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Traveling with family members spanning two, three or even four generations offers a unique opportunity to create priceless memories. With time for interaction between grandparents and grandkids, aunts, uncles, cousins and sometimes even great grandparents, the experience strengthens our family bonds. But when it comes to planning a large family vacation, choosing the right location is key to a stress-free memory-making trip.
The Biggest Challenge
The biggest challenge to planning an extended family getaway is finding a place that will appeal to everyone.
You need a resort or destination that balances the right amount of togetherness with enough space to give everyone the option of spending time apart.
You need activities that will satisfy the active preschoolers, the sullen teenagers, the foodie millennials, the wine-loving parents and the nap-happy adults.
In other words, planning multigenerational travel is not always easy. But it is rewarding!
We love traveling with our extended families, from watching cousins who live on other sides of the country bond as they play in the pool to reconnecting with our adult siblings and watching grandparents and grandkids see one another in a whole new light.
We love sharing tips and stories with our fellow Traveling Grandparents. Join our private Facebook Group to become part of our community!
So, how do you start planning a multi-gen trip? By choosing the right family vacation destination.
Things to Consider for Your Extended Family Trip
There are four main considerations:
- How much?
- Who pays?
- When can you go?
- What does everyone love to do?
Who Pays and How Much?
Who pays is the most important question. If grandma and grandpa are paying, they generally get more say in the rest of the vacation planning.
But, if everyone is paying for their own family, then how much the trip will cost becomes a negotiation. If the goal is to have everyone together, you don’t want anyone to drop out because they can’t afford the trip.
When Can You Go?
Next is scheduling. For people who are working and learning remotely, that can be easier. But if you need to balance work, school and sports schedules, it can be a challenge. Advance planning usually helps.
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What Does Everyone Love to Do?
Finally, you need to take an honest look at your extended family’s unique personality.
Grandparents who are used to luxury travel may not enjoy a family road trip vacation as much as a family that loves camping. Similarly, a resort without play areas or a children’s menu may not be the best for families with young children. If some family members are prone to motion sickness, it may be better to leave the cruising for another trip.
Travel Tips for a Successful Multigenerational Family Vacation
No matter where you choose to go, one of the key things that I’ve found makes for a multigenerational family vacation everyone will enjoy is being flexible in the planning. Start with some plans in mind but be willing to adapt.
Another key is making sure that there’s separate downtime for everyone. While grandparents may love their little ones, they may not be ready for all the energy they bring. Remember, the end goal is for everyone to head home with happy memories!
Once you’ve figured out who pays and how much and when everyone can go and what they want to do, it’s time to choose the right destination. Here are some of our favorite extended family vacation ideas.
Try an All-Inclusive Resort for Your Beach Vacation
All-inclusive resorts take the work out of planning an extended family vacation while keeping the finances simple. Larger all-inclusive resorts include several dining options, opportunities for water play and plenty of entertainment choices. Families can do as much or as little as they like together. Parents can spend time together exploring the spa while grandparents and grandkids build sandcastles on the beach.
Choosing the Right All Inclusive
The key thing to remember is that all inclusives come in many shapes and sizes with varying offerings. When TravelingMom Editor Cindy Richards was looking for an all-inclusive resort for her large family trip, she needed one that was small enough to make it easy for her legally blind 87-year-old mother-in-law to get around but still had enough on-site activities to keep two teenagers happy.
TravelingMom Kendra Pierson headed to Beaches Resort in the Turks and Caicos for a family vacation that included her mom. It’s a vacation her sons still talk about. They played with Elmo and Big Bird while watching awe-inspiring sunsets. It was a new place for them to explore together but still left her mother with enough space to have a relaxing vacation.
Take to the Water on a Family Cruise
Some people refer to all inclusives as “cruise ships on land.”
We like both types of family vacations — all inclusives and cruises — for the same reason: All your family has to do is show up. With everything from kids’ clubs to casinos and nightlife, large cruise ships keep the entire family entertained. Your family can also choose to spend every day doing whatever they enjoy most, then come together for a big family dinner that night.
Cruises are an easy choice for a multi-generational trip. With a cruise, once the destination is selected all your family has to do is board and go. Cruises offer so much for different ages from casinos and shows to kids clubs and nightlife. Your family can also choose how much or how little time to spend together.
More than Mega Ships
Don’t just think about the traditional large cruise ships either. Another option for the family who has done it all could be a European river cruise. In addition to cruising along the river, stops in picturesque villages and cities allow families to see another side of Europe without worrying about the logistics of changing hotels.
For some good old-fashioned fun, a vintage sailboat cruise promises to be an unforgettable experience. Companies like Star Clippers offer tall ship sailing itineraries in the Caribbean as well as Europe. Generally recommended for children ages 8 and up, these tall ship sailing adventures make an ideal multigenerational trip.
When the boat drops anchor, marine platforms serve as a launching pad for water sports including kayaking, snorkeling, skiing and paddleboarding. And the more adventurous family members can even climb up the mast to a viewing platform.
If you prefer a more laid-back sailing experience in the United States, you won’t go wrong with a Maine windjammer cruise. Join the crew as they hoist the sails as you sail alongside iconic lighthouses.
Family Fun Awaits in the Theme Parks
A trip to either Walt Disney World or Disneyland is a great option for families that love theme parks. Disney’s exceptional customer service can accommodate just about any challenge your family may have, from food allergies to mobility issues.
If it’s the first trip to Disney World, don’t worry about doing all the parks. Focus on exploring the Magic Kingdom which boasts several of Disney’s best rides for grandparents and kids.
If your family members visit the parks often, consider booking an exclusive experience or try a new park.
More Florida Theme Parks
Another Florida favorite for family vacations, LEGOLAND entertains the entire family with fun rides, amazing displays and places to explore, although the park is best for the 12-and-under set. Teens, however, can find plenty of fun at LEGOLAND Water Park, one of the best ways to escape the Florida heat.
On a recent trip here with my grandkids, they had a blast in both parks. From building new LEGO creations to an impromptu dance party as they dried off in the fun air dryer machines at the water park, the experience earned several “best day ever” exclamations.
If you have older kids or teens in your extended family group, consider a theme park vacation at Universal Studios.
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Sleep Outside in Luxury on a Glamping Trip
Chances are not all family members will embrace the idea of sleeping in a tent. I know some of mine wouldn’t. But bump the experience up to the luxury level on a glamping trip and even the skeptics in the family will be on board.
Glamping delivers opportunities to stargaze, roast marshmallows for s’mores and catch up on family stories around the campfire. And when the day ends, you can bed down in luxury.
Glamping resorts stretch all across the United States offering a wide range of amenities and activities.
Glamping at Westgate River Ranch
One of my favorites is in Florida: Westgate River Ranch. When I took my 6-year-old grandson there, it was the perfect way to enjoy the great outdoors without sacrificing creature comforts and without complaining (from me).
Benjamin was delighted at the real canvas tent complete with zippers and tie-backs. I was THRILLED with the king-size bed, two additional twin-size beds and two chest of drawers.
And I was even more thrilled with the air conditioning – yes, air conditioning in a tent. Do you have any idea how fabulous that is in Florida? Family adventure options range from a petting zoo to an airboat ride on the Kissimmee River and we took full advantage of all of these.
Glamping Near Moab
For a more traditional camping/glamping experience, head to Canvas Moab. It’s a great way to spend the night in luxury after a day hiking the national parks near Moab, Utah. Tucked between Arches National Park and Canyonlands National Park, adventures abound for the entire family.
Hiking, mountain biking and climbing rank among the top activities in the area. But even those less adventurous family members will embrace the beauty of Utah.
A trip like this works best for older kids and teens. It’s also important to consider accessibility needs within your group. While my grandkids are always up for rock climbing and I can hike for miles, older grandparents might not have enough stamina to keep up.
For a more citified experience, there’s even glamping in New York City. Really.
Try a Dude Ranch, No Riding Required
If yours is a particularly outdoorsy family, a dude ranch vacation offers myriad ways to spend the day outside in the fresh air.
Head to Colorado where you can spend your days hiking or horseback riding along ranch trails and take in the Rocky Mountain views. And just because Aunt Mabel doesn’t like horses is no reason to forego a dude ranch for your extended family trip. There are plenty of things to do besides horseback riding.
Book a Vacation Rental
When planning a large family vacation, accommodations matter. My extended family spans four generations with ages ranging from 10 to 81. We usually book a vacation rental large enough for the whole family in a location with a variety of activities. We typically choose a place in the mountains in the southeast since we can all get to this region easily.
The shoppers in the family will check out local antique stores or art galleries in nearby small towns. The adventurers might choose whitewater rafting, zip-lining or fishing. At the end of the day we all meet up to spend the evening playing games or telling family stories together.
Resorts that Work for Extended Family Vacations
Numerous resorts across the country work well for extended family getaways. Here are a few of my family’s favorites.
Palm Island Resort in Cape Haze, Florida
Located on Florida’s Southwest Gulf Coast approximately 50 miles north of Fort Myers, Palm Island has kept all four generations of my family happy for decades. We spend the days searching for shark’s teeth on the beach, fishing in the surf and exploring the island by golf cart or bicycle.
We love the old-style Florida charm of this resort. Villas come with fully equipped kitchens and laundry facilities. Villas are clustered in groups around swimming pools with Hydro Spas and gas barbeque grills and the beaches are never crowded.
We have everything we need to prepare our own meals (although we manage at least one night eating at the island’s Rum Bay restaurant, where the yummy specialties include native grouper and baby back ribs).
For active pursuits, there are 11 tennis courts. Lessons and clinics are available with the resort’s tennis director. Family adventure packages can be arranged through several independent companies for fishing, sightseeing, sandbar eco-adventures and wildlife viewing. Rental items like kayaks, canoes, boogie boards, rafts, and snorkeling gear help to maximize the water fun.
The island’s resident pirate, Red Beard and his trusty parrot add more entertainment for the kids. Happily teaching the little ones how to make sand art and pirate beads, Red Beard also regals them with stories of his fights with the evil Pirate Blackbeard.
Basin Harbor Club in Lake Champlain, Vermont
For more than a century, Basin Harbor Club in Lake Champlain, Vermont, has been a destination for families to play, relax and reconnect. Situated at the edge of shimmering Lake Champlain, the resort’s large verandahs and summer sounds of wooden screen doors slamming as children run in and out evoke a nostalgic vibe.
A full menu of scheduled activities includes fitness boot camps, golf lessons, and tennis. For the younger family members, Kids Clubs offer arts and crafts, sports, fishing, and games like Capture the Flag, scavenger hunts and water carnivals. Movie night in the pool was a big hit with my grandson, Marshall, mostly because “Star Wars” was playing.
Adirondack chairs scattered throughout the resort invite you to sit, sip a glass of wine and soak in the sunshine as it glistens off the lake. Or enjoy a little family competition with classic lawn games like croquet, badminton, giant chess and volleyball. Paddle boats, kid’s boats and a giant water trampoline helped my grandkids make full use of the lake.
Lodging options include 45 charming guest rooms located in four guest houses: The Main Lodge, The Homestead, Champlain House and Summit. If you prefer more togetherness, there are 74 private lakeside cottages ranging from studio to 3-bedrooms, each with its own unique personality…just like your family members.
Old Kinderhook Resort at the Lake of the Ozarks, Missouri
This is the place for golfers and spa lovers. The resort’s centerpiece is a Tom Weiskopf signature golf course carved from the Ozark Hills. The challenging course includes valleys, waterfalls, hills, trees, water hazards and elevation changes, along with breathtaking views.
If you need a little help with your game, book a lesson with one of the resort’s pros. I needed a LOT of help with mine and although my instructor tried his best, it was clear I’m better off hiking or enjoying an afternoon at the spa!
In between rounds of golf and massages, there’s a whole region of outdoor wonders to engage the whole family at the Lake of the Ozarks, from boating and fishing to hiking and caving. An ideal trip for older kids, teens and adults, family members can go their own ways during the day and meet back up to share stories of the day’s adventures.
Even better for extended families, Old Kinderhook offers a wide variety of options for lodging. The Lodge at Old Kinderhook overlooks the golf course and offers 84 impeccably decorated rooms.
Other lodging options include golf cottages, patio homes, villas and estate homes with three to four bedrooms scattered throughout the golf course. So you can have your own rooms or rent one big house for the whole family to hang out together.
No matter where you choose to go for your extended family vacation, we hope these planning tips and ideas will help you in your quest to make treasured memories together!