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9 Day Travel Itinerary: Maui by Jeep


Hula Dancers in Lahaina. Maui, Hawaii.
Hula Dancers in Lahaina. Maui, Hawaii.

Maui is a magical place where diverse cultures blend as if they all belonged. The island offers visitors from the main land a chance to explore a rich Hawaiian history in a modern American setting. Visitors experience both the excitement of an exotic island, and the familiarity of home.


This 9 day Working Joe Travel Itinerary is designed to help you capture a bit of the ‘aloha’ spirit at this unique vacation destination. We hope you find this trip planner the right blend of nature, culture and creature comforts. HipaHipa! (Cheers!)


On the island, Hawaii’s second biggest, there are several micro-climates. While it is sunny on the west coast, it may be foggy in the Iao Valley, and snowing on Mt. Haleakala. There are rain forests, a 10,000-foot volcano, and the vast Pacific Ocean to influence the weather.


Maui is meant to be enjoyed outdoors. The breathtaking scenery always feels near and accessible. On the island, contemporary and traditional language, food, and customs mingle. In the air, there is a warm kinetic energy. Perhaps the nicest part of visiting Maui is getting to experience its peaceful, laid back personality.

An autumn day in Maui, Hawaii
An autumn day in Maui, Hawaii
Maui Travel Itinerary At-A-Glance
Terraced fields in Maui, Hawaii.
Terraced fields in Maui, Hawaii.

For more ideas on traveling to Maui read our blog posts on:

Maui Travel Tip: Getting to Hawaii from most of the continental United States involves a full day of travel and time zone changes. If you are planning to burrow in and enjoy the beach, a 7-day vacation is plenty. If you plan to explore the island, Joe and I recommend tacking on (at least) an extra day so you have a bit of time to relax. Also, sites on the island are spread out. A rental car gives you maximum flexibility (we rented a Jeep).


Maui Lodging Tip: We recommend booking a room on the west coast for easy access to great beaches. There are many beautiful locations to choose from such as Kapalua, Lahaina, or Kihei. Joe and I liked the Ka’anapali area. It had a nice mix of budget and luxury shopping, restaurants, and lodgings as well as a 4-mile long beach with a paved walkway. There is also a shuttle between Kaapanali and Lahaina so you can travel up and down the coast without ever getting in your vehicle.

The Maui Coastline, Hawaii
The Maui Coastline, Hawaii

TRAVEL ITINERARY

Day 1: Travel Day


After a long day of travel – touch down! Pick up your rental car. It is wise to opt for a four-wheel drive if you plan to explore roads off the beaten path. (Our bright red Jeep was fun!) Drive to a nearby motel in Kahului or Wailuku. We stayed at the locally owned Maui Seaside Hotel. It was clean, with comfy beds, and a nice view of Kahului Bay. Before turning in, we sat outside looking through palm trees at the bay. In the morning, we woke to a massive cruise ship that seemed to be anchored beside us. It was a splendid surprise!

Maui Seaside Hotel, Maui, Hawaii
Maui Seaside Hotel, Maui, Hawaii

Day 2: Wailuku Town, Kahekii Highway, and Kapalua Coastal Trail


Have a hearty breakfast, and set out for a road trip through the old plantation town of Wailuku. The streets are full of wooden storefronts and coffee shops where you will see locals hurrying about. The historical sites here are on a small scale, but they are authentic and lovingly maintained.


Before leaving town, stock up on drinks and snacks. There are few places to stop as you journey around the West Maui Forest and Mount Pu’u Kukui. The 40-mile drive will start on Hwy. 3400, which turns into Hwy. 340 (Kahekili Highway), and then Hwy. 30 after the Nakalele Blowhole.

Nakalele Blowhole, Maui, Hawaii
Nakalele Blowhole, Maui, Hawaii

The curvy, cliff-hugging road (an ancient Hawaiian footpath) will introduce you to Maui’s rugged, undeveloped northern tip. You will pass timber-lands, ranches, and villages. There will be occasional farm stands and artist galleries, but mostly there will just be you and the incredible coastline.


Be forewarned, long sections of the ‘highway’ turn into a one lane road with overgrown vegetation and occasional pull-offs so vehicles can pass each other. There are few guardrails, poor cell service, and when it rains there are frequent rock slides. Nevertheless, if you are a confident driver and have a reliable vehicle, this untamed drive could be a highlight of your vacation.

View of the one lane Kahekili Highway, Maui
View of the one lane Kahekili Highway, Maui

About 35 minutes into the trip, look for the Kaukini Gallery. Some of Hawaii’s best artists sell paintings and handicrafts here. The property has great views of the Kahakuloa Valley. It is a good place to stretch your legs, and take a bathroom break.


A bit farther down the road, you will come to a series of scenic lookouts and nature points that are fun to explore. As you pass Honolua, begin looking for signs for Kapalua (and the Ritz Carlton Hotel).


Once there, park in the lot by Kapaulua Bay. Grab your camera and begin hiking along the Kapalua Coastal Trail (3.5-mile round trip). Flowers, pine trees, and native plants line the path. Waves crash upon jagged lava rocks that are just a short distance away. In the sun, the water turns an incredible sapphire blue. When you get to the beautiful DJ Fleming Beach, turn around and retrace your steps.

Livestock Grazing | Maui Hawaii
Livestock Grazing | Maui Hawaii

On the return trip, if it after 3 pm, stop at Merriman’s Kapulua Restaurant. There are views of the surf and swaying palms on three sides of the eatery. The menu is American, the food is fantastic, and this might be the most romantic late afternoon lunch you will ever enjoy. (Make a reservation.)


Navigate back to Highway 30 and head to your resort. Finish the day with drinks by the pool. Note: For more information on this drive see our post on the Kahekili Highway.

Jagged Lava Coast | Maui Hawaii
Jagged Lava Coast | Maui Hawaii

Day 3: Beach Day, Ka’anapali, and Whalers Village


Spend the day at the pool or beach closest to your resort. (If you are not close to the beach, check out the 4-mile golden sand Ka’anapali Beach.)

Fishing boats in Maui, Hawaii
Fishing boats in Maui, Hawaii

In the late afternoon, make your way to the Whalers Village Seaside Mall in Ka’anapali. Designer shops, beach side dining, and lush landscaping are hallmarks of the plaza.


In addition to great shopping, there is a free museum, The Whale Center of the Pacific. Also, look for the Martin and MacArthur store that features fine jewelry, art, and woodworking made in Hawaii.


At 6pm every day there is a free Hula show next door to Whalers Village at the Ka’anapali Beach Hotel (snack and drinks are available for a fee). The outdoor show is sweet and endearing.


Hula Dancing, Maui, Hawaii
Hula Dancing, Maui, Hawaii

At sunset, take a stroll along the 3-mile Boardwalk that runs the length of Ka’anapali Beach. The lovely path will take you past surf side restaurants, exquisitely landscaped resorts, and evening surfers. Dine at one of the many beach side restaurants or pubs along the path.


Day 4: Haleakala (House of the Sun) National Park


Haleakala National Park is an expansive wilderness area and biological reserve encompassing a 10,023’ dormant volcano and 5 climate zones (ranging from alpine to rain forest). A steep road leads to the summit. One portion of the drive contains 33 switchbacks in rapid succession.

NASA Earth Observatory | Haleakala
NASA Earth Observatory | Haleakala

The weather at Haleakala’s peak is unpredictable and usually about 30’ colder than at the beaches. A drive to the mountaintop involves slipping into and out of the clouds. The summit’s ‘crater’ is clearest at sunrise when there is often a crowd to witness the sunrise.

Summit 'crater' of Haleakala, Maui, Hawaii
Summit 'crater' of Haleakala, Maui, Hawaii
Biking in Haleakala National Park, Maui, Hawaii
Biking in Haleakala National Park, Maui, Hawaii

There are many ways to experience the park (hiking, horseback riding, helicopter, or zip lining). Joe and I choose a morning Bike Tour. We were bussed in a small group to the summit where we had time at the crater and Visitor Center. We then went biking some 23 miles down the side of the volcano.


We cycled past pineapple fields, pastures, and views that seem to go on forever. As we coasted along there were periods of fog, sun, and rain. There was a fair amount traffic, but we never felt unsafe or out of control. It was just a bit of pedaling and phenomenal, exhilarating fun. Highly recommended!

Biking the slopes of Haleakala. Maui, Hawaii
Biking the slopes of Haleakala. Maui, Hawaii

TRAVEL TIP: The trip to the park from the Ka’anapali region is about 3-hours round trip. The drive, plus time spent in the park makes for a long day, so it is best not to plan an evening activity. Layer clothing and wear closed toe shoes. There is no food, drink or gas sold in the park so stock up before entering.


Day 5: Beach Day and the Feast of Lele


Beach day. Enjoy!


Tonight, ready for an evening of intimacy and romance. Drive to Lahaina for the Feast of Lele (make reservations). This 3-hour beach luau will include dinner and high quality, culturally respectful entertainment.


After being greeted with a lei, you will have time to view local artisans demonstrating their crafts. Before dinner, each party is seated at a private table. The performance takes place on a stage that is set against the backdrop of the ocean. The show, featuring Hawaiian music and dance, begins at sunset. The overall effect of the songs, costumes, fire, sand and sea breezes is spectacular! Highly recommended.

Feast of Lele Dancers | Maui Hawaii
Feast of Lele Dancers | Maui Hawaii

Day 6: Snorkeling, Lahaina, and Dinner at the Plantation House

Begin the day with a drive to Maalaea Harbor. The harbor serve as coast guard headquarters, and a base for water adventures. There are many to choose from – jet skis, parasailing, scuba trips, and whale watching. Joe and I took a snorkeling trip to the Molokini Crater.

The crater is home to some of Maui’s best snorkeling. We choose a tour that first dropped anchor at the Molokini Crater (known for having abundant species of tropical fish), with a second snorkel stop at a nearby turtle habitat. Our vessel was a catamaran that held 20-30 people. As the boat skimmed across the water, dolphins swam and played beside us. At one point, the captain let me take the wheel of the boat. Great fun.

Sailing, Maui Hawaii
Sailing, Maui Hawaii

After your water adventure, explore the town of Maalaea, and then meander back up the coast checking out the beaches along the way. When you get to the Lahaina Town and Harbor, stop to stroll the streets of this interesting village.


Storefronts with a small town, tropical vibe line the commercial district. The businesses here once catered to whalers, missionaries, and Hawaiian royalty. Today, tee shirt shops are interspersed with historical homes, ships, and other landmarks. You can easily spend an afternoon (or day!) here.

Lahaina, Maui, Hawaii
Lahaina, Maui, Hawaii

Tonight, romance is once again on the menu. Make a sunset reservation to have dinner at Kapalua’s Plantation House Restaurant. Sitting high on a hill, the dining room has open sides. Spectacular landscapes of rolling greens, the mountains, and the sea surround. Tables are arranged on tiers so everyone has a view. With the elegant décor, soft lighting and open-air, you cannot help but feel decadently relaxed.


Day 7: The Road to Hana

Eucalyptus Trees, Maui Hawaii
Eucalyptus Trees, Maui Hawaii

We are off to explore Maui’s northeastern coast on the Road to Hana. The windy 50-mile coastal drive (Hwy 36) snakes along the less developed side of the island. The (roughly) 3-hour road trip from Kahului to Hana begins by taking you through a series of small Hawaiian towns.


Get an early start. Motor about 10-miles past the Kahului Airport to the community of Paia. Here you can gas up, and then fill up at Charlie’s Restaurant and Saloon. The diner has been serving up meals to surfers and tradespeople since 1969. Joe and I found the atmosphere friendly, and the food plentiful. Plus, we got a kick out of having breakfast in the front dining room while a healthy contingent of locals enjoyed beers in the backroom.

Surfing | Maui Hawaii
Surfing | Maui Hawaii

Our next stop is just past mile marker 9 at the Hookipa Beach Park. Park in the lot, and then sit on the grassy banking overlooking the surf. In the water below, surf boarders will be vying for the best waves. The park is where some of the world’s best wind surfers come to practice their sport. If you are lucky, you may see a few dancing across the sea. Joe and I really enjoyed watching these talented athletes.


Over the next 40-miles, communities along the route will become smaller and fewer. You will pass magnificent coastline, terraced crops, and patches of bamboo, bananas and eucalyptus. There will be a stunning array of scenic outlooks, hiking trails, and waterfalls to explore.

Pasture Land, The Road to Hana
Pasture Land, The Road to Hana

Joe and I recommend getting a good map and marking off a few must-see stops. Then be spontaneous. Pause at the places that look most interesting. Don’t be surprised if at the entrance to trail heads you see random hippies, handymen, and farmers selling their wares from the backs of their pickups. This is an earthy, unusual area.

Bamboo & Buddhist Flags | Maui Hawaii
Bamboo & Buddhist Flags | Maui Hawaii

You have reached Hana when you come upon the Hana Ranch Center, a small commercial zone. There is a pier, park, and bay in town. Check out the Hasegawa General Store for provisions and souvenirs. From this area, you can travel on to the nearby beaches (black, red, and grey sand), a lighthouse, nature tours, horseback riding, or a host of other activities.

Hours later on the ride home, just as you pass Paia, look for Mama’s Fish House Restaurant. This colorful, fun, beachy eatery has been serving up fresh seafood to happy customers for many years. For more information on this drive check out our post on the Road to Hana.


Day 8: Beach Day – Wailea Beach


Your last day in Maui has to be a beach day. Enjoy the sun and water around your resort. Or, if you still have any gas in the tank, explore the southern tip of Maui – the only location we have not yet dipped into.


Wailea is about 30-miles south of Ka’apanali. It is a lovely resort town on the leeward side of the island. If you go, leave early so you can find public parking. Look for the lot between the Grand Wailea and Four Seasons hotels.

Maui's jagged lava coastline.
Maui's jagged lava coastline.

Get the lay of the land with a jaunt along the Coastal Nature Trail (3-mile round trip). This beautifully landscaped path weaves along in front of luxury resorts. You will pass magnificent ocean vistas, black lava points, and blossoming native species.

Later, stake out a piece of the crescent shaped Wailea Beach. The sand is golden. The water is clear and gentle. You can bring your own beach gear or pay a resort fee at one of the big hotels and have access to their chairs, restaurants, and other amenities.


On the way home, stop in Kihei at Buzz’s Wharf for a last supper in Maui. Inside or out, there are terrific views and the American style menu has an Hawaiian flair. Overlooking a marina, it is a great place to chill a while before returning to your hotel to pack.

A marina in Maui, Hawaii
A marina in Maui, Hawaii

Day 9: Head home. Aloha! Laura and Randy

For more ideas on traveling to Maui read our blog posts on:

Feast of Lele dancers, Maui, Hawaii.
Feast of Lele dancers, Maui, Hawaii.


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