The Ultimate 5 Day Maui Itinerary

This is a guest post by Caresa. You can find out more about her at the end of this article.

It’s no secret that planning a vacation is quite overwhelming. Between doing research on your destination, choosing your accommodations, and finding activities, it can get pretty stressful. Luckily for you, I have put together the perfect 5 day Maui itinerary to make your trip planning a little smoother.

The island of Maui, Hawaii is known to be its own little paradise – from breathtaking beaches, perfect weather, phenomenal locals, to fun activities all around. It doesn’t get much better than this. It’s listed as one of the best mother-daughter getaways in the USA!

I have had the pleasure of visiting Maui twice already and each time, it never fails to amaze me. In this Maui 5 day itinerary you will find nothing but the best tips to create the perfect vacation.

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Maui 5 Day Itinerary | Footsteps of a Dreamer

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Related: Best 2 Weeks in Hawaii: Itinerary & Travel Tips

Maui 5 Day Itinerary

Day 1

Snorkel to Molokini Crater

Out of all the Maui activities to check out on the island, snorkeling in Maui’s pristine clear waters has to be among the most popular. Start off your day with a snorkeling trip to Molokini Crater. Known as Hawaii’s most popular snorkeling destination, this tour lasts roughly around five hours. Although there are many different tour companies to bring you to the crater, Pride of Maui offers the best tours on the island. The tour comes with all the gear needed for an amazing snorkeling experience, breakfast, lunch and my personal favorite part of it… Open bar on the way back. You really can’t beat that one.

Lunch at Down the Hatch

If you’re staying in or near Lahaina, one restaurant that is an absolute must to add to your Maui 5 day itinerary is Down the Hatch. Located right in the heart of Lahaina, this restaurant is to die for. Not only is the food amazing but Down the Hatch also offers live music. A fair warning though, it does get extremely busy so finding seating can be a difficult task sometimes since it’s a seat yourself restaurant.

Down The Hatch Maui Hawaii | Footsteps of a Dreamer

Relax at Ka’anapali Beach

After your adventurous day, there is nothing better than ending it by laying out a towel and relaxing on Ka’anapali Beach. Watch the sunset as the day comes to end, preparing for the night to come, before a new day makes its way through.

Drinks at Maui Brewing Co

As the night arrives, you might be in the mood to kick back and unwind — and what better way to relax than enjoying a nice beer at Maui Brewing Co. This awesome bar also comes with an ice bar to keep your drinks cold at all times.

Maui Brewing Co Maui Hawaii | Footsteps of a Dreamer

Day 2

Zip-line through the Maui Mountains

If you are looking for more adventurous things to do in Maui, you must add zip-lining through the mountains to your Maui 5 day itinerary. Since those scenic sights are not witnessed too often, it was an absolutely breathtaking and magical experience. When I went zip lining, I went with Skyline Eco-Adventures in Kula, HI. Everything from the tour guides to the experience was absolutely exceptional.

Lunch at Kula Lodge

Located about three miles from Skyline Eco-Adventures, you will find the Kula Lodge. A million five star reviews wouldn’t be enough for this restaurant. Kula lodge is located at 3,200 feet elevation and is just down the road from Haleakala National Park. I highly recommend eating outside as you will be blessed with some magnificent views of Hawaii.

Kula Lodge Pizza Maui Hawaii | Footsteps of a Dreamer

Check out Ali’i Kula Lavender Farm

As you start making your way back down to town, you will come across Ali’i Kula Lavender Farm. It is on the way back down from Kula Lodge and a sight that you don’t want to miss. The sweet fragrance of lavender will come creeping up your nose as you witness fields of beautiful lavender flowers. It only costs a few dollars to get in, and the farm also makes for some awesome photo ops!

Lavender Farm Maui Hawaii | Footsteps of a Dreamer

Explore Downtown Lahaina

After making your way back into town, end your night by letting your wanderlust run free in downtown Lahaina. With so many awesome bars, restaurants, shops, and boutiques there is so much to do in this little town. It’s also a 3 minute walk from the beach, just in case you decide to just take it easy the rest of the day. It also makes for a great place to stay while in Maui.

Day 3

Breakfast at The Gazebo

They aren’t lying when they say that breakfast is the most important meal of the day. Start your day off right with some nice breakfast at The Gazebo, located in Lahaina.

Road to Hana

This one goes without saying, but you can’t just visit Maui without adding the Road to Hana to your 5 day Maui itinerary. The Road to Hana is world famous, and if you plan on making stops it will be a day long trip. Depending how many stops you make, the drive can last up to 12 hours, but it is worth every single minute. Also, make sure to remember your nausea medication since the Road to Hana is equipped with 620 turns and 59 bridges. The roads are extremely narrow so drive carefully and pay a lot of attention to other drivers. Along the way there are so many beautiful sights and hikes, including but not limited to The Bamboo Forest and The Seven Sacred Pools. For more information, you can check out this detailed Road to Hana Guide.

Road to Hana Maui Hawaii | Footsteps of a Dreamer

Dinner at Mama’s Fish House

Maui is known for having some of the best seafood out there. I mean, considering it is so close to the ocean, I would certainly hope so. After the Road to Hana make sure to check out Mama’s Fish House for an amazing dinner with a killer ocean view. Mama’s Fish House is almost a 5 star restaurant and it earned every single one of its stars fair and square. Plus, it’s one of Maui’s best gluten free restaurants!

Day 4

Hike Waihee Trail Hike

As much as I love a nice relaxing day by the beach, when I was in Hawaii I made it a point to go on at least one hike. The hike I decided to go on was Waihee Trail Hike located near Wailuku. This hike definitely has the best of both worlds. You will get a panoramic ocean view on one side and a mountain view on the other side. It is a little strenuous at first, but it gets easier. and is around 4 miles round trip.

Waihee Trail Hike Maui Hawaii | Footsteps of a Dreamer

Lunch at Cafe O’Lei

After your Waihee Trail Hike, make sure to stop at Cafe O’Lei for a nice lunch to refuel your body. The seafood at Cafe O’Lei is amazing, and it is known for its famous Mahi Mahi.

Check out Big Beach/Little Beach

Everyone knows that Maui has some gorgeous beaches, but one thing that many people don’t know is that one of the most beautiful beaches in the world resides in Maui. Located in Kihei, Big Beach is hands down the best beach on the island and also listed as one of the world’s most beautiful beaches. It has crystal clear water along with perfect, golden sand. Also, another little secret that the majority of people don’t know is that only a short hike away from Big Beach is Little Beach. Little Beach is a clothing optional beach and just as beautiful as Big Beach. If you do decide to check it out, make sure to wear lots of sunscreen. Otherwise you will have sunburns places no one should ever experience sunburns.

Big Beach Maui Hawaii | Footsteps of a Dreamer

Drinks at the Grotto Bar

The Grotto Bar was one of my favorite bars in Maui with the best atmosphere. It is located in the Hyatt Regency in Lahaina and the bar is inside a cave surrounded by waterfalls.

Grotto Bar Maui Hawaii | Footsteps of a Dreamer

Day 5

Watch the Sunrise at Haleakala

There is no better ending to your trip than watching the sunrise at Haleakala. Although, it will be an early wake up call, that is one view you are not going to want to miss. Many companies offer tours to watch the sunrise, but a tour guide is not required. As you stand above the clouds, it is a perfect way to start the last day of your perfect vacation.

Stand up Paddle Boarding

Another famous activity to add to your 5 day itinerary Maui, is stand up paddle boarding. Makena Landing is a huge spot for paddle boarders who come from all over the world. Whether you’re a beginner or an expert, paddle boarding is such a fun activity. Although, if you’re a beginner, I would suggest taking some lessons before going out by yourself. The Maui waves are no joke.

Standup Paddle-Boarding Maui Hawaii | Footsteps of a Dreamer

Lunch at Matteo’s Osteria

Everyone loves Italian food. Matteo’s Osteria is a magnificent Italian joint on the island. It holds 4 stars and has an amazing atmosphere along with some delicious cuisine!

Dinner Cruise

Another great Maui activity, which is the perfect end to your day is a sunset dinner cruise. Along with delicious food, live entertainment and an open bar, there is no better way to watch the sunset on such a beautiful island.

Sunset Dinner Cruise Maui Hawaii | Footsteps of a Dreamer

Maui Tips

Here are my tips on the best transportation arrangements, lodging accommodations, and what to pack for the ultimate Maui vacation.

What to Pack for Maui

Me being from Las Vegas, our packing guide is a whole world of difference than Maui’s. Maui weather is perfect almost all the time, so you will really only have to worry about which summer outfits and swimsuits to bring. Although, it did rain a few times when I was there, so make sure to prepare for rain. Oh, and also don’t forget the bug spray! The mosquitoes over there have no mercy!

For more information, check out this detailed Maui packing list.


Maui is a relatively small island. When I first arrived, it was around midnight. Therefore, when I tried to call for an Uber there was none available. I would suggest renting a car so you are free to explore the island as you wish without being restricted on time or racking up your Uber bill.

Where to Stay in Maui

After doing an extensive amount of research, I found out that hotels in Maui are a lot more expensive than AirBnb’s. When searching for my week long home, I found amazing deals on AirBnb, and I even ended up getting a balcony with an ocean view!

Caresa Guest Post | Footsteps of a Dreamer Hi there! My name is Caresa. I am a travel and fashion blogger at This Spontaneous Life. I just recently sold all my belongings to become a minimalist and be able to travel the world without limitations.

Want more from Caresa? Check out her website or follow her on Instagram!

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Maui 5 Day Itinerary | Footsteps of a Dreamer

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