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Off the Beaten Path Itinerary

Unique Tour of Maui

Looking for things in Maui you haven’t seen before or want to avoid popular spots for a more secluded and unique tour of our island? Take a look at our off the beaten path itinerary to find new adventures to add to your Maui vacation plans!

Day 1

Start off your morning right with a delicious breakfast in your vacation rental!

Then you’re off to the beach, a bit traditional, but you are in Hawaii! If you need a bit more thrills to add to your morning at the beach, you may wander down to Makena and visit Little Beach for its famous cliffs and claim to fame as a nude beach. You’ll definitely enjoy the views on the drive to this part of the island.

For lunch, you’re on the hunt for the Shark Pit, a food truck company that specializes in Asian fusion and Hawaiian dishes.

Ending the day back at the beach might not seem so off the beaten path, but visiting the Traveler’s Choice 2014 beach at Ka`anapali beach at sunset is an experience not to be missed. Every evening, up at Black Rock, you can watch a cliff diver reenact the amazing dive and feat of Maui’s King Kahekili.

Day 2

Today you’re going to experience a part of Hawaii’s culture that isn’t always associated with our tropical islands: horseback riding! In 1838, King Kamehameha II invited vaqueros from California to teach the Hawaiian people to manage cattle and since then we’ve been home to paniolo (Hawaiian cowboys) and you can head into Makawao to visit Piiholo Ranch to see real paniolo in action. This ranch is about an hour away from Kahana Sunset but is home to seven generations of Hawaiian wranglers and cowboys. The guides are extremely knowledgeable about Hawaii’s history and you can experience this part of Maui on a two or three-hour private ride. If riding in a saddle isn’t your definition of a fun morning, they do have zipline tours at the ranch as well!

While in Makawao, visit the Komoda Store & Bakery for their legendary cream puffs or guava filled doughnuts.

Later in the afternoon or evening you’re going to immerse yourself in a Hawaiian tradition and take a hula lesson! The Hawai`i Hula Company offers private lessons and will come to you so you can learn in your vacation condo or if you’re feeling confident you can learn out on the beach. You’ll not only learn basic steps and hand motions, but you’ll also learn about the history of hula and its connection to our culture.

Day 3

Now that you’ve acclimated to the time change on Maui, it’s time to get up in the early hours of the morning to visit Haleakala and watch the sunrise from this impressive vantage point. Known as “house of the sun” you won’t regret your early a.m. wake-up call. After watching the sunrise, you can enjoy the variety of hiking or biking trails in the park. For the super adventurous, there are sunrise bike tours of Haleakala where you’ll take a shuttle up to the top and then bike your way around the park.

We recommended packing some energy bars, fruit, or snacks for a treat after your busy morning at the park.

On your way back to Lahaina from Haleakala National Park, take a detour to Maui Wine for a complimentary tasting. Feel like royalty as you step into the King’s Cottage, originally built in the 1870s for King Kalakua who would visit the region to relax and entertain. Delight on island favorites such as the pineapple wine or method sparkling wines. Complimentary tastings are offered daily from 10 a.m. to 5:30 p.m. or you can take a guided tour of the historic estate at 10:30 a.m., 1:30 and 3:30 p.m.

Tonight, you’re heading to Whalers Village, which is a tourist destination but is a great spot to get a bite to eat and take in some more of Hawaii’s culture with free hula lessons, lei making, coconut husking demonstrations, and more. Or, if you’re visiting us October – April, Whalers Village is a prime location for whale watching as humpback whales migrate to our Hawaiian waters.

Day 4

Today you’re going for a long stroll as you’ll probably want to sleep in after your early wake-up call the morning before. Head out onto the Lahaina Historic Trail and see if you can find all 62 historical markers. It’s truly a walk back through time and gives insight into Hawaii’s rich and culturally influenced past.

After your walk, take a rest by catching a historic train: The Sugar Cane Train! As one of the last railroads in operation on Hawaii, the Sugar Cane Train or the Lahaina Kaanapali & Pacific Railroad is a fun and unique way to see our lush landscape.

Day 5

Surf’s up today, but not for you! You’re off to the Surfing Goat Dairy farm, about an hour away. Not only can you take tours and meet the goats, but you can sample and of course buy some of their delicious cheese. If you could bring back some of the goat cheese truffles, we’d appreciate it!

On your way back, stop at Iao Valley State Park to see the iconic needle. You may bump into other visitors but the trek is worth it as this is the spot of the Battle of Kepaniwai where King Kemehameha I defeated Maui’s army in 1790.

If this night is a Friday for you, you’re off to the Art Night in Lahaina. Each Friday, from 7 to 10 p.m., you can walk along Front Street and visit the art galleries to meet the artists, enjoy music, and perhaps purchase a locally made piece of art to take home with you. Enjoy a relaxing evening at your vacation condo to round out your distinctive Maui adventure.