I’ll never forget the moment I first stepped onto Maui’s sun-soaked shores. Maui greets you with the scent of saltwater and the rustle of palm fronds, creating a sense of tranquility that’s hard to describe and even harder to forget. Whether you’re here for beaches, adventure, or just to slow down and soak in the island vibes, this 5-day Maui itinerary is packed with fun things to do on Maui that made my trip unforgettable. From sunrise at Haleakalā to the winding Road to Hana, here’s exactly how I spent five perfect days on the Valley Isle.
Epic 5 Day Maui Itinerary
Day 1: Arriving in Maui + Relaxing in Kihei or Wailea
Morning: Arrive and Get Oriented
After landing at Kahului Airport (OGG), I picked up my rental car a must if you plan to explore the island freely. I recommend booking in advance, especially during peak seasons. From the airport, it’s about a 25-minute drive to Kihei or 35 minutes to Wailea. I chose Kihei for its laid-back vibe, proximity to affordable dining, and central location for exploring the island.
Tips:
- Download Google Maps offline or use the GyPSy Guide app to get audio tips during your drive.
- Try to book a flight that arrives before noon so you can check in early and make the most of your afternoon.
- Pick up a local SIM or activate international roaming if you’ll be navigating frequently.
Check-in and Essentials Stop
Once I dropped off my bags at the hotel or vacation rental, I headed to a nearby grocery store (try Foodland, Safeway, or Times Supermarket) to grab some essentials. I bought local fruits like papayas and apple bananas, stocked up on water and beach snacks, and made sure I had reef-safe sunscreen and a cooler bag. If you’re planning early hikes or long beach days, it’s helpful to grab portable breakfast options too.
Afternoon: Beach Time and Shave Ice
After a long flight, the best way to unwind is by hitting the beach. I headed to Kamaole Beach Park III, a peaceful stretch of sand with grassy areas for picnics, a calm swimming area, and excellent facilities (restrooms, showers, and shaded benches). I laid out a towel, dipped into the warm Pacific, and let jet lag melt away.
Later in the afternoon, I made the short walk to Ululani’s Shave Ice. I chose the classic rainbow combo with li hing mui powder and a snow cap topping it was the perfect refreshment in the island heat.
Tips:
- Kamaole Beach Park I is great for snorkeling when the water is clear; bring a mask and reef shoes.
- Beach gear rentals (chairs, umbrellas, snorkels) are available in town if you didn’t pack your own.
- Ululani’s has locations in Lahaina, Kihei, and Kahului so if you love it, you can enjoy it more than once!
Evening: Dinner and Sunset Walk
For dinner, I chose Coconut’s Fish Cafe, a casual spot known for generous portions and fresh, local catch. The grilled mahi mahi tacos were stacked high and full of flavor. They also offer vegetarian options and local brews if you want to toast your arrival.
After dinner, I strolled along Keawakapu Beach. It’s often quieter than other South Maui beaches and offers one of the best sunset spots on the island. The beach has tide pools at the northern end, perfect for some casual exploring before dusk.
Optional Add-On:
- If you’re feeling energetic and want a taste of West Maui, drive to Black Rock in Ka’anapali for the torch lighting and cliff diving ceremony just after sunset. It’s about a 45-minute drive but a memorable experience if you’re up for the evening adventure.
Day 2: Epic Road to Hana Adventure
Early Morning:
Start Before Sunrise The Road to Hana is one of the coolest things to do in Maui, and it’s truly about the journey, not the destination. I left Kihei by 5:30 AM to get a head start on the day. This winding, 64-mile drive along Maui’s northeastern coastline includes over 600 curves and 50+ one-lane bridges.
Preparation Tips:
- Fill your gas tank the night before there are no gas stations past Paia.
- Bring a packed cooler with breakfast, snacks, and lots of water.
- Wear comfortable hiking sandals or water shoes for muddy trails.
- Download offline maps and the Shaka Guide app for real-time GPS audio commentary.
- Keep some small bills handy, many roadside stands along the Hana Highway only accept cash, especially for local treats like banana bread..
Top Stops Along the Way:
- Twin Falls: First waterfall stop, with a short trail to a refreshing swimming hole. Great for early photos before the crowds.
- Waikamoi Ridge Trail: An underrated loop trail through a lush bamboo forest. Peaceful and perfect for stretching your legs.
- Ke‘anae Peninsula: A picturesque lookout point and cultural spot. You can also grab homemade taro bread at Aunty Sandy’s Banana Bread stand.
- Ching’s Pond (optional): A roadside plunge pool just past mile marker 16. Be cautious it’s a local spot and not patrolled.
- Wai‘anapanapa State Park: This park features Maui’s striking black sand beach and fascinating coastal formations. Since it’s a popular spot, you’ll need to reserve entry online before visiting.
Lunch at Hana Farms: This open-air tropical café is a delicious stop just before you reach Hana town. I had the teriyaki chicken bowl and their famous banana bread both were fresh and flavorful. You can also browse handmade crafts and local honey.
Afternoon:
Hamoa Beach + Optional Red Sand Beach Once in Hana, I made my way to Hamoa Beach, a crescent-shaped shoreline with soft gray sand and vibrant turquoise waves. Parking is limited, so arrive early in the afternoon. There are showers and restrooms nearby.
If you’re feeling adventurous, Kaihalulu Red Sand Beach offers a striking visual contrast with its rust-colored shoreline. The trail is tricky it involves navigating a narrow, slippery cliffside path, so wear good shoes and avoid visiting during rain.
Safety Tips:
- Red Sand Beach is on partially private land access is tolerated but not formally sanctioned.
- Be cautious of high surf and strong currents at both beaches.
- Always respect local signs and never trespass.
Evening:
Drive Back or Stay Overnight By late afternoon, I started the drive back along the same coastal route. It took about 2.5–3 hours without major stops. If you prefer a more relaxed pace, book a night at Hana-Maui Resort or a vacation rental and enjoy the quiet serenity of this lush area.
Optional Stops on Return:
- Wailua Falls: A roadside waterfall just beyond Hana no hiking required.
- Coconut Glen’s: Vegan ice cream made from coconut milk. Their unique flavors were a sweet end to a long day.
Final Tips:
- Don’t attempt to loop around via the southern route unless you’ve researched road conditions. It’s often unpaved, remote, and not always rental-car friendly.
- Be courteous: pull over for faster cars, honk before blind curves, and avoid blasting music near quiet residential areas.
Day 3: Haleakalā Sunrise + Upcountry Maui
3:00 AM
Wake-Up for Sunrise at Haleakalā Waking up at 3 AM might sound rough on vacation, but trust me it’s worth every yawn. Watching the sun rise from above the clouds at Haleakalā National Park was one of the most awe-inspiring experiences I’ve ever had. The air at the summit is thin and biting cold, even in summer, so pack a thick jacket, gloves, and a beanie. If you don’t have warm clothes, some visitors wrap up in hotel blankets no shame in staying warm!
To access the summit for sunrise, you’ll need a reservation through recreation.gov. These sell out quickly, so book as early as you can (up to 60 days in advance).
Tips:
- Arrive at least 60–90 minutes before sunrise to account for parking and walking to the overlook.
- Bring a flashlight or headlamp for safety in the dark.
- Be mindful of wildlife on the road Nēnē (Hawaiian geese) often appear near the summit.
- Use the Haleakalā Visitor Center bathrooms before settling in to watch the sunrise.. It gets cold (really cold), so bring a jacket and book your sunrise reservation in advance on recreation.gov.
Tips:
- Arrive at least 60 minutes before sunrise to secure a parking spot.
- Use your headlights responsibly and be mindful of cyclists.
6:30 AM
Sunrise + Silversword Sighting The view is surreal at over 10,000 feet elevation, it feels like you’re on another planet. I also saw the rare silversword plant that only grows here.
Late Morning: Kula Lodge Brunch After descending the volcano, I stopped at Kula Lodge for brunch with panoramic views and fresh papaya bowls.
Midday:
Upcountry Delights After a relaxed brunch at Kula Lodge, I explored Maui’s charming Upcountry a quieter, cooler region on the slopes of Haleakalā that feels worlds apart from the beach. Here’s what I visited:
- Ali’i Kula Lavender Farm: Nestled at 4,000 feet elevation, this peaceful farm offers panoramic views of the West Maui Mountains and central valley. I wandered through fields of blooming lavender (especially vibrant from June to August), sipped lavender tea, and browsed handmade soaps, honey, and essential oils in the gift shop. Don’t miss the Secret Garden trail if you have time for a short, meditative walk.
- MauiWine: This historic estate in Ulupalakua offers a unique chance to try wines made from local pineapple and grapes. The King’s Cottage tasting room is set among towering trees and rolling hills. I recommend doing a tasting flight and taking a guided tour to learn about the winery’s 150-year-old roots and royal connections.
- Surfing Goat Dairy: Quirky and fun, this working goat farm lets you get hands-on. I joined the “Evening Chores & Milking Tour,” where I fed goats, learned about cheese-making, and even tried my hand at milking. Their gourmet goat cheese is award-winning my favorite was the Maui Secret (a soft chèvre with garlic and herbs).
Tips:
- The Lavender Farm is especially photogenic during the early afternoon light.
- Many upcountry spots close by 4 PM plan ahead!
Evening
Explore Paia Town + Dinner I drove back through Paia, a bohemian surf town on Maui’s North Shore known for its artsy shops, vibrant cafes, and laid-back vibe. I parked near Baldwin Avenue and strolled through a mix of locally-owned boutiques, surf stores, and art galleries. Alice in Hulaland had some great souvenirs and quirky finds, and I browsed beachy jewelry at Maui Hands.
Hungry after a long day of exploring, I headed to Flatbread Company, one of Paia’s most popular eateries. The restaurant has a cozy, rustic vibe with a wood-fired oven at its center. I ordered the Kalua Pork flatbread with local pineapple and goat cheese, plus a side salad made with fresh Upcountry greens. They also have vegan and gluten-free options, which makes it a great pick for groups with different dietary needs.
Tips:
- Arrive before 6:30 PM to avoid long wait times.
- Parking in Paia can be tricky look for spots on Baldwin Avenue or near the Paia Community Center.
- Save time for a post-dinner walk on Paia Bay Beach, just a short stroll behind the gas station.
Bonus Tip:
- Stop by Mana Foods in Paia to grab organic snacks and local produce.
Day 4: Snorkeling + Beach Hopping in South Maui
Morning:
Snorkeling at Molokini & Turtle Town I joined a morning snorkel tour to Molokini Crater and Turtle Town with Redline Rafting, and it was easily one of the highlights of the trip. Molokini is a partially submerged volcanic crater about 3 miles offshore. Its crescent shape protects the inside reef, creating crystal-clear visibility often up to 150 feet. We spotted a variety of marine life, from butterflyfish and eels to the occasional reef shark.
After Molokini, we headed to Turtle Town, a stretch of coral reef off the coast of Makena where Hawaiian green sea turtles are often seen feeding and resting. Floating silently as these gentle creatures swam past me was a surreal experience.
Tips:
- Choose a smaller boat tour for fewer crowds and access to better snorkeling spots.
- Bring a rash guard for sun protection and to avoid chafing from snorkel gear.
- Motion sickness? Take Dramamine the night before and again in the morning.
- GoPros or waterproof phone cases are perfect for underwater shots.
- Some tours offer breakfast and snorkel gear check in advance.
Late Morning:
Return and Poolside Rest After a salty, sun-filled morning, we returned to the dock by late morning. I grabbed a fruit smoothie at Akamai Coffee on the way back and then headed to my hotel pool for a well-earned lounge session. A shaded lounger, chilled drink, and some downtime helped balance the adventure-packed morning.
Afternoon:
Makena Beach (Big Beach) Around 2 PM, I drove south to Makena State Park, home to one of Maui’s most iconic beaches Big Beach. Stretching nearly two-thirds of a mile, this golden beach is perfect for sunbathing, beach walks, and scenic photos. The shore break can be intense though, so I only went in for a quick dip.
For a more secluded experience, I climbed the lava trail over the hill at the north end to reach Little Beach. It’s smaller, clothing-optional, and attracts a more bohemian crowd. Sundays are especially lively with drum circles and fire dancing at sunset.
Tips:
- Pack water, snacks, and an umbrella there’s no shade or food vendors onsite.
- Arrive early or late in the day for easier parking.
- Be cautious of the shore break; it’s not ideal for beginner swimmers.
- Restrooms and showers are located at the Big Beach entrance.
Evening:
Sunset Picnic + Food Truck Dinner To wind down the day, I stopped by the Kihei Food Truck Park, a casual spot with plenty of options. My picks? Thai Mee Up for chicken pad Thai and Tacos La Bahia for fish tacos with mango salsa. I packed everything to-go and headed to Keawakapu Beach, just a short drive away.
This beach has soft sand, calm waters, and a peaceful vibe perfect for a picnic dinner. As the sky turned pink and the waves gently lapped the shore, I couldn’t imagine a better way to close out a day of sea, sand, and snorkeling.
Additional Tip:
- Bring a lightweight blanket or beach mat for your picnic.
- If you have time before dinner, stop at Island Gourmet Markets to grab local drinks or dessert for your beach picnic.
Day 5: Iao Valley, Lahaina, and West Maui Beaches
Morning:
Iao Valley State Park Nestled in the lush mountains near Wailuku, Iao Valley State Park is steeped in both natural beauty and cultural history. The valley was the site of the Battle of Kepaniwai in 1790 and holds deep spiritual significance for Native Hawaiians. I arrived just after sunrise to find the park tranquil and lightly misted by the morning rain an almost mystical setting. The short, paved path leads to a scenic overlook of the Iao Needle, a towering rock formation that rises 1,200 feet from the valley floor. The trail is easy, family-friendly, and includes interpretive signs about the area’s ecological and cultural importance.
Tips:
- Check weather beforehand; the valley is frequently misty or rainy, which adds to its magic but can make trails slippery.
- Bring bug spray and a light rain jacket.
- There’s a $5 entrance fee and $10 parking fee for non-residents (credit card only).
Late Morning:
Head to Lahaina From Wailuku, I drove about 45 minutes to Lahaina, once the capital of the Hawaiian Kingdom and a major whaling village in the 1800s. While many parts of the town are undergoing recovery, Front Street remains partially open and still offers a mix of shops, local artists, and the resilient spirit of the community. I stopped at the Baldwin Home Museum, the oldest house on Maui, and wandered under the massive Banyan Tree, which covers nearly an acre.
Tips:
- Parking can be tricky; the Lahaina Cannery Mall or outlets have public lots.
- Check local websites for updates on access and open businesses due to ongoing wildfire recovery efforts.
Lunch:
Down the Hatch I grabbed lunch at Down the Hatch, a casual open-air eatery tucked into the Wharf Cinema Center courtyard. Their lava lava shrimp and mahi sliders lived up to the hype. Portions are generous, and the relaxed courtyard seating often features live acoustic music.
Alternatives:
- Paia Fish Market (also in Lahaina) for grilled fish plates.
- Choice Health Bar for acai bowls and vegan-friendly bites.
Afternoon:
Ka’anapali Beach + Black Rock Snorkeling After lunch, I drove north to Ka’anapali Beach, a resort-lined stretch of soft sand and swaying palms. The beach is easy to access and great for swimming, sunbathing, or grabbing a cocktail at one of the nearby resorts. At the northern end, Black Rock (Pu’u Keka‘a) is a popular cliff diving spot and excellent for snorkeling. I spotted tropical fish and even a green sea turtle while floating near the rocks.
Tips:
- Bring a dry bag, snorkeling mask, and water shoes.
- Restrooms, showers, and public beach access paths are available behind the resorts.
- Watch for cliff divers at sunset it’s a local tradition here.
Evening:
Sunset Dinner in Kapalua To wrap up the trip, I made a reservation at Merriman’s Kapalua, one of Maui’s most celebrated farm-to-table restaurants. The open-air dining terrace looks out over Kapalua Bay, and timing your reservation with sunset is an absolute must. I ordered the macadamia-crusted mahi mahi with a local pineapple martini and soaked up my final moments on the island.
Alternative:
- For a more casual coastal meal, The Gazebo in Napili is perfect for a breakfast or lunch flip if you’re starting Day 5 later. Their macadamia nut pancakes are legendary, but expect a wait.
Final Note: If your flight is late the next day, consider exploring nearby Napili Bay in the morning or stopping at Leoda’s Kitchen and Pie Shop in Olowalu for one last treat try the coconut cream pie!
To enhance your 5-day Maui itinerary and align it with top-ranking travel guides, consider incorporating the following elements to provide a more comprehensive and engaging experience for your readers:
Additional Activities and Experiences
Attend a Traditional Luau
Immerse yourself in Hawaiian culture by attending an authentic luau. Options like the Old Lahaina Luau or the Feast at Lele offer traditional Hawaiian music, hula dancing, and a feast of local dishes. This experience provides insight into the island’s rich cultural heritage.
Explore Maui Ocean Center
Visit the Maui Ocean Center in Maalaea to learn about Hawaii’s marine life. The aquarium features exhibits on native Hawaiian species, coral reefs, and cultural connections to the ocean. It’s an educational stop suitable for all ages.
Discover Upcountry Farmers Markets
Experience local flavors and crafts at Upcountry farmers markets, such as the one in Kula. These markets offer fresh produce, handmade goods, and a chance to interact with local vendors, providing a taste of everyday life on Maui.
Visit Botanical Gardens
Enhance your itinerary with visits to Maui’s botanical gardens:
- Kula Botanical Garden: Located on the slopes of Haleakalā, this garden showcases a variety of native Hawaiian plants, waterfalls, and a koi pond.
- Maui Nui Botanical Gardens: Situated in Kahului, this garden focuses on the conservation of native Hawaiian plants and offers educational exhibits.
Beach Alternatives and Activities
Relax at D.T. Fleming Beach
Located in Kapalua, D.T. Fleming Beach is known for its scenic beauty and excellent facilities, including picnic areas and restrooms. It’s a great spot for swimming and bodyboarding, especially during the summer months.
Experience a Helicopter Tour
For a unique perspective of Maui’s diverse landscapes, consider booking a helicopter tour. These tours offer aerial views of waterfalls, volcanic craters, and the island’s lush terrain, providing unforgettable photo opportunities.
Culinary Experiences
Dine at Local Favorites
Enhance your culinary journey by dining at renowned local establishments:
- Tin Roof: A casual eatery in Kahului offering Hawaiian comfort food crafted by Chef Sheldon Simeon.
- Star Noodle: Located in Lahaina, this restaurant serves Asian-inspired dishes with a modern twist.
- Mama’s Fish House: Situated in Paia, it’s famous for its fresh seafood and oceanfront dining experience.
Packing Tips for Maui
Packing smart can make your Maui adventure more comfortable, safe, and enjoyable. Here’s a detailed checklist of must-have items to help you prepare for every climate zone from the beaches to the summit of Haleakalā:
- Lightweight clothing + layers: Breathable fabrics like linen and cotton are ideal for warm days. Bring a few long sleeves or a light sweater for cooler evenings.
- Hiking sandals + water shoes: Essential for trails with stream crossings (like Twin Falls) and slippery paths (like Red Sand Beach).
- Reef-safe sunscreen: Opt for mineral-based sunscreens without oxybenzone or octinoxate—these ingredients are banned in Hawaii to protect coral reefs.
- Portable cooler: Great for storing drinks, snacks, and lunch during day trips like the Road to Hana.
- Snorkel gear: Optional but helpful if you plan to snorkel independently at places like Black Rock or Ahihi-Kinau.
- Reusable water bottle: Stay hydrated on the go many parks and resorts offer refill stations.
- Dry bag for electronics: Protect phones and cameras during boat tours or beach days.
- Light rain jacket: Especially useful in Iao Valley and the Hana region where sudden showers are common.
- Daypack or small backpack: Ideal for carrying sunscreen, snacks, maps, and gear during hikes.
- Bug spray: Helpful in rainforest areas and during early morning or dusk outings.
- Travel-size first aid kit: For minor scrapes and blisters during hikes.
Pro Tip: Leave some room in your luggage for souvenirs like local coffee, macadamia nuts, or handmade crafts!
FAQs: 5-Day Maui Itinerary
What’s the best time to visit Maui?
April to October offers dry weather, but December to March is great for whale watching.
Do I need a rental car in Maui?
Yes. Maui’s attractions are spread out, and public transportation is limited.
Is the Road to Hana safe?
Yes, but drive slowly and be prepared for sharp curves, one-lane bridges, and sudden rain.
Can I swim at all beaches?
Most, yes. But always check conditions, some beaches have strong currents.
Final Thoughts
Five days in Maui gave me a taste of everything: lush rainforest hikes, once-in-a-lifetime sunrises, relaxing beach days, and unforgettable food. This itinerary mixes adventure with downtime so you can truly enjoy the island’s magic without rushing. I left with sandy flip-flops, a sun-kissed smile, and a camera roll full of memories, and I’d go back in a heartbeat.
If you’re dreaming of Maui, I hope this guide gives you the inspiration (and the blueprint) to plan your own epic escape.
