Best Way to Spend 5 Days in Maui Itinerary

I absolutely love Hawaii- it is one of my favorite places on Earth. I had only been to Kauai and Oahu so when I found a Cyber Monday flight deal to Maui, I knew I had to go and see what this island had to offer and it didn’t disappoint! I have put together what I believe is the perfect 5 days in Maui Travel Itinerary!

Best Places to Stay

South Side:

Fairmont Kea Lani Hotel:

Staying at the Fairmont Kea Lani was so dreamy. The hotel is very luxurious, has 3 swimming pools, multiple restaurants and has its very own beach. You seriously don’t even have to leave the resort because there is so much to do here including lots of fun activities for families and their kids. I have written an entire post about my stay here.

THERE Maui House:

THERE Maui House is the perfect place to stay if you are traveling with family or a group of friends. It is very spacious with a full living room/entertainment area with a huge couch and tv for movie nights after playing in the sun all day. There is also a full kitchen which is super nice so you can go grocery shopping and save some money on food since a lot of the restaurants in Maui can be on the more expensive side.

The hosts Klara and Brandon live in the house next door in case you need help with anything and they are so sweet and accommodating. I loved the decorations in the house and it was very cute and cozy. They also have two decks which are both so nice. One even has a succulent wall which was really adorable. One of the perks of staying here is that you are in a quiet and safe neighborhood close to tons of beaches, shops and restaurants. Also, they have boogey boards and other outdoor gear that you are free to use during your stay which is so fun!

Use this

West Side: Royal Lahaina Resort

Rental Car:

Click here to book your rental car from my favorite rental car website for great deals!

DAY 1 Central Valley Adventure – Maui Travel Guide

5 days in Maui may not seem like a lot of time and I agree I could spend so many more days here, but I assure you there is plenty of time to relax or adventure depending what you want to do!

9 AM- Fairmont Breakfast Buffet

Start the day off with a hearty breakfast at the hotel. This is one of the best breakfast buffets I’ve ever had! There was so much to choose from including an omelet bar which was sooo good! They also had an area with fresh baked goods every morning like various banana breads, muffins and an amazing macadamia nut sticky bun that was to die for! They also served fresh juice every morning and this was seriously the best way to start the day!

11 AM- Iao Valley State Park

Iao Valley State Park is a definite must while on Maui, as we were pulling up, it felt like we were pulling up to Jurassic Park! There is a small fee to get into the state park, but I think it is worth it. The state park is pretty small and a great place for families because there are mostly just beautiful walks all around, not really any arduous hikes. There were some really beautiful garden areas here along with the defining feature of the park “The Needle”- a mountain peak that sticks straight up like a needle.

1 PM- Lunch at the Mill House

The Mill House is a farm-to-table restaurant located at the Maui Tropical Plantation, only about a 15 minute drive from Iao State Park so it is perfect to do these two on the same day. I absolutely loved walking around the Maui Tropical Plantation and seeing all of the different flora and fauna- it was absolutely beautiful! There was a small river with a stunning green mountain backdrop. There were also a lot of really cute ducks walking around that you can pay to feed if you want- something that is really fun for kids (or kids at heart!)

After walking around a bit, we headed to our lunch reservation at the Mill House (Reservations are required in advance as this place is one of the most popular restaurants on Maui!) The setting of the Mill House is absolutely stunning. There is normally outdoor dining, but unfortunately it was raining on the day that we came so we had to eat inside, but the views and ambiance were still beautiful. I absolutely loved the design of the inside of the restaurant- it was so unique and there was even part of a train inside which was really cool!

Now on to the food- it was sooo good! The food is so fresh because it is all produced right on the island and it was truly to die for. The rolls were probably the best I have ever had. Our group tried a hamburger, fries, a beef pasta and a taro risotto and everyone was happy! They are also really well known for their craft cocktails/mocktails and there are so many to choose from. You can’t go wrong and all of them are beautifully presented. I was so excited that my drink came out in a cup that looked like a pineapple- such a fun touch!

3 PM- PaiaHo’okipa Beach

After lunch, we decided to head to the nearby town of Paia because I had heard great things about it. Paia did turn out to be a cute little town with colorful little cafes, murals and boutiques everywhere. We had fun wandering around for a little while taking pictures by murals and looking in some of the boutiques. There are some popular food places in this area as well in case you didn’t eat at the Millhouse.

After Paia, we headed 8 minutes down the road to Ho’okipa Beach and it was one of my favorite beaches on the whole island of Maui! It is famous for it’s huge waves and surf and sea turtles! Tons of sea turtles come up on the beach to rest. We saw at least 30 of them which was so special! (Make sure to stay a safe distance away as not to bother the cute little turtles).

6 PM- Sunset

No Maui travel guide would be complete without mentioning sunset. The sunsets in Hawaii are gorgeous so you’ll want to catch as many as possible! Before dinner, head back to your hotel to freshen up and catch the sunset. The sunsets were gorgeous from my balcony at the Fairmont, a great view would also be down at Fairmont’s own beach- Polo Beach.

7 PM- Dinner at Ko

Ko is Fairmont Kea Lani’s award winning signature restaurant- offering plantation-inspired cuisine featuring Hwaiian, Chinese, Filipino, Portuguese, Korean and Japanese menu items. This meal was so delectable and a definite must when on Maui. I tried to be adventurous and tried a lot of new things which were really delicious. All of the food tasted very fresh and I loved the sauces and everything they were cooked in.

Day 2 Pool, Beach and Luau – 5 Days in Maui Itinerary:

10 AM Breakfast

Wake up and have another breakfast at the Fairmont buffet. If you are not staying at the Fairmont, Kihei Café is a popular breakfast café on the south side of Maui.

11 AM- Pool Time

There is so much to do in Maui, that you might want to be go, go, go, but it’s important to remember to have a day to relax! We decided to spend the afternoon at the Fairmont and spend time in their 3 different pools. One was an adult’s only pool and one of the pool’s even had a waterslide and swim up bar! We decided to try out the pool cabanas and it was amazing! You rent a cabana for the day to relax in and you have your own personal butler that brings around snacks and drinks constantly. They leave a cooler with you with various juices, water and soda and snacks like macadamia nuts and fresh pineapple! It was the best way to spend the afternoon!

sitting in a cabana with tropical back drop and holding a banana

2 PM- Beach Time

After hanging out at the pool and cabana for awhile, we decided to check out the beach- Polo Beach. If you are staying at the Fairmont, they will bring you beach chairs to lounge on and an umbrella- which is so nice. They also have snorkel gear you can check out for an hour. If you really want to, you can take a walk on the beach pathway that connects several of the beaches on the South side together. However, Polo Beach is a really nice beach so you might just want to hang out here for the rest of the afternoon.

My flower crown was made by a local named Andrea, she is so sweet and talented and if you want to get one on Maui, check her out at @petite.maui on Instagram.

5:30 Old Lahaina Luau

I had a ton of fun going to this luau! One of the things I love about traveling is experiencing different cultures so I absolutely love going to luaus because I enjoy seeing the dances and entertainment from so many Polynesian cultures! And of course, trying so many different foods too! Old Lahaina Luau is the most popular luau in Maui for good reason! The setting is incredible right next the beach so you get to watch the sunset right at the luau. The performances and stories/history of Maui were incredible. I loved the food, but especially the dessert! Oh and also, they had guava butter for the rolls which ended up being so incredible! I felt like this luau made our Maui trip extra special.

5 Days in Maui Itinerary

DAY 3 South Side Beach & West Side Road Trip: Travel Guide to Maui

10 AM- Big Beach

Makena Beach, otherwise known as Big Beach, is one of the most beautiful in all of Maui and perhaps the most popular beach on the South side for it’s pristine sand and it’s turquoise blue waters. This beach is the perfect place to go swimming and the water feels so nice! While sitting at the beach, I noticed there was a pathway to come up to this viewpoint looking over the beach so I had to go check it out and it was totally worth it! This cliff side also shows you views over Little Beach- but be warned, Little Beach is a clothing optional beach so that person you are seeing is probably not wearing a nude- colored swimsuit like I first thought! Haha.

12 PM Makena Cove

Just a half mile down the road from Big Beach is Makena Cove- a beautiful and secluded cove where you won’t find many other tourists. This area is popular among locals and wedding photographers. It can be hard to figure out where to park for Makena Cove because this is a residential area and the streets aren’t very wide. We just kept going down the street until we found a parking spot. We hung out here for a little while and it was a great place for pictures with all of the cool lava rock everywhere.

1 PM- Lunch at Peggy Sue’s Diner

After hanging out at the beach all morning, head over to Kihei for a bite to eat. There are so many food options, you can’t go wrong! I initially headed to this are to try out Coconut’s Fish Café- known for their famous fish tacos and I planned to go to Wow Wow Lemonade after- also famous, but for their lemonade. Both places looked really good and were really busy. However, I ended up falling upon a diner right next to Coconut’s Fish Café. I absolutely love old school diners and our group was in the mood for cheeseburgers since we had so much seafood for dinner a couple nights before. The Diner was called Peggy Sue’s and it was so cute. This is definitely another great food option! I had the chicken fingers combo and a rootbeer float and both were delicious, but the ambiance of the diner was definitely the best part.

2 PM- West Side Road Trip- Stop for a snack

After lunch, we headed up to the West side of the island to see what it had to offer! The drive was very scenic and beautiful and you are along the ocean for most of the way! We decided to stop for a quick snack break at Olowalu Fruit stand. The food truck was so cute and my friend ordered a drink right out of a pineapple which was so fun! They have tons of fresh fruits and even some fruit samples which was nice! Right next to Olowalu is the very popular- Leoda’s Pies. They are most famous for their- you guessed it- pies! They make tons of different flavors and they come in mini sizes so you can take them to go with you!

3 PM- Kapalua Bay

There are a lot of beautiful beaches on the West side, but I had heard great things about Kapalua Bay. I was excited to check it out because it was said to be less busy than some of the other nearby beaches and have amazing snorkeling. The beach was indeed very beautiful and I don’t have a picture from the actual beach because I put down my camera for once and had a blast playing around and swimming in the water. It was great! The setting was beautiful inside of a secluded cove. I recommend heading over to Snorkel Bob’s before you come here and renting some snorkel gear- it’s very cheap and definitely worth it!

6 PM- Sunset at Lahaina Beach

We transferred hotels and checked into the Royal Lahaina Resort – a beautiful property in a beautiful area right on the beach. After our long day and road trip adventure, my husband and our friend took a quick nap and I woke them up right in time for sunset. We were able to just walk right down to the beach to see the sun setting. This beach was huge! Tons of different resorts are lining it so there were a lot of people out to catch the sunset, but that didn’t take away from this beach’s charm.

7 PM- Dinner at the Beach Club

After sunset, we headed over to the Aston Kaanapali Shores, an Aqua-Aston Hospitality property because I heard great things about their dinner at the Beach Club. Our server was seriously so helpful and gave us so many tips for Maui which was so nice! We loved our smoothies and the food! We had teriyaki skewers, calamari and a chef special for the appetizers and they were great. My husband tried the ribs for dinner which were so good and I had the BBQ chicken with pineapple flatbread and it was very flavorful, it was amazing! For dessert, our server convinced us we had to try the macadamia nut pie even though we were so full. You always have room for dessert, right? It did not disappoint- it was phenomenal!

The Beach Club is in a really beautiful area and I think it would actually be a good place to come for lunch or during sunset so you can really appreciate the beautiful surroundings!

DAY 4 Road to Hana – Maui Itinerary:

5:30 AM- Head to the Road to Hana

We had a very early wake up call this morning because we were planning to head to the Road to Hana and we wanted to try and beat a great majority of the tourists.

6:30 AM- Stop in Paia

We stopped in Paia on our way to the Road to Hana to fill up on gas- definitely make sure you do this! We also made sure to take a bathroom break and we got some snacks and a quick breakfast to go. If you don’t see anything to suit your fancy at the gas station, there is a really cute store a few miles away from the Road to Hana called Jaws and I wish I would have stopped there. It looked adorable!

Road to Hana

I will probably end up writing a Blog Post just about the Road to Hana because I have so much advice and suggestions, but you can’t have a Maui travel guide and not have the road to Hana, so here is a basic overview. There are so many stops on the Road to Hana- it can be overwhelming! Try and do as much research as you can before and at least have a handful of places you know are must do’s for you.

There are probably going to be cool stops that you are going to have to pass up just because realistically there is not time- unless of course you stay in Hana (which I would really love to do one day to explore this area more in depth!) One reason you want to get here as early as possible is because parking is very limited so if you get here hours and hours after everyone else, there might not be a place to park in some of the places you really wanted to see.

Another reason is that you will want to be out of the Road to Hana area before dark. This can already be a dangerous and sometimes scary road so I can’t imagine driving it in the dark. There is a backside of Hana road, but it is said to be even more dangerous and scary than the Road to Hana itself so I didn’t want to risk it- so like most people- we drove back the same Road to Hana route.

Road to Hana Highlights: 5 days in Maui itinerary

Here are some of my very favorite places that we stopped on the Road to Hana!

Keanne Lookout/Aunty Sandy’s Banana Bread

Puak Ka Way Falls

Koki Beach- Red Sand Beach

Black Sand Beach

Bamboo Forest

DAY 5 Snorkeling, Haleakala Crater and Upcountry

Although this is the final day of your 5 days in Maui Itinerary don’t worry there is still so many amazing things to do!

8 AM- Snorkel Molokini Crater

Snorkeling in Maui is definitely a great experience! Molokini Crater is a crescent shaped island just off of Maui that is incredible for snorkeling because of all of the marine life over there, including sea turtles! The snorkel tour is so fun because the crew is amazing and makes sure that you are taken care of. Two meals are included with your tour! Lunch includes things like kalua pork sliders, fresh pineapple and mac salad! The lunch is delicious and definitely an added bonus. The snorkel tour also goes to this area commonly referred to as “Turtle Town” after Molokini Crater so you get to try out snorkeling in two different locations which is so cool! I highly recommend going on this tour.

One of the things I love about this tour is that it is perfect for the whole family! If you have never been snorkeling before, they will teach you how to snorkel. If there are members of your family who don’t want to snorkel, that’s ok too because they have a glass bottom viewing room so you can see the marine life right from the boat! This would be perfect for my dad and grandparents who don’t want to get in the water!

12 PM- Haleakala Crater

Haleakala Crater is a dormant crater on Maui with incredible views. Many people visit during sunrise or sunset. Be aware if you visit during sunrise, it is very packed and you will have to wake up really early. Also, you will need to purchase a $1 permit in advance. Unfortunately, there were no slots left when I went to purchase a permit. Sunset is equally as beautiful and you are literally above the clouds. The views are incredible! I actually was really surprised by how much I loved the drive up to the crater. I felt like I was in Ireland or New Zealand- not Maui. It was absolutely stunning. For my itinerary, it didn’t work out to go to the crater at sunset or sunrise, but I thought it was still worthwhile going during the day!

However, we had quite the adventure. The weather did not want to agree with us and apparently in the Winter, it can actually snow up by the crater. Haha so we drove all the way up and could not see a thing and the roads were getting snow packed so we had to head down the mountain immediately. Make sure to check the weather forecast while you are in Maui and you might have to switch your itinerary around a little bit.

2:30 PM- Upcountry Maui

After you visit the crater, spend a bit more time in upcountry. This area is beautiful after all! Two of the top activities I recommend are the Surfing Goat Farm and the Lavender Farm. I thought the Surfing Goat Farm sounded too cute/funny to pass up. (They are not actually surfing in the water haha). This is a working goat farm and you can take tours to meet the goats and learn about the farm for an extra fee. We decided to just visit and say hello for free and not take the extra tour. Basically, there are surf boards all over the goats’ pen that they hang out on which is so cute.

Also, in upcountry there is a Lavender Farm which is really beautiful. You are pretty high up so you get amazing views of Maui and the ocean. The gardens are really beautiful to walk around and the lavender is stunning- not to mention smells really good! Eat lunch at the nearby Kula Lodge.

4:30 PM- Wailea Shops, Shave Ice & Wailea Grand Resort

After spending time in upcountry, we headed back down the mountain to get some beach time, unfortunately it was raining pretty hard so we had to improvise. (Tip: this happens a lot in Maui so you might have to improvise your itinerary on the fly a lot and bring rain jackets! I forgot mine at home and it was one of my biggest regrets!) Since it was raining, we decided to check out the Wailea shops. This shopping area is very upscale and has some really adorable boutiques. After window shopping, we decided we needed some Shave Ice so we stopped by Uluani’s Shave Ice and it was sooo good!

We then walked around the Wailea Grand Resort because it’s where Just Go With It with Adam Sandler and Jennifer Aniston was filmed. We had just watched the movie so we thought it would be fun to walk around and see the property. The property was truly incredible!

6 PM- Sunset at Wailea Beach

Wailea Beach is really beautiful and the perfect place to catch your last sunset in Maui!

7 PM- Pizza Food Truck

To end the epic day, try Outriggers Pizza in Kihei. It is an unassuming food truck, but the pizza is so delicious! It had great reviews online and apparently it is really starting to make a name for itself. Guy Fieri has even been there before! My husband and our friend said it is some of the best pizza they have ever had! We tried pepperoni, chicken bacon ranch and spicy buffalo chicken. The chicken bacon ranch was our favorite! It is the perfect stop before heading home on your red eye flight.

Depart Maui

After an amazing 5 days in Maui it is sadly time to depart. You might be leaving, but it’s never good bye, just a see you later or hopefully see you soon!