Maui, Hawaii, will always hold a special place in my heart as it is where I went for my Honeymoon, and it was the perfect balance of relaxation and adventure. My husband and I are adventurous travelers, so although we appreciate some beach time, we definitely needed somewhere we could go on hikes and explore more than just the resort we stayed at.

If you are planning a honeymoon, anniversary trip, family vacation, or just want to experience the best of Maui, this 5-day Maui itinerary blends relaxation at the beach, scenic drives, and thrilling hikes.

This itinerary is built based on staying in Ka’anapali, although it can easily be adapted to stay anywhere in Maui. If you do choose to stay in Ka’anapali, I recommend the Westin Maui Ka’anapali

5-Day Maui Itinerary

Day 1: Beach Day

Ka’anapali Beach

Start your trip with a good beach day! If you are staying on Ka’anapali Beach, this will be right out your door. This is one of Maui’s most famous stretches of sand, with 3 miles of shoreline perfect for swimming or sunbathing! Head to Black Rock at the north end of the beach, which is great for snorkeling, and you can often see sea turtles and cliff divers.

Ka’anapali Village & Whalers Village

After some time in the water, head over to Whalers Village for shopping and lunch at Monkeypod Kitchen or Maui Brewing Co.

Luau

You have to have a Luau in your Maui itinerary! It is a great way to experience Hawaiian culture through communal dining with delicious local food, music, and hula dancing. There are so many luau’s around Maui, but a few to note in Ka’anapali are the Wailele Luau and Old Lahaina Luau.

Day 2: West Maui Adventure

Waihe’e Ridge Trail

Now it is time for some adventure! Start your morning with the Waihe’e Ridge Trail hike. This was one of my favorite hikes in Maui as it really shows off the green lucious mountains. It is a 4-mile round-trip hike and takes you through views of the West Maui Mountains, Makamakaole Falls, and the ocean. Go early in the morning before clouds roll in for the clearest views and fewer people.

Nakalele Blowhole

On your way back to your accommodation, drive along Maui’s rugged coastline to see the Nakalele Blowhole, where the ocean water shoots into the air through a natural rock formation. It is really quite entertaining to watch! It is also a beautiful surrounding area.

Relaxation

Take the afternoon to relax by the pool or beach.

Dinner

One of my absolute favorite dining experiences in Maui was at Takumi, a tiny, tucked-away restaurant offering Omakase. We sat at the counter, and what made it so unforgettable was being able to chat with the chef throughout the meal, with each of our dishes prepared right in front of us. It was such an intimate experience, and the food was prepared so delicately and was delicious! It was a truly memorable experience!

Day 3: Road To Hana

Road To Hana

The Road to Hana is a must when you are in Maui! It is a scenic drive to many viewpoints and hikes along the way. The drive itself is the main star of the adventure, with A TON of curves and one-way bridges, but it is really great scenery along the way!

If you want a complete Road to Hana guide, check out my full blog post here.

My recommendation is to drive all the way to the Pipiwai Trail first (past Hana) and then, on your way back, stop for lunch and viewpoints along the way back. And definitely start early and give yourself the entire day to enjoy the drive at a relaxed pace.

My Favorite Stops to Include:

• Pipiwai Trail Hike and Seven Sacred Pools: One of Maui’s most famous hikes inside Haleakalā National Park (we’ll explore more of this amazing national park later in the itinerary). Pipiwai Trail takes you through a bamboo forest and ends at the stunning Waimoku Falls, and Seven Sacred Pools leads you to a series of natural pools.

• Wailua Falls: One of the many easily accessible waterfalls you will pass.

• Black Sand Beach at Waiʻānapanapa State Park: A beautiful stretch of coastline with volcanic sand. Note: You need a reservation to enter the park.
• Hāna Farms Roadside Stand, Pizza Oven, and Bakery: Lunch spot where you can enjoy pizza on beautiful grounds.

• Garden of Eden Arboretum: A beautifully maintained garden showcasing tropical flowers, exotic plants (such as rainbow eucalyptus!), ocean views, and peacocks! (fun fact: part of Jurassic Park was filmed here).

Dinner

The last stop of the day is to catch your dinner reservation at Mama’s Fish House. When I told people I was going to Maui, this was the number one thing everyone said to do! So, now I am passing it on to you 🙂

Day 4: Ocean Adventure and Relaxation

Snorkeling Tour

Book a snorkeling tour to explore the crystal-clear waters around Molokini Crater or Turtle Town. You will swim among schools of tropical fish, colorful coral, and sea turtles. I would recommend a morning tour, as they tend to have calmer seas and better visibility. Also, if you are traveling to Maui during whale season (December – April), you might get to see these massive creatures while on the boat. 

Spa

Have an afternoon filled with a relaxing spa. Most resorts have wonderful spas, but here are two to check out: the Westin Ka’anapali Spa or the Spa at Black Rock.

Dinner

Have dinner at Japengo, located at the Hyatt Regency in Ka’anapali. It has a beautiful setting overlooking the ocean and is perfect for watching the sunset with a cocktail in your hand. The menu blends Hawaiian flavors with Asian influences, so you can find fresh seafood and sushi.

Day 5: Haleakalā National Park

Sunrise at Haleakalā Crater

If you are up for getting up early, then you are in for an epic experience. You can watch the sunrise above the clouds at Haleakalā. Note: You have to make a reservation in advance if you arrive at the park before 7 am.

If you do not want to get up super early, that is okay! You can still have an amazing day filled with hiking at Haleakalā National Park.

Hiking In Haleakalā National Park

I absolutely LOVED Haleakalā National Park and was in awe the whole time. First, the drive up was so curvy, and you just kept climbing! (You will go up to ~9,700 feet!) Next, I hiked in two different areas, which were so different from each other that it was crazy. One was rocky, green, and lucious, and the other was a sandy, volcanic landscape and felt like I was on the moon!

I have two recommendations for how to do the Sliding Sands Trail and the Halemauʻu Trail. 

1. You can hike the Sliding Sand Loop, which takes you from Sliding Sands Trailhead to Halemau’u Trailhead for a total of ~11 miles. This gives you the ultimate experience of point to point that allows you to see it all. Logistically, it is recommended you park at the Halemauʻu Trailhead parking lot, and then you walk out to the “hiker pick-up” area on Haleakala Highway and hitchhike to the Visitor Center, where you will start your hike. This way, your car will be waiting at the point you end at.
2. You can hike a couple of miles each way on both the Sliding Sands Trail and the Halemauʻu Trail. You can make this less mileage in total, but you still get to see the two different areas.

Sliding Sands Trail (Keonehe‘ehe‘e Trailhead): The Sliding Sands Trail was the area that felt like I was on another planet. It has a wide, volcanic landscape. Take the hike all the way down to the crater if you are doing the loop; otherwise, even a shorter hike will give you incredible views and intriguing rock formations. There are a lot of switchbacks and elevation on this hike.

Note: When I did this hike, it was incredibly windy and raining, with not great views. This is saying a lot since I still loved the hike so much, so hopefully you have better luck than I did, but just know the weather is unpredictable here, so that may happen!

Halemauʻu Trail: The Halemauʻu Trail also takes you down to the crater with steep switchbacks, but with a completely different landscape of greenery and rocks. Again, if you are doing the loop, you can go down to the crater, but if not, you can hike a few miles each way for still an incredible experience.

Lunch at Kula Lodge

After a day of hiking, stop at Kula Lodge for a well-deserved meal with great views of Maui in a cozy cabin atmosphere.

Relaxation and Dinner

Spend the rest of the afternoon and evening relaxing and having dinner near your accommodation for a casual last night in Maui.

Tips for Your Maui Itinerary

• Car Rental is Essential
• Pack for Variety: You will want swimsuits and sandals for the beach, hiking shoes for the trails, and a warm jacket for Haleakalā’s chilly summit.
• Respect the Land & Culture
• Do you have time before the airport on the day of your departure? Check out Kanaha Beach Park, a local favorite and a great spot to watch kite surfers, enjoy a picnic, and just relax with ocean views before your flight.

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Maui is a dream destination for a reason. With this 5-day Maui itinerary, you will get the perfect balance of relaxation and adventure through sunbathing, spa time, snorkeling, hiking, and scenic drives. I am so excited for you to plan your Maui trip!

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