4 or 5-Day Maui Itinerary for First Time Visitors

While it is tempting to spend a week or two sunbathing by Maui’s beaches, some of us don’t have the luxury of time. With a direct 6.5-hour flight from the West Coast, we’ve done several long weekend visits to the islands for years. If you have limited vacation time and yet still want a short getaway, this is a 4 or 5-day Maui itinerary for first time visitors.

Though, there is so much more to Maui or the Valley Isle beyond its beaches. This itinerary, based on some of our past visits, will include cultural, adventure, outdoor activities, popular attractions and of course, plenty of beach time thrown in.

Day 1 Maui Itinerary

Most flights from the mainland USA usually arrive right around lunchtime. This gives visitors plenty of time in the afternoon to stop at some attractions before checking in at the hotel. Try to request for an early check-in and you may get lucky.

If you’re hungry, these are the places we usually go since it is near the airport. Our first stop is usually Geste Shrimp. This is actually a food truck and has been around for awhile.

We love their garlic shrimp plates that rival those we’ve found in Oahu’s North Shore area. There are many food trucks parked along with Geste Shrimp across from the Costco store.

If you have a Costco membership, there is one less than two miles from the airport. It is a great place to go for pizza, sandwiches and snacks or to stock up if you’re staying someplace with a kitchen.

If you like poke (marinated seafood chunks), they sell a variety here. This is usually my husband and son’s first meal after getting off the plane on any of the Hawaiian Islands.

No matter where you eat after landing, we recommend ordering the items for takeout and going to Kanaha Beach near the airport to watch the kite surfers. They are a delight to watch as they perform their daring moves. It’s also a great place to have a picnic and stretch your legs before heading to your hotel to check in.

After a long flight and waiting around airports, this first/arrival day is the perfect day to unwind in the afternoon up to the early evening. There is no better way to start your Maui getaway than relaxing at the beach after checking in.

Rest and Beach Time

If you’re staying in the Ka’anapali area/west and your hotel room isn’t ready yet, the Honolua Forest Trail also called the Enchanted Forest is a short drive away. This scenic trail is filled with native Hawaiian plants, ferns, banyan trees leading to picturesque Honolua Bay and cove.

End your travel day with a walk on the beach for some sunset viewing. Maui offers some of the most glorious sunsets we’ve seen. Some of the most popular spots for sunset viewing are at Ka’anapali Beach, Makena Beach, or Kapalua Bay Beach.

Day 2 – Water Activities and Hike

It’s time to see and experience Maui’s water activities and short hikes. Due to the time difference, we always wake up early to catch the sunrise. It’s one of the few times we are grateful for jetlag. So, start your day early by watching the sunrise.

Beach and Water Activities

Maui has over 30 miles of beaches and boasting some of the best in the world. There is no shortage of water sports activities from surfing, kite/wind surfing, snorkeling, kayaking, stand up paddling, parasailing or swimming here. If you want to sunbathe or just have a stroll, there’s plenty of sandy shores too.

There are several companies that offer various snorkeling and scuba tours. Some can be combined with whale or dolphin watching tours. One of the most popular is a snorkeling trip to the Molokini Crater.

Located about two miles from Maui’s south shore area, this volcanic caldera offers one of the world’s best areas for spotting diverse marine wildlife. Other favorite snorkeling spots in Maui include Honolua Bay, Kapalua Bay and Maluaka Beach. Ka’anapali Beach and Baby Beach are great for families to check out.

Iao Valley State Monument

If you have some time for a short hike or walk, Iao Valley State Monument is a fantastic pit stop. It’s a great place to learn about Hawaiian culture, history and seeing the native plants on the ethno botanical loop and lookout trail. The Iao Needle and stream also provide a beautiful backdrop.

Other short hikes/walks to take depending on your location are the 3.5-mile Kapalua Coastal trail that snakes through four of Maui’s bays along a wooden boardwalk and volcanic rocks. The paved Wailea Coastal Walk along the south shore is also a wonderful stroll through five white sand beaches, top-notch seaside resorts and the chance to see humpback whales during winter and sea turtles along the shore.

Luau Time

After a busy day of activities, it’s time to enjoy some Hawaiian culture, music and food by attending a luau at night. This Hawaiian festivity is something not to be missed especially if it’s your first visit.

Luaus offer a glimpse into the Hawaiian and Polynesian culture with food and entertainment that usually includes hula dancers and fire throwers. It also has a buffet of local dishes like kalua pig (roasted pig), poi (taro potato), macaroni salad, lomilomi salmon, haupia (cocout pudding), teriyaki, fresh tropical fruits and of course drinks like Mai Tai, Pina Colada and Blue Hawaii.

Visitors also witness an Imu ceremony to see how a pig is cooked in an underground oven. It’s a wonderful glimpse into the Polynesian and Hawaiian culture and food.

A major bonus is that these luaus are usually by the beach offering fantastic views of the ocean and the sunsets. The most popular luaus are Myths of Maui Luau at Royal Lahaina Resort, Old Lahaina Luau and the Sheraton’s Luau show.

Day 3 – Haleakala National Park and the Upcountry

Start your day early for a visit to Haleakala National Park, known as the “House of the Sun”, and the up county area. If you can, watching the sunrise at Haleakala is a bucket list item for many people. We’ve never been early risers so we have never gone around to doing this.

Reservations must be made to enter the park to watch the sunrise between 3AM and 7AM via recreation.gov. There are also various tour operators that offer sunrise viewing options. The drive to the park takes about an hour from the airport area so plan accordingly.

Haleakala Park is an amazing and unique park. The summit district rises high above the clouds to over 10,000 feet. It is a sight to behold with an otherworldly landscape.

Bring extra layers of clothing since it is a lot colder at the summit and be aware of possible altitude sickness. Keep an eye out for the Hawaiian goose or nene along the road. There are several hiking trails that range from .5 mile to 11 miles depending on your endurance and time.

Go to the visitor’s center to see which trails are open. If you’re traveling with kids, be sure to participate in the Junior Rangers program to learn more about the park.

Maui Upcountry Area

After spending a at least a couple of hours at Haleakala, it’s time to explore Maui’s upcountry area known for the many farms lining the mountain slopes. Two of our favorite quick stops are Ali’ Kula Lavender Farms and Surfing Goat Dairy Farm. Please check with them before you visit to see what is available due to current conditions and restrictions.

The 13.5-acre farm is filled with about 55,000 lavender plants and 20 different lavender varieties in addition to other varieties of tropical flora and succulents. The views are beautiful and there’s a sense of calmness around the property with lavender scent wafting through the air.

There are guided tours and also a self-guided tour version using a pamphlet. It’s a great way to learn more and explore the farm. Admission to the farm is three dollars per person with senior and military discounts. Children ages 12 and under are free.

Surfing Goat Dairy Farm is a working goat farm and is a family favorite among visitors and locals. They offer several tours that allow visitors to watch, pet or feed the resident goats.

They also produce award winning gourmet goat cheese that are quite delicious. This is a wonderful stop for families and animal lovers.

Sunset/Dinner Cruise

End your day with a relaxing sunset dinner cruise which sometimes doubles as a dolphin or whale watching tour depending on when you’re here. Many of these cruises are usually about two hours and offer live entertainment, drinks and dinner. It’s a great way to see a different perspective of Maui’s coast. Check out Pride of Maui or Maui Princess Dinner Cruise to book your excursion.

Day 4 – Drive the Road to Hana

The Road to Hana is also often on many people’s things to do in Maui. This is definitely a lot more about the journey than the destination itself, which is the quaint town of Hana. The infamous road is 64+ miles with about 617 hairpin curves and 59 one-lane bridges that usually take about 2.5 hours of driving one way with minimal stops.

This road takes visitors past some very scenic spots that include beaches, tropical rainforests, waterfalls and cliffs. With the travel time and many pit stops in between, this trip usually takes a whole day.

Some of the most popular stops are Ho’okipa Beach Park to watch the wind surfers, Twin Falls, Maui Garden of Eden, Wailua Valley State Wayside, Halfway to Hana Stand to buy what many people claim the island’s best homemade banana bread. Upper Waikani Falls, Pua’a Ka’a Falls and State Park at Mile marker 22 and Nahiku Marketplace is a great place to stop for lunch, Wai’anapanapa State Park (home of the black sand beach) and Kaumahina State Wayside Park.

If you don’t feel like driving, there are several tours wit from Get Your Guide with experienced drivers and knowledgeable tour guides. These tours know where all the best pit stops are and the best places for photo ops. A bonus is you can really enjoy the roadside scenery a whole lot more with some expert guidance.