Perfect 5 Day Maui Itinerary and Luxury Travel Guide

Maui is the perfect United States destination for a honeymoon, babymoon, family vacation or really any occasion. This 5 day Maui itinerary explains everything you need to know about Maui to plan an unforgettable luxury Hawaii vacation.

I have been to Maui 6+ times, and plan to visit many more. The people, weather and natural beauty of Maui are what keep me returning time and time again.

Keep reading to discover where to stay in Maui, what to do and what to eat. Learn from my many trips, many mistakes, and long lasting memories.

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5 Day Itinerary for Maui

This 5 day Maui itinerary includes a balance between relaxation, culture, and adventure. It provides a mix of beach days, day trips, and excursions.

It also includes visits to the three most popular areas of Maui – Wailea, Lahaina, and Hana.

Keep reading for the top things to do in Maui and how to easily fit it into a 5 day itinerary.

Day 1: Arrive, Explore Wailea, and Attend a Luau

Welcome to your Maui vacation! The first plan of action for your 5 day Maui itinerary is getting checked into your resort.

If you arrive early in the day, spend some time exploring the grounds and relaxing at the pool or beach.

To get the vacation started off right, one thing you must do in Maui is visit a Hawaiian luau. One of the most compelling things about Maui is the wonderful, rich, culture.

Found at many major resorts and private locations, luaus are a fun feast and celebration. Expect a large buffet serving local foods such as Kalua pork, macaroni salad, poi and much more. On stage, watch the history of Maui depicted through dance.

Some of the best Luau’s in Maui are hosted at the Grand Wailea Resort or the Andaz Maui. Their food is the best in my opinion, and I appreciated the open bars.

To prepare for a luau, come hungry and dress in your best tropical attire. When at the event, respect the dancers and culture by giving your full attention.

2: Take a Full Day Snorkeling Tour to the Molokini Crater

Hawaii is one of the best snorkeling locations in the world and Maui has some incredible spots. One of the best places to snorkel in the world is at the Molokini crater, off the coast of Maui.

This day tour to the Molokini crater visits the crater, and another great snorkeling location, turtle town.

The tour includes breakfast and lunch, since you will be on the boat for most of the day. It also has bathrooms, showers, and comfortable seating on board.

Following the snorkel tour, return to your hotel for sunset cocktails and dinner. I’m sure you will be tired after a day of swimming.

3: Take a Day Trip to Lahaina

If you are not staying in Lahaina, a day trip is a great way to experience the charm of the cute, local town. The best way to get to Lahaina is by renting a car, which is discussed above.

Once you arrive in Lahaina, spend time walking the main street, stopping in local shops. Find tropical clothing, souvenirs, local food products and luxury jewelry.

Be sure to stop by the banyan tree at the edge of town to take some photos and marvel in its large size.

Lahaina is also a great place to try some tasty eats. For lunch, stop at either Cheeseburger in Paradise or Kimos.

Both are situated next to the water and serve casual American fare. For dessert get a shave ice or dole whip (or both).

Note – Lahaina suffered devastating wildfires in 2023, so consider alternate plans while the town recovers

4: Spend the Day Relaxing at Your Resort or Take a Whale Watching Tour

A Maui vacation isn’t complete without some relaxation time at the pool or beach. On day 4, I recommend enjoying your resort and the Hawaii sunshine.

Alternatively, if you want to get out, a whale watching tour is super fun!

Whale Watching

Whale watching season in Maui is from December to February when the humpback whales are migrating to warmer waters.

During this time of the year, you can easily spot whales from shore. To find them, look for water spouts approximately 300 feet offshore. Once you spot a spout, keep an eye out for breeching whales.

If you prefer, there are many whale watching tours that go out on boats or kayaks. This option will typically guarantee a sighting and will get you closer to the whales.

If you’re up for the adventure, check out this whale watching snorkel tour.

5: Explore the Road to Hana

The Road to Hana is one of the top things to do in Hawaii. This 40-mile road starts on the north shore then travels along the east shore of Maui and passes many waterfalls, lookouts, and beaches.

For a great Road to Hana day trip, leave your hotel early in a rental car and proceed to the surfing town of Paia. From Paia, follow the Hana highway, stopping along the way to see the sites.

Best Stops on the Road to Hana:

• Ho’okipa beach
• Ke’anae peninsula
• Waianapanapa State Park black sand beach
• Haleakala National Park

Once you arrive in Hana, enjoy a delicious lunch at Braddah Hutts then continue home. Since this is a long day, be sure to come prepared with gas, snacks and extra phone and camera batteries.

My number one tip for the Road to Hana is to utilize this phone guide to help you navigate the roads, learn about the area, and keep yourself from getting lost.

This Road to Hana day trip will take a full day, so plan to leave early and arrive back to your hotel around dinner time.

Since this is the last night of your 5 day Maui vacation, treat yourself to a delicious final dinner.

Where to Stay in Maui

I have either stayed at the below resorts myself or have had them highly recommended by friends and family. With so many great hotels and resorts on the island, this should help narrow it down.

Fairmont Kea Lani

First, my absolute favorite hotel in Maui and one of my favorite hotels in the world. The Fairmont Kea Lani has stunning grounds, personable staff, and approachable luxury in every detail.

Each room at the resort is a suite with high-end furnishings and spacious living areas. the large ocean-front villas are perfect for larger groups or those seeking a bit of privacy.

The three pools are tailored to adults, families, and young children, respectively.

There are two restaurants onsite serving high-end cuisine as well as a casual pool restaurant and café. The willow stream spa provides a wide variety of services and relaxing treatments.

What makes me return to the Fairmont Kea Lani Maui time and again is the fantastic, friendly staff that makes the resort feel like a home away from home.

Read my full Fairmont Kea Lani villa review

Grand Wailea Maui

The Grand Wailea is the most-family focused resort on this list. Owned by Waldorf-Astoria, you can expect their high level of service and luxury.

The rooms are spacious but a bit outdated. However, if an amazing pool is a priority for you, this is the best place to stay. The impressive pool area has multiple pools, waterslides, and swim-up bars.

Hana-Maui Resort

Hands down, if you choose to spend any time in Hana, the Hana-Maui resort is the best resort in the area. This beautiful beachfront resort emphasizes the natural surroundings, with open, airy rooms and large private balconies.  

This resort is conveniently located near many of the restaurants and tourist sites in Hana for easy convenience. Onsite, they have a gym, restaurant and two pools.

The Westin Maui Resort & Spa

If you choose to stay in the Kaanapali area of Maui, the Westin is a great option. As with all Westin properties, the service is exceptional, the rooms are updated, and the amenities meet all your needs.

Onsite at the Westin Maui, you will find 5 restaurants, a large pool, a fitness center, and a spa. Nearby, easily walk to the beach or Whaler’s village shopping center.

Where to Eat in Maui

This Maui travel guide would not be complete without suggesting where to eat on the island. A great thing about Maui is the variety of cuisine and price ranges of food you can find (all of which is delicious).

Nick’s Fish Market

Cuisine: Seafood
Location: Fairmont Kea Lani, Wailea

Nick’s Fish Market is my favorite high-end restaurant in Maui. It is a great spot for a celebration or date night. The food at Nick’s showcases fresh local ingredients with gourmet preparation.

Some of my favorite dishes are the seared scallops with goat cheese tortellini, macadamia crusted catch of the day and the filet mignon.

Humble Market Kitchen

Cuisine: Asian-Fusion
Location: Wailea Beach Resort, Wailea

Humble Market Kitchen is a high-end Asian fusion restaurant with stunning views of Wailea beach and the ocean. The restaurant has a comfortable atmosphere with elevated food.

Once I tasted the complimentary edamame starter, I knew I was in for a great meal.

I recommend the catch of the day, beef short ribs and the cauliflower starter. Be sure to try a cocktail from their unique and inventive drink menu.

Kimos

Cuisine: Casual American
Location: Lahaina

During your day trip in Lahaina, Kimo’s is a great causal lunch spot. The large deck has stunning views of the ocean.

Their Mai Tai’s are delicious and come in a fun tiki glass. For food, I recommend the poke stack, burger and the hula pie for dessert.

Mama’s Fish House

Cuisine: Local Seafood
Location: Paia

Mama’s Fish House is often rated the number one restaurant in Maui and will show up on every Maui travel guide. Unfortunately, I have been unable to get a reservation at this popular spot.

Visitors rave about the service, location, and quality of the fresh caught seafood. Be sure to book a reservation at Mama’s at least two months ahead of time for an unforgettable dinner in Maui.

Braddah Hutts

Cuisine: Hawaiian BBQ
Location: Hana

Braddah Hutts is a food truck in Hana serving up the best Hawaiian BBQ. Located on the property of the owner and chef, this casual food truck will not disappoint.

I recommend stopping here as part of your road to Hana drive. You cannot go wrong with any of the dishes but I recommend the barbecue chicken or kalua plate.

Maui Brewing Co.

Cuisine: Bar Food
Location: Kihei

Maui Brewing is great for a casual dinner or happy hour. This large warehouse has brewing facilities, a large restaurant and outdoor patio.

There are 20+ beers on tap, great pizza, burgers and appetizers. Maui brewing’s outdoor patio has a turf lawn and games, making it a great family spot.

Different Regions of Maui

Maui, while relatively small, has a few different key tourist areas. Many people wonder which area of Maui they should visit. Lets break down how to make that decision:

Hana: Hana is located on the east coast of Maui at the end of the famous “road to Hana”. Hana is known for natural beauty, eco-tourism, and proximity to Maui’s national parks.

I recommend at least seeing Hana by completing a one-day road trip. If you have time in your itinerary, plan to stay 1-2 nights in this cute jungle town.

Lahaina/Kaanapali: The town of Lahaina and nearby resort area of Kaanapali is the most-visited area of Maui. Located on the west coast of Maui, Lahaina is known for local shops, fun restaurants and many tourist activities.

It also has lower priced accommodations compared to Wailea, the luxury area of the island. If are seeking a lower price point, stay in Lahaina. Otherwise, opt for visiting in a day trip.

Wailea: Wailea is my personal favorite area of Maui. Known for high-end luxury and 5-star resorts, Wailea is the most exclusive and pricey area of the island.

Located in west Maui, Wailea also tends to have drier and warmer weather than other areas of the island. If it fits in your price point, I highly recommend using Wailea as your home-base then taking day trips to the above areas.

Getting around Maui

While Maui is a relatively small island, it has many different regions to explore. As mentioned above, it is recommended to visit at least the Wailea, Hana and Lahaina areas.

To see all these locations, many people opt to rent a car for the duration of the their stay. Cars run around $100 per day depending on the season and which vehicle you choose.

Having a car will allow you to explore beyond your resort area, drive to a variety of dining options and have the freedom to run errands at your pleasure.

If you choose to rent a car, arrange before you arrive as they sell out quickly. Once you land in Maui, follow the signs to the rental car facility to retrieve your vehicle.

Alternatively, if you choose not to rent a car, taxis and rideshare options are readily available. Typically, a taxi or rideshare will be $50-$75 from the airport to Lahaina or Wailea.

If you plan to stay at your resort most of the trip, this option may be better for you.

On my recent trip to Maui, I chose to do a hybrid of the above options. Since I knew my plan ahead of time, I chose to rent a car for only two days. These days were the Road to Hana and day trip to Lahaina.

Ultimately, your decision depends on what about Maui you plan to experience each day.

5 Day Maui Packing List

Summary of this Maui 5 Day Itinerary

Overall, your Maui vacation will be wonderful whether you do all the activities on this list or choose to relax at your resort the entire time. Be sure to take advantage of the local beauty, explore the Hawaiian culture and get to know all the amazing people.

For a different Hawaiian vacation, consider traveling to Oahu. The city of Honolulu is an interesting contrast to the smaller towns of Maui.

Related Posts:

• 12 Best Restaurants In Maui – The Top Restaurants In West Maui
• 120 Maui Captions for Your Hawaiian Vacation Photos
• Complete One Day Road To Hana Guide
• Guide To One Day In Lahaina Old Town, Maui Hawaii
• Fairmont Kea Lani Villas And Resort Review
• 7 Best Hotels In Wailea Maui For A Luxury Hawaii Vacation
• What To Expect At The Grand Wailea Luau

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