The Ultimate Maui Itinerary for First Time Visitors

black rock beach at Wainapanapa State Park in Hana

About this Maui Itinerary

Maui is an extraordinary place.  It has a unique combination of adventure and relaxation. In this Maui itinerary, you will have opportunities for outdoor adventures as well as pure, do nothing relaxation! Snorkel, surf, watch the sunrise at 10,000 feet elevation, devour macadamia nut pancakes by the plate full and test your nerves on the road to Hana.  I have included all this and more.

This Maui itinerary is tailored to those staying in West Maui, but if you decide to stay in South Maui, plan extra travel time for the activities listed on the west side. Also, I like to stay in a condo when I visit, as it allows me to save some money on food and gives me the feeling that I’m at my home away from homes. However, if you prefer a resort where you can get room service, this itinerary will work for you as well.

This Maui itinerary is designed to be a self-driving guide. So I make the assumption you will have a rental car.  Yes, Maui has a bus system, and yes you can take tours, but I feel this island is best seen with your own vehicle.  It gives you more flexibility and allows for spontaneity.

When to Visit: Anytime. You can often get discounted airfare from late March to early June and also from September to November. December thru May is whale season and if you want to visit during the winter book around 6 months in advance as this is a popular time for travelers.

Getting Around: Car rental makes the most sense in Maui.

Weather: Nice year round.  November-March tends to be the rainiest.

Maui Itinerary Highlights: Road to Hana, Haleakala National Park, Ka’anapali Beach, Kapalua Bay, and Coastal Trail, Molokini Snorkel Tour, Try Hawaiian Shave Ice, Warren & Annabelle’s, Hawaiian Luau

Length of Stay Recommended: 7-14 days

How to use this map: Click on the icons to see the address and get directions using Google Maps, you can also click the star next to Maui Itinerary to add this to your own Google Maps. And the icon to the left of Maui Itinerary will show you a list of all the regions and locations I have saved for each.

Day of Arrival:

You will fly into Kahului Airport, which is only a 5-minute drive to Costco & Wal-Mart. Depending on when your flight lands, I recommend taking time right after you get your rental car, to head to Costco and Wal-Mart to shop for your stay. If you’re staying at a condo, this is a great way to save money on your trip.  Buy stuff to BBQ, cases of water, fresh fruit, salads, pb&j sandwiches, etc.

It is much cheaper to purchase your stuff here, rather than closer to the resorts.  If you are a member of Costco, make sure to stop off at their bakery and pick up a pineapple coconut loaf with macadamia nuts. This paired with a cup of Hawaiian coffee while sitting on the lanai is the perfect way to start a day!

Tip: Make sure you purchase reef safe sunscreen. In 2021, Hawaii will implement a ban on the sale of sunscreen containing the coral-harming chemicals oxybenzone and octinoxate.

Day 2: Haleakala National Park

On your first full day, you will most likely wake up early. So why not be adventurous today and head to Haleakala to watch the sunrise. You must have a reservation to enter the park between the hours of 3am-7am. It costs $1.00, and you can reserve 2 months in advance which I highly recommend you do! Make sure to pack warm clothes & bring a blanket; it gets surprisingly cold up there!

Sunrise at Haleakala has all the details on how to get there, what to pack and what you need to know for an unforgettable day trip to Haleakala.

Take time to enjoy Maui’s Upcountry before heading back to your resort or condo. I have marked a few places you might want to stop on the map. Hali’imaile General Store, Maui Pineapple Tours, Piiholo Ranch Zipline are just a few of the possibilities. Upcountry Maui is full of wonderful options and is worth staying a night or two on a future trip to Maui.

Tip: If you can’t make it to the sunrise, sunsets here are spectacular too, so enjoy your day exploring Upcountry Maui, do a day hike in Haleakala’s crater and then enjoy a gorgeous sunset and star gazing afterward.

Sunrise at Haleakala National Park Maui

A breathtaking sunrise captured over a sea of clouds.

Tip: Try to snorkel first thing in the morning, prior to 11 am for the best snorkeling conditions.  The trade winds tend to kick up in the afternoon and visibility is reduced.

Day 3: Kapalua Beach & Kapalua Coastal Trail

After breakfast head over to Kapalua Beach for some spectacular snorkeling. Get here early as the parking lot fills up quick!  I have seen turtles, eels, and all sorts of colorful fish here.  It is one of my favorite snorkel beaches that I return to multiple times a visit.  Plus it’s a beautiful beach! They also rent paddleboards, kayaks, snorkel gear and beach umbrellas from a hut on the right side of the beach.

After you’ve had your fun at the beach, consider walking the Kapalua Coastal Trail.  One of the highlights is the Dragon’s Tooth area connected to the trail.  The Kapalua Coastal Trail trail is about 2 miles in length and stretches from Kapalua Beach to  D.T. Fleming Park. It does get a little rocky in parts, so you may want to wear strap-on sandals or tennis shoes versus flip flops.

Tonight treat yourself to a Hawaiian Luau. I recommend Old Lahaina Luau for an authentic luau experience. If you want to see fire dancers,  Legends of Kāʻanapali Lūʻau is another good option. If you’re staying in South Maui consider Te Au Moana.

Day 4: Road to Hana

Give yourself a break from the sun by getting up early and driving to Hana.  No Maui itinerary would be complete without including the road to Hana. The drive is an adventure in itself. It has 620 curves in the short 52 miles!  You will see gorgeous waterfalls, hike thru dark lava caves, walk across black sand beaches and so much more! Plan the whole day for your drive to Hana.  Get up early to beat the crowds and tour buses. Read our Road to Hana Guide to learn more about how to plan for this incredible day trip while in Maui.

Tip: To see the Seven Sacred Pools at Ohe’o before the crowds arrive, drive all the way here first, then see all the sights in reverse order back down.  Better yet, camp at Wainapanapa State Park (reservations required) or snag a first come first serve site at Kipahulu Campground.

Maui Sea Turtle eating on rocks

Honu is what the Hawaiians call these beautiful sea turtles.

Day 5: Ka’anapali Beach

After yesterday’s drive to Hana, you will want a relaxing day at the beach.  Pack up your sunscreen, water and beach gear and get ready for a day at Ka’anapali Beach.  This beautiful sandy beach stretches for almost a mile.  It is also where the famous Black Rock is at.  Get an early start and snag a free parking spot if you can. There are a few public parking areas scattered along the parkway. Look for beach access signs near parking areas. Otherwise, you can park in the parking garage for Whalers Village, where you can get a 3-hour validation if you purchase something at one of the stores.

There is excellent snorkeling at Black Rock when the conditions are calm. Just be careful as this area can also get some massive waves and currents near the rock. Watch the adventurous people who make the climb up Black Rock to jump off. Be careful if you are snorkeling and keep an eye on those jumping to make sure you don’t get in their way. I have seen eels, shark, turtles, octopus, and lots of fish all around Black Rock.  Even if the snorkeling isn’t great during your visit, it is still a spectacular beach for swimming and sunbathing.

When you get hungry or would like to do some shopping, head down the beach away from Black Rock and go to Whalers Village, there are lots of places to eat and shop. Additionally, there is the Whalers Village Museum worth taking a peek at.

Maui Sunset

One thing not to be missed is enjoying the beautiful sunsets in Maui.

Day 6: Molokini & Kihei

You have a lot of tour options when planning a trip to Molokini.  I recommend Kai Kanani Sailing; they are a smaller boat with a fantastic crew!  I loved my trip to Molokini with them. Other options would be Pride of Maui Molokini and Turtle Town tour, or if you want a more all-inclusive option, Ali Nui Maui includes transportation with their packages.

Most tours leave from South Maui, so if you are staying in West Maui, make sure to consider how long it will take you to get there when choosing your tour time.  Grab some breakfast at Kihei Caffe and then head to Kama’ole Beach II or III to enjoy more snorkeling and beach time. When you’ve had your fill of the beach, get some gelato or shave ice and enjoy all that South Maui has to offer.

Day 7: Napili Bay

Eat breakfast at The Gazebo. You must try the macadamia pineapple pancakes and fried rice!  Oh and have the coconut syrup on your pancakes.  Yum! Get there early, before it opens if possible, and be prepared for a line.  The line moves fast, and if you’re lucky, you’ll get a seat with a view overlooking the ocean.  After breakfast, take a little time to walk along the water and explore the tidal pools while your food settles.

Then head off to Napili Bay to find a good spot on the beach.  This is the perfect beach to do some body surfing, but please exercise caution as these waves get huge! Oh and make sure you put your beach bag as high up as possible, or it will get wet!

Tonight, head to Warren & Annabelle’s to be entertained with comedy & magic.  You’ve got to trust me on this one, I have gone to this show two different times, and each time it was different, and both times I thoroughly enjoyed myself.  It is a great way to spend an evening! Make sure to book ahead of time.

Day 8: Day of Relaxation

Today is a good day for you to experience some of that “do nothing” relaxation I mentioned before.  Grab your favorite book, sunglasses & sunscreen, and find the nearest beach umbrella and chair.  And if napping in the sun isn’t relaxing enough, why not get a relaxing massage at a local spa.

Tip: Always carry extra water with you. You can freeze water bottles the night before at your condo and then you will have cold water in the car as it melts throughout the day.

Day 9: Historic Lahaina

Surf’s up!  Today why not try one of the favorite pastimes for locals and learn to surf! It is easier than you think.  I recommend Royal Hawaiian Surf Academy located right in Lahaina. You will walk to the harbor where they will teach you to surf.  Or if you prefer a smaller group size away from the crowds, you can try Maui Surfer Girls. They offer small group size lessons at Ukumehame Beach Park.

After your surf lesson, grab some lunch before starting this self-guided walking tour of historic Lahaina. When you finish the walking tour, head up Front Street and cool off with gelato at Ono Gelato and Espresso Bar. They have a couple of tables in the back of the store with views over the water. If gelato isn’t your thing, then head to Ululani’s Hawaiian Shave Ice and enjoy more of this delicious treat!

Banyan Trees in Lahaina, Maui

These Banyan trees in downtown Lahaina are incredible to see!

Day 10: Honolua Bay, Nakalele Blowhole & Olivine Pools

Drive to Honolua Bay for an amazing snorkel spot in a marine life conservation area.  Make sure you’ve got all your essentials packed in a beach bag, including good walking shoes. You will have a short hike through a “jungle” before reaching the rocky beach. Snorkeling is best on the right side of this protected bay.  You have to swim about 600 feet offshore to get to the reefs, so I recommend you wear a life vest if you have any concerns at all about swimming that far. Plus sometimes it is very shallow over the vast reefs, so I prefer a life vest as it helps me float over the reefs and avoid touching them. There are portable toilets at the beginning of the trailhead, but no other facilities at the beach.

After you finish snorkeling, grab some shave ice or a fresh coconut at the Coconut Caboose you passed right before the parking lot to Honolua Bay. Then continue up the road towards the Nakalele Blowhole & the Olivine Pools.  You want good shoes for getting to the Olivine Pools and the Nakalele Blowhole. It is a very steep and rocky climb. Please use caution when visiting here! If it is windy, or rainy or there are huge swells, don’t risk your life! People have died here after being swept away by large waves.  So don’t put yourself close to the edge or anywhere this could happen.  It isn’t worth it. These are beautiful places to visit,  but caution and safety have to take priority over everything else.

If you’re still feeling adventurous, you can continue up the road past the Olivine Pools and explore the historic town of Kahakuloa. Just know that this stretch of road will give the road to Hana a run for its money with some of its narrow curves and sheer drop-offs. But if you do make the drive, make sure to try the local banana bread and shave ice!

Day 11: Olowalu

Book a kayak tour and explore the reef at Olowalu, mile marker 14.  Another excellent option for this fantastic reef system is to rent a stand-up paddleboard; you can paddle out to the reef and then snorkel off your board whenever you wish! Afterward, get some of the best pie in Maui at Leoda’s Kitchen & Pie Shop. I highly recommend the banana cream pie and coconut cream pie.  Honestly, I got the banana cream pie by mistake and was blown away by how good it was! Drive towards Kahului and visit the Maui Ocean Center to learn more about all the marine life you have been snorkeling with for the past week.

Olowalu Paddleboarders

The view from my stand up paddleboard.

Day 12: Relax

I think by now it’s time for another do nothing day!  So grab that book you’re reading and find a cozy spot to curl up.  Perhaps today is a good day to spend shopping for souvenirs or eating your fill of Maui Gold pineapples and fresh coconut. A great spot to get fresh coconut is at a store called the Farmer’s Market; they will cut the top off for you so you can drink its refreshing coconut water. Then scrape out the meat back at your condo and let it dry out a little before enjoying your fresh coconut. And if you’re hungry for lunch, just down the street from the Farmer’s Market, you’ll find delicious fish tacos at The Fish Market. If you’re looking for something else to do, you might consider a glass blowing class and create a unique souvenir.

Day 13: Customize Your Day

Today is your day to decide what you want to do. This Maui Itinerary is packed with lots of snorkeling and beach activities. Perhaps you’d like to do some more relaxing or better yet, more shopping? Or if you’re like me and you can’t get enough of the ocean, why not rent a SUP for the day. Take the ferry to the island of Lanai or book a dolphin snorkel cruise to Lanai or sunset dinner cruise with the Pacific Whale Foundation. Perhaps you need a little more adventure, get some spectacular views over Maui as you’re flying down a zip line! You decide!  This is your last full day in Maui, make the memories you want to make.

rainbow on Kapalua Coastal Trail

Catching a glimpse of a rainbow along the Kapalua Coastal Trail.

Day 14: Day of Departure

Sleep in and then have macadamia pancakes one last time before you have to check out. If you have a late flight check out these 7 things to do in Kahului near the airport.  Make the most of your last day in Maui!

Customize this Maui Itinerary

You can customize this itinerary to fit a vacation of 7, 10, or even 14 days.  Feel free to change days around as suits your needs and tailor the activities to your interests.  This Maui Itinerary covers the “must-see” highlights of Maui.  However, there is so much more to see and do, you can’t do it all in one trip, and you wouldn’t want to try.  Leave that for your return trip. Because if there’s one thing I’ve learned about Maui, it’s that you’ll miss it before your plane leaves the ground.

Final Thoughts

Hawaii is made up of beautiful islands with a unique culture and history. Make sure to take time to learn about the Hawaiians and their rich heritage.  Be respectful of this beautiful area and do your best to preserve it for future generations.  And if you want to learn ways you can do even more while on your vacation to Maui here are some great volunteer opportunities.

Make sure to check out our Road to Hana guide and Sunrise at Haleakala to help you plan your trip to Maui.

Mahalo & Aloha!

2 Comments

  • Rachel at Reply

    Wow!! What an incredible blog!! May be useful for my Hawaii trip.

    • Charity at Reply

      I’m glad you enjoyed it. Make sure to check out the other articles in this series for your trip planning. Maui is a beautiful place, that has something for everyone. I am sure you will love it!

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