The festive season is made for gathering. From multigenerational family holidays and long-awaited reunions to getaways with friends and milestone celebrations, travelers are finding new ways to spend the season together — often taking cherished traditions somewhere new. Festive travel offers the chance to create new traditions while enjoying the moments that make this time of year special.
Look Beyond the Room
The right property should do more than accommodate everyone — it should add something to the celebration. For festive FIT groups, advisors should consider how accommodations, dining, seasonal programs, and resort experiences come together to create a stay that feels special while meeting the needs of everyone traveling.
Accommodations for Everyone
The right accommodations can make it easier for families and friends to stay connected while still having the space they need. A mix of guestrooms, suites, villas, residences, and connecting options gives advisors greater flexibility to accommodate different family structures, preferences, and budgets within the same group.
Festive Dining
Gathering around the table is often an important part of the holiday experience. Look for resorts with multiple restaurants, special holiday menus, celebratory dinners, and dining options that make it easy for the group to come together. Thoughtful festive dining can turn a traditional holiday meal into a memorable part of the getaway.
Seasonal Programming
Seasonal programming can transform a resort stay into a true festive experience. Tree lightings, visits from Santa, holiday markets, festive entertainment, children’s programs, New Year’s Eve celebrations, and other resort traditions give advisors more opportunities to match the property with the type of holiday experience their clients are looking for.
Experiences Across Generations
For multigenerational groups, variety matters. Pools, beaches, spas, golf, kids’ clubs, cultural activities, and excursions can appeal to different ages and interests while creating opportunities to spend time both together and independently. A resort with a broad range of experiences gives each traveler something to enjoy without requiring the entire group to follow the same itinerary.
The right setting can make gathering for the festive season feel effortless. These resorts offer the space, variety, and experiences that can make them especially appealing for families and friends traveling together.
For families and friends who want room to spread out while staying connected, Casa de Campo Resort & Villas offers a natural fit. Private villas provide space to gather together beyond the traditional hotel room, while the resort’s extensive dining, golf, beaches, and activities give travelers plenty of freedom to create their own days. Different generations can pursue their individual interests before coming together for meals, celebrations, and time at the villa, creating an easy balance between togetherness and flexibility.
Set along O‘ahu’s North Shore, The Ritz-Carlton O‘ahu, Turtle Bay gives multigenerational groups the opportunity to experience Hawaii together while leaving plenty of room for individual interests. A broad mix of resort and island experiences makes it possible for different ages to enjoy the destination at their own pace, whether that means relaxing by the ocean, exploring the outdoors, enjoying wellness experiences, or simply slowing down together. For festive FIT groups, the variety can make planning for multiple generations feel more seamless.
For travelers dreaming of a classic winter holiday, Montage Deer Valley provides a mountain setting made for the festive season. Ski access and winter activities can fill days outdoors, while dining and inviting gathering spaces offer plenty of opportunities to reconnect afterward. Families and groups of friends can spend their days on the mountain before settling in for relaxed evenings together, combining the energy of a ski getaway with the warmth and tradition of a holiday escape.
Fairmont Mayakoba offers a warm-weather alternative for festive groups looking for variety and easy access from the U.S. A broad mix of accommodations, dining, wellness, nature, and recreational activities makes it easier for advisors to accommodate different preferences within one FIT group. Travelers can spend time at the beach, explore the resort’s natural surroundings, enjoy wellness experiences, or simply relax before gathering again, giving families and friends the flexibility to make the festive getaway their own.
The holidays give families and friends a reason to come together. Travel gives them a new place to do it.
Whether clients are gathering several generations for a holiday in the sun, bringing friends together for a winter escape, or celebrating a December milestone somewhere new, advisors can help transform the festive season into an experience everyone shares.
With Classic Vacations’ Preferred portfolio, advisor resources, and support, bringing those moments together can be easier than ever.
Ready to turn the next big moment into a small-group getaway? Explore Big Moments, Small Groups for inspiration and discover flexible ways to bring families and friends together at luxury resorts.
FIT groups of fewer than 10 rooms: Book online or connect with Reservations at +1 (800) 221-3949.
Groups of 10 rooms or more: Contact Groups@ClassicVacations.com or submit the Group Request Form.
Looking for festive inspiration? Explore Classic’s Festive Availability to discover Preferred hotels and resorts ready to welcome your clients for the holiday season.
