Home 9 Lifestyles & Wellness in Highlands NC and Cashiers NC 9 Multi-generational Family Adventure

Multi-generational Family Adventure

Careful planning and wise decisions form the foundation of family travel that’s treasured for a lifetime.

Written by: Hilary Wilkes

Issue: July 2025

We’ve all said, “there just isn’t enough time,” or heard from family and friends, “we never get to see you.” After spending two years as a “together but separate” society, our craving for connection and quality time together is at an all-time high.

With many families and friend groups returning to their pre-pandemic routines – busy with work, youth sports, and volunteer organizations – but still aiming to stay connected to loved ones, multi-generational travel has experienced a surge in recent years and is a great way to embark on new adventures and create lifelong memories across different age groups.

From economy to luxury budgets, and from long-haul to local destinations, the travel industry is poised to provide options for every group’s needs, and the possibilities are endless.

Cruise lines have long been leaders in providing spaces to excite and invite all ages. With kid and teen clubs, a variety of shipboard entertainment and dining options, and itineraries that cater to adventurous groups (think Alaska) or those more inclined toward fun in the sun (think Caribbean), a cruise can offer a turnkey experience with significant savings for kids and groups. Port excursions are also available at a range of activity levels, allowing travelers to easily explore independently before reconnecting with the group. Some cruise lines include excursions at every port in their package, taking the guesswork out of unforeseen expenses.

If your family is eager for immersion in the natural world, an African safari is the ultimate bonding experience. A guided game drive is the perfect place to unplug and just “be” – all while enjoying the thrill of observing the big five (lion, leopard, elephant, rhinoceros, and African buffalo) and so many more animals, along with the most amazing landscapes, sunrises, and sunsets you’ve ever seen.

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Lodges like the Bush Lodge in Greater Kruger Sabi Sabi region are perfect for guests young and not-so-young.

Their EleFun center is a kid-pleaser and the ideal place for children to stay if they are not yet safari-ready, or just want to play.

The center also serves as a day care for staff, and young guests have the opportunity to interact with peers from around the world.

Many tour companies like Tauck, Backroads and Trafalgar offer family-specific itineraries, including river cruises, both stateside and abroad. You can fill a tour with just your group or go with others and make new friends along the way. With every detail handled, including flights, accommodations, transfers, and tours, these companies excel in maximizing your dollars and time, and often offer special rates or incentive trips to groups.

Finding a home to share in a high-interest destination is a great way to stretch your budget and spend quality time together during the trip. The rental market offers a wide range of options that can comfortably accommodate many guests but be mindful as you investigate.

Utilizing local agencies can give you peace of mind that your needs can be met by someone accessible to the property. Websites like Airbnb and VRBO can give you an idea of pricing in an area as you research where you’d like to go. When booking abroad, consider using a travel advisor to provide you with options that have been vetted through their partners.

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The Brinson-Wilkes Family on vacation at Massanutten Resort in Virginia.

As you work to plan your next multi-generational or multi-family trip, keep these things in mind:

– Set clear expectations for each guest’s budget and financial requirements before the trip (including deposits, trip insurance, and credit card guarantees) and during the trip (such as excursions, meals, and gratuities). Utilizing favorable exchange rates in countries like Canada and South Africa is a great way to bridge the gap between varying budgets.

– When booking a group, be sure to inquire about group discounts, including those for milestone anniversaries or birthdays.

– Be realistic about the physical abilities within the group. Make sure the itinerary includes something for everyone and leaves room for downtime.

– Working with a travel advisor can streamline the planning process, access additional savings and deals, and ensure your trip is seamless from start to finish, allowing everyone to relax and enjoy themselves.

Don’t forget that many travelers experience the joys of the trip long before even leaving home. Daydreaming about the sand in your toes, the yummy food, or the awe-inspiring sites you’ll see is half of the fun. Include everyone in the conversation so they can get excited too!

Hilary Wilkes is a local travel advisor and works personally with clients to plan trips around the world. She also plans and leads group trips through her family’s store, Highland Hiker. Learn more at scouttravelco.com and highlandhiker.com.

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