Best Multi-Gen Travel Destinations: Maui

Maui is often called a lover’s paradise. While this Hawaiian island has a decidedly romantic vibe, it’s far more than just a place for couples.

Excitement, adventure and a well-deserved change of pace (think: island time) awaits, making Maui an ideal destination for travelers of all ages, all of which makes Maui a fantastic destination if you’re considering a multigenerational trip.

Vacations that include at least three generations and extended family are trending, and they’re a great way for family members of every age to catch up and create unforgettable memories.

Families planning a multigenerational trip have the opportunity to add a stay at Maui Bay Villas by Hilton Grand Vacations into the mix. Slated to open in September 2021, Maui Bay Villas is a stunning beachfront timeshare resort situated on Maalaea Bay. Enjoy easy access to the beach and the option to book multi-bedroom condo-like suites, complete with full kitchens.

After securing your suite at this luxurious new property, you’ll want to map out your “must-dos.” Here are our top picks for every generation on the journey.

Baby Boomers

Baby Boomers (those born between 1946 and 1964) looking for the ultimate scenic tour of Maui should consider driving the Road to Hana. This 64-mile highway winds around the eastern perimeter of Maui. Along the way, you’ll pass cascading waterfalls, national and state parks, expansive vistas, charming towns and a whole lot more. Check out the top Road to Hana sights to make the most of your time.

If you’ve got a golfer in your group, Maui’s 14 world-renowned golf courses, many of which regularly host professional tournaments, will be a plus. One standout course is the Arnold Palmer-designed Kapalua Bay Course.

Another is The King Kamehameha Golf Club that’s home to a clubhouse designed by Frank Lloyd Wright. Warning: You might find it hard to focus on your game with views that include lava flows and endless ocean expanses.

History buffs in your crew will appreciate a visit to Alexander & Baldwin Sugar Museum. Located next to Hawaii’s largest working sugar factory, the museum unpacks the critical role sugar played in Maui’s early years.

Gen X and Millennials

Each one of Maui’s world-famous beaches has its unique flavor to entice the 30-to-50 somethings in your group. Don’t worry if you’d rather not drive. As an Owner or Guest at Maui Bay Villas, you’re within walking distance of a private beach. If freshwater is more your style, this beachfront resort is home to a super pool with waterslides, a kids’ play area and a grill area.

Travelers up for an adventure can consider a visit to Ka’anapali Beach, which is well worth the drive. This perennially popular spot along Maui’s northwest shore beckons visitors with white sand beaches, crystal clear waters and a busy boardwalk.

If shopping is your jam, check out nearby Whalers Village. This open-air, beachside mall has more than 90 stores and restaurants along with free events like hula shows and lei-making demos.

Around sunset, head over to Black Rock on Ka’anapali’s north shore to watch the daily cliff diving ceremony. Living history actors gather with torches each evening to recreate the dive made by a traditional Hawaiian king.

Another way to get your blood pumping is with a hike along the Kapalua Coastal Trail. This 2.5-mile trail takes you past dramatic shorelines, beaches, lava fields and more. It’s an easy hike for all skill levels.

After all that activity, cap off your day with a cold one at the Maui Brewing Company. The award-winning brewer offers hyper-local craft beers like Pineapple Mana Wheat and Coconut Hiwa Porter. Sample them at a beer tasting or take a 45-minute guided brewery tour at their Kihei location. Make sure to book your tour ahead of time.

Another option is to enjoy an evening snack and nightcap at Maui Bay Villas. Choose between the indoor dining area or take your eats and libations outdoors to enjoy seating by the pool.

Generations Z and Alpha

A natural marvel sure to captivate the littlest travelers is Nakalele Blowhole in eastern Maui. However, the crazy explosion of water that bursts through this hole in the ocean shelf will have travelers of all ages watching in awe. You’ll need to follow a short trail to see it, so wear good shoes.

If your kids have energy to burn, consider a visit to Haleakala National Park. The 30,000-acre park is home to Hawaii’s highest peak, five climate zones, and rare plants and animals. Two popular areas are the Summit Area and the Kipahulu Area. While Summit is rocky and volcanic, Kipahulu is full of lush greenery and waterfalls. You can see all the incredible scenery on foot, by car or a mix of both.

For something super relaxing, head over to Napili Beach on Maui’s northwest shore, where outer reefs keep big swells out, making it a great place for families to snorkel, paddleboard and swim. In tune with all Maui’s beaches, Napili personifies tropical paradise and beams with white sand beaches and pristine blue water.