9 Day Travel Itinerary: Maui by Jeep
- Laura
- Apr 3
- 9 min read
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Maui is a magical place where many different cultures blend, and seem to belong. The Hawaiian island offers visitors a chance to explore a rich Hawaiian history in a modern American setting. On a Maui itinerary, visitors from the US can experience both the excitement of an exotic island and the familiarity of home.
Maui is meant to be enjoyed outdoors. The breathtaking scenery always feels near and accessible. 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. This 9 day Maui travel itinerary is designed to help you capture a bit of the ‘aloha’ spirit.
We hope you find this trip planner the right blend of nature, culture and creature comforts. Our itinerary includes all of the best things to do in Maui. We take you to the Kehekili Highway, Road to Hana, Wailea Beach, Lahaina Town, Haleakala National Park, and more.
MAUI HAWAII WEATHER
Maui Hawaii is the second biggest of the Hawaiian Islands. It has several micro-climates; meaning while it is sunny on the west coast, it may be foggy in the Lao Valley, and snowing on Mt. Haleakala. There are rain forests, a volcano, and the vast Pacific Ocean to influence the weather which averages in the 70' F throughout the year.
BEST TIME TO VISIT MAUI
While temperatures remain fairly steady throughout the year, Maui experiences the most sunny days from April through October. For manageable crowds, lower prices, and pleasant weather the best time to visit Maui is in the shoulder months of April, May, June, September, and October.
MAUI HAWAII HOTELS
We recommend looking at Maui Hawaii hotels on the west coast for easy access to great beaches. There are many beautiful locations to choose from such as Kapalua, Lahaina, or Kihei. Randy and I found the Ka’anapali area to be a nice mix of shopping, restaurants, and lodgings as well as a 4-mile long beach.
Consider these well-reviewed Maui Hawaii Hotels:
GETTING TO MAUI & GETTING AROUND
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, Randy and I recommend tacking on (at least) an extra day so you have a bit of time to decompress. Sites on the island are spread out. A rental car gives you maximum flexibility.
Click here to compare air fares to Maui
Click here to compare car rentals fees in Maui
BEST TOURS IN MAUI HAWAII
Maui is a big island with gorgeous scenery. Even if you rent a car, tours can be a great way to take in the beautiful landscapes and learn about the local culture. In this section we have listed some of the best things to do in Maui. In addition, where appropriate, we have added tours and excursions to the itinerary below.
MAUI 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. Drive to a nearby motel in Kahului or Wailuku.
Day 2: Wailuku Town, Kahekili Highway, and Kapalua Coastal Trail
Start your road trip with a drive 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.
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.
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.
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, then hike the Kapalua Coastal Trail (3.5-mile round trip). Flowers, pine trees, and native plants line the path. Waves crash upon jagged lava rocks. 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.
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. 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.
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.) Or, if you are feeling adventuresome, book a water-based excursion:
In the late afternoon, make your way to the Whalers Village Seaside Mall in Ka’anapali. Enjoy the designer shops, beach side dining, and lush landscaping of the plaza. Onsite, visit the free Whale Center of the Pacific museum.
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.
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. Or, take a sunset dinner cruise:
Day 4: Haleakala (House of the Sun) National Park
Haleakala National Park is an expansive wilderness area encompassing a 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.
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.
There are many ways to experience the park (hiking, horseback riding, helicopter, or zip lining). Randy 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 biked some 23 miles down the side of the volcano.
We cycled downhill past pineapple fields, pastures, and views that seem to go on forever. As we coasted along there were periods of fog, sun, and rain. It was a bit of pedaling and phenomenal, exhilarating fun. Highly recommended!
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. There is no food, drink or gas sold in the park so stock up before entering. Here are two Haleakala tours to choose from:
Day 5: Beach Day and the Feast of Lele
Beach day. Enjoy!
Tonight, enjoy a traditional luau. A luau is a celebration feast that often includes Hawaiian music, dress, cultural demonstrations, and food. Expect menu items like kalua pig, poi (mashed taro root), and salmon dishes. Here are a few well-established Maui luaus.
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. Many trips to the Molokini Crater leave from this destination.
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. As the boat skimmed across the water, dolphins swam and played beside us. Great fun.
Check out these snorkeling trips:
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, stop to stroll the streets of this interesting village which is fast recovering from a devastating fire that occurred in August of 2023.
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 spectacular views of rolling greens, the mountains, and the sea. Tables are arranged on tiers so everyone has a view. (Make a reservation.)
Day 7: The Road to Hana
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.
If you don't want to miss any of the scenery, try one of these tours:
If you decide to drive, get an early start. Have breakfast in Paia at Charlie’s Restaurant and Saloon. The diner has been serving up meals to surfers and tradespeople since 1969. The atmosphere is friendly, and we got a kick out of having breakfast in the front dining room while a contingent of locals enjoyed beers in the back.
Up the road, past mile marker 9, park at the Hookipa Beach Park. Sit on the grassy banking, and watch the surf boarders vying for the best waves. The park is where some of the world’s best wind surfers come to practice their sport.
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.
Randy 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. Along the route you will likely see random hippies, handymen, and farmers selling their wares from the backs of their pickups.
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) and a lighthouse.
Day 8: Beach Day – Wailea Beach
Your last day in Maui has to be a beach day. Enjoy your resort. Or, take a drive to Wailea (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.
Walk 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.
Day 9: Head home.
Aloha! Laura and Randy
For more ideas on traveling to Maui read our blog posts on:
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