Best 5 Day Maui Itinerary

Maui Hawaii is one of the most beautiful places on earth, and it was a privilege to explore its gorgeous lands and seas on a recent adventure trip! We explored jungle trails, tried out some marvelous snorkeling beaches, were awed by some stunning ocean cliffs and ate some amazing food. Enjoy our version of the Best 5 Day Maui Itinerary!

1. Day One

Leoda’s Pie Shop

This roadside stand sheltered by the most gorgeous monkey pod trees growing in an arch completely covering the road was ABSOLUTELY AMAZING. An open air fruit and food stand offers fresh local produce and some unique Hawaiian treats in flavors like Li Ming Hui, Pineapple, Guava, Coconut, and others you’d expect from a tropical island. Next to this stand was a magical smoothie bus, but it’s manned by the owner only and lines are really long!!! Try anything involving guava and coconut, or classic strawberry banana. https://www.leodas.com

Whaler’s Village

Stay here for a luxe ocean view experience with a perfect white sand beach. The waves can get intense!!! We spent the first day getting to know the ocean. This was our start to the 5 Day Maui Itinerary! Our accommodation was just west of the small town of Lahaina, in a very luxurious resort area which even featured its own shopping district and a wide variety of restaurant choices.

Whaler's Village, our luxe lodging home base for our 5 Day Maui Itinerary

We were a large family party so we stopped at Costco on the way out from the airport in our rental car to provide ourselves with breakfast and lunch options to help with costs. Everything is a bit more expensive on the island, with most costs being about 20% more than mainland. Condos are equipped with great kitchens so we did a lot of cooking for breakfasts or quick lunches.

The best part of the condo which we rented for the week was the gorgeous ocean views and the sound of the waves to rock you to sleep. It’s also a great location halfway from the snorkel location to the east at Black Rock and to the west for the surfing beach.

Beaches are lovely clean sand with enough waves to be exciting, but not so wild that families with young children wouldn’t venture in. You can definitely get knocked down by a wave if you aren’t paying attention, and it can be a bit shocking to get rolled face first into the sand. (It’s also a bit exciting….)

We spent most of the first day playing in the waves on the beach. The water is a really warm 75 degrees and it was quite a shock to this northern fish! It’s also fantastically clear and an uncanny aqua blue. For someone used to fresh water, I was shocked by how buoyant I was! It’s hard to dive down without bouncing back to the top, and there’s rather a lot to look at down there!!

Weather note: It is SO easy to burn in Hawaii. The weather in late April was incredibly perfect and it was tempting to get a bit of a tan but don’t chance it. The sunscreen is a must if you don’t want to spend a week in paradise in pain. I used a ton of it, and don’t bother bringing it from the mainland as it has to be reef-safe. It’s for sale absolutely everywhere and many of the hotels have dispensers right as you leave the sidewalk for the beach. The Whaler didn’t provide it but there was plenty for purchase.

Which brings us to… Shopping!!

Maui Hack—These marvelous convenience stores on the southwest side of Maui called ABC Stores will sell you everything you forgot to pack. Plus, the famous olulani (?) flower is featured on a lot of gorgeous jewelry, but it’s by far the best deal at ABC and the jewelry is silver and very very pretty. You can also buy your Hawaiian irregular pearls at ABC, in big strings ranging from $15-$30. I came home with an anklet, earrings, and several bracelets before I decided I should restrain myself from buying any more Shiny Things. I know it’s a tourist thing, but it should be part of your 5 Day Maui Itinerary!

For higher end jewelry, there is so much to choose from in Whalers Village, with the most advertised being Maui Diver Jewelry. Pearls are really big, of course, but there are some beautiful things made out of blue or black coral too!

Clothes!–Pack very casually for Maui, which is a very laidback and sandy vibe, although some light and pretty dresses and light colored pants are nice for dinner and after the sun goes down around 6:30. I spent most of the time in sporty crop top/shorts swimsuit and flowered coverup, although a loose flowered jumpsuit or white linen pants hit the spot right around dinnertime.

Day Two

Running on the Beach

I’m a distance runner and no day seems complete that doesn’t start with a sunrise run, and what luxury to run along such a gorgeous beach! The paved walkway in the resort area is a favorite, and if you follow it east towards Lahaina there is a paved trail that continues all the way to town. The view is much rockier with waves crashing into great black lava boulders. Keep your eyes on the sea as you may see breaching whales farther out or the famous sea turtles in the surf near shore. I saw a small turtle crashing about in the surf and it was amazing he didn’t seem to mind getting bounced off the rocks!

Surfing at Whaler’s

Some of our party were surfers, so we headed down the beach to the east towards Lahaina where there was easy access to some great but not too threatening waves. It was really fun to watch! The rest of the party swam the waves, and I acclimated to snorkel gear and fins. One of our party got caught in the riptide and had a hard time getting home, which was a sobering lesson on how to deal with the ocean—basically, don’t fight the waves, float and swim carefully parallel to shore and the waves will eventually spill you out on the sand.

Most people who get in trouble in riptides get exhausted from trying to fight straight to shore, but the backwash of the waves will carry you farther out at that point so it’s much better to come in on a very long diagonal and DON’T PANIC. Less confident swimmers really need flotation devices of some kind in case the waves pull you out farther than expected, and they can be pretty brutal on this portion of the beach.

The waves are impressive here if you aren’t used to ocean. If you turn your back when coming into shore, you WILL get clobbered. The other rule is that you need to walk backwards into and out of water when wearing fins or they will trip you up and you will also get clobbered by a wave. The ocean is  a pretty powerful beast here!! But you can’t have a 5 Day Maui Itinerary without making friends with the great Pacific.

We really enjoyed Star Noodle for dinner–it was perfectly amazing–but the recent tragic fires in Lahaina have made this experience out of the question for now. Lahaina has all our thoughts and prayers and support, and we have wonderful memories of it.

Clothes–I know these are bikini beaches, but keep in mind you can inadvertently lose your suit to an overexcited wave. A cropped halter-top from Apana and board shorts was the perfect choice to go from swim to shop or lunch. Star Noodle is an upscale restaurant and while we were all still beach casual, we dressed up a bit more than sandy swimsuits for this one.

Day 3

Snorkeling Onolua

We drove up just north of the village of Kapalua to a small cove known for beautiful snorkeling. It was my first experience and I nearly hyperventilated at my first sight of Pretty Fishies. We walked about half a mile through a jaw-dropping jungle populated by—not kidding—wild chickens. The chickens have totally taken over the beach and will poach your food so mounting a Chicken Guard with one of your party isn’t a bad idea. This stop is both on our Maui Snorkeling Guide and our 5 Day Maui Itinerary. https://foodieontheroad.com/maui-snorkeling-guide/

The rocky beach is a little challenging to enter with fins, and you really DO need them. The waves aren’t high here, but remember to walk backwards until you can start swimming. One of the party scraped feet on the exit and it was pretty painful. Avoid getting too close to the rocky sides of the cove, but just a little out from there is pretty magical.

Onolua was a fantastic snorkel experience, with great visibility and very diverse wildlife darting in and out of the gorgeous corals. I had a wonderful time diving to the corals with my GoPro chasing fish I’ve only ever seen in aquariums. This first experience was a wonderful stop on our 5 Day Maui Itinerary.


Maui hack: to dive with a snorkel, make sure to point your head straight down until your fins are underwater, and kick down hard. Otherwise you pop right back up like a bobber. Remember to blow out and clear the tube!! This is a slightly more advanced location than the snorkel tour boats, but with general caution it’s a life-changing memorable destination on our 5 Day Maui Itinerary.

Gear–You can rent snorkel gear very cheaply from most of the resorts, and it’s worthwhile usually to rent for a week and take advantage of the better gear than the ones in the ABC Store. However, buying a mask for $15 and fins for $30 isn’t a bad option, it’s just that the rented gear works a bit better. Next time, I would just take that option.


After snorkeling we headed up the coast to a cave-riddled point with a tiny hole that exploded periodically with water just like a spouting whale. While you don’t want to get too close, it’s an unforgettable sight. The climb down is kind of like the surface of Mars, all red dirt and uncanny rock formations, and the waves are hugely powerful here. You won’t forget this stop on the 5 Day Maui Itinerary.

The cliffs of the Blowhole, a highlight of our 5 Day Maui Itinerary

Clothes—for snorkeling and surfing, wear a long-sleeve rash guard shirt which also have the benefit of looking cool AND keeping you from getting fried. If you can, rent or bring a wetsuit because it makes all the difference in how long you can stay out. Deeper water is cooler and you don’t always realize you are getting chilled because there is so much to look at!

Day Three

Black Rock

Due to some showers in the afternoon forecast, we spent morning on the beach at the Whaler to take advantage of the sunshine, and it’s only a short walk from there up the coast to the snorkel spot at Black Rock. This is very popular but sometimes visibility is down due to a lot of wave action. It’s very important to stay within the rocky point of Black Rock as there is a very strong current that can sweep you out quickly just beyond it. Snorkeling here is unique and amazing. Bright fish and schools flock this area near the rocks and there’s a lot to see.

Turtles love this spot, and I swam beside a huge male who calmly turned his head and looked at me with mild curiosity. Turtles are very protected and it’s required to give them space and not crowd them, but they are also generally pretty unfussed by sharing the sea with humans. Once in awhile they will accidentally swim right into you in a “scuse me pardon me” sort of moment, so don’t panic if they do. They are HUGE, weighing hundreds of pounds, and a pure gentle miracle of creation. https://foodieontheroad.com/maui-snorkeling-guide/


We headed northeast into the Upcountry, which is much more local and wilder landscape than the resort areas. Those of our party that had come before said that this was their favorite part of Maui, and you can even stay on a banana plantation! 

Twin Falls

Wailele Farm in the Ho-Olawa Valley gives public access to the gorgeous Twin Falls, with beautiful trails through the jungle to a magical hanging rock outcrop with a lacy fall over the edge. You can swim through the misty blue green pool to get a shower under the cool and refreshing waterfall and explore the shallow cave area under the waterfall. It’s like something from another world, unearthly gorgeous. It’s a must see on your 5 Day Maui Itinerary.


Hiking and surfing are a big part of this area, and on days with good visibility, there is a great climb to the top of Mount Haleakala which is 10,023 ft up!! We didn’t make this hike due to heavy cloud cover but would love to come back and try it.

Surf Beach at Ho’okipa

We went along the coast to a great spot where there was an overlook to watch surfers on Ho’okipa Beach casually challenging some killer huge waves. Not a spot for novices but very very fun to watch!!! There were probably 50-60 very experienced surfers of all ages at each wave spot. This is not a beach for tourist surfing as it’s extremely wild! But even just watching is highly recommended on your 5 Day Maui Itinerary!

Paia Village

Paia is a tiny town in the upcountry with great food and drink options. This is a fun local place for dinner and shopping to end the day. The town has a beach with a great sunset too! I wish we had had more time to shop and explore–make sure to make this part of your 5 Day Maui Itinerary,

Day Four


We had a spectacular and memorable time shopping, eating, and exploring Lahaina, just two miles from Whaler’s Village. It was one of the highlights of our 5 Day Maui Itinerary. Unfortunately, catastrophic wildfires in 2023 recently destroyed this historic town, leaving only our memories. We grieve with Maui in this time of tragedy.

For more information about how to help the residents and businesses of Lahaina, see this recent article in USA Today.


Day Five

Snorkel Tour Pride of Maui

This portion of our trip was also covered in my review of Best Maui Snorkeling Guide Stops: https://foodieontheroad.com/maui-snorkeling-guide/


Snorkel Tour with Pride of Maui to Molokini Crater and Turtle Town was an absolutely epic adventure which we cannot recommend highly enough. A highlight of our 5 Day Maui Itinerary!!! Non swimmers, strong swimmers, old, and young all had fun on this well-run tour. They are well stocked with gear from flotation to snorkel to wetsuits, and even—for the adventurous—a Snuba Tour, which is a cross between snorkel and scuba in which you are attached to an air hose in a group and can go down about 12 ft (added $68 cost).

The basic tour is $198 and we didn’t regret any of it. WOW. The staff took good care of everyone and made sure it was a smooth and memorable experience. From continental breakfast to outstanding snorkeling at two amazing locations to grilled lunch on the boat and an open bar after, it was a wonderful way to experience the underwater world of Maui in a very safe and happy way.

The End

Although the face of Maui has changed with the recent fires, we hope that this beautiful place will recover and flourish again. Some of these places have changed and many were spared, so come and explore this beautiful piece of tropical paradise. We hope you enjoyed our 5 Day Maui Itinerary!

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