Extended Weekend in Maui, Hawai'i

Maui’s main airport is located in Kahului, where you’ll land and begin your island adventure. Since a car is essential for exploring beyond your hotel or resort, this is also where you'll pick up your rental car. I found more affordable rental options just 10 minutes away at Enterprise on Hana Hwy. Given the time zone change, you’ll likely arrive in the late afternoon or evening. If you’re lucky, you’ll have just enough time to grab your car, check into your hotel and catch a stunning Maui sunset. I would recommend catching a sunset near Kihei. Start your evening at South Maui Gardens Food Truck oasis for a quick bite, then stroll to nearby Kalama Park to enjoy the sunset views.

Upon entering Haleakalā National Park, be prepared to pay a $30 day pass fee or present your Annual National Park pass for entry. This day is a “choose your own adventure” experience, with a range of options to explore the park’s landscapes. If you’re after breathtaking panoramic views, drive to the summit of Haleakalā Volcano and stop by the Haleakalā Visitor Center. At 10,000 feet, clouds will surround you and treated to 360-degree views of the island below.

For a short but rewarding hike at the summit, try the White Hill Trail (Pa Kaoao Trail) for stunning views and a taste of the area’s unique terrain. White Hill Trail on AllTrails.

For the more adventurous, consider the Sliding Sands Trail, a challenging 11-mile trek that takes you through volcanic landscapes. The hike offers diverse terrain, including volcanic cinder fields and desert-like surroundings. To access the trail, park at the Halemau'u Trailhead parking lot and walk to the designated hitchhiker pick-up point. If you’re not comfortable hitchhiking, consider securing a permit for an overnight hike, completing the full 22-mile round-trip. Or organize a shuttle with friends. I only waited a couple of minutes before a friendly family offered me a ride to the summit, where you can use restrooms before starting the trail.

Be prepared for rugged conditions — bring at least two liters of water, snacks, and wear sturdy footwear. The terrain is dry and windy, with occasional rain showers. The hike typically takes around 5.5 hours to complete.

Another bucket-list experience is catching the sunrise at Haleakalā, though it requires a permit, which tends to sell out quickly. Limited reservations for sunrise tickets open at 7 pm the night before your visit, with only 30 or so tickets available, so they go fast. Or if you’re planning, reservations are released three months in advance and can be reserved here: Sunrise Permit Reservations.

Snorkeling is an absolute must-do when visiting Hawaii, and Molokini Crater is a historic destination that should be at the top of your list. Formed by an eruption over 230,000 years ago, Molokini is now a protected marine sanctuary, offering some of the clearest waters in Hawaii and an array of marine life. It’s the perfect spot to dive into the underwater world. Most tours depart Wailuku, where you'll board the boat for a 5-hour adventure. Many operators offer onboard lunch and the chance to snorkel alongside sea turtles, colorful tropical fish and other marine species in this crescent-shaped crater. Whether you're a seasoned snorkeler or a first-timer, Molokini promises an unforgettable experience in the heart of the Pacific.

The Road to Hana is one of Maui’s most iconic drives. It is a 64-mile journey along the island's coastline, connecting Kahului to the small town of Hana, with countless scenic stops along the way. Your adventure begins at mile marker 2, where you'll visit Twin Falls. Take a moment to stretch your legs and grab a bite of Aunt Sandy’s famous banana bread. Next, head to Ho'okipa Beach Park, a prime spot for watching surfers ride the waves. For a splash of color, stop by the Maui Garden of Eden, home to tropical flowers and vistas.

As you continue your drive, there will be plenty of opportunities to stop for snacks and enjoy the scenic beauty. Highlights include the picturesque coastal views and lush landscapes. But gas is limited, so fill up before you depart for your road trip. Your destination is the charming town of Hana. Explore its quiet beauty before continuing to hike Wailua Falls (mile marker 45) or relax at Hamoa Beach (mile marker 51). I highly recommend making the trek to Hamoa Beach — its beauty and seclusion make it a perfect spot to unwind before heading back.

Afterward, make your way back along the Road to Hana. Make your reservation at Black Sands Beach within Waiʻānapanapa State Park for a swim or simply to enjoy the black sand shore. Reservations are required for entry, so be sure to book ahead: Waiʻānapanapa State Park Reservations.

To wrap up the day, stop for dinner at the Paia Fish Market Restaurant in the town of Paia, known for its fresh seafood. If you have time, cap off your day with a visit to Ho'okipa Beach Park, where you can watch surfers catch waves as the sun sets over the horizon. This drive offers the perfect blend of adventure, relaxation and natural beauty, making it an unforgettable Maui experience.

For those looking to enjoy the scenery along the way, consider booking a guided tour. This drive can be long and dangerous, so proceed on-own with caution.

I highly recommend booking an evening flight to maximize your time on Maui, giving you a full day to unwind and enjoy the island’s beaches. My personal favorite is Kamaole Beach, a beautiful spot on the south side of the island that’s perfect for a relaxing day by the sea with calm waters. The area boasts a collection of beaches, each offering something unique: Ulua Beach is ideal for snorkeling. Wailea Beach is great for family-friendly fun, and Maluaka Beach offers peaceful views and a more tranquil atmosphere.

This side of the island is home to luxurious resorts and hotels, making it a popular area for tourists looking to experience the beauty and amenities of Maui. It’s the perfect place to relax, but also offers plenty of opportunities for exploring the vibrant beachfront and dining.

Considering adding in some hikes to your Maui adventure. Iao Valley State Monument is a must for a quick, short walk along a paved path to view the Iao Needle. For those looking for a challenge, consider Waihe'e Ridge Trail — a 4.2 mile trek gaining 1500 feet of elevation over a span of two miles, overlooking the Waihe’e Valley.