Top Five Vacations with Extended Family

'Ohana Check In Polynesian Village Resort WDW

Top Five Vacations with Extended Family

Throughout the years, I’ve found some of the most rewarding experiences included multi-generations of our family. Looking ahead to your next vacation, consider one of these amazing places to gather with your loved ones.

Top Five Vacations for Extended Families

1. Disney’s Hilton Head Island Resort

It’s no secret that I love all destinations with Disney in its’ name. And I cherish the memories we made with my in-laws at Disney’s Hilton Head Island resort.

Hilton Head Island South Carolina
Hilton Head Island

With villa type accommodations, families can reserve the set-up that works best for them. On our visits, we booked a two-bedroom villa. Grandparents took the master bedroom and bathroom while we sheltered in the second bedroom complete with two queen beds and a full size bathroom. This was the perfect set-up for our getaway with extended family.

With a shaded outdoor deck, we were able to play cards at the picnic table and enjoy homemade sandwiches outdoors for lunch. In the evening, we explored the restaurants that the island had to offer.

Picnic table on villa's deck. These have now been replaced with round wooden tables.
Picnic table on villa’s deck. These have now been replaced with round wooden tables.

The resort offers many activities for all ages — nature walks, kayaking, swimming, bike riding, and more. While the villa is in a wooded area, there is a beach lodge on the ocean with another pool and oceanside activities.

Why so special? It’s a combination of a cabin, beach, and Disney trip all in one!

Attractions: Bike riding, miniature golf, lighthouses, beach activities, and more.

Dining: Tide Me Over Cafe, Signals, many island offerings

Lodging: Disney’s Hilton Head Island Resort



2. Any Cruise Ship

With extended family, we have sailed with Disney and Royal Caribbean cruise lines. Once aboard, there are a plethora of activities to enjoy. Families can meet up for a show, a meal, or to soak up the sun on deck.

Disney Magic
Disney Magic

During the in-between times, each person can delve into their own vacation pastimes. Mom heads to the solarium to read a book (and maybe sip a strawberry daiquiri), Dad goes to a beer tasting event, Grandma tries her luck in the casino, Grandpa takes a walk on deck, Aunt gets a spa treatment, and Uncle climbs the rock wall. Where are the kids? Probably in the youth activities area where they are dancing with characters, playing dodgeball, drinking smoothies with new friends, etc.

Family gathering inside Animator's Palate aboard the Disney Dream
Family gathering inside Animator’s Palate aboard the Disney Dream

Attractions: Depending on your ship, you’ll have Broadway-style shows, rock climbing walls, miniature golf, scavenger hunts, trivia contests, ice skating, dancing, shopping, and more. Plus, countless offerings at the ports of call.

Dining: Room service, formal dining rooms, extra-cost restaurants, casual buffets, fast food counters, and snack locations.

Lodging: I recommend Disney Cruise Line and Royal Caribbean Cruise Line for plenty of activities for kids.

3. Outer Banks, NC

I have fond memories of traveling to this location with my in-laws. Each time we visited, we selected a different beach house to rent so that everyone had their own bedroom and bathroom. We made sure that we had places to congregate such as a game room with pool table, outdoor deck for stargazing, and living room/dining room for building puzzles, playing games, and watching movies.

Outer Banks, North Carolina
Outer Banks, NC

This is a great set-up for traveling with family members of all different ages. Those relatives that like to sleep in late, rise early, and/or take afternoon naps, can escape to their own havens within the beach house. And then everyone can choose what activities they want to participate in. I recommend collecting shells at the beach, bike rides, climbing sand dunes at Jockey’s Ridge, a visit to Wright Brothers memorial, and a ride to see the amazing lighthouses throughout the Outer Banks.

On a family trip, riding bikes is a fun activity for all ages
On a family trip, riding bikes is a fun activity for all ages

An excursion for ice cream is a must in the evenings. One of my favorite all-time places for ice cream is Kill Devil’s Frozen Custard. It’s fun to try the special of the day!

Attractions: Cape Hatteras Lighthouse, Currituck Beach Lighthouse, Wright Brothers National Memorial, Jockey’s Ridge State Park

Dining: Kill Devil’s Frozen Custard, Bob’s Grill

Lodging: Currituck Club

4. Gatlinburg/Pigeon Forge, TN

Here’s where you’ll want to reserve a cabin. Be careful to watch for location challenges as some cabins are at high elevations. This may make traveling to your hideaway difficult, especially in the winter. You’ll also want to steer clear of any rentals with steep driveways and/or stairs, especially if a family member has mobility concerns. I’m thinking of your restless toddler, midlife husband with a bad back, and/or a grandparent in need of a knee replacement.

Great Smoky Mountains National Park
Great Smoky Mountains National Park

This type of vacation works for various ages because there is room to spread out. If you plan accordingly, everyone benefits from a bit of privacy plus a healthy dose of family togetherness.

To increase the magic of this type of trip, I recommend going over a holiday such as Thanksgiving or Christmas. Sure, there are some logistics to work out (how to make your favorite recipes or where to hide the gifts) but once these issues are solved, you’ll have time to gather, nap, watch the game, and take a scenic walk.

Choose a cabin that will accommodate your family -- big or small!
Choose a cabin that will accommodate your family — big or small!

If you plan to hideout in your cabin for your visit, be sure to stock up on groceries before arrival. I recommend heading out for at least one pancake breakfast during your visit. You’ll want to get out for at least one hike near your cabin or at the nearby Great Smoky Mountains National Park. When cabin fever strikes, attractions abound in this area. Send the thrill-seekers to race go-karts while the more sedate vacationers explore local shops.

It’s a peaceful getaway whether you stay for 3 nights or a week!

Attractions: Great Smoky Mountains National Park, Dollywood, The Village Shops, Titanic Museum Attraction, Tanger Outlets, MagiQuest, WonderWorks

Dining: Pancake Pantry, Smoky Mountain Brewery, McAlister’s Deli, Flapjack’s Pancake Cabin, Mellow Mushroom

Lodging: Cabin rental or Wilderness at the Smokies

5. Walt Disney World Resort

My first visit to Walt Disney World was with my Mom and grandparents at age 11. Ever since, this has been a favorite place to vacation with family. And our son has been going to WDW since the age of 2 — many of these trips with grandparents in tow.

Cinderella's Castle
Cinderella’s Castle is a welcoming sight!

When planning a trip with people from toddlerhood to senior status, you’ll want to make sure that everyone is comfortable with the lodging, meals, and park touring plans. I highly recommend touring in the morning, returning to your resort for an afternoon rest (an escape from the HOT sun and HUGE crowds), then returning to tour in the evening. During the afternoon rest period, family members can take a nap, go for a swim, take a stroll around the resort, or board a bus to go to Disney Springs to shop. Also, keep in mind whether younger ones need a stroller or older ones an electric scooter. What matters most is that everyone is comfortable.

Making memories at the Once Upon a Christmastime Parade, Magic Kingdom
Making memories at the Once Upon a Christmastime Parade, Magic Kingdom

What I’ve learned is that a trip to WDW doesn’t have to be a race to see every attraction, show, character, or restaurant. Your trip will be more memorable by slowing down and soaking up the magic. Choose a few must-do attractions for each day and then let magical moments happen spontaneously. Some of my favorite memories are watching our son chase a squirrel in Liberty Square while his grandparents laughed heartily, seeing our son and grandparents hug Pooh Bear, watching our son squeal with delight while waiting for a parade with his aunt and uncle, and so much more.

Attractions: Disney Parks, Water Parks, Disney Springs

Dining: Hotel food courts, Signature restaurants, Casual counter-service

Lodging: A Disney resort that fits your budget. My favorites: Pop Century, All-Star Music, and Art of Animation (value); Port Orleans French Quarter and Port Orleans Riverside (moderate); Grand Floridian and Animal Kingdom Lodge (deluxe).

Look for more information on these amazing vacation destinations in future posts.

Of course, I now want to hear from you. Let me know your top vacation spots when traveling with family members of all ages! Please chime in so I can add your ideas to my bucket list.

Kimberly LaPaglia

Kimberly shared her passion for Disney when she was selected for the inaugural Walt Disney World Moms Panel and then as the first Disney Cruise Line panelist. As a Disney Mom, she helped countless families plan their own dream-filled journeys. Blending her love for research, travel, and writing, Kim has been an editor for Disney Food Blog for nearly 8 years. At The Castle Concierge, she blogs about travel, parenting, celebrations, and the road to empty nesting.

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