The Ultimate 5 Day Maui Itinerary You'll Want to Steal (2024)

I visit Maui every year, so I’ve become an expert at planning a 5 day Maui itinerary. Whether you prefer lounging on the beach, outdoor adventures, shopping, or food, Maui has it all…but it can make planning a trip to Maui overwhelming if you want to fit it all in!

To make it easier, I’m sharing all my tips for planning 5 days in Maui. I’ll break down the best area to stay, where the locals eat, the best snorkeling beaches, easy hikes, shopping areas, and more. Then I’ll put them all together into my ultimate Maui 5 day itinerary!

Maui experienced catastrophic fires August 9, 2023. Please consider donating to help locals recover from devastating loss.

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Planning Your 5 Day Maui Itinerary

Here’s important information about Maui you should know before you embark on your journey.

How Maui compares to the other islands

Depending how you count them, there are as many as 130 islands in Hawaii! However this includes small rocky areas that aren’t really habitable, so in reality, there are 8 islands people are referring to when they talk about visiting Hawaii. These include Hawaii, Maui, Oahu, Kahoolawe, Lanai, Molokai, Kauai, and Niihau.

The four most popular Hawaiian islands to visit include Hawaii, Maui, Oahu, and Kauai.

Here’s what each of these Hawaiian islands is best known for:

Hawaii – Referred to as “the Big Island” and is known for volcanoes and weddings/honeymoons.
Maui – Known for agriculture, golf, and whales. It’s more arid on the west side of the island and lush on the east.
Oahu – The most touristy of the islands thanks to the state’s capital, Honolulu, and worldwide surfing recognition. Lots of shopping and food.
Kauai – Where Jurassic Park was filmed because of its greenery, hiking, and rainforests. It’s quieter and lush.

Someone once told me that Maui is the best island if you want a mix of everything with less tourists than Oahu. I have to agree with that.

All of the islands have beautiful beaches, so for me I like spending 5 days in Maui above all the other islands because it has an incredible food and makers scene (so many artists!) and a bit more to do than, say, the quiet island of Kauai. If you love these things too, Maui is likely the island for you!

The best time to book 5 days in Maui

Many people say the shoulder seasons of April – May and September – October are the best times to visit Maui, but I usually visit between January – March. While this is Maui’s “winter” and known as the rainy season, I’ve never had rain completely ruin my trip before. There are so many micro climates on Maui that weather changes quickly.

The reason I like planning my 5-day Maui itinerary January – March is because it’s less hot and that’s when the majestic humpback whales are in migration. Because of the way Maui is situated, its western shores are known as “whale soup” because the water is warmer and attracts these marvelous creatures. I’ve literally been a few feet away from a humpback whale every year I’ve gone during whale season!

A downside to planning your 5 day Maui itinerary in January – March is that it’s a popular time for other people to visit. Most people in the US don’t get tropical weather year round, so they escape to Maui when the kids are on winter break.

The worst part about this is it drives up hotel and flight costs. I’ve never found it to be unbearable, either price or tourist wise, but if you don’t care about seeing whales or milder temperatures, visiting during the shoulder seasons may be the better choice to save money.

Best Area to Stay in Maui for This Itinerary

Planning where you’ll stay is key to making the most of this 5 day Maui itinerary. I have a whole article on where to stay in Maui, with detailed pros and cons of each area, plus information on which area is best for different attributes like affordability, snorkeling, beaches, etc. I highly recommend reading it and checking out the cool places I found to stay in each part of the island.

Here’s a quick summary of my favorite areas on Maui. I’m a busy bee when I travel (versus lounging at my resort’s pool), so I make sure to stay in areas that are easily accessible to other areas of the island. Here are where I consider the best areas to stay in Maui:

Lahaina – This area on the southwest coast of the island has a touristy strip, but a great food scene and is usually sunny. This is where I usually stay because you can find affordable beachfront hotels.
- Note, this area is affected by the wildfires, so staying north in Ka’anapali is better at the moment if you want to stay in west Maui.
Kihei – This area is along the southern coast of the island and has some of my favorite restaurants in Maui. I find this to be the most centrally located, with good access to all areas of the island and full of locals. It’s the location we always consider staying in besides Lahaina.

Pro tip: I usually stay at Lahaina Shores Beach Resort because it’s the most affordable beachfront property I’ve found an isn’t crawling with tourists like the big resorts. However, they aren’t accepting reservations right now because of the fires, so Sugar Beach Resort in Kihei is a similar alternative we stayed at during our last trip.

Here are some other areas you’ll hear about, but why I don’t think they’re the best areas to stay in Maui:

Pā’ia – This small surfer town is along the north coast about 15 minutes from the airport. It has great vibes and shopping, but the waters are rougher and the main road gets crowded with Road to Hana traffic since it’s at the start of the famous drive. This makes it difficult to explore other areas of the island.
Ka’anapali – This is where all the ritzy resorts are along the northwest coast of the island. It has some of my favorite snorkeling beaches in Maui, but it’s not as accessible as the rest of the island. It’s close to Lahaina so I usually reserve it for visiting vs. staying.
Wailea – This is another posh area of the island known for fancy stores, resorts, and golf courses. It’s a bit south of Kihei, but more expensive. It’s too quiet and devoid of local small businesses for me.
Upcountry – This is where all the farmland is. I love how it’s virtually free of tourists, but it’s far from beaches and not as accessible for exploring other areas of Maui.
Kahului – This is where the airport is. It has some fabulous restaurants near the Maui airport, but it’s commercial (think where Home Depot would be located) and there isn’t a ton of beachfront accommodations.
Hana – This is the eastern coast of Maui. It’s beautiful and remote, but on a terribly inaccessible road for exploring the rest of the island (you can’t exceed 30 mph). It also has terrible cell reception and gets windy and rainy.

The Ultimate 5 Day Maui Itinerary

When I think about how to spend my dream 5 days in Maui, this is it! Follow this itinerary and you’ll explore the majority of the island with a mix of both the must-visit attractions and locals-only hang outs.

Some ground rules before jumping in:

A lot of places, particularly restaurants, are closed Sundays. Some restaurants are even closed Saturdays, so plan your trip accordingly.
Avoid weekends for major attractions. The Road to Hana, Pā’ia, Molokini Crater, and Haleakalā National Park are very crowded on the weekends, so try to do those on a weekday!
You must rent a car. This 5 day Maui itinerary assumes you’ll have one!
Stay in Kihei or Wailea. However, this itinerary will also work if you stay in West Maui. You’ll just need to swap a few breakfast options around.
I can customize this itinerary for you. If it doesn’t fit your schedule or include your favorite things, l’m happy to create a custom itinerary just for you.

Pro tip: I found Expedia has affordable Maui rental cars. Book your car in advance for the best prices.

Day 1: Check out Maui’s best small towns

Pro tip: Since Pā’ia gets crowded on weekends with people trying to access the Road to Hana, make sure this day’s itinerary lands on a weekday.

Get an early breakfast at Kihei Caffe

Kihei Caffe is a popular order-at-the-counter breakfast and lunch spot in Maui. They serve comfort food like eggs Benedict, pancakes, loco moco, and more. The hearty fare will be the perfect fuel for a busy day!

My go-to order always includes the macadamia nut pancakes and crab cake eggs Benedict. The kalua pork loco moco is also interesting, as you don’t see that mash up of these two classic dishes that often. Also, don’t miss their coffee. They serve some of the best I’ve had at a restaurant on Maui!

Head to Pā’ia to shop local makers

Picking up gifts and souvenirs whenever I travel is important to me, so I’m always on the hunt for where to find goods made by locals. I always make a stop in the small surfing town of Pā’ia during my 5 day itinerary to Maui because I think it has some of the best shopping in Maui. It’s 15 minutes from the airport along the north coast and is full of artsy shops perfect for picking up the best Maui souvenirs.

I usually just stroll up and down the streets and pop into stores of interest, but don’t miss Wings Hawaii, which makes everything it sells, and Pearl Butik for exquisite linens.

Pro tip: Feeling adventurous? You can rent e-bikes from Maui Sunriders in either Kihei or Pā’ia. One of the funnest things I’ve done on my one 5 day Maui itinerary is bike from Kihei to Pā’ia. But if that’s too much for you, Maui Sunriders also recommends a bunch of shorter bike rides around Pā’ia.

Get lunch at Tin Roof

Tin Roof is owned by Top Chef finalist and fan favorite, Sheldon Simeon. It’s in a tiny strip mall outside of Pā’ia and only does takeout. But what this spot lacks in ambiance, it makes up for in flavor, so it’s worth the detour.

I make sure to visit this restaurant near the Maui airport in Kahului every year, so make sure to add it to your Maui 5 day itinerary. Everything I’ve ordered is good, but the two must-get dishes include the mochicko chicken and poke bowl. The first dish has double-fried chicken with a crazy flavorful topping of miso sauce, gochujang aioli, and furikake that they charmingly call a “dime bag mix”.

The poke is made with melt-in-your-mouth fresh fish that changes daily. It’s also generous with the sweet sauces and dime bag mix, which makes it much different than other pokes you’ll find on the island (or in Seattle for that matter).

If you have room, I also enjoy their saimin noodles!

Head to Makawao for some more shopping

Another great Maui shopping area to stop at during your 5 days in Maui is Makawao. This is another quaint town full of artists about 15 minutes away from Pā’ia toward the Upcountry. Again, I like to just pop into stores that interest me, so save time to meander! As you do, don’t miss Maui Hands and The Monarch Collective.

Pro tip: You’ll be near all the amazing Upcountry farms. If you’re interested in a tour, check out this Maui Pineapple Tour to taste sweet, Maui grown fruit!

Get dinner at NyloS

website | area: Pā’ia (get directions) | cuisine: farm-to-table | reservations accepted? yes, recommended | known for: being the only tasting menu in Maui

What better way to celebrate a day of shopping than to finish with a swank meal? On your way back from Makawao you’ll pass Pā’ia, home to Maui’s only multi-course tasting menu restaurant called NyloS.

You may read you should go to Mama’s Fish House. Trust me, skip it. It’s definitely not worth the exorbitant prices. NyloS is better and just as special, if not more!

While it’s also pricey and doesn’t have the water views that Mama has, NyloS is owned by a certified sommelier and chef who has worked in some impressive kitchens around the world. He uses that experience to create whimsical, over-the-top dishes that are just as flavorful as they are beautiful.

Day 2: Do the Road to Hana

You can’t go to Maui without driving the Road to Hana. Do you need to do it more than once…probably not. But I’ve done it multiple times and have had a grand day every time.

The Road to Hana is 64.4 miles along the eastern coast of Maui. On a highway you could drive that distance in an hour, but since this is considered one of the most harrowing roads in the world, it’ll take you at least 5 hours if you drive the whole way without stops. I don’t remember going over 40 mph anywhere, and most of the time it’s closer to 30 mph.

But don’t worry, the Road to Hana isn’t that scary.

Before I went, I envisioned we’d definitely drive off a cliff, but if you’ve driven the Amalfi Coast it’s pretty similar with less traffic.

If you’d prefer not to drive yourself, check out these tours:

Tips to make your Hana trip successful

I have a whole article on the best Road to Hana itinerary, but here are some of my fast tips:

If the road is open, drive the Road to Hana “backwards”. Most people start clockwise through Pā’ia in the north of Maui, but I prefer starting counter clockwise in the south to avoid traffic (always check for road closures first, though). Use Waiakapuhi Lava Fields as your starting point in Google Maps and drive east on Highway 31. The coast on this part of the Road to Hana has more interesting ocean views, so it’s best to see that during daylight when you’re less fatigued. The stretch of the Road to Hana from Pā’ia has the road weaving through rainforest and gets monotonous after a while.
Start early. It doesn’t have to be the crack of dawn, but I often start my drive around 11 AM and every time I’m like, “We ran out of time.” One of the funnest things to do is stop at random things that catch your eye, so leaving time to do that is key.
Download offline Google Maps. This is important if you definitely want to make certain stops because the cell service on the Road to Hana is basically non-existent.
Gas up beforehand. There’s only one gas station in Hana.
Prepare for all weather. One time I went and it was rainy and freezing. Another time it was humid and I was dying in workout leggings. So bring layers!
Bring cash. A lot of the fruit stands are cash only.
Consider this audio tour. If you want to learn more about the area as you drive, consider downloading this Road to Hana Audio Tour.

Now that we got through those ground rules, let’s begin your Road to Hana itinerary!

The backside of Road to Hana is currently closed, so you can’t drive the road backwards at the moment. Therefore, you’ll need to skip breakfast at Grandma’s and do this itinerary in reverse until it reopens.

Get breakfast at Grandma’s Coffeehouse

If you’re looking for the best breakfast place in Maui, this is it. It’s a little roadside bakery and cafe in Kula on the way toward the Road to Hana (if driving backwards). The must-get order you? Coconut-crusted French toast. It’s so flavorful and the perfect way to start your day before hiking.

Stop at Laulima Farms Fruit Stand

website | area: Hana (get directions) | reservations accepted? no | pro tip: cash only

Fruit stands are a big thing along the Road to Hana. I love how entrepreneurial the locals are along the route. You’ll find everything from honor-system stalls at the end of a residential driveway (where you leave money vs. pay an attendant) and more established fruit stands. A lot of them also sell homemade food goods like banana bread (in fact, going on a hunt for the best banana bread on the Road to Hana is a thing).

My favorite fruit stand to stop at is Laulima Farms near the popular Pīpīwai Stream Trail. If you’re doing the Road to Hana backwards, this will be toward the beginning of your journey.

This stand sells goods from its farm, including coffee, fruit, and different cleaning supplies and beauty products. It’s cash only, like most of the fruit stands, so prepare for this. And make sure to get the fruit sampler platter to try fruits you likely haven’t had before. Eat it in the bamboo garden for a truly magical rest stop.

Hike Pīpīwai Stream Trail (the bamboo forest trail)

website | area: Hana (get directions) | distance: ~3.5 miles round trip there and back | elevation gain: ~1,000 feet | pro tip: parking is $30 per car

One of my favorite, easy Hana hikes is the Pīpīwai Stream Trail, also known as the “bamboo forest hike in Maui”. It’s part of Haleakalā National Park and has a mix of landscapes to keep things interesting.

For example, it starts in a wooded area and then opens up to a view of a waterfall in the distance. Then it goes back into the forest before opening up to this magical bamboo arching over the path. Lastly, there’s a stream that you can cross to get right under Waimoku Falls.

We didn’t go behind the waterfall because unfortunately it was raining when we went and we were a tad grumpy, but this is a fabulous easy/moderate Hana hike worth stopping at during your 5 day Maui itinerary.

Get lunch in Hana

Hana is the main town on the Road to Hana, so it’s where you’ll find the majority of restaurants. Hours can be unreliable and crowds don’t always mean good food, so stick to these spots to ensure you eat well:

Kilo’s Kitchen – Excellent Hawaiian grindz and burgers made with local beef.
Thai Food by Pranee – A food roadside stand notorious for being closed, but worth a stop if not.
Ae’s Thai Kitchen – A good alternative to Pranee’s. Get the green curry.

Explore Wai’ānapanapa Black Sand Beach

website | area: Hana (get directions) | distance: ~3 miles there and back | elevation gain: 200 feet | pro tip: book your reservation 30 days in advance

The Wai’ānapanapa Black Sand Beach is on the Road to Hana and it’s my favorite stop on the drive. You’ll immediately notice the black sand on the small beach near the parking lot, but the coolest part is that the volcanic rock along the coast makes for a gorgeous hiking trail. It’ll make your visit much more enjoyable if you do the hike because the crowds thin out once you get past the beach.

Pro tip: Non-residents need make a reservation up to 30 days in advance to visit Wai’ānapanapa State Park. You’ll need to pay both an entrance fee (~$5) and vehicle fee (~$10).

Visit a lava tube cave

website | area: Hana (get directions) | distance: ~0.5 miles there and back | pro tip: there’s a $15 per person entry fee

The Hana Lava Tube is one of my other favorite stops on the Road to Hana. It’s on private property and feels as if you’re trespassing, but on their lot is a hole with stairs down to a cave formed by lava years ago.

Your entry fee includes good quality flashlights. If you go late in the afternoon, you may have the cave to yourself. This makes it both super eerie and super cool! Make sure to wear good shoes because the terrain in the cave is uneven.

Meander the rest of the Road to Hana

The best part of the Road to Hana is stopping at viewpoints, waterfalls, and cute roadside stands that catch your eye. I have a lot of stops pinned on the map below, but here are some of my other favorite stops to try and fit into your 5 day Maui itinerary:

Hana Farms – One of the more built-up stands that has flushing toilets.
East Maui Chocolate – A farm stand that grows cacao and sells chocolate.
Coconut Glen’s – Awesome vegan ice cream made with coconut. Don’t miss the lilikoi flavor if available.
Wailua Valley State Wayside – A nice viewpoint overlooking the lush valley with waterfalls in the distance.
Keanae Lookout – A rocky volcanic beach with beautiful water views.
Aunt Sandy’s – Excellent banana bread served warm.

Get dinner at Nuka

You’ll pass by Haiku as you leave the harrowing part of Road to Hana and head toward Pā’ia. It’s a great spot to grab a meal among locals, as most tourists never make it here.

Nuka is a small sushi restaurant in Haiku’s quaint downtown area. I typically avoid getting sushi in Maui because it pales in comparison to Seattle’s best sushi restaurants, but Nuka is the exception.

The quality of fish Nuka serves is superb. The local tuna is some of the best I’ve had at your everyday grade, and I love the little lime art the chef makes. Order the tuna macadamia nut roll and sashimi and you’re in for a satisfying meal to end a long day.

Pro tip: Too long of a wait at Nuka? Colleen’s at The Cannery is a good alternative across the street. If available, don’t miss the warm bacon spinach salad.

Day 3: Go snorkeling and beaching

No trip to Maui is complete without some snorkeling. Here’s how I’d plan my perfect 5 days in Maui around it.

Get up bright and early to snorkel Molokini Crater

It was my first trip to Maui that helped me realize I friggin’ love snorkeling. I’m not sure why because it scares the shit out of me. For reference, it was only this past year that I stopped covering my ears while I snorkel. But there’s something magical about seeing creatures you never get to witness in the wild right beneath you, so this is a must during your 5 day Maui itinerary.

The most popular Maui snorkeling spot is Molokini Crater. It’s a few miles off the southern cost of Maui and is only accessible by boat. Yes, it’s kinda scary to think you’re in the middle of the ocean. But yes I’ve done it multiple times and love it.

Since the water is calmer in the morning, all tours I’ve found start at the ass crack of dawn between 6-7 AM. Book far in advance to reserve your spot.

When choosing what tour group to go with, pay attention to the size of the boat. Some of the boats can hold up to 100 other people! Try to find a boat with under 25 for a more intimate experience.

Molokini Crater aerial view — *Photo courtesy of Boss Frog’s*

Molokini Crater Tours

Here are some small group tours worth considering:

I definitely encourage adding a snorkeling tour of Mokolini Crater to your 5 day Maui itinerary. I’ve seen a manta ray, sea turtles, and even a friggin’ shark! Plus, if you go during whale migration season in January – March, you will definitely see whales as you boat to the snorkeling destination. I’ve seen them every time…as in a few yards away from them breaching like crazy!

If snorkeling isn’t your thing, I encourage you to go on a non-snorkeling, whale-watching tour instead if you’re visiting between December – April. Here are some whale watching options:

Get lunch at Da Kitchen

I’ve been coming to Da Kitchen every year since I started coming to Maui. They used to have two locations where they served an extensive menu of Hawaiian classics like loco moco, saimin, and more. The pandemic hurt them and they had to close their locations, but luckily they reopened a smaller location in a strip mall in Kihei.

While they don’t have as extensive of a menu anymore, they still have their famous loco moco. It is seriously the best loco moco I’ve ever had. The gravy is deeply flavored thanks to onions and mushrooms, and the meat is moist. I also like to ask for chicken katsu on the loco moco like they used to have on the menu at their original location. If you can only go to a few restaurants on Maui, make sure this is one of them!

Get dessert at Sugar Beach Bake Shop

website | area: Kihei (get directions) | cuisine: sweets | reservations accepted? no | known for: malasadas and key lime pie

There’s a very popular pie restaurant in Lahaina that you’ll read about having to go to when you visit Maui. However, Sugar Beach is better (yes, I did a very official taste test). This is another spot I know locals eat in Maui because a local recommended it to me and it’s always crowded.

One of Sugar Beach’s specialty is key lime pie with lilikoi (Hawaiian for passion fruit). I love ordering a mini pie and enjoying it on the benches outside. The key lime is more curd-pie like than cream-pie like, which I love, and is the perfect balance of acidic and sweet.

Their malasadas are also a must if you’re able to get them before 10 AM when they typically sell out. The dough is really flavorful and the filling divine.

Pick up local coffee at Akamai Coffee

website | area: Wailea, Kihei, and Kahului (get directions) | cuisine: coffee shop | reservations accepted? no

One of the things I was surprised to learn is that Maui coffee is expensive. In my mind I was like, “Maui. Tropical. Coffee!” However, the truth is most Hawaiian coffee is grown on the big island. Since Maui is so remote, grocery food is pricey.

I love coffee, but I typically don’t spend over $20 a bag max. It’s almost impossible to find Maui coffee for this price…I’ve seen it as high as $60 for 12 ounces!

However, Akamai isn’t too bad at ~$24 per bag. They’re making excellent roast coffee from Maui-grown beans and their cafes are super cute with swing chairs and homey decor.

Walk the Hoapili Trail

website | area: Kula (get directions) | distance: ~3.5 miles one way | elevation gain: ~100 feet | parking? yes

This is one of my favorite walking trails in all of Maui. It’s part of the Ahihi-Kinau Natural Area Reserve and consists of black lava rock that weaves along the coast. You’ll get stunning views of the coastline, plus see wild goats. The trail is quite long, but you can take it as far as you want and turn back.

Pro tip: A little bit before the parking lot for Hoapili Trail is Kanahena Cove (also called Ahihi Cove by locals) where you can snorkel. Park in the parking lot just past the cove. It can get rougher in the afternoons, but it’s worth checking out if you’re comfortable with the waves!

Lounge and snorkel at Maluaka Beach

area: Wailea-Makena (get directions) | public access? yes | parking? yes, but limited

If you Googled where you can swim with turtles in Maui, you inevitably read about Turtle Town. What’s confusing is it sounds like a specific location, but it’s more the general area where you can see a lot of turtles along Maui’s south shore. However, I did some digging and read that locals consider Turtle Town to be accessible via Maluaka Beach.

Maluaka Beach is a lesser known beach a bit north of the popular Makena Beach in Kihei. It’s small and in a residential area, so bring snorkel equipment with you. Since it’s a bit off the main road, less people go to it, so you may have the snorkeling all to yourself.

This is both a good and potentially bad thing. The good is that you can experience the wildlife without a ton of tourists. The bad is that the snorkeling here is a touch more intimidating because you lose sight of the shore.

What I mean by this is that the coral starts at either side of the beach and then wraps around the coast. If you want to explore it all, you need to swim along the coast in open water without the safety of the beach. It’s not particularly challenging, but I was definitely a touch freaked out being out of sight of the shore when there was no one else in the water. Also, the coral is closer to the surface here so it can be a bit alarming when you think a wave may be pushing you too close.

Again, I don’t consider myself a super strong swimmer and did it.

I think it’s more a confidence thing. I’ll definitely say it felt like a hidden gem compared to other snorkel beaches, but it didn’t have the safety of people and a shore in sight. If you’d prefer to have the safety of other people, consider taking this Maui Turtle Town Kayak and Snorkel Tour or this Clear Kayak and Snorkel Adventure with a professional guide.

Pro tip: Sea turtles aren’t afraid of the surface. I actually almost ran into one because I was so busy looking down while snorkeling! Remember it’s your responsibility to keep a safe distance and avoid touching them.

Get dinner at South Maui Fish Company

website | area: Kihei (get directions) | cuisine: seafood | reservations accepted? no | pro tip: this food truck sells out fast, so get there when they open for dinner

South Maui Fish Company is one of my favorite poke places in Maui. It’s owned by friends who grew up in Puyallup, WA. They had a dream of fishing in Maui, so they moved to the island to make it a reality.

Now you can try their fresh-caught fish in various raw and cooked preparations. The must-get is the daily poke specials, which you can get half-and-half on a plate to try both. Besides exceptionally fresh fish, I love how they serve poppy seed pineapple slaw on the side. It’s so interesting and refreshing!

Enjoy dessert at Maui Pie

website | area: Kihei (get directions) | cuisine: pi | reservations accepted? no

I love that pies are a thing in Maui. You’ve had Sugar Beach Bake Shop. Now try my other favorite version at Maui Pie.

You’ll find a bunch of pie flavor options for sale by the slice. My go-to order is the lilikoi curd pie and strawberry mango. Both are served on Maui Pie’s signature crust and have the perfect balance of fruity flavors.

Day 4: Haleakalā National Park and the Upcountry

Get ready to experience one of the bucket list adventures in Maui: a visit to Haleakalā National Park! The Haleakalā National Park crater is accessible via the Upcountry, Maui’s farmland, so it makes sense to visit farms on the same day during your 5 day Maui itinerary.

The national park is a popular destination for sunrise viewing, but it requires a reservation months in advance. I’m here to tell you that you can avoid the crowds and have an equally amazing time going later in the day.

However, if you want to go at sunrise, here are some tours to consider that will pick you up at your hotel:

If you don’t care about sunrise, use this itinerary for making the most of this day.

Grab breakfast at the Cinnamon Roll Place

website | area: Kihei (get directions) | cuisine: pastries | reservations accepted? no | pro tip: order ahead to skip the line

The Cinnamon Roll Place is a small bakery in a strip mall serving excellent pastries, including gluten free options. The menu consists of scones, bread pudding, banana bread, an egg wrap, and of course their famous cinnamon rolls. I love how the cinnamon spice is more pronounced with a zing similar to a stick of gum. The tang goes beautifully with the creamy icing!

Pro tip: Looking for something healthier? Check out the smoothie and acai bowl counter at nearby Hawaiian Moons Grocer.

Check out the farmers market & Maui Swap Meet

If it’s Saturday, check out Maui Swap Meet and the Upcountry Farmers Market.

The Maui Swap Meet is a flea market and craft fair that happens every Saturday from 7 AM – 1 PM near the airport in Kahului. It has some junky stuff to sift through, but it’s worth a visit because you’ll pass it on the way to the Upcountry. It gets crowded, so the earlier you get here the better.

The Upcountry Farmers Market is a small farmers market that runs super early from 7 AM – 11 AM on Saturdays. It’s where the locals go for fresh produce and a quick bite. Make sure to grab a sushi hand roll from Maui Cones!

After you check out the farmers market, head to the food cart pod on the other end of the parking lot and then grab a beer at Mahalo Aleworks, which is tucked behind the western part of the shopping center.

Visit the Upcountry farms & farm stands

You’ll be a world away from the ocean as you climb toward Haleakalā National Park. This fertile land is Maui’s agricultural hub, as you probably noticed from the countless sheep, goat, and grassy pastures.

There’s no better way to experience Maui’s bounty than by visiting as many farms as possible. There’s seriously a farm for every type of produce or animal product you can think of. My favorite thing to do is map out a few to visit and hit them up one after the other.

Here are some of my favorite farms to visit:

Kula Country Farms – A larger farm stand with u-pick strawberries.
Surfing Goat Dairy – A great stop for cheese or a farm tour where you can take care of the goats!
Maui Bees – A little farm stand with honey tastings and products for sale.
O’o Farm – A coffee farm that does tours and farm lunches.

Pro tip: Prefer a guided tour? Check out this private Upcountry tour that visits Kula Farms, a tea farm, and a lavender farm!

Get lunch at Pukalani Superette

website | area: Pukalani (get directions) | cuisine: Hawaiian | reservations accepted? no | known for: cheap bento boxes

Pukalani Superette is a serious locals-only hidden gem in the Upcountry. It’s a convenience store a bit off the main drag, so many tourists never pass it on their way to the crater.

However, a stop here is a must for some of the most affordable eats on the island. For ~$8 you can get a large portion of hot food or cold takeaway items. My go-to is the chili chicken and chow fun bento box, so grab that one if it’s available!

Pro tip: Want to fit in more eats? Check out nearby Kalei’s Lunchbox for more local grindz. Get the breaded beef teriyaki!

Go wine tasting at Maui’s only winery

website | area: Kula (get directions) | reservations accepted? yes

There’s only one winery on Maui aptly called MauiWine. It’s in the Upcountry on the way to the Road to Hana if you’re driving it counter clockwise. It has beautiful grounds…there’s even an old plantation prison house on the grounds! But what really stands out is the fact that it’s making wine in a climate not exactly hospitable to grapes.

The tasting flight will include wines supplemented with grapes from California since the vineyard’s yields are low, but try the estate grown wines using the grapes they’re able to grow on the island. And don’t miss the pineapple wines…they aren’t as sweet as you’d imagine!

Visit Haleakalā National Park

website | area: Kula (get directions) | reservations accepted? No, unless you want to go for sunrise. Then it’s required.

Haleakalā National Park is a large area that spans from sea level to more than 10,000 feet above. There are actually two sections: the Summit and Kīpahulu Districts. Kīpahulu is near the backside of the Road to Hana (you were in it when you did the bamboo forest trail on day 2). On this day, you’ll explore the Summit District.

Since you’ll be close to the top of the volcano, make sure to dress in layers because it gets surprisingly cold. You can buy a pass in advance for $30 per vehicle, or get it upon entering the park with a credit or debit card (the park is cashless).

There are a bunch of hiking trail options, but even just from the visitors center the peak is wildly impressive. The beautiful red, rocky landscape makes you feel like you’re on Mars! On a clear day you can see uninterrupted views of the ocean to the west.

If you prefer a guide, here are tour options you may find interesting:

Haleakala Maui Sunset Tour
Haleakala Golden Hour Downhill Biking Tour
Haleakala Slingshot Navigation Self-Guided Tour (this car is so dope!)

Get dinner at Tamura’s Fine Wine & Liquors

Tamura’s is my third favorite poke on the island. I know this is where locals eat on Maui because I would have never found it without a local’s recommendation…it’s literally inside a liquor store. Once you walk in and turn left, a seafood counter case will magically appear with at least 8 different pokes.

Eat as the locals do and grab a bowl of 2 pokes and eat on the bench in the parking lot. Tamura’s is probably the best value poke given how much fish you’ll get, so come hungry!

Sample beers at Maui Brewing Co.

website | area: Kihei (get directions) | reservations accepted? no

There aren’t a ton of breweries on Maui, but obviously I sought out the ones that exist. Maui Brewing Co. is the largest craft brewery in Hawaii and has two locations in Maui: one in Ka’anapali and one in Kihei. They serve some great beers, my favorite being the coconut porter. You can also do a brewery tour and eat at their full-service restaurants.

Pro tip: Love beer? Take a Maui Brewery Tour and visit 3 breweries, including Maui Brewing Co.

Don’t want the night to end? Finish your evening with a Maui Sunset Luau Dinner Cruise or Te Au Moana Luau at a Resort.

Day 5: Check out Maui’s north coast

I prefer the north coast of Maui over the Road to Hana because it’s more accessible and less crowded. Get ready to explore this hidden gem on the last day of your 5 day Maui itinerary!

Get an early breakfast at Sam Sato’s

area: Wailuku (get directions) | cuisine: Hawaiian | reservations accepted? no | known for: dry mein

Sam Sato’s is a local institution that’s been around since 1933. This no-frills spot is known for dry mein, a brothless version of saimin with soft noodles made of wheat and egg. You may be thinking, “Noodles? For breakfast?!” I’m here to tell you yes, do as the locals do and get here for shortly after they open at 7 AM.

Chinese cooks working at Sam Sato’s actually invented dry mein. The noodles are tossed with a sauce and topped with things like char siu pork, bean sprouts, and green onions. You’ll also get a small bowl of chicken broth on the side for customizing the brothiness of your meal.

Another item you should add to your order is the Lima Manju. It’s a dessert similar to mochi, but made with flour and lima beans instead. You’ll be hard pressed to find them on many other menus!

Pro tip: Sam Sato’s is notorious for being randomly closed. If that’s the case when you visit, another option is Waikapu on 30, a locals-only spot with incredible pork laulau. If you want more traditional breakfast options, don’t miss Bamboo Grille.

Hike Waihe’e Ridge Trail

website | area: Kahului (get directions) | distance: ~4 miles round trip there and back | elevation gain: ~1,500 feet

This is a hike near the north shore of Maui. I read somewhere before I went that it’s an easy-moderate hike that takes you along beautiful inland ridges.

The latter part was accurate, but let me tell you, this is not easy at first. It’s uphill right from the start so it can burn you out fast. I pulled a muscle in my calf walking up the paved section from the parking lot to the trailhead (not even joking).

However, if you can deal with the burn, it mellows out a bit and is a beautiful Maui hike. It’s like you’re in those mountains they take drone video of in Jurassic Park! The hike should take you about 3-3.5 hours without too many stops.

Stop at Karen Lei’s Gallery

website | area: Wailuku (get directions) | best for: picking up souvenirs

After Waihe’e Ridge, you’ll begin your drive along the northeast coast of Maui. One of the first stops you’ll come across is Karen Lei’s Gallery, a seemingly random gift shop full of handmade goods. I love popping in to pick up souvenirs and take in the pretty valley views from their property.

Get Julia’s Best Banana Bread

area: Wailuku (get directions) | cuisine: Hawaiian treats | reservations accepted? no, this is a roadside stand

A bit further along Maui’s north coast is a bright green roadside stand selling the best banana bread on the island. Julia sells super moist breads with different mix ins, as well as jams, cookies, and juices. Don’t miss the guava jam if it’s available. It makes a great souvenir! I also loved the pineapple mango juice.

Pro tip: Julia’s was randomly closed 2 times before I finally got to try it on my 3rd visit. Expect typical island hours…which means it may not be open!

Also, this green farm stand pictured below is their old location, but they moved further west. Follow the directions above and you’ll find it.

Explore the northeast coast

After you get some souvenirs and snacks, you’ll be ready to explore the rugged northeast coast of Maui. The road is harrowing like Road to Hana, so drive slow and make sure to only pull over at designated spots.

The beauty of a coastal drive is that there are a ton of viewpoints and easy hikes to explore. The beauty of it is that you can stop on a whim at whatever looks interesting. But if you want more guidance, don’t miss these spots:

Olivine Pools Trailhead – A short 1/2-mile walk to pools and lava rocks.
Ohai Trail – An easy ~1-mile hike along the coast.
Acid War Zone Trail – A short ~2-mile trail through rocks that look like they’ve been eaten by acid.

Check out Nakalele Blowhole

website | area: Wailuku (get directions) | distance: ~1.2 miles round trip there and back | elevation gain: ~275 feet

The most popular stop on the northern coast is Nakalele Blowhole. It’s accessed via a short and relatively easy Maui hike, with a bit of a scramble down toward the water. You’re going to get sprayed so keep fancy camera gear at home! And keep your eye out for the heart-shaped hole formed between the rocks near the blowhole.

Visit D.T. Fleming Park

website | area: Kapalua (get directions) | public beach? yes | parking? yes

This beach is north of Kapalua and is said to be a good snorkeling beach, though I haven’t gone in the water yet to vet that statement. What I did vet was that it’s near Dragon’s Teeth, which is an epic walking trail in Maui. It gets its name from the way the jagged rock formation resembles teeth thanks to the way the lava rushed into the ocean a long time ago. You’ll get sprayed with water, so prepare to get wet!

If time, head to Kapalua Bay Beach for more snorkeling

area: Kapalua (get directions) | public beach? yes | parking? limited

This crescent shaped bay is one of my favorite snorkeling spots in Maui. It’s a touch difficult to find because the beach access is through a parking lot that hides the water from the road. However, once you find it you’ll come across a sweet little beach. It can be a bit crowded, but the snorkeling is a ton of fun.

This is one of my favorite snorkeling beaches in Maui because the coral is further below you so there’s some distance between you and the fishies. I’ve also swam with sea turtles here, so if you’re looking for where you can swim with turtles in Maui, this is a good beach for that.

Pro tip: Consider renting snorkel equipment, beach chairs, and umbrellas for the duration of your trip. I always rent from Snorkel Bob because there are convenient locations across the island and you can drop off your gear at any one.

You can also visit the nearby Napili Bay Beach for more great snorkeling.

If time, unwind with a treatment at a spa

It’s not a vacation to Hawaii for me if I don’t include a visit to a spa in my 5 day Maui itinerary. Every year I make the rounds at the luxury spas on Maui. Here are my favorites in northeast Maui.

Pro tip: If you don’t have time to fit in a visit to a spa, have it come to you! Book a Private Spa Experience in Your Hotel.

Spa Montage Kapalua Bay

Fun story about my experience at Spa Montage Kapalua Bay. I got violent food poisoning the day I was supposed to go. I was not about to pay the steep cancellation fee, so I went. A distinct memory is writhing in a pool lounge chair, too afraid to go in the water for fear I’d have an accident (TMI?). I was convinced something was about to go down on the massage table.

Yet despite this terrible memory, I remember Spa Montage as pure bliss. You walk into the spa and are immediately greeted with an open-air lobby that has views all the way to the beautiful Hawaiian landscape. The outdoor spa pool is beautiful and there’s a path leading to private massage huts.

I got a massage in one of those huts and, no, I didn’t have an accident. I was so relaxed that I was able to forget how violently ill I was…until I made it home. 😉 If a Maui spa can leave that impression despite dire circumstances, it’s good in my book!

The Spa at Ritz-Carlton

The Spa at Ritz-Carlton Kapalua is near Spa Montage in Ka’anapali. It has a female-only or co-ed grotto pool, steam and dry saunas, and a relaxation room with super cozy chaises. They use Eminence products, which is what I use at home so you can feel good about the quality.

Pro tip: Before the pandemic you used to get free access to the Ritz’s grounds with a spa treatment, but unfortunately they stopped doing this. I was devastated to learn this, as being able to live as the other half lives made this my favorite spa in Maui.

Eat dinner at Joey’s Kitchen

website | area: Ka’anapali (get directions) | cuisine: Filipino-Hawaiian | reservation accepted? no | known for: casual comfort food

Joey’s is a casual, order-at-the-counter spot perfect for ending your 5 day Maui itinerary. It has the soul of the island in its food and charm, so even if there’s a wait, persevere.

When you get to order, don’t miss their pork lumpia, mac salad, loco moco, and mochiko chicken. All are comforting versions of the Hawaiian and Filipino classics.

And there you have it! My ultimate roundup of Maui tips organized into a 5 day Maui itinerary. Hopefully this helps you when planning your trip to Maui.

As you can tell from the ~7,000 words in this post, I love Maui. It’s a place I feel at peace immediately after I step off the plane. I guess what they say about vitamin D is real because I feel like a happier version of myself.

Save this guide to Pinterest for later as I’ll update it as I discover more places that make me smile.

Pro tip: I can customize this itinerary for you so it has exactly what you like to do. Check out my travel planning services.

My Maui map

Want to curate your 5 day Maui itinerary? Here is the map I curated over many years of planning a trip to Maui. It includes my favorites mentioned here, plus places I need to try or others I visited and thought were just ok (read the pin descriptions for more info!). If you have other recommendations, contact me because I’d love to add them to my map!

Explore more of Hawaii

Still need to play more of your 5 day Maui itinerary? Check out my other guides for more ideas of things to do on this magical island:

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