The Best of Maui in Five Days

If you’re headed to Maui for a short visit, this itinerary will show you the absolute best of the island in just five days! You will take in Maui’s majestic volcano at sunrise, snorkel with rare sea life, travel the famous Road to Hana and taste the best shave ice anywhere. This island has both white and black sand beaches, a cooling tropical breeze and some of the most delicious fresh fish around, prepared to perfection. Plus, the warm ocean waves are always nearby, for a visual treat or a refreshing dip.

Tips to Know When Visiting Maui
The best time to visit Maui is anytime. The tropical climate is consistent year-round. Daytime highs are in the mid-80s in the summer and around 75 in the winter months.

November through March is considered the rainy season, but rain showers are short and soon clear skies and sunshine will return, leaving the island stunningly green. Often when one side of the island is cloudy, the other side is bright and sunny!

January through March is prime for whale watching. Off Maui’s sunny west and south shores, the ocean is  sheltered by the islands of Molokai, Lanai and Kahoolawe in our four island County, making this the premier place to see humpback whales breaching and dolphins playing.

Arrival day is generally reserved for getting groceries, using our contactless check in to your condo, and breathing in the relaxing, fragrant air of the island. You’re on Maui now!

To get the most of your time in Maui, follow this itinerary, starting the day after you arrive:

Day 1: Hit the Beach

Start the day going to one of Maui’s beautiful beaches. Head to Lahaina and check out Baby Beach, named for the fringing reef that creates a calm lagoon for splashing around or floating on a lounger. Get directions and see our other favorite beaches here. Beaches are best before noon, so when you’ve had enough sun, duck into Down the Hatch for a cool drink or lunch (happy hour starts at 2pm!). Then spend the afternoon checking out the shops and harbor area of this former whaling capital. You can also do a walking tour of museums, or check out the many fine art galleries. Another option is to visit Maui Ocean Center in Maalaea. We highly recommend this world class aquarium and marine park. It is a great primer for identifying ocean species you might encounter, has an amazing 3D whale movie, and one of the best gift shops on the entire island. Be sure to make aquarium reservations in advance, as the park uses this method to keep crowds to a minimum.

Staying at Kuleana Resort is an excellent choice for West Maui based activities.

Day 2: Explore the Ocean

Ready to get up early? It’s a great day to go on a snorkel or dive charter to Molokini or Turtle Reef. One of Hawai’i’s most spectacular natural treasures is the wide variety of marine life found in the nearshore waters of the state. Over 400 species reef fish inhabit Hawai’i’s coastal waters, many found nowhere else in the world. Tours leave out of Maalaea Harbor or Lahaina Harbor. If your destination is Molokini Marine Preserve, we suggest staying in Maalaea. It makes getting up early so much easier! A charter out of Lahaina is great for an afternoon snorkel to Turtle Reef. Set against the backdrop of a partially collapsed pier, you are bound to see an abundance of green sea turtles, and likely some reef sharks on this relatively shallow, easy dive.

For ocean charters and any other activities, we recommend booking through Maui Sights and Treasures. No high pressure sales tactics here!

Day 3: Sunrise at Haleakala Crater and Upcountry Tour

To take in the sunrise at Haleakala National Park, what we call the “House of the Sun” or simply “the crater,” you will want an early wake-up call and an advance reservation.  Check sunrise time for your desired date, then backtrack from there. Driving time from Wailea or Lahaina is about two hours. Allow time to get up, dressed, grab something to eat and fill your coffee mug. Since this is a popular attraction – who wouldn’t want to see the sunrise above the clouds from an active volcano – you will want to get there at least 30 minutes before sunrise. The activity does draw a large crowd. It will take some time to navigate the winding 38-mile road, but it will be worth the drive and early wake-up call. The views from the crater are stunning- not just the volcanic landscape, but also the 180-degree bi-coastal view of Maui and distant islands.

A word of caution: be sure to dress in layers as temperatures at the 9,740-foot summit will be about 30 degrees colder than at sea level. We are not kidding- wear a t-shirt, sweatshirt and coat, long pants, shoes and socks for this alpine environment. Pack a change of clothes- shorts and flip flops, to change into as you descend to warmer layers of the mountain.

Not a fan of getting up pre-dawn? No reservations are needed to enter the park after 9am, and the views are just as spectacular. Pay at the entry and save your receipt. Your National Park entry is good for three days, and you can use the receipt when you go on the Road to Hana, stopping at Kipahulu to visit the “Seven Pools” area and the Pipiwai trail. Staying in South Maui will shave off some travel time to both Haleakala and Hana.

Once you leave Haleakala National Park, find a bite to eat at Kula Lodge upcountry, or drive out to Grandma’s Coffee or the Ranch Store in Ulupalakua for more spectacular views.

Getting up early, tiredness may kick in by afternoon, so consider a relaxing evening barbequing dinner at your condo, and catch sunset on the beach. Local tip- if you are grilling some of our local warm-water fish, cut your cooking time to half of what you normally would at home. A light spritz of cooking spray on the grill and a sprinkle of dry Hawaii seasoning on the  fish if you desire is all the prep needed. When the skinless filet just starts to turn opaque, flip it over.  Total cooking time is about 6 minutes on a hot grill, depending on the thickness of the filet. Top with mango or pineapple salsa for an easy island-style main course.

Day 4: Take a Helicopter Tour over Maui County

If you do one “splurge” activity on your Maui vacation, this is it. The island view from a helicopter is spectacular. You’ll see hidden valleys, mountain peaks and waterfalls not visible from the ground level, and learn about the island, too. The pilots are well-versed in the island’s historical past and geography. They may even point out pods of whales, dolphins or manta rays. Since Maui County consists of four islands, we recommend a tour that takes in both West Maui and the sea cliffs of Molokai. A more budget friendly, yet still amazing option is an East Maui tour. Plan a morning tour between 8 and 11am for the best viewing weather.

After landing, explore the shops and restaurants of nearby Paia town. A fresh ono, ahi or mahi mahi sandwich at Paia Fish Market is worth the wait. Be sure to try Uilani’s shave ice across the street for dessert – it is some of the best. Plan on parking in the lot to the right as you come into town (before the gas station), or a block up Baldwin avenue on the left (turn at the traffic light) and walking the quaint little town. Parking on the street is hard to come by.

Day 5: Drive the Road to Hana

Many think the road to Hana is the highlight of a Maui vacation- but that’s if you take our local suggestions to heart. Also known as Highway 36, it is one of the most famous roadways in the country. The trip is 52 miles of winding curves, with 56 bridges, some only one-lane, so be prepared to stop. Hairpin turns reveal stunning jungle cliffs. It will take about 3 hours to drive, but you will want the entire day to stop along the way, walk in a nature reserve or take a short hike, view waterfalls and ocean vistas.

Here are the tips to make your journey on the Road to Hana successful.

  • Get up early. From where ever you are staying, check the drive time on your GPS to Paia. Arriving in Paia to start your journey around 6am is ideal. Later in the morning the drive gets very busy and parking is difficult.
  • You will need advance reservations to visit Waianapanapa State Park, a sprawling oceanfront park with a black sand beach and shallow caves. Reservations are taken by time of day. If you leave Paia by 7am and make a few stops, you should reach the park around 10am, so choose the 10am to 12:30 time slot. Another option if you plan to hike the Pipiwai trail is to make few stops along the way, and go directly to the Kipahulu entrance of Haleakala National park. Then you can stop at sights on the way back, and choose 3pm – 6pm timeslot for your Waianapanapa visit. Plan on leaving the park by 4:30- you don’t want to be driving the curvy road back to Paia in the dark.
  • This is an epic road trip, where the journey is the adventure. Pack some snacks and beverages!
  • Use an app like Shaka Guide. This narrated tour not only tells you the best places to stop, it is filled with history and cultural information, is humorous and has some cool Hawaiian music. Download the paid app on Wi-Fi before leaving your accommodations, then activate it on your phone and connect it to your car’s Bluetooth before heading out. The app runs on GPS, so will continue to work on your tour even when cell service drops out, but needs to be set up in advance.
  • Don’t park in areas posted “no parking,” on private property or anywhere blocking traffic. Fines are hefty and it is considered really rude locally.
  • Avoid “going all the way around” or taking a reverse tour to Hana during winter months. Much of the route past Kipahulu to Upcountry is unpaved and can be treacherous with flash floods. Your rental car contract forbids it- if you have any car troubles on your journey, you will be stranded as there is no cell service. This is a rural, local area, not a tourist area, so please don’t enter non-public areas.
  • Don’t bring anything along that you can’t carry with you when you leave the car, with the exception of a small cooler for snacks in the trunk. Unfortunately, break-ins are common along the Road to Hana. Do not travel with luggage or leave expensive cameras, laptops or other items in the car, including the trunk.

If you change the itinerary around, try to keep Haleakala and Hana within 3 days of each other so you don’t pay again for admission. If you scuba dive on day 2, you cannot go to high elevations on day 3, so swap Haleakala with Hana.

There is plenty more to see and do on Maui, but this itinerary takes in some of the most popular bucket list items. Have a wonderful vacation on Maui, and come back when you can stay longer!


2023-01-17T21:16:25+00:00December 1st, 2022|Beach, Culture, Dining, Entertainment, Ocean|

Share This Story, Choose Your Platform!

Destination Maui Vacations
Administrative Office: 380 Huku Li'I Place, Suite 206
Kihei, HI 96753
Copyright © 2023 Destination Maui Vacations. All Rights Reserved.