I traveled to Maui, Hawaii for my 25th birthday! The biggest (well, only) perk of turning 25 is being able to rent a car without fees.. so of course I had to make it special!
Maui is home to the famous Road to Hana where you get to explore hidden beaches, swim in waterfalls, see red & black sand beaches, and drive a winding and challenging road. What better road trip to celebrate my 25th than that?!
Whether you like to relax on the beach, do some thrilling excursions, or dive into the culture of Hawaii.. Maui is the perfect location for everyone!
In this 5 day Maui Itinerary, I go over the stuff you need to know before going (when to go, where to stay, what to pack, etc.), a full Maui Itinerary for 5 days, and a bonus section at the bottom of this guide in case you want to extend your trip! 🙂
Here we go…
There’s a chance this free guide contains affiliate links. This means that if you make a purchase through some of these links, I may make a small commission (at no extra cost to you) that goes towards little Rosie’s dog treats! This trip was also graciously hosted by Kaanpali Resort Association, Hyatt Regency and Aston at the Whaler. As always (and per FTC Guidelines), all opinions are my own!
Maui Itinerary Overview
Day 1: Explore Kaanapali Beach & Best Luau on the Island
Day 2: Ultimate Road To Hana Itinerary
Day 3: Snorkeling at Black Rock & Sunset Catamaran Cruise
Day 4: Golf (Or Tour Recommendation) + Best Sunset Spot on the Island
Day 5: Explore the Untouched Beauty of the North Side of Maui
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Where to Stay on Maui?
West Maui is the most popular place to stay, specifically Kaanapali Beach! This is where you will have access to all the best resorts, best restaurants, best beaches, best snorkeling, best golf courses, and more (are you seeing a trend here?)!
There are many resorts along this stretch of beach, so I decided to split my time between two hotels to see which one I liked best!
The first one I stayed at was the Aston at the Whaler, which was amazing! It is a condo style hotel, so you will have a huge balcony, full kitchen, living area to relax in, and it is a very quiet property. The hotel was also in the best area of Kaanapali beach, located right in between Black Rock Snorkeling (best on the island) & Whaler’s Village (where all the restaurants & shops are).
The rush after COVID (when I went) was WILD. You would have to make reservations 2 weeks out or… you aren’t eating! It was really nice to have a full kitchen and dining area to eat breakfast / lunch at.
For the second half of my stay, I stayed at the Hyatt Regency, which was BEAUTIFUL! It’s a resort-style hotel, so you will have a large pool with waterslides, swim up bar, cabanas along the beach, and several restaurants on the property. Not to mention they also have penguins, flamingos, and swans on the property.. which for an animal lover, that’s all I could ask for! 🙂
The Hyatt is on the southern end of Kaanapali Beach, which has it’s pros and cons! It’s a little less than a mile walk to Whaler’s Village (where all the restaurants and shops are), but I think it’s worth it because the beach area in front of the Hyatt is so quiet and peaceful! Plus, a walk on the scenic Kaanapali Boardwalk isn’t the worst thing 😉
Overall, I think it will depend on what kind of experience you’re looking for!
Looking to head to a local fish market and cook yourself an amazing dinner in a full size kitchen? Then the Aston at the Whaler is for you!
Want to relax on a lawn chair and keep the Pina Coladas coming? Hyatt is for you!
The Ultimate 5 Day Maui Itinerary!
Okay, time to get into the good stuff!
Your 5 Day Maui Itinerary can look very differently depending on what you like to do on vacation, but for me, I like to have a perfect mix of sight seeing, adventure, tours & relaxing!
At the bottom of this Maui itinerary, I list a ton of bonus ideas for you to either extend your trip or swap out something!
Let’s dive in!
Day 1 – Explore Kaanapali & Luau at Hyatt Regency
On your first day, you are likely adjusting to the time change and dealing with the worst part of travel… jet lag! Have a slow morning with walks on the beach, grab a fresh fruit acai bowl for breakfast, dip your toes in that warm Hawaiian water, and explore the shops at Whaler’s Village!
TIP: I always aim to get my souvenir shopping out of the way on the first few days because there is nothing worse than scrambling to get it done on your last night of vacation!
Whaler’s Village is the most popular spot on Kaanapali Beach where you will find tons of restaurants, local boutiques, souvenir shops, and can sign up for last minute tours.
Start your first night in Maui off with a BANG! There is nothing more “Hawaii” than attending the best Luau on the Island.. Drums of the Pacific Luau!
This Luau touches on the culture and history of Hawaii, while also tying in modern jokes / entertainment! And on top of that, you are fed a 4 course meal + bottomless drinks.
The show is from 5:30pm – 8:30pm nightly (except for Thursdays). Click here to check it out!
Day 2: Road to Hana
Road to Hana is one of the most famous road trips in the USA, and for good reason! This challenging, scenic and winding road is a bucket list drive for many.. including myself!
I traveled to Maui for my 25th Birthday specifically for this road trip. I am a big fan of making every birthday memorable, and for my 25th, I wanted to do an epic road trip because the main perk to turning 25 is being able to rent a car without fees! 🙂
And what’s more epic than renting a jeep to explore the Road to Hana in Maui? Ya, nothing.
But enough about me.. back to the Itinerary!
Road to Hana in Maui is a LONG day. We woke up before the sun rose and drove back around sunset. And if you’re like me, you’ll get stressed knowing that’s still not enough time to see everything!
With that being said, it is 1000% worth it.
There is no place in the world where you can swim in waterfalls, see black AND red sand beaches, and hike through bamboo forests all in the same day.
I’ve created a full itinerary specifically for Road to Hana because there’s so much to know, you can read that here!
Day 3: Snorkeling at Black Rock & Sunset Catamaran Cruise
Road to Hana is a massively exhausting day, so you will want to make sure you plan to have a relaxing day to follow.
If you are staying on Kaanapali Beach (my recommendation) the best snorkeling on the island is easily Black Rock. OR if you want to sound like a local, it’s formal name is Pu’u Keka’a!
REMINDER: Only use reef safe sunscreen if you plan to go in the ocean! My favorite brand is Sun Bum!
Along this stretch of lava rock is a huge coral reef, cliff jumping opportunities, and tons of friendly turtles. During my trip to Maui, I snorkeled during different times of the day and you constantly are seeing something different.
In the morning, the water was calm and crowds were minimal, which brought out huge schools of fish. In the afternoon, the turtles made their way to the beach and were SO friendly!
TIP: If you don’t want to lug snorkeling gear in your suitcase, you can rent snorkel gear from the Aston at the Whaler’s Beach shack!
For your evening plans, get ready for your favorite thing on the itinerary.. Sunset Catamaran Cruise with Teralani Sailing!
Guys. I really can’t rave about this tour enough, it was amazing! We launched right off Kaanapali Beach, the second we took off they were handing out drinks (not pre-mixed mai tais, but actual drinks), had a professional photographer on board, and we saw a huge pod of spinner dolphins playing in the wake of the boat!
They have different tour options, but I would highly recommend doing the sunset dinner cruise. 🙂
PSST… This was listed as a recommendation on my Things to do in Maui for Couples guide!!
Day 4: Golf & Sunset at Sand Bar in Sheraton
Kaanapali has amazing golf courses with incredibly scenic views! There is one course that sits right behind all the resorts & Whaler’s village (Kaanapali Golf Course) and two on the northern end (The Bay & The Plantation).
I wouldn’t consider myself a big golfer, but that’s my fiance’s favorite activity. So, he takes endless photos of me and I take him golfing… fair trade, right? 😉 That’s why it was listed on my things to do in Maui for couples guide – you can read that here!
In all seriousness though, the golf courses are beautiful. They were well kept and had ocean views on almost every hole!
TIP: Not a golfer? I would swap this out with a fun tour! Click here to browse tours in Kaanapali Area.
After golf (or for whatever you swapped it with), head back to your room to freshen up for the best sunset spot on the island!
The Sand Bar at the Sheraton is easily the best spot to enjoy the sunset on Maui. This bar is on their top floor with a big deck and plenty of seating. If you get there about 1.5 hours before sunset, you’ll have no problem securing chairs along the glass for sunset.
Every night, the Sheraton does a torch lighting ceremony during sunset. A “Hawaiian Warrior” runs through the property, lighting all the torches. Then he runs down the beach and hikes up the Black Rock to light the torches on top of the cliff.
Right at sunset, he cliff dives off the top! It’s a really fun ceremony to watch, especially from the viewing area at the Sand Bar!
Day 5: Head North to explore Honolua Bay, Tide Pools & Iao Valley
On your last day, it’s time to head up north to explore a completely different side to Maui!
You will be doing a loop, seeing many different sites. Here is a rough itinerary for the day:
- See those beautiful, ridged mountains on the Waihee Ridge Trail
- Go swimming in natural tide pools at Olivine Tide Pools
- See Nakalele Blowhole Viewpoint
- Walk through a fairytale forest at Honolua Bay Access Trail
- Snorkel in crystal clear water at Honolua Bay
- Back to Kaanapali Beach!
If you drive this entire route all the way through, it’s about 2 hours of driving total. BUT it will be a full day considering you are doing a hike, swimming in tide pools, and snorkeling!
Stop 1: Waihee Ridge Trail (~1 hour from Kaanapali Beach)
The drive from Kaanapali Beach to Waihee Ridge Trail is about an hour. This is a gorgeous hike, but with that comes crowds. If you want to secure parking, you will want to get there early (before 8am).
The hike itself should take you about 2 hours to complete and is rated as moderate! Click here for all the hike’s details.
TIP: If you don’t want to hike and / or don’t want to wake up early for parking, swap it out with this scenic walk instead! You’ll still get all the beauty of Iao Valley, but it will be quicker + more relaxing. 🙂
Stop 2: Olivine Tide Pools (~30 Minutes from Waihee Ridge Trail)
These all natural tide pools will make you feel like you are on the edge of the world! If you have never swam in natural tide pools before, you need to read up on safety.. Yes, I know that sounds incredibly dorky, but these can be very dangerous if you don’t know what you’re doing.
If the waves are big and crashing into the pools, do not go in! They can come up and sweep you out. The ocean is more powerful than you think. It is recommended to not go in the pools during high surf months (winter) because the waves are bigger!
Also, stay closer to the land, not towards the ocean. The lava walls are a lot more fragile on these ends, and chances of a big wave hitting you towards the edge are much higher.
TIP: You will 1000% need wet socks! You will need to walk across lava rock to get to the tide pools. I know wet socks are not cute, but you know what’s REALLY not cute? Cuts all over your feet!! Click here to snag some off amazon.
Stop 3: Nakalele Blowhole (~10 Minutes from Olivine Pools)
Similar to the tide pools, you need to be careful viewing the Nakalele Blowhole! Many tourists thought it was fun to look into the blowhole and they got sucked in! There are many safe viewing platforms to see the blowhole, so just be smart and you’ll be fine 🙂
I would recommend just viewing this from the parking area, because it’s time to head to stop #4!
Stop 4: Honolua Bay Access Trail (~15 Minutes from Nakalele Blowhole)
Where many elopements are done in Hawaii is the magical Honolua Bay Access trail through the forest. During the afternoon when the sun is beginning to set, you will get these beautiful light rays shining through the hanging vines.
This flat, half mile trail is the “hike” to get to stop #5!
Stop 5: Snorkel at Honolua Bay
This protected bay will have crystal clear waters and tons of coral to explore! Keep in mind there are no restrooms, water stations, or snorkel rentals on the beach. You will need to pack all of that stuff in.
When you arrive at the rocky beach, swim out and start exploring!
TIP: If you are wondering where the best snorkeling is in the bay, head to where the catamarans are! They likely are dropping off their tours in the most popular spots. 🙂
Rather do a catamaran snorkeling tour? Here are ones that takes you to Honolua Bay!
Stop 6: Back to Kaanapali Beach (~15 Minutes from Honolua Bay)
After your long day of exploring, head to the best restaurant on the island… Japengo! This sushi restaurant has oceanfront views and to-die-for sushi.
Joseph and I are HUGE sushi connoisseurs and are rarely “wowed” by sushi restaurants… but guys. This place is a must! What better way to end your last night in Maui?!
Make sure you make a reservation well in advance because I’m not joking when I say it’s the best restaurant on the island.. they book up fast!
Bonus Ideas to Extend Your 5 Days in Maui Itinerary!
If one of the activities on this itinerary didn’t interest you, I would recommend swapping them out with one of these fun ideas!
** I have done this, and I have to say.. it was a very cool thing to see a crater, but the snorkeling was better at Black Rock in Kaanapali Beach! BUT I did go to Molokini on a very windy day where the water was very choppy, so take my opinion with a grain of salt. 🙂
- Day trip to Lanai (another Hawaiian island that is just a short boat ride away!)
What is cool about Maui (specifically Kaanapali Beach) is that you can see three, neighboring Hawaiian islands right off the shore! One (Kaho’olawe) cannot be accessed because it was used for bomb testing and there are still potential bombs on the island, but the other two (Moloka’i & Lanai) can be accessed by ferry / boat tours.
- Whale Watching Excursion (only in winter / early spring months)
This is HIGH on my bucket list, but I traveled to Maui a few months too late! If seeing whales in the wild is something that interests you, I would 1000% book a tour! Maui is one of the best places in the world to spot whales because there is a huge migration that happens annually.
- Go to a Sunflower Field
Maui has a sunflower farm that is not too far from Kaanapali Beach! The sad news is, they only bloom a short period of the year, which is late summer (July / August). Here is the address.
I REALLY wanted to do this because it looks unreal! But, I already made my fiancé wake up before sunrise for Road to Hana on our trip, so… next time 😉
NOTE, you can do this on your own or with a tour! If you do it on your own, you will need to make National Park reservation in advance. Click here to make your reservation!
If you are not a sunrise person, but still want to see Haleakala National Park, you can sign up for a bike riding tour! This tour is super fun because it comes with your park reservation and will drop you off at the top of the mountain. From there, you just relax and cruise down 🙂
If you’ve never ziplined before, Maui is the place to do it! I actually did this on my first trip to Maui a LONG time ago when I went with my parents, and it was my favorite memory of Hawaii. 🙂
There are certain waterfalls and hidden gems that can only be accessed by helicopter. I also really wanted to do this tour, but ever since Kobe Bryant’s tragic accident, my Fiancé won’t step foot onto a helicopter!
If you do a helicopter tour, be sure to share your experience in the comments so I can live vicariously through you! 🙂
When to go to Maui
Lets be honest here.. there is truly no bad time to go to Maui! This beautiful island is sunny and warm year round, making it the perfect destination for any season!
Depending on what you want out of your trip, here are my recommendations:
Looking for the least amount of crowds? If you are looking for the least amount of crowds on your Hawaiian vacation, I would recommend traveling in the winter season (November – March) or shoulder seasons (April – May & September – November).
Want the least chance of rain on your vacation? Hawaii’s rainy season is during the winter months, so if you are trying to avoid the rain, I would recommend traveling during their dry season (April – October)!
Want to experience a whale watching tour? Maui is the perfect spot for whale watching. If this is on your travel bucket list, plan your trip sometime between November – March. This is when thousands of Pacific Humpback Whales are doing their annual migration. Click here for an awesome whale watching tour!
What to Pack for Maui?
I never want to bore you with a long packing list, especially because you came here to read an itinerary! But, I do always like to recommend just a few must-have’s for this specific trip! Here are my top 5 absolute must-have’s for Maui:
In 2018, Hawaii banned standard sun screen that contains chemicals that are harmful to reefs. It was the first state in the USA, which was long over due! It is SUPER important that you are only using reef safe sunscreen not just because it’s illegal not to, but because the chemicals in regular sunscreen can cause hundreds of years of damage to a coral reef.
I solely used Sun Bum, which you can get right on Amazon! It has a good smell, doesn’t make you feel super greasy, and didn’t make me break out!
If you are weird about using the same mouth piece and snorkeling gear as other people, bring your own! You can get some good pairs on amazon before your trip and the best part is.. you can read reviews to make sure you are getting a good quality pair! Click here for the cutest baby pink set!!
3. Cute Sun Hat
I get all my hats from Olive and Pique, which are seriously the cutest hats! My specific hat I wore on all my travels is the “Jana!” These are on the pricier side, and a lot of people don’t like to bring expensive hats on vacation because they can get banged up in your suit case.
The closest dupe I could find for you was this one from ASOS (SUPER affordable)!
I am not a sunglass snob AT ALL. I buy 99% of my sunglasses off amazon because I am the most irresponsible sunglass owner on the planet! When you are traveling, you should bring a cheap pair to take with you in the ocean / pool, shove in your bag when you’re in a rush, and not care if you lose!
I have this adorable two pack! They are super sturdy, so adorable, and the best part.. extremely affordable!
5. Go Pro
If you plan on doing any snorkeling.. I’m sorry, but you NEED a go pro. If you see a friendly turtle swimming up to, you are going to want to take a photo of that epic moment!
At the very least, be sure to get a waterproof phone case to take your phone for some photos!
Is 5 Days in Maui Enough?
YES, I would say that is plenty of time to enjoy Maui. Of course, you could easily spend more time on the island, but overall, I think that is plenty of time to see most of the island and relax.
What Time should you start the road to Hana?
EARLY! I started before sunrise and it was still a full day without seeing everything. Just keep in mind that Hana is on the wet side of the island, so it rains A LOT. When I went early in the morning, it rained constantly until about 10am. If you want warm weather with the least chance of rain, you might want to start a little later in the day. Be sure to check out my full Road to Hana Itinerary here!
Is Maui Expensive to Visit?
It can easily be expensive, but there is 100% a way to do Maui on a budget! If you stay at an Airbnb or condo style hotel (like the Aston at the Whaler that I mentioned earlier), you can shop & cook most of your meals! And of course, just make sure you are booking pretty far in advance to secure the best rates. 🙂
What is the best area to stay in Maui?
I stayed in Kaanapali Beach area and loved it! You are surrounded by great restaurants, golf courses, beautiful views, luaus, and the best snorkeling on the island. If it’s your first time visiting Maui, it doesn’t get any better than Kaanapali. Click here to read my guide on fun things to do in Kaanapali Beach area!
Do I need a rental car to get around Maui?
If you plan on just relaxing on the beach, then probably not! But if you want to explore other areas of the island like Road to Hana, then yes you do! If you plan to see at least half of the things on this itinerary, I would definitely recommend renting a car. Click here to browse car rental options!
Okay, that’s a wrap!
Maui is the ultimate vacation location for any type of traveler! In this 5 day Maui Itinerary, I tried to include the perfect mix of relaxing, fun excursions / tours, and adventure!
This was my second time visiting the beautiful island of Maui and I don’t think it will be my last! This island has a little bit of everything and I think is the perfect first island to visit out of all the Hawaiian islands. 🙂
Hope you loved the itinerary, if you have any questions don’t hesitate to ask away in the comments!
Still finalizing your trip to Maui? Be sure to check out these other Maui guides:
- Things to do in Maui for couples!
- Ultimate Road to Hana Itinerary – All the Best Stops!
- 30 Fun Things to do in Kaanapali Beach!
- Which Hawaiian Island is best?!
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