Pack up the family and dive in to a dreamy Kaanapali Beach vacation with a private condominium rental at Kaanapali Alii. These unique villas provide a whole home vacation well-suited for family and group travel. Rentals include a fully-equipped kitchen and spacious dining room, sizeable living room, large bedrooms with ensuite bathrooms, and a private furnished lanai to enjoy your breakfast outdoors while overlooking an incredible ocean view. Families will also enjoy use of a full size ensuite washer and dryer, along with access to gas barbeque grills to make your own meals poolside.
Kaanapali Alii has all the perks of a traditional resort, like the incredible freshwater swimming pools featuring waterfalls, and daily housekeeping services, yet caters to travelers who prefer a more spacious vacation rental that feels like a home away from home. When booking direct with Kaanapali Alii, there are no resort fees for amenities including free WiFi, beach towels and chairs, and free parking. Didn’t rent a car? Take the free Kaanapali Trolley escorting visitors along the Kaanapali Resort beach strip, to Kaanapali golf courses, and to Whalers Village.
Neighboring Whalers Village is a central hub for food, entertainment, and shopping. Families will love the children’s play area and free movie nights, while those in search of local goods will enjoy perusing retailers like Blue Ginger, Glass Mango Designs, and Tori Richard. This is also my go-to destination for picking up island treats at Honolulu Cookie Company, Island Vintage Coffee, and the ever-popular ABC Stores.
While your stay at Kaanapali Alii is well-suited for home-cooked meals and beachside barbeques, I recommend sampling the incredible flavors at Whalers Village eateries. For a quick bite at lunch, head to Joey’s Kitchen to savor Loco Moco or Huli Huli Chicken. Be sure to try Joey’s Ahi Potstickers for a truly mouthwatering app packed with flavor. For a romantic evening along the beachfront, book a table at Hula Grill during sunset. Set the mood with a refreshing Lilikoi Mojito or a pint of Barefoot Brew—a golden ale with a hint of honey brewed exclusively for Hula Grill. I recommend sharing the lobster, shrimp, and scallop potstickers before ordering pan-seared Hawaiian Snapper or a beautiful ribeye steak from Double R Ranch. Finish off with a Hula Pie easily shared between loved ones. An oceanfront table is perfect for watching the sun set over the waves, while live music entertains with island favorites in the background.
For a flavorful evening out with the family, visit Leilani’s On The Beach and discover their award-winning menu. Start with jumbo crab cakes and a Maui Fresh salad featuring local produce, then dig into the daily catch to savor fresh local fish or try the Maui Onion sirloin for a savory plate. The Keiki Menu provides child-size servings of island tacos, crispy chicken, cheeseburgers, and salads. For a sweet finish, linger over Leilani’s apple banana bread pudding.
The next day, treat your family to the breakfast buffet at Kaanapali Beach Hotel’s Tiki Terrace. You’ll find local flavors abound daily, while Sunday offers a champagne brunch option. Next door, the Grab N Go coffee bar is a great venue for espresso beverages and fresh fruit parfaits. While at Kaanapali Beach Hotel, visit their Hale Hoʻokipa to sign up for cultural activities including hula or ‘ukulele lessons, or to learn about traditional lei making. Their beachfront activity center also offers daily rentals of snorkel gear, body boards, kayaks, and SUP boards. Or, for a real treat, sign up for the Waʻa (Canoe) Paddle Tour for a 90-minute paddle where you’ll also take in a bit of cultural history.
For even more local history, take a free walking tour of nearby Lahaina Town. Stroll under the limbs of a Banyan Tree planted in 1873, trace King Kamehameha III’s footprints to the palace-turned-courthouse, and visit one of Lahaina’s oldest buildings with a tour around The Baldwin Home Museum. Before heading back to Kaanapali, visit the Maui Ocean Center for an immersive experience with the new 3D humpback whale theater. Settle in for a feeding session to watch sharks, rays, and colorful fish interact in a mesmerizing world beneath the surface. And let the kids get up close and personal at tide pools with sea turtles and living coral.
Once you’ve experienced Maui Ocean Center, head back to Kaanapali for a snorkel session at Black Rock in front of Sheraton Maui Resort and Spa. See if you can identify the sea life you’ve just met at the aquarium as they swim around you in this easy-entry snorkel hub. Later, witness the torch lighting and cliff diving ceremony that takes place nightly at Black Rock.
Throughout Kaanapali, you’ll find year-round celebrations of culture and heritage, while annual events like the Hawaii Food and Wine Festival highlight regional chefs and island cuisine. Any time is a great time for a Maui vacation, so for more information and planning tips, visit the Kaanapali Beach Resort website.
Lori A. May is a Seattle-based travel writer.
Photos by Lori A. May and CT Shier.