized dining. Requests for multi-bedroom beachfront villas are up, and suites and connecting rooms appeal to families who want time together with some privacy.
Securing that kind of space takes lead time. Luxury travelers are booking six to 12 months out for preferred villas, suites and flight schedules, and holiday inquiries began building toward the end of June. Clients booking within 90 days of travel have to weigh availability, pricing and higher airfares, and multigenerational groups that need several room categories have fewer options. Thanksgiving and the weeks leading into Christmas and New Year’s are expected to be the busiest periods, though some travelers are departing Dec. 27 or later to celebrate Christmas at home first.
Why It Matters
Airfare is the cost to watch with clients who haven’t committed. Christmas tickets are running more than 20 percent above last year, according to travel booking company Hopper, which puts current fares at a 10-year high driven by jet fuel costs. Any Christmas trip booked today already falls inside that 90-day window, so advisors have a concrete reason to confirm air and accommodations together now for clients still deciding on December. Lead with the space these groups are asking for, such as a multi-bedroom villa with private transfers, and quote the full trip, flights included, so a multigenerational group can weigh one total rather than tracking fares on its own.
For more information, visit classicvacations.com.
