The Perfect 5 Day Maui Itinerary for First-Time Visitors
Maui is one of those rare destinations that feels like a dream the moment you arrive. With golden beaches, lush rainforests, and volcanic peaks rising above the clouds, it’s easy to see why so many travelers call it their favorite Hawaiian island.
A few years ago, I visited Oahu on a family vacation, and that trip left me yearning for more of Hawaii. Ever since then, I’ve dreamed of exploring Maui, the island that so many people describe as the perfect balance of natural beauty, relaxation, and adventure.
While you could spend weeks exploring, 5 days gives you just enough time to experience the best of Maui.
In this guide, I’ll share my 5 day Maui itinerary filled with scenic drives, beaches, local eats, and tips to help you plan your trip.
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About Maui & Map
Maui is the second-largest Hawaiian island, known as The Valley Isle because of the broad isthmus that separates its two major volcanic mountains, Haleakalā in the east and the West Maui Mountains in the west. This unique shape gives the island its distinct figure, often described as looking like two islands joined together.
The island offers incredible geographic diversity:
- The eastern half is dominated by Haleakalā National Park, where you can stand above the clouds at the 10,000-foot summit of a dormant volcano.
- Central Maui is home to lush valleys and towns like Wailuku and Kahului.
- West Maui boasts resort destinations such as Lahaina, Kāʻanapali, and Kapalua.
- South Maui features beautiful beaches and laid-back resort towns and communities like Wailea and Kihei.
Maui Travel Essentials
Best Time to Visit: Maui has a really ideal climate, so there’s no “bad” time to go to Maui. April through October will be dry and sunny weather. Winter months bring cooler temperatures and rainy season, but December-March is the best time to see humpback whales.
Getting There: Fly into Kahului Airport (OGG)
Getting Around: A rental car is essential. I recommend booking early through Discover Cars for the best rates.
Recommended Duration: At least 5 days
Where to Stay: Wailea (South Maui) and Kāʻanapali (West Maui) are the most popular.
Things You Should Bring
- Reef-safe sunscreen – we got this zinc based water resistant sunscreen
- Snorkel gear – we brought this anti-fog mask set because we don’t like to rent the mouthpieces.
- Swimwear
- Beach cover up
- Underwater action photo & video camera – this one is affordable
- Underwater action cam (GoPro) – best if you want high quality underwater shots
- Waterproof phone pouches
- Lightweight, breathable outfits
- Sandals
- Walking shoes / sneakers
- Warmer layers (jackets, pants) if you’re planning on going up to Haleakalā
- Hats – the sun on Maui is no joke!
- Packable beach blanket
Where to Stay in Maui
I recommend staying in West Maui, or South Maui.
Kaanapali – West Maui
You can find resorts here, Whaler’s Village shopping center, and restaurants. The beach here is great for snorkeling and cliff jumping, and there is a golf course.
Sheraton Maui Resort & Spa
Westin Maui Resort & Spa
Kihei – South Maui
A bit more budget friendly compared to Kaanapali or Wailea. It’s practical, but not as upscale as the other areas. There’s lots of local restaurants, bars, and more vacation rental condos.
Wailea – South Maui
You’ll find ultimate luxury in Wailea. This area has endless stretches of sand and upscale resorts.
Four Seasons Resort
Andaz Maui at Wailea
A Quick Note About This Itinerary
Maui is the second largest island in Hawaii, known for its incredible variety of landscapes and experiences. From volcanic peaks and lush rainforests to golden beaches and scenic drives, there’s so much to do that you’ll never fit everything into one trip.
This Maui travel itinerary is perfect for you if:
• You want to visit some of the most popular places on the island
• You’re looking for a little bit of everything—beaches and mountains
• You want a balance of relaxing days and active exploring days
As many of you know, the island of Maui suffered devastating wildfires in 2023, which deeply affected the community of Lahaina. I visited in 2025, and while restoration efforts have begun, much of Lahaina remains closed to visitors. Out of respect for the residents and ongoing recovery efforts, this itinerary does not include stops in Lahaina.
If you’re visiting Maui, please stay updated on local guidance, support local businesses responsibly, and remember that Maui is still welcoming visitors to other parts of the island. Tourism continues to play an important role in helping the local economy recover.
Day 1: Arrival + Relax
Welcome to paradise!
Pick up your rental car at Kahului Airport and head to your hotel. Depending on where you’re staying, the drive will take 30–45 minutes. We stayed in Kāʻanapali, so this itinerary will be based on that area. However, you can easily modify it depending on where you’re staying.
If you’re coming from mainland USA or other parts of the world, you’ll likely have traveled a long way to get here. Check in to your hotel and spend the rest of the arrival day unwinding and settling in, so that you are well rested for the rest of the trip and to beat the jet lag.
Before heading in to our hotel, we did stop by Foodland for some fresh poke. Foodland & Tamura’s are 2 chains of grocery stores on the island and they have the best poke! Make sure to stop by one at some point in your trip.
If you’re staying near Kāʻanapali, I highly recommend The Sandbar at the Sheraton Maui. This stylish lobby bar features an open-air terrace with direct views of Black Rock, making it one of the best places to watch the evening cliff dive ceremony. It’s a great place to unwind with a cocktail while enjoying the sunset and the ocean breeze and to ease into this Maui 5 day itinerary.
Day 2: Paia, Ho‘okipa Beach, Upcountry Maui + Haleakalā Sunset
Good morning! Let’s start day 2 in Maui.
Breakfast & Coffee
Your first stop will be Tin Roof Maui, which is super popular on social media and for a good reason! We went right at opening so it wasn’t very busy. We got their Mochiko Chicken as well as the pork belly, and I personally liked the pork belly more. Make sure to get the garlic noodles with it!
I highly recommend trying Akamai coffee while you are in Maui. In addition to regular coffee menu, they have 3 signature drinks which is the Hawaiian Honeybee, Road 2 Hana, and Oatmeal Cookie. The Hawaiian Honeybee had hints of coconut and honey, and it was delicious.
There’s a 3 locations including Wailea, Kihei and Kaluhui. We went to the Kaluhui location which is actually a truck in a parking lot, but trust me, the coffee here is worth the stop!
Paia
After a caffeine charge, drive to Paia, a charming surf town filled with colorful boutiques, coffee shops, and art galleries. There wasn’t a ton to do here, but it was fun to wander the streets with all the cute beach shops.
Mama’s Fish House in Paia is probably the most well known restaurant on the island, but almost impossible to get a reservation to. We booked our trip last minute so we weren’t able to get a reservation, but if you can do it, definitely try it and let me know how good it is! I do hear they take walk-ins if you go before opening at lunch so this would be a good day to try this.
Ho’okipa Beach
Just a short drive away is Ho‘okipa Beach Park, one of Maui’s best spots to watch surfers riding massive waves and sea turtles resting on the sand. Probabilities of seeing turtles are higher in the afternoon around 3-4 pm, but we got here around 2 pm and saw more than 30 turtles sunbathing.
Upcountry
From there, continue uphill toward Upcountry Maui, a region of rolling hills, farms, and panoramic ocean views. Most popular things here include:
- Ali‘i Kula Lavender Farm for scenic walks through lavender fields
- Ocean Vodka Organic Farm & Distillery for a tasting
- Kula Bistro for a casual meal
Unfortunately we didn’t have much time to explore Upcountry because we were trying to make it to sunset at Haleakalā. If I were to do it over, I would have had an earlier start to the day and spend more time in Upcountry.
Sunset at Haleakalā
Now in the afternoon, drive to Haleakalā National Park for one of the most breathtaking sunsets you’ll ever see. Standing above the clouds as the sky turns shades of pink, gold, and violet is a once-in-a-lifetime experience.
While sunrise on Haleakalā gets all the fame, I decided to go for sunset instead. It takes several hours to get to Haleakalā summit from West or South Maui, and that means you have to leave your hotel at around 3 am to see sunrise.
You can read my full Haleakalā Sunset Guide for more information on how to get to Haleakala National Park and what the experience is like. This is one of the best things to do on Maui.
Bring some warm layers because it gets cold at 10,000 feet. You’ll want to arrive at least an hour before sunset to get parking and enjoy the full color shift as the sun dips below the horizon.
Day 3: Beach + Luau
Today will be a bit more relaxing, especially after the long drive yesterday. Let’s spend the morning snorkeling and enjoying the sandy beaches of Maui.
But first of all, I was on the hunt for this pineapple bowl acai bowl from Maui Fruit Ninja. They are a family owned business, and are at different locations with their truck each day. You can check their location for the week here. On this day they were located in Ka’anapali so this was perfect.
The bowls are either pineapple or papaya, and they have acai, strawberry sorbet or mango sorbet.
We chose the pineapple combo with a scoop of acai and strawberry sorbet, all the fruits, added on granola and hawaii honey, and topped it off with extra dragonfruit.
This was the best acai fruit bowl I’ve ever had! Highly recommend you look at their schedule and get it during your trip to Maui.
Ka’anapali Beach
Now for beach time.
If you’re in West Maui, Ka’anapali Beach is great for snorkeling. We brought our own snorkel gear from home because I don’t like using mouthpiece that has been used by someone else… but we rented floating belts from the rental shop by the beach.
As soon as we started snorkeling by the Black Rock, we saw turtles in the water and this was one of the most exciting things on our trip. There were about 3 turtles literally a few feet away from us. They are gentle and beautiful creatures, and you should be respectful and NEVER touch them.
Another option for this day would be to do a snorkel tour, like this one to the Molokini Crater and Turtle Town.
Luau
In the afternoon after a great time at the beach, we got ready for a luau. If you’re not familiar, a luau is a traditional Hawaiian feast or celebration with food, music and dancing.
There are several different options for luaus on the island, including Old Lahaina Luau, and Grand Wailea Luau just to name a few.
The food and performances vary as do the prices, so I recommend reading reviews to choose the one that suits you the most.
We went to the Maui Nui Luau which takes place at the Sheraton Maui where we were staying, so we didn’t have to venture far. There was live music and traditional dancing in a beautiful setting, and the food which was served in buffet style, was delicious. The food honestly exceeded my expectations! This was a great way to learn more about Hawaiian culture, and to end the night.
Day 4: Road to Hana
The Road to Hana is known as one of the most scenic drives in Hawaii. It’s a full-day trip that winds through lush rainforests, a black sand beach, and cascading waterfalls. Today you’ll be going on this epic road trip.
The roads are windy and narrow, with several bridges that turn into a single lane. My husband is a good driver and he didn’t find it too difficult, but I do recommend only doing the drive if you feel comfortable.
You should aim for an early morning start, 6-7 am if possible.
This way you’ll get a full day and have plenty of time to stop by the most popular stops along Road to Hana. There are lots of possible Road to Hana stops, and I recommend looking at them prior to the day and deciding the absolute must stops for you as this may vary based on preference.
One thing to note is that there is no cell service throughout most of Road to Hana. This means you can’t rely on Google Maps for the drive. After some research I downloaded the GuideAlong Road to Hana audio tour guide, and I highly recommend it!
The app uses GPS to locate where you are, and will provide you with audio guides of different places along the Road to Hana as you drive.
It’s a good idea to bring some snacks and water for the way because there really aren’t any places for food for a long stretch. The Road to Hana starts in Kaluhui (near the airport), and passes through the town of Paia and a lot of people pick up food here. You should check out this store called Kū’au Store that has cute surfboards lined up outside. They have different fruit juices, coffee (get the Mac Nut Vanilla Latte!), prepared foods and even poke.
Road to Hana Stops
The stops along Road to Hana are marked by mile markers (MM).
I won’t go through all the stops on Road to Hana here, but some of the most popular ones include:
- Ho’okipa Beach (MM 9) – the beach with turtles and windsurfers (can skip this if you came here on day 2 itinerary)
- Twin Falls (MM 2) – first waterfall stop just outside of Paia
- Garden of Eden Arboretum (MM 10) – a beautiful botanical garden
- Ke’anae Peninsula(MM 16) – stunning ocean views and this is where the famous Aunty Sandy’s banana bread is located.
- Halfway to Hana (MM 17) – a small market, and official half way point.
- Wai‘anapanapa State Park (MM 32) – home to the famous black sand beach (reservation required)
- Hana Town (MM 34) – a quaint historic town
- Wailua Falls (MM 45) – a picturesque roadside waterfall
- Pipiwai Trail (MM 42) – a 4 mile round trip hike with a famous bamboo forest in Haleakalā National Park (Kipahulu side of the island, not the summit).
- ‘Ohe’o Gulch / Seven Sacred Pools (MM 42) – also within the Haleakalā National Park.
Some places along the Road to Hana require entrance fees or parking fees.
Please avoid parking illegally along the Road to Hana and blocking the roads. It’s a narrow road and locals who live along this road need to use it on a daily basis.
You should also stop by Coconut Glen’s, where they sell coconut milk based ice cream (non-dairy). It’s on Hana Highway at Mile Marker 27.5.
And just after passing by Coconut Glen’s, we found this cute fruit stand and had to stop by. The owner, Kai the Coconut Guy, was the kindest and gave us a bunch of samples to try. We got a coconut which he skillfully opened for us and along with a bamboo straw.
These small businesses will appreciate cash so bring some cash with you!
Whether you stop your journey at Wai’anapanapa State Park, Hana, or the Haleakalā National Park, you’ll have to turn around and drive back the same way. If you continue the same direction past the national park, you’d drive around the south side of Maui and the roads here are rough, unpaved. Locals do not recommend driving here.
We did not do Haleakalā National Park’s Pipiwai Trail or the Seven Sacred Pools because we actually didn’t leave as early as we should have, and we wanted to start heading back before sunset. Road to Hana is already not an easy road to drive on, so you really want to avoid driving it in the dark.
Wai’anapanapa State Park
You’ll need reservations for Wai’anapanapa State Park, and limited quantities are sold for each day so I would reserve this sooner than later.
It’s $10 per vehicle and $5 per person.
Reserve tickets here. There’s 4 time slots per day: 7 am, 10 am, 12:30 pm, and 3 pm.
After returning from Road to Hana, we had dinner at Monkeypod Kitchen in Whaler’s Village, an oceanfront outdoor mall with boutiques, restaurants and shops. You have to try their Mai Tai! It’s topped off with honey-lilikoi foam, and tastes like heaven!
Day 5: Beach + Food Trucks + Iao Valley
Welcome to the last full day in Maui.
Wailea Beach & Makena Beach
Today you’ll visit the white sand beaches on the south side of Maui. Both Wailea Beach and Makena Beach are considered some of the best beaches in Maui.
First, I picked up coffee from Kraken Coffee, just around the corner from Wailea Beach. I got Mocha Wao, a white chocolate macadamia nut coffee. Yum!
Wailea Beach is a public beach, so there is a parking lot and restroom facilities here. It is beautiful, located along an upscale resort area. If you’re not swimming, the beach path is really nice to walk along.
About 10 minutes south of Wailea Beach is Makena Beach, or the Big Beach. Makena Beach is a State Park, so there is a fee. Just like all other state parks, the parking fee is $10 and it’s $5 per person. Unlike Wai’anapanapa, this lot just had a kiosk where you pay.
The waves here are less developed compared to Wailea Beach, and while you can swim here, you should take caution as it’s known to have powerful shore breaks, and rip tides. There are lifeguards, but always be cautious.
If you walk a short path over the hill from Makena Beach, there is Little Beach which is more secluded, and clothing-optional.
Food Trucks & Shave Ice
After spending hours at the beach, you’ll drive a little over half hour to Kahului to hit up the food trucks. This area has some of the best food trucks! BRING CASH!
We got:
- Geste Shrimp Truck (Spicy shrimp and pineapple shrimp)
- Thai Mee Up (pad thai)
Next you’ll have to get shave ice from Ululani Hawaiian Shave Ice at least once on your trip. You can go to the one in Kahului which is just 3 minutes away from the food trucks, or the one in Wailuku because this is on your way to the next destination.
Iao Valley State Park
After some delicious shave ice, you’ll head to ʻĪao Valley State Park.
It’s a short 15 minute drive from Kahului to Iao Valley, a lush green park known for its misty mountains and the iconic Iao Needle.
Type in Iao Valley State Monument on your GPS and once you arrive, you’ll have to pay entrance fees or show proof of reservation. It’s the same $10 per car, $5 per person as it’s a State Park. You can reserve here in advance, but for this one it’s okay to do it same day. We made our reservations while eating shave ice.
You don’t need a ton of time here. There’s a pretty botanical garden you can walk through and then it’s a short stroll up a scenic path to the viewpoint for the Needle.
In the evening, have your final dinner on the island and take in the gorgeous sunset one last time.
Final Thoughts on 5 Day Maui Itinerary
There you have it, my 5-day Maui itinerary! I hope this helps you plan your next Maui adventure.
Hawaii is one of my favorite places in the United States, and I can’t wait to return to explore more!
