10 Maui and Kaanapali Activities

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Full of calming scenes, panoramic vistas, mouthwatering Hawaiian food, and places to explore, Maui just makes life worth living.

Here are 10 of our most cherished Maui memories and recommendations for how to fill your getaway itinerary!

Walking Distance Activities

You won’t get bored at The Whaler on Ka’anapali Beach. From adventures on the water, to lazy afternoons on the beach, to romantic dinners at some of Hawaii’s most enticing oceanfront resorts—you can find a lot of ways to live well without ever getting in the car.

  1. Stroll Whalers Village. Your next-door neighbor, Whalers Village, has a great collection of shops, from designer (Kate Spade and Louis Vuitton) to beachwear (Honolulu Surf Co. and Tommy Bahama). I like Sephora and the Walking Company, and then, afterward, frozen yogurt at Haagen-Dazs. For a full meal, try Hula Grill or Leilani’s on the Beach, both located at the Whalers Village. At Leilani’s, order the Maui Fish Tacos! They’re made with Mahi Mahi and they’re incredible. Rated #1 on the island!
Leilani's at the Whalers Village near the Whaler Penthouse Studio Rental

Leilani’s at the Whalers Village. Credit: Joe Nevill

  1. Go to a luau. A delightful way to spend an evening, and you don’t have to go far. From our experience, Ka’anapali Beach Hotel’s luau is the most authentic—and it’s right next door to The Whaler! Watch hula dancers, learn a little about Hawaiian history, and enjoy a buffet of Hawaiian cuisine outside on the hotel’s lanai.
Luau on Kaanapali Beach

Luau on Kaanapali Beach. Credit: Brian

  1. Have an oceanfront BBQ on The Whaler grounds. Among our favorite Maui memories are the oceanfront cookouts at The Whalers shared BBQ areas. Grab your favorite grill foods at the Safeway in Lahaina, a bottle of wine, and a couple of plastic wine glasses from our collection at the condo (glass is not allowed at the BBQ grills). While you grill and sip wine, take in the stunning sunset from the shaded umbrella table.

Want to stay even closer to your condo? You can’t get much closer than our ocean-view lanai, another spectacular place for a sunset meal!

  1. Spend a day on the beach. This one isn’t exactly a secret. But if you don’t spend a day at Ka’anapali Beach you’re missing out. A beach shack outside The Whaler rents out loungers, covered canopies, and umbrellas so your long, beachy afternoon doesn’t leave you sunburned. Meanwhile, Hawaiian wildlife (like sea turtles, spinner dolphins and sea birds) may show up to say “hi”!
Ka'anapali Beach outside The Whaler Resort

Ka’anapali Beach

If you get bored of lounging, you can try a range of activities like scuba, snorkeling, sailing, surfing, whale watching (seasonally) and more. To arrange these activities, we like to go to Trilogy, located right next door to The Whaler.

  1. Create the most romantic evening of your life. Planning to propose? Celebrating a new marriage…or a 50-year one? You can have a romantic evening of a lifetime right here on Ka’anapali Beach. Start with dinner at one of the 5-star resorts nearby, like Japengo at the Hyatt or the Black Rock Kitchen at the Sherton. Call in advance for reservations. Then hit the beach (or boardwalk) for a twilight stroll as the moon and stars appear.
  1. Go golfing. We have two championship golf courses right across the street: Royal Ka’anapali and the Ka’anapali Kai. They’re so close, in fact, that you can see them from our condo’s lanai! Book your tee times in advance.
View from the penthouse studio rental at the Whaler Resort

Golf course view from the condo’s lanai

Driving Distance Activities

Many of our guests choose to rent a car so they can explore the rugged beauty of Maui beyond Ka’anapali Beach (and easily get to and from the airport). Here are 3 driving destinations to add to your list.

  1. Drive the Road to Hana. An iconic Maui adventure! The Road to Hana is a 64.4-mile journey (each way) with exhilarating curves suspended above the Pacific, cascading waterfalls, and incredible vistas. Along the way, sample Hawaiian cuisine at roadside stands or take short hikes to natural wonders.

Fully experiencing the entire road often takes more than one day, so if you want to come back to the penthouse condo after your drive, leave early in the day and plan to cover a shorter distance. Begin the journey in Lahaina.

Road to Hana, near our penthouse studio rental at the Whaler

The Road to Hana. Credit: Ted

  1. Visit Lahaina. For another, different beach and a whole new set of delicious restaurants, drive just 3 miles to Lahaina. This former whaling village features historic walking tours and lovely shops and dining all up and down Front Street. For lunch, we like Kimo’s, a renowned Lahaina oceanfront restaurant with delicious pupus and seafood specialties.
  1. Hike Haleakala National Park. Get up close at personal with a volcano at Haleakala, Maui’s otherworldly National Park. In our adventurous days, my husband and I rode on horseback to the volcano’s crater, then spent the night in a wilderness cabin. We couldn’t hear a sound. No birds, no animals, no flights overhead, no cars—nothing. It’s just quiet. After supper, we sat out to look up at the sky and it felt like we could touch the stars. It’s an experience I’ll never forget.

For hiking options, check out the hiking guides we provide in the apartment. We’ve hiked all over these mountains, and I’m happy to answer any questions you have! For your safety, be sure to stick to the designated and marked trails.

Haleakala Crater

Haleakala Crater. Credit: lamoix