Getting the whole family together for a vacation sounds wonderful. Getting your grown kids to use their precious vacation days, coordinate the grandkids’ schedules and agree on where to go? That’s the hard part. As a mom of four grown daughters and grandmother of 10, I’ve learned that the best multigenerational trips have something for everyone.
Highlights:
- Tropical Escapes: True tropical vacations in Hawaii, Puerto Rico and the U.S. Virgin Islands without leaving the country
- Outdoor Adventures: Hiking in Zion, water sports in the Florida Keys or a Colorado dude ranch vacation
- Beach House Getaways: Renting a beach house gives the whole family room to spread out, slow down and spend time together
- Theme Park Magic: Disneyland proves that Disney trips aren’t just for little kids
- Shared Experiences: Learn something new together, from beekeeping on Mackinac Island to ukulele lessons in Hawaii
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Learn a Little Aloha Together on Kauai, Hawaii
Property: Sheraton Kauai Coconut Beach Resort | Address: 650 Aleka Loop, Kapaa, HI 96746 | Phone: 808-822-3455 | Hours: Open 24/7
Kauai is one of those destinations where I can’t imagine anyone in the family complaining about being invited. You get beaches, waterfalls, hiking, snorkeling and some of the most beautiful scenery in Hawaii. It works especially well because your family doesn’t have to spend every minute doing the same thing. Some days really can be beach, shave ice, sunset, repeat.
- The Magic: Ukulele classes where Grandma, Dad and the grandkids can all be complete beginners together and something to continue to learn together at home
- What We Love Best: Oceanfront infinity pool with complimentary bicycles, sunrise yoga and hula lessons
- Must-Try Recommendation: A scenic boat trip along the Na Pali Coast to chase waterfalls and snorkel
- Spontaneous Moments: Unwinding with simple local shave ice at sunset
Go Completely Car-Free on Mackinac Island, Michigan
Property: The Inn at Stonecliffe | Address: 8593 Cudahy Circle, Mackinac Island, MI 49757 | Phone: 906-847-3355 | Hours: Open daily
There is something wonderfully old-fashioned about arriving somewhere and realizing nobody needs to get back in the car. I remember visiting Mackinac Island as a kid with my parents and grandmother, and it’s as cute and quaint as you might think it is. Getting around by bicycle, horse-drawn carriage or on foot makes the island feel like an adventure, especially for grandkids.
- The Magic: Suiting up in beekeeper gear to explore the property orchard with a local beekeeper
- What We Love Best: A historic estate set on 15 acres away from the busiest part of downtown
- Must-Try Recommendation: Renting bikes to explore the island and eating famous Mackinac Island fudge
- Family Laughs: Looking ridiculous in beekeeping photos while learning together
Take the Whole Family Skiing in Jackson Hole, Wyoming
Property: The Lodge at Jackson Hole | Address: 80 Scott Lane, Jackson, WY 83002 | Phone: 307-739-9703 | Hours: Open 24/7
A ski vacation solves one of the biggest challenges of multigenerational travel: not everyone wants to do the same thing at the same pace. Beginners take lessons, experienced skiers head for challenging terrain and non-skiers explore town. If you’re a grandma like me, you can always volunteer for hot chocolate duty when the kids come in from sledding.
- The Magic: Reconnecting at the end of the day after everyone explores at their own pace
- What We Love Best: Comfortable home base that gives non-skiers a relaxed place to land
- Must-Try Recommendation: Wildlife watching and cozy dinners in downtown Jackson
- Grandma Duties: Official hot chocolate duty when the grandkids come in from sledding
Learn Something New in the Florida Keys
Property: Grassy Flats Resort & Beach Club | Address: 58182 Overseas Highway, Marathon, FL 33050 | Phone: 305-998-4590 | Hours: Open daily
The Florida Keys are easy to love across generations with beautiful drives, snorkeling, fishing, kayaking and quirky roadside stops. Grassy Flats Resort & Beach Club offers paddleboarding, kayaking, sailing, wakeboarding and more. It doesn’t matter if Grandma would rather watch from a beach chair while the grown kids test their balance. Some of the best dinners happen with different stories to tell.
- The Magic: Included kayaks and paddleboards so trying something new isn’t a major excursion
- What We Love Best: Three-bedroom suites sleeping up to six with full kitchens and multiple balconies
- Must-Try Recommendation: Testing your balance with paddleboarding or wakeboarding on the water
- Scenic Stops: Exploring roadside stops along the Overseas Highway drive
Take Your Grown Kids Back to Disneyland, California
Property: Disneyland Hotel | Address: 1150 West Magic Way, Anaheim, CA 92802 | Phone: 714-778-6600 | Hours: Open 24/7
Disneyland hits differently when your kids are grown and have kids of their own. Ride big rides together, let parents take little ones back for naps while grandparents stay with older kids, or split into groups and meet for nighttime entertainment. Staying at the Disneyland Hotel makes midday breaks easy with retro pools, Monorail waterslides and whirlpool spas.
- The Magic: Revisiting a place you took your own children and seeing it all over again through your grandchildren
- What We Love Best: Retro-themed pools and two Monorail waterslides for easy hotel break days
- Must-Try Recommendation: Meeting back up for nighttime fireworks and entertainment
- Park Strategy: Splitting into smaller groups to avoid moving a giant pack all day
Rent a Vacation Home and Explore Southern Utah
Property: St. George Vacation Rentals | Address: 1845 W. Canyon View Drive, St. George, UT 84770 | Phone: 435-275-4419 | Hours: Open daily
When our family went to Southern Utah last year, renting a vacation property through St. George Vacation Rentals gave us room to actually hang out together. Our home had multiple pools, hot tubs, pickleball, basketball and playgrounds. Zion National Park is about 45 miles away, offering trails for every ability, from gentle walks to the famous chains on Angels Landing.
- The Magic: Having a kitchen, living room and common space to actually spend time together
- What We Love Best: Multiple resort pools, hot tubs, pickleball courts and playgrounds for downtime
- Must-Try Recommendation: Exploring trails in Zion National Park tailored to your group’s abilities
- Bucket List Hikes: The 5.4-mile Angels Landing hike with its 1,488-foot elevation gain and famous chains
Give Everyone a Caribbean Vacation in St. Thomas, U.S. Virgin Islands
Property: The Westin St. Thomas Beach Resort & Spa | Address: 5 Estate Bakkeroe, St. Thomas, U.S. Virgin Islands 00801 | Phone: 340-249-0100 | Hours: Open 24/7
U.S. citizens can get a true turquoise-water, white-sand-beach Caribbean vacation in the U.S. Virgin Islands without pulling out a passport. The Westin St. Thomas Beach Resort & Spa offers multiple pools, a beach, kids club, watercraft rentals and a spa. Charter a boat for the day to go snorkeling like we did, explore the island or ferry to St. John for world-class beaches.
- The Magic: Combining a resort vacation with easy island hopping to pristine beaches on St. John
- What We Love Best: Multiple oceanfront pools and watercraft rentals right on site
- Must-Try Recommendation: Taking a catamaran out on the water for a snorkeling excursion
- Relaxation Focus: Grandparents relaxing while grown kids and grandkids get out on the water
Combine a Caribbean Resort With Old San Juan in Puerto Rico
Property: Caribe Hilton | Address: 1 San Geronimo Street, San Juan, Puerto Rico 00901 | Phone: 787-721-0303 | Hours: Open 24/7
Puerto Rico is an easy passport-free Caribbean trip combining beaches, history, food and nature. Caribe Hilton sits on a peninsula near Old San Juan, offering a secluded beach and oceanfront pool complex. Explore historic Spanish forts, hike El Yunque National Forest and save one evening for a 1-hour-15-minute drive to Fajardo to kayak through a bioluminescent lagoon.
- The Magic: Nighttime kayaking through mangrove channels in Laguna Grande to see microscopic organisms illuminate the water
- What We Love Best: A secluded 17-acre beachfront resort sitting right near historic Old San Juan
- Must-Try Recommendation: Wandering Old San Juan’s colorful streets and massive Spanish forts
- Day Trips: Planning a day trip to explore lush trails in El Yunque National Forest
Rent a Beach House Close to Home
Not every multigenerational vacation needs a flight, resort or packed itinerary. Sometimes you just need a big house near the beach and everyone you love under one roof. We’ve done this with our family countless times, and they’ve been some of our best and easiest family trips.
We rent a house, hit the beach when we feel like it and have plenty of space to hang out when we don’t. Friends love doing the same in Florida and the Carolinas. Galveston works for Texas families, while the Jersey Shore is an easy option in the Northeast.
A vacation home gives you a kitchen for easy meals, separate bedrooms for privacy and plenty of space to gather. Best of all, the beach provides the entertainment.
- The Magic: Getting everyone under one roof without needing to entertain each other every minute
- What We Love Best: Easy beach days with no reservations, tickets or complicated schedules
- Must-Try Recommendation: Find a beach destination your family can easily reach and rent a house big enough for everyone
- Family Time: Cooking together, playing games, taking beach walks and having nowhere you absolutely have to be
Try a Colorado Dude Ranch Vacation
Property: C Lazy U Ranch | Address: 3640 Colorado Highway 125, Granby, CO 80446 | Phone: 970-887-3344 | Hours: Open daily
A dude ranch works like a summer camp where everyone gets to go. Lodging, meals and activities are all in one place. At C Lazy U Ranch in Granby, Colorado, the summer children’s program serves ages 3 to 17 with age-divided groups for horseback riding, swimming, fishing and ropes courses. Grandkids get adventures while grown kids and grandparents enjoy true downtime.
- The Magic: A summer camp vibe where grandkids make friends while grown kids get a real vacation too
- What We Love Best: Supervised youth programs dividing kids ages 3 to 17 into age-appropriate adventure groups
- Must-Try Recommendation: Horseback riding through mountain trails and fishing in pristine streams
- Ranch Life: All-inclusive lodging, meals and activities right on property
Frequently Asked Questions
The bigger the family, the earlier I would start. Finding dates that work for grown kids, school schedules and everyone’s vacation time can be harder than choosing the destination. For our family, I like to get the dates on everyone’s calendar first, then worry about the details. Large vacation homes and connecting hotel rooms are also much easier to find when you book early.
Destination fit matters more than age. Younger grandchildren thrive at Disneyland, Hawaii resorts or pool properties, while teenagers get excited about skiing, hiking, horseback riding or snorkeling. Choose destinations offering experiences that genuinely appeal to adults as well.
Every family handles finances differently. Some grandparents cover total lodging while grown children pay for transportation, activities or meals. Talking about money before anyone books avoids awkward conversations and keeps expectations clear for everyone involved.
Combining group space with private bedrooms offers the best experience. Vacation rentals, multi-bedroom suites and connecting rooms provide shared kitchens and living rooms for gathering while preserving private quiet space when family members need personal downtime.
Stop trying to make everyone do everything together. Schedule a few anchor family experiences, then encourage smaller groups to split up. Reconnecting over dinner to share separate daytime stories creates a far more relaxed, enjoyable trip.
SheBuysTravel writers have been where you’re going. We share our ground-truth experience to save you time, money and energy, making your trips easier. Been There. Bought That. Since 2006.
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