Planning a trip to Maui but don’t know how much time you should allot for your island adventure?  No worries, I’ve lived on Maui for over 12 years and I put together a Maui itinerary that covers the whole island.

This post contains multiple sample itineraries ranging from a Maui 3 day itinerary, a Maui one week itinerary and all the way to two weeks on Maui.  These itineraries will help you maximize your time, allow for flexibility for unexpected adventures and enjoy those much needed relaxing beach days.

In this article, I recommend staying in a few different places all over the island especially if you are visiting Maui for multiple weeks.  This allows you to experience multiple areas of Maui on a more intimate level.

It is possible to drive around the whole island of Maui in a day, so if you are looking for a Maui itinerary 7 days or less, stay in the same Maui accommodation.  Just pick and choose your day trips.

A locals guide Maui Itinerary

For full transparency, I have sprinkled some affiliate links in this post which gives me a small commission at no extra cost to you if you decided to make a purchase. As always, I would never recommend a product or service that I didn't truely believe in. If you find this post useful, you can also treat Jess to a cup coffee by clicking the icon on the bottom of the page. This will allow me to continue to create more content for you to enjoy ☕️. 

Maui 3 day Itinerary

  • 2 Days: Choose West Maui or South Maui
  • 1 Day: Road to Hana or Haleakala Summit

Maui 4 day Itinerary 

  • 2 Days: West Maui
  • 1 Day: Road to Hana or Haleakala Summit
  • 1 Day: South Maui

Maui Itinerary 5 days 

  • 2 Days: West Maui
  • 1 Day: Road to Hana 
  • 1 Day: South Maui
  • 1 Day: Haleakala Summit

Maui Itinerary 7 Days 

Maui Itinerary 10 Days

Maui Itinerary 14 Days 

How to get to Maui

Did you know that the Hawaiian Islands are the most isolated island chains in the world?!  That means no matter where you coming from its going to be a long flight.

Maui has many direct flights from the mainland especially on the West coast.  Even if you can’t find a direct flight connecting through Honolulu isn’t terrible, from HNL to OGG (airport code for Kahului on Maui) its only a half hour flight.

Check Flights ↓


Once arriving on Maui I ALWAYS recommend that you rent a car/jeep.  The islands public transportation is very limited and time consuming.  Having your own wheels only amplifies your Maui vacation and gets you to where you need to be.

book your jeep ↓


The Best time to Visit Maui

Best time to go to Maui

Maui basically has two seasons, summer and winter.  Summer season is April through October and winter is November through March.  Temperatures only vary by a few degrees between seasons.  It’s a tropical paradise that has warm weather all year round.

When to go to Maui will depend on what you want to do.  If you want to escape the cold then visiting in the winter months is a no brainer.  But the BEST part about visiting Maui during the winter months is for the whales.  🐳

Every year over 10,000 North Pacific Humpback Whales make their way to the warm shallow waters of Hawaii to give birth.  Official whale season is mid-December to mid-May.   Make sure you go on as many whale watching tours as you can!

Hurricane season is from June through November and thankfullyHawaii isn’t prone to hurricanes as much as other islands in the Caribbean. 

The last 2 weeks of December during the holidays is the busiest time of the year.  Make sure you book your accommodations, rental cars, popular activities and make restaurant reservations in advance.  It’s crowded, everybody wants to spend Christmas in Hawaii.

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Day 1: arrive-head to West Maui

Ka’anapali is the popular resort area on West Maui.  Just because its popular doesn’t mean that its not stunningly beautiful!  I recommend basing yourself here for the next few days, its centrally located near tasty restaurants, shops and sits on a long, gorgeous stretch of golden sand beach.

There are several top notch resorts to stay at perfect if you’re on your honeymoon.  If you’re only able on a 4 day Maui itinerary stay in West or South Maui the whole time.

Lahaina, Kapalua, Kahana or Napili are other towns on West Maui are other excellent options for accommodations.  Below I’ll list my top hotel pick for each area.  For a detailed guide.

Where to Stay in Lahaina

Old Lahaina House

Located a block away from the beach and walking distance to many bars, restaurants and shopping.  There’s a great beginner surf spot in town perfect to take a surf lesson.

Where to Stay in Kaanapali

The Royal Lahaina

I love the stretch of beach that the Royal Lahaina resort sits on.  It has a small pool and bar on sight but you come here to lounge on this end of the beach which is never busy.  This is one of the oldest resorts on Maui, about a ten minute drive to Lahaina.

The Westin Nanea Ocean Villas

Located on a beautiful beach with excellent snorkeling, you are likely to spot sea turtles often.  Some rooms have a kitchen.  The Westin Nanea Ocean Villas are right in the action and walkable to several of the best things to do in Kaanapali.

Where to Stay in Napili / Kahana

Napili Sunset Beach Front Resort

Condo style with kitchen, lanai (Hawaiian patio) and amenities for the beach.  Located on Napili Bay as well.

Napili Kai Beach Resort

Located on the beautiful Napili Bay which has world class snorkeling.  The Sea House Restaurant has one of the best happy hours on the island.

Where to Stay in kapalua

Montage Kapalua Bay

Luxury, Luxury, Luxury.  Perched above Ironwoods beach you’ll find this picture perfect resort.  World class golfing located 5 minutes away.  You won’t be disappointed.  This is a great place to stay on your honeymoon.

No matter where you’re staying it’s gonna be on a beautiful white sand beach and perfect day involves a pina colada and boojee pool.

If you’re staying in Ka’anaapall go all the way to the end of the beach by the Sheraton and jump off black rock, this is one of the best things to do in Kaanapali. It’s a 20 feet jump off the cliff into the water.  

Every night at sunset the tiki torches are lit and a man jumps into the water.  This is also a great snorkel sight, I almost always see a turtles! 🐢

Eat dinner at Monkeypod, one of the best restaurants in Kaanapali and is walkable from any hotel on the Ka’anapali walkway.  They have a great happy hour  & reverse happy hour, a huge selection of beer and poke tacos.

Day 2: Explore West Maui

Explore West Maui by driving North,  but first stop and have breakfast at Down the Hatch, the Gazebo or Plantation House.  Down the Hatch has some of the best breakfast on Maui.  The Gazebo is more casual, it’s even BYOB.  The Plantation House sits atop the beautiful Kapalua golf course.

The coastline is jaw dropping and there are many places to pull over, get out of the car and take pictures as you drive West Maui.  A few of the best stops include Honolua Bay, Slaughterhouse, Olivine Pools, the Blow Hole, Mahana Ridge, the Ohai Trail and Julia’s Banana Bread.  For a more detailed post

I have to warn you that the road gets sorta sketchy at some parts.  Meaning very twisty and narrow.  There’s one section that is a long stretch of one lane road on the side of a mountain.  If theres people going both ways, someone will have to backup.  So be aware. 
TRAVEL TIP:  If you would prefer to follow along to an audio tour as you explore the coast line of West Maui, I recommend the Shaka Guide!  The Shaka guide tours are great for independent explorers who want the freedom to explore on their own terms, but like to learn about the spots they’re visiting.

The tours use GPS to offer turn-by-turn directions and audio narration with stories and music.  This will leave you with a deeper understanding and connection to Hawaii.

Spend the rest of the afternoon at the pool or beach before you head to Lahaina to eat dinner.  A few of my favorite restaurants are Fleetwoods, Down the Hatch and Star Noodle.  For a larger list of the best restaurants in Lahaina

Extra days for the 14 & 10 day Maui itinerary 

If you’re only the 7 or 10 day Maui itinerary you’ll have a 1 or 2 extra days in West Maui.  Learn to surf, sip pina coladas the pool, bask at the beach, go diving, go for a snorkel.

If you’re here during whale season (December 15-May 15)  go on a whale watching tour.  I’d plan ahead if you plan on doing excursions, tours fill up fast especially in peak season.

Camping on Lanai. Manele Bay

Extra day  on 14 day Maui itinerary: Day trip to Lanai

Did you know that there’s a ferry that runs from Maui to Lana’i?  This is a great way to explore Lana’i on a day trip from West Maui. 

The ferry runs 5 times a day and cost $60 round trip.  You can look up times  here.  The boat ride is a quick 45 minutes until you dock at Manele harbor.

Spend the day relaxing at the picture perfect Manele Bay (pictured above ↑), enjoy a short hike to along the coastline to Puu Pehe, petting cats at the cat sanctuary or renting bikes to explore the island.  However you decide to spend your day, it’ll be a great island hopping adventure.

Road to Hana Maui Hawaii

Day 3: Drive the road to Hana

Today’s the day you’ve been waiting for, driving the road to Hana.  The Hana Highway is 52 miles of winding road, 59 one lane bridge and 620 curves and hairpin turns.

The road takes you through lush rainforests, by flowing waterfalls, and offers jaw dropping seascape views.  Get an early start as it’ll be a long day of waterfall chasing.  
The road to Hana is easily a highlight of someones Maui vacation.  A few of my favorite stops are Twin Falls, the Painted Forest, Honomanu Bay and the star Wai’anapanapa State Park.  For a more detailed guide on all the best stops

Locals Tip:  Get off-the-beaten path and avoid the crowds by driving the back road to Hana.

Tips for driving the road to Hana 

  • PULL OVER and let the locals pass. If they are riding your ass it’s not because they’re trying to be mean it’s their way of asking you to “let them pass.”
  • Pack plenty of snacks & beverages for the drive, it’s a long day.
  • Avoid sites located on or beyond private properties, and areas that lack visitor welcoming signage.
  • Park in designated parking stalls.  Don’t be “that guy” and block the road for everybody.
  • Don’t expect much service, cell service and WIFI will be very limited on this journey.
  • Please respect the Aina (land)!  Theres nothing that irks me more than to see litter and trash strewed about.  Pack it in, Pack it out.
  • Lastly, Do Not park underneath a mango tree, those sweet things have an evil side!
TRAVEL TIP:  If you would prefer to follow along to an audio tour I recommend the Shaka Guide!  The Shaka guide tours are great for independent explorers who want the freedom to explore on their own terms, but like to learn about the spots they’re visiting.

The tours use GPS to offer turn-by-turn directions and audio narration with stories and music.  This will leave you with a deeper understanding and connection to Hawaii.

Where to stay in Hana

You will be staying in Hana for 2 nights.  Hotels & AirBnB’s are limited.  Planning accommodations ahead of time are crucial.  Here’s what I recommend.

Wai’napanapa State Park

On the iconic black sand beach has camp grounds and cabins which are always a highlight in my book.

Haleakala National Park

Where the famous Pipiwai Trail starts.  I love camping in Hana.

Aina Kupuna

Great location for this jungle oasis.  Equipped with amenities for the beach this one bedroom place has a kitchen and parking.  Perfect for a night or 2 while you explore the surrounding area.

Travaasa Hana

Luxury in the jungle.  The Travaasa (part of the Ritz Carlton) is one of Hana’s only luxury resorts.  Explore during your days and relax in the evenings on the beautiful grounds witch ocean views and an amazing hot tub.  

A perfect stay on your Maui itinerary and one of the best resorts in Maui for your honeymoon.

Beautiful banyan tree on the Pipiwai trail inside Haleakala National Park Maui

Day 4: explore Hana

Hana is a magical place, I wish I got to more often.  When you think of Hawaii you probably think of waterfalls, lush rainforests and tropical flowers, Hana embodies all of this.

Start your day early with sunrise at the red sand beach.  Getting to this beach is half the adventure as you have to ‘scale’ a cliff to get there.  If you did it right and booked a stay at the Hana Hotel for a few nights ask anyone at the hotel to point you in the right direction to the beach, its located directly next door.

Bring a towel or blanket to sit on, along with a long sleeve shirt.  There are tons of sand flies buzzed around that tend to get annoying so be prepared. It will be a sunrise you’ll never forget.

After sunrise at red sand beach head to the Surfing Burro to grab breakfast and coffee.  There aren’t many food options in Hana so planning out your meals are crucial.  Most places close early or are only open 4 hours a day.
Breakfast burrito at one of the few Hana Maui Restaurants

READ NEXT:  Where to Eat in Hana

Next head 20 minutes down the road to Haleakala National Park stopping to take some pictures at Wailua Falls along the way.  This is the Kipahulu District of Haleakala National Park.

Park at the visitor center and take the short Kūloa Point Trail to the Kūloa Point at the mouth of ‘Ohe’o Gulch.  The ‘Ohe’o Gulch or commonly known as Seven Sacred Pools is a series of waterfalls that fall into pools.

Now start hiking the Pipiwai Trail.  This is one of the most popular hikes on Maui and once you hike it, you’ll understand why.  This 4 mile hike takes you past ancient banyan trees, through a dreamy bamboo forest and finally ends at the spectacular 400 foot Waimoku Falls.

Most people hike this trail are coming over for the day.  This means that most hikers do not start til afternoon.  You’ll be getting here fairly early around 9 so you’ll have the trail all to yourself.  It’s a videographers dream.  Just check out the pictures.

Pipiwai Trail in Hana HI
Hawaii travel guide with I'm Jess Tracveling
I'm Jess Traveling, travel blogger on Maui in Hana Hawaii
Most of the time when I come to Hana, I camp inside the Park.  There’s shade, grills, bathrooms and its a 5 minute walk to the Pipiwai trailhead.  If you’re traveling Maui on a budget, camping is a great option.  Make sure you get all of your supplies before you leave.  Hana has a 2 general stores but they are limited and pricey.
Finish the day lounging at Hamoa Beach and let your dreams melt away.  Remember to plan ahead for dinner.  Find out your options here.
Black Sand Beach Hana HI

Extra days for the 14 & 10 day Maui itinerary 

If you’ve chosen to carve out more time in Hana, you’ve made the right choice.  There is so much adventure to have in Hana its a dream.

If you crave thrill then make sure you check out Venus Pools which is my favorite place to go cliff jumping. There are several rocks that you can jump off of  into a natural swimming hole that range in different heights.  Then scramble up the lava rocks.  Rinse and repeat.

I would also rise for yet another sunrise but this time at Wai’anapanapa State Park.  I recommend this sunrise over the red sand beach because there’s more to explore, its more open and its absolutely beautiful.  Just because Hana is remote doesn’t mean there’s a shortage of things to do.   

* As of March 2021 you must make reservations to visit Wai’anapanapa State Park.  You can do so here.

Unusual things to do on Maui-2

Day 5: drive to South Maui

Get ready to be in the car for more than a couple of hours.  Drive the back way from Hana to South Maui.  The drive is beautiful.

Make sure you stop at St. Joseph’s to snap a few pictures of the beautiful church perched on the cliff with views of the ocean below.

Another off-the beaten path must stop is at the Maui Honey Bee Sanctuary.  The beautiful grounds overlook the ocean and I was surprised to have only discovered this spot in February!

Great souvenirs/gifts are handmade ‘Hive to Home’ and ‘Bees to Body’ products.  I bought the local lavender honey and put it in my coffee every morning. ☕️  This is one of the most unusual things to do in Maui

Where to stay in South Maui

If you want to splurge stay at one of the top end resorts in Wailea.

Andaz Resort

If you want a beach front resort that you’ll never want to leave.  The Andaz has 4 outdoor infinity pools, a couple on-site bars and restaurants, and top notch service.  Spend your days relaxing pool side with a lava flow (a Pina colada with strawberry).  Close to the best beaches on Maui, high end shopping and all the best things to do in Wailea.

Hotel Wailea

On you’re honeymoon?  The Hotel Wailea, Relais & Châteaux is an adults only resort with the finest views, luxury and facilities.  This is a top honeymoon resort in Hawaii.

Fairmont Kea Lani

Located on a perfect beach.  The Fairmont has several pools, hot tubs, restaurants and bars on sight.  Koa’s has a great happy hour and is located at the adult pool.  Walkable to the beach and a free shuttle to the shops at Wailea.
If you’d rather not spend insane resort prices stay at a vacation rental in Kihei.

Relax at the pool or at one of the pristine beaches nearby…I mean it is a vacation after all.  And you’ll be able to walk to all the things to do in Kihei.

Sunrise atop Haleakala National Park a top thing to do in Maui

DAY 6: Surise at Haleakala or Explore Upcountry

Okay so this requires a 3:30 am wake up call and a reservation booked in advance but watching the sunrise above the clouds atop Haleakala is an incredible experience.  It is a shorter drive to the top when you are staying in South Maui so that’s why I’m suggesting to do it this day.

The drive up to the summit of Haleakala is about 1 -1.5 hours.  There’s even tours you can book that drive you to the top of the summit for sunrise then unload bikes and you get to coast 26 miles down the slopes of Haleakala Paia town.  Make sure you bring a sweater, it gets cold at the summit of 10,000 feet.

Sliding Sands trail, Haleakala Crater I'm Jess Traveling

My preferred way of exploring the crater is by hiking down, through and out of the crater.  You do this by hiking down Sliding Sands Trail and connecting with the Spur Trail towards Holua and eventually onto the Halemauu Trail.

After a grueling 4 or 5 miles worth of switchbacks you’ll end up where you parked your car.  (From the car you hitch hike to the summit to begin the hike).

If hiking is not your thing and you’re over these early morning wake up calls, sleep in and spend this day exploring Maui’s Upcountry and the North Shore.  Upcountry is the area on the Haleakala side of Maui away from the shoreline.  The town of Paia (you drove through this cute town at the beginning of the road to Hana) is about a 10 minute drive from Upcountry.

Sip organic vodka made from sugarcane at the Ocean Distillery or sample goat cheese at the Surfing Goat Dairy Farm.

Pau Vodka Upcountry Maui Hawaii
Surfing Goad Dairy farm in Upcountry Maui
Mama’s Fish House is a staple of Maui and a great place for lunch, make reservations ahead of time.  You’ll love the hippie/surfer vibe that the town of Paia gives off.
I'm Jess Traveling

Day 7: beach day all day

Alas its the last day on your 7 day Maui itinerary your so plan on doing nothing today but lounging at the beach or pool.  My favorite beach is Big Beach located down in McKenna.

It’s a 5 mile long white sand beach that carved into a perfect crescent. You can climb up the side on rocks on the far East side of the beach. It gives a great viewpoint.

If you continue over the rocks you’ll be at little beach which happens to be a nude beach.  On Sunday nights they have a naked drum circle. To  ensure a perfect beach day don’t forget to bring these items to the beach.

Travel Tip:  Respect the ‘Aina and do your part to help protect the ocean by only wearing reef safe sunscreen.  This is a requirement in Hawaii and should be around the world. 

Extra days for the 2 week Maui itinerary

If you’re staying 2 weeks, spend your final 2 extra days enjoying the fantastic beaches that are in that area. Secrets Beach, Wailea Beach and Kam III are some of my other favorite beaches.

Make sure you carve out a morning to drive down to La Perouse.  The drive is picture perfect and gives you a small town Hawaii feel.  Hike as far or as little as you want on the Kings Trail.  You’ll see goats running around towards the beginning of the path.  Lava rocks surrounded the and sometimes jut into the path.

Molokini is the crescent shaped atoll you can see from the Southern part of the island.  Here is where you can find some of the best snorkeling on Maui.

7, 10 or 14 Day Maui Itinerary with I'm Jess Traveling
7, 10 or 14 Day Maui Itinerary with I'm Jess Traveling