Maui Hawaii Family Vacation Itinerary -

Known as “The Valley Isle”, the island of Maui, the second largest Hawaiian island, is filled with pristine beaches, countless water sports, unparalleled hiking, and of course, one of the most famous roads in the world, the Road to Hana.

For travelers that only have a limited time to enjoy Hawaii, Maui is the perfect jumping off point for a week-long adventure. Staying on one island for a full week allows you to experience the full essence of the unique Hawaiian culture. There will be a bit of time for relaxing, a day-long epic road trip, and some of the freshest cuisine you’ll ever taste.

Maui Vacation Week Itinerary -

How to Experience One Perfect Vacation Week in Maui,  Hawaii

Day 1: Arrival into Maui, Settling In

Chances are, if you are coming in from the U.S. you will be arriving into Maui in the mid-afternoon. After grabbing your rental car, stop at one of the many grocery stores Kahului (only a few minutes from the airport) to stock up on drinks and snacks. We recommend spending your first few nights in the Kaanapali or Lahaina area. Located in West Maui, this is the thriving hotel zone with beautiful resorts and bustling downtown areas.

You’ll be tired from the long flight, but don’t turn in too early! Enjoy some time at your resort, relaxing and getting to know the area. Sip on a cocktail and watch the sunset on your first night in paradise.

Where to eat in Maui:
  • Hula Grill Kaanapali
  • Leilani’s on the Beach
  • Japengo
Where to stay in Kaanapali/Lahaina:

Hyatt Regency Maui Resort and Spa: As one of the top resorts on all of Maui, the Hyatt Regency Maui stands out with its beautiful oceanfront location on Kaanapali Beach and world class amenities and spa. Whether you are sitting poolside or beachside, this resort will have a little something for everyone. The Hyatt Regency also offers an on-site luau performance combining traditional cuisine and customary Hawaiian entertainment.

Kaanapali Beach Club: located minutes from Lahaina, the Kaanapali Beach Club combines comfort and convenience for guests of all ages. All rooms feature private balconies with either mountain or ocean views. Nearby activities include snorkeling, hiking, local entertainment, water sports, and horseback riding. Guests can enjoy local cuisine at the on-site restaurant or sit poolside with tropical cocktails. It’s a true home away from home!

Day 2: Bright and Early Snorkel and Whale Watching Tour

Let the jetlag work in your favor this morning by scheduling an early morning snorkeling or whale watching tour. This will allow you to get out on the waters before the crowds and hopefully see some impressive tropical fish or massive whales. Make sure to book a tour that includes the Molokini Crater. This area offers the most diverse sea life and reefs to explore. After the tour, enjoy some lunch, and an afternoon at your leisure with some beach lounging.

Insider tip: It’s best to do any snorkeling or whale watching tours (Dec-Apr) at the beginning of your trip. High winds or lack of whales can often delay the tours so scheduling them for the beginning of the trip allows for any delays to be rescheduled to later in the week.

If you don’t feel like sitting on the beach, head north to explore the northwestern part of Maui. With excellent hiking, beautiful bays, and some of the most scenic vista driving in all of Maui, this area is worth the drive! Popular stops along the way include: Honolua Bay, Lipoa Point, Punalau Beach, Nakaele Blowhole, Olivine Pools, Kahakuloa, and Waihe’e Ridge Trail.

Where to eat:
  • Old Lahaina Luau
  • Monkeypod Kitchen
  • Belle Surf Café
Suggested tours in Maui:

Maui Kaanapali Vacation Planning -

Day 3: Explore Lahaina/Kaanapali

Today is another relaxing day to enjoy Maui’s western coasts. If you didn’t get the snorkeling or whale watching tour in yesterday, today’s the day to do it. Enjoy a leisurely breakfast at your hotel or head into town early to pick up some fresh coffee and tropical acai bowls to enjoy on the beach.

Spend some time in Lahaina today to explore the art scene, do some shopping, and eat just a bit of everything. If adventure sports are your thing, book a zip-lining or helicopter tour for the best views on the island. Or head to the beaches south of Lahaina for some surf lessons on the legendary waves of Maui. Close out the day with a beautiful sunset catamaran cruise.

What to do in Lahaina an Kaanapali:

Front Street: As the main street of Lahaina, Front Street is where you’ll find all the best shopping, dining, art galleries, surf shops, and just an all-around lively, fun vibe. Spend some time popping in and out of the local shops and enjoy all that this area has to offer.

Banyan Tree: The famous Banyan Tree of Lahaina was planted there almost 150 years ago! No trip to Lahaina would be complete without seeing it. Covering nearly 200 feet, this massive tree is a spectacle to behold.

Kaanapali Beach: If your resort isn’t located on Kaanapali beach, this area is still worth a visit. Stretching over 6 miles along the coast just north of Lahaina, Kaanapali Beach is the perfect place to enjoy a nice beachy picnic and bask in the Hawaiian sun.

Where to eat:
  • Maui Tacos
  • Duke’s Beach House
  • Roy’s Kaanapali
Suggested Tours in Lahaina an Kaanapali:

Road to Hana Vacation Tours in Maui Hawaii -

Day 4: Road to Hana

Today is a big day so be sure to be up bright and early. You will want to utilize as much of the day as you can! Known as one of the best drives in the world, the Road to Hana is filled with lush scenery, incredible waterfalls, and stunning beaches along the way. The road is not for the faint of heart or the nervous driver because of its hairpin turns and proximity to the cliff’s edge. With that in mind, a slow speed and careful driving will get you to Hana without any issues.

It is highly recommended to overnight in Hana Town so that you can take your time and enjoy everything the road trip has to offer. Even though it’s only about a 65 mile-long journey, expect to be on the road for at least 10 hours, including all the amazing stops along the way. It’s all about the journey so stop at anything that strikes your fancy and just enjoy the ride!

Insider tip: Be sure to fill up on gas and snacks in Paia. There won’t be any place to fill up along the way. You will most likely lose cell phone service once you get into the drive so it’s a good idea to also download offline maps. It’s pretty hard to get lost though.

Top Stops on the Road to Hana:

Twin Falls: located at mile-marker 1, the Twin Falls are one of the most well-known stops along the way. It’s a half mile hike to get to the falls and the views are entirely worth it!

Huelo Lookout: This is a quick stop to enjoy beautiful views of east Maui and enjoy a snack from the fresh farm fruit stand.

Keanae Peninsula: This area is known to show visitors a glimpse of “Old Hawaii”. There are botanical gardens to explore and a perfect place to get out and stretch your legs a bit before continuing on.

Hanawi Falls: Another popular spot if you’re looking to chase some waterfalls. The best viewpoint is from the Hanawi Falls Bridge.

Nahiku Marketplace: Stop here to explore some gift shops, art galleries, and enjoy the delights of the roadside food vendors.

Wai’anapanapa State Park: This area really has it all with a black sand beach, blowholes, sea arches, hiking trails, and stunning panoramic views. Take some time to here to explore it all.

Wailua Falls: This is considered to be one of the most beautiful waterfalls in Maui so it is definitely not to be missed!

Seven Sacred Pools: One of the most popular stops, the Seven Sacred Pools or Ohe’o Gulch, is located about ten miles past Hana. Bask in the beauty of the freshwater pools and cascading waterfalls as you take a dip and enjoy the end of your journey.

Where to eat on the Road to Hana:

Roadside food vendors/trucks: In true Hawaiian fashion, a road trip would not be complete without a stop or two at a food truck. This is a must along the Road to Hana!

Where to stay in Hana:

Hana Maui Resort: With a perfect location in Hana Town, guests can rest up and enjoy the beautiful ambiance at the Hana Maui Resort after a long day on the road. This secluded resort offers guests breathtaking views and exceptional service, all the while keeping with a traditional Hawaiian cultural flare.

Day 5: Return to Wailea or Kaanapali

Today, you have a couple of options. If you felt like you missed some things along the Road to Hana you can backtrack the same way that you came because you will be heading back to the western coast. Alternatively, you could continue on along the south coast on the Pilani Highway. Until recently, this was a rugged road, only accessible to 4WD vehicles. Now it is mostly paved with only a few sections of unpaved dirt road. Unlike the lush, rainforest along the Road to Hana, the Pilani Highway is spotted with grassland and pastures on one side and deep ocean cliffs on the other. The southern view of the Haleakala Volcano is a solid fixture along the route.

Your second decision today is where to stay for the last few nights of the trip. You have the option of heading back to the Kaanapali/Lahaina area or splurging a bit by staying in the ritzier Wailea area in southern Maui. For the purposes of changing things up, let’s focus on Wailea.

No matter which way you choose to get there, enjoy the day by leisurely making your way to Wailea and checking into your new resort. Spend the evening relaxing after a very long last couple of driving days.

Where to eat in Wailea or Kaanapali:
  • Monkeypod Kitchen
  • Ka’ana Kitchen
Where to stay in Wailea:

Andaz Maui at Wailea Resort: This top resort in Maui boasts some of the most premium beachfront property and views. With farm-to-table dining options, stunning rooms, and exceptional service guests will never want to leave this luxury oasis!

Grand Wailea Maui: As a Waldorf Astoria resort, the name says it all. Guests can expect to be pampered in the ultimate luxury all the while enjoying truly magnificent ocean views. With multiple pools and restaurants, a world class spa, and beach front access, every guest will feel relaxes, welcome, and at home.

Maui Hawaii Vacation Bike Tours -

Day 6: Haleakala Sunrise Tour and Biking

If you are a morning person, today will be your day to shine. After your 3am wake-up call head out on the road toward the Haleakala Volcano for a sunrise you won’t soon forget. Make sure to bundle up as it will be very cold at that elevation!

To avoid the crowds, make sure you arrive early to pick the best viewing spot. The parking lot will fill up quickly as well so it’s very important to be there as early as possible.

Insider tip: you must make a reservation to enter the National Park if you are going at sunrise. Visit to to do this. And plan for traffic on the way to the summit—you don’t want to get up at 3am only to miss sunrise!

After enjoying the sunrise, spend the rest of your morning exploring the area and taking in the incredible views of the volcano. Many people choose to bike ride down the volcano’s switchbacks. Bike rental and transportation are available as self-guided or through a tour. Stop in for lunch in the nearby town of Makawao. Next head back north to Ho’okipa Beach or Baldwin Beach to see the sea turtle soaking up the sun that you watched rise this morning.

Spend the rest of the afternoon in Paia if you didn’t already hit this area on your way to Hana earlier in the week. This funky little town is a perfect shopping stop and has some great eateries. If you have time head over the to Iao Needle National Monument for some amazing views.

Where to eat:
  • T. Komoda Stone Bakery
  • Paia Fish Market
  • Surfclub Tacos
Suggested tours:

Maui Hawaii Vacation Luau Tips -

Day 7: Kihei, Wailea, and Makena with Evening Luau

It’s time to get in some relaxing after yet another action-packed day. Enjoy a morning at leisure and then get ready to head out to some beaches in the southern part of the island.

South of Wailea along Makena Road you’ll find that this is the perfect area for hiking out to the lighthouse, and strolling on the black sand beach. If you’re lucky, some whale spotting. Further along the drive is Makena Beach which is the place to park yourself for a relaxing day in the sun. A great snorkeling spot around here is the Ahihi-Kinau Area Reserve. Enjoy lunch at one of the many food trucks along Makena Road.

Head back to your resort before dinner time because it’s time to get ready for an amazing final night experience – a Luau! Depending on where you are staying your resort may offer their own entertainment so be sure to inquire about that or book online ahead of time. With authentic Hawaiian cuisine and incredible cultural entertainment, this activity is not to be missed!

Where to eat:
  • Maui Brewing Co.
  • Bistro Molokini
  • A local Luau event

Day 8: Morning at Leisure, Departure

Alas, all good things must come to an end. Enjoy your last morning in paradise with some famous Hawaiian coffee and a nice walk along the beach. Say Aloha to this beautiful island and bask in the memories of your perfect week in Maui as you make your way back home.

We can make your Maui vacation happen, effortlessly!

To experience the best on your Maui Hawaii vacation, leave the planning to the experts at Sunset Travel & Cruise! Our team of seasoned travel agents will work with you to plan the perfect getaway, without the hassle of doing it all yourself. We make it incredibly easy and take your vacation planning to the next level. Contact us today!


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