5 Day Itinerary Maui: The Perfect Island Adventure with Practical Tips
Over the years, we’ve island-hopped across Hawaii multiple times, visiting all four major islands, Maui, Oahu, Kauai and the Big Island, in every season. But there’s something about Maui that keeps calling us back. This 5 day itinerary for Maui is crafted from our personal experiences.
Maybe it’s the way Haleakalā glows at sunrise or how the Road to Hana feels like a journey through Eden. Either way, we’re hooked. We’ve snorkeled Molokini, sampled upcountry wines, watched baby whales leap from the water and tracked down the best vegetarian eats across the island. If you’re planning your dream Maui vacation, let us be your virtual guides.
Note – The wildfires of 2023 did affect some of the destinations, but based on photos I’ve seen from others, you should have no problem having a fun time. Just be respectful to the residents and give them their space.
Best Time to Visit Maui for You
We’ve been lucky enough to experience Maui in every season, sometimes chasing the sun, sometimes chasing waterfalls (yes, we sang that line while driving through Hana). Each visit taught us something different about the island’s rhythm and honestly there’s no bad time to be in Maui. But depending on your vibe, some seasons might just click better than others.
Related Read: For more reasons to fall in love with this state, don’t miss our Reasons to Visit Hawaii blog.
Winter (December–February):
If you’ve never seen a whale breach before, winter in Maui will steal your heart. We remember standing on the Lahaina shoreline, sipping coffee one morning, when a mama whale launched completely out of the ocean like it was a dance performance just for us. It was surreal. The island is lush and alive during this time, but it’s also when everyone else has the same idea so yes, it’s more crowded and accommodations are expensive. Still, for those magical ocean moments alone, it’s worth it.
Spring (March–May):
This is Maui’s best-kept secret. Everything is still green from the winter rains, but the skies tend to stay clear and bright. We hiked through Iao Valley in April once, and the trails were empty except for the sound of birds and rushing streams. The jacaranda trees in Upcountry Maui bloom around this time too and lavender blossoms floating above emerald hills. It’s peaceful, less touristy, and perfect for anyone who loves nature without the noise.
Summer (June–August):
If your dream Maui trip involves long beach days and warm, golden evenings, summer delivers. It’s hot, it’s sunny, and the ocean is calm and inviting. But you’ll be sharing it with a lot more people. We usually adapt our days by waking up early, doing our adventures before noon, and spending the afternoons napping or swimming. It’s busy but there’s a high-energy buzz in the air that can be fun too.
Fall (September–November):
This is hands-down one of our favorite times. The weather is still amazing – warm ocean, sunny skies but the crowds have thinned out, and prices start to dip. We once had a whole stretch of Big Beach practically to ourselves in late October. It felt like the island was exhaling, relaxing into its off-season pace. If you’re the kind of traveler who values serenity over scenes, you’ll love this window.
Quick Tip: No matter when you visit, pack a light jacket or hoodie. Evenings, especially if you’re venturing up Haleakalā, can get surprisingly chilly. Maui may be paradise, but even paradise has a microclimate or two.
Top Things to Do in Maui
There’s no shortage of adventures in Maui. Here are our personal top picks:
- Snorkeling at Molokini Crater: Early morning trips are best for calm waters. We did a catamaran tour and loved the clarity of the reef. Bonus: breakfast onboard included fresh fruit and a vegetarian tofu scramble.
- Sunrise/Sunset at Haleakalā National Park: Yes, the 2 a.m. wake-up is brutal. But the view is worth it. Make sure to reserve in advance and bring warm clothes, it gets cold up there!
TIP: If you aren’t early risers (like us!) then sunset is also a great time for amazing views! - The Road to Hana: One of Hawaii’s most iconic drives. We suggest staying overnight in Hana if possible. Our highlights included Wai’anapanapa State Park’s black sand beach and a banana bread stop that was life-changing.
- Upcountry Maui: Lavender farms, paniolo (Hawaiian cowboy) culture, and laid-back vibes. We spent a whole day here just soaking it in.
- Beach hopping: From Big Beach’s wild waves to Baby Beach’s calm waters, there’s a stretch of sand for everyone.
- Whale watching (in season): January to March is peak. We went on a sunset sail and saw dozens.
Related Read: Check out our post on Unique Things to Do in Hawaii for other Hawaiian islands including Maui!
5 Day Itinerary Maui
Pro Tip for First Time Visitors
As you are exploring Oahu by car for the first time, consider using the Shaka Guide app, especially if you are visiting for the first time. This GPS-based audio tour provides insightful commentary, local tips, and turn-by-turn directions as you drive around the island. It enhances your road trip experience by sharing Hawaiian history, cultural insights, and hidden gems that you might otherwise miss. Whether we were cruising along the scenic east coast or navigating through North Shore’s surf towns, Shaka Guide was a fantastic way to discover this Hawaiian island as a first time visitor at your own pace.
1st Day: Arrival + Beach Chill + Sunset Luau
Morning: Arrival & Rental Car Pickup
Welcome to paradise! After landing at Kahului Airport (OGG), we grabbed our rental car, a must-have for Maui. Whether it’s zipping up to Haleakalā or stumbling upon hidden banana bread stands, having your own wheels gives you the freedom to explore at your pace. We’ve learned this the hard way on our first trip, relying on limited shuttles and missing out on some amazing detours.
Midday: Settle In + Lunch
We usually book our first few nights in Kihei or Wailea, close to postcard-perfect beaches and delicious food options. On this trip, we checked into a cozy Airbnb just a two-minute walk from the sand. By the time we unpacked, we were starving. We went to Tin Roof in Kahului, I ordered the garlic noodles with tofu which was good. But honestly, the food truck across the street surprised us even more, a crispy tofu poke bowl with mango slaw that we still talk about.
Quick Tip: book something with easy beach access so you can sneak in morning dips before breakfast.
Afternoon: Beach Time
Maui’s pace is naturally slow, lean into it. We spent the afternoon exactly how we think all first days should be: barefoot on the sand, floating in the ocean. Kamaole Beach Park I (Kam I) is one of our favorites for easy access, calm waters, and soft sand. After a long flight, there’s nothing better than letting the Pacific soothe your travel fatigue.
Evening: Old Lahaina Luau
As the sun dipped, we rinsed off the salt, changed into our favorite aloha wear and drove to Old Lahaina Luau for our welcome dinner. The oceanfront setting, traditional storytelling, and graceful hula performances brought Hawaiian culture to life in the most memorable way. As vegetarians, we appreciated their thoughtful plant-based options from taro cakes to coconut-laced desserts.
2nd Day: Haleakalā Sunrise + Upcountry Maui
Early Morning: Haleakalā Sunrise
This was actually our first time visiting Haleakalā and while most people swear by the famous sunrise, we’re not early risers. Sunrise means setting your alarm for 2:30 a.m., layering up like you’re heading to the Arctic (yes, it’s that cold at the summit) and making a 1.5-hour winding drive in the pitch dark.
Quick Tip: You need an advance reservation (via Recreation.gov) for sunrise, you can book up to 60 days ahead and they sell out fast. or you can book a guided tour that includes pickup and breakfast.
Optional: But we decided to go a different route, sunset. And honestly? It was magical. As the sky started to change, the clouds dipped into the crater and the whole scene glowed in golden pinks and purples. It looked strikingly similar to every sunrise photo we’d seen without the 2:30 a.m. wake-up call. There were fewer people, no rush to find parking, and we had plenty of space to just sit in silence and soak it all in.
Mid-Morning: Breakfast with a View
On the drive back down, we stopped at Kula Lodge, perched on a hill with sweeping views of Maui’s lush Upcountry. Their open-air lanai made us feel like we were still in the clouds. We ordered a veggie omelet and toast with pineapple jam and just sat there, exhausted and giddy.
Late Morning to Afternoon: Lavender Fields + Wine Tasting
Next, we visited the Ali’i Kula Lavender Farm. Picture purple rows of lavender against a backdrop of green hills and blue sky. We wandered slowly, sipping lavender-infused tea and taking way too many photos. The scent was relaxing, and the views were some of the best of the entire trip.
Just down the road, we pulled into MauiWine for a tasting. We were skeptical about pineapple wine but it was one of the most delicious wine tastings I have ever had. Light, crisp, and surprisingly refreshing after a long morning of adventure. We sat under the old trees outside, glasses in hand, enjoying a rare moment of total stillness.
Afternoon: Exploring Makawao
On our way back down to sea level, we stopped in Makawao, a little cowboy town with artsy flair. We wandered into local boutiques, peeked inside a glass-blowing studio and bought cinnamon rolls from a bakery that smelled like a hug. Makawao isn’t flashy, but it has soul.
Evening: Dinner in Paia or Back to Kihei
Upcountry dining is limited, so we drove toward Paia for a casual dinner and enjoyed our beautiful drive there. If you’re tired, head back to Kihei instead, there are plenty of dining options there too. Either way, Day 2 is best wrapped up with full bellies, tired legs and that blissful kind of Maui quiet you only get after sunrise hikes and lavender-scented walks.
3rd Day: Molokini Snorkeling + Relaxed Beach Day
Early Morning: Snorkeling at Molokini Crater & Turtle Town
We were up before dawn again, but this time for a more laid-back kind of adventure. With sleepy eyes and warm layers, we boarded a catamaran bound for Molokini Crater. The breeze was crisp, the sea calm, and the sky slowly waking up with us. As the boat cruised out from the harbor, we huddled in towels, sipping our coffee and watching the horizon change colors.
When we arrived at Molokini – a crescent-shaped, partially submerged volcanic crater, the ocean looked like liquid sapphire. Jumping in was like diving into a screensaver: colorful reef fish darting everywhere, and the water so clear we could see the bottom 100 feet below. Later at Turtle Town, we floated beside a massive green sea turtle. Watching it glide effortlessly past us was a moment we both agreed we’ll never forget.
Late Morning: Onboard Breakfast + Return to Shore
Back on the catamaran, we tucked into a surprisingly satisfying breakfast. Tropical fruit, granola and a tofu scramble that made Ishi and I very happy. We stretched out on the bow, sun on our faces, salty and smiling as we cruised back to shore.
Afternoon: Wailea Beach Bliss + Golden Hour at Secret Cove
We headed straight for Wailea Beach, one of our favorite places to unwind. It’s gentle, quiet, and easy to find a peaceful patch of sand. We grabbed a casual lunch from a nearby beach café (poke bowl for Ishi, veggie wrap for me), then rolled out our towels and let the ocean breeze lull us into the kind of nap you only take on vacation.
Later in the day, we made a short stop at Secret Cove Beach. Tucked between lava rocks and shaded by palm trees, it’s a postcard-perfect spot that’s popular for weddings. We arrived just in time for golden hour, and watched a couple say their vows as the sky turned pink and the waves rolled in gently behind them. It felt like stumbling into someone else’s beautiful story.
Evening: Spa + Dinner
With the sun setting behind us, we treated ourselves to a beachside massage back at our hotel. Picture this: ocean sounds, scented oils, and an open-air cabana. It was the most indulgent hour of our entire trip and totally worth it. For dinner we went to Moku Roots and had their delicious Taro Burger!
Related Read: For more plant-based options check out our Best Vegetarian and Vegan Restaurants in Hawaii post.
4th Day: Road to Hana
Early Morning: Set Off Before the Crowds
We woke up with that giddy road trip feeling, snacks packed, playlists queued and cameras charged. Around 7:00 a.m. we hit the road with the Shaka Guide playing in the background. Starting early is essential to avoid getting stuck behind the long line of cars that eventually snake their way along this iconic, winding drive.
Our first adventure was at Twin Falls, just a short walk off the road. The trail is easy and lush, and the falls are incredibly refreshing. Since we arrived early, we had the waterfall pool all to ourselves, the chirping birds, and a little spray on our skin. The dip woke us right up.
Mid-Morning: Ke‘anae Peninsula
A little further along, we turned off at the Ke‘anae Peninsula, a rugged coastal spot where the waves crash against black lava rock with dramatic force. We were mostly there for the banana bread, Aunt Sandy’s is legendary for a reason. We ate a warm slice fresh from the oven, still steaming, and instantly decided we needed one more for the road (no regrets).
Late Morning to Early Afternoon: Wai‘anapanapa State Park
Next up was Wai‘anapanapa State Park, home to Maui’s famous black sand beach. Walking barefoot across the volcanic sand while the surf rolled in felt like stepping onto another planet. We explored the caves, watched the waves explode against the cliffs, and lost track of time watching crabs dance between the rocks.
Quick Tip: Wai‘anapanapa State Park requires timed entry reservations via gowaianapanapa.com. Make sure to book in advance!
Mid-Afternoon: Optional Waterfall Stops or Chill Drive to Hana
From here, you can keep stopping at waterfalls, botanical gardens, and lookout points or just coast into Hana like we did. We chose to slow things down and made it to our rental by mid-afternoon. Hana isn’t about flashy resorts or Instagrammable moments, it’s about peace and space to breathe.
Evening: Sleepy Hana Vibes & Dinner Under the Stars
Our place had no TV, spotty Wi-Fi and honestly we loved that. We made a simple dinner, sat out on the porch with our feet up and listened to the palm trees rustling in the breeze. It felt like we were in a different world, still Maui, but more raw and untouched.
Quick Tips: The Road to Hana often have spotty or no cell service. so ensure you download offline maps.
5th Day: Iao Valley + Farewell
Morning: Slow Start & Iao Valley Serenity
After four full days of exploring, snorkeling, and chasing sunrises, we gave ourselves permission to sleep in. No alarms. No agenda. Just the soft light of morning filtering through the curtains and the scent of salty breeze drifting in. It’s a luxury that feels especially indulgent in Maui.
Optional for the Morning: Hike the Pipiwai Trail
If you’re up for a bit of a trek, wake up early and hike the Pipiwai Trail in nearby Haleakalā National Park. It takes you through a bamboo forest that creaks and sways as you walk, ending at the stunning Waimoku Falls. It’s about 4 miles round-trip and hands-down one of the most rewarding hikes we’ve done on any island
Late morning, we headed to ʻĪao Valley State Park, a short drive from central Maui but a world away in energy. As soon as we entered, it felt like the island exhaled. Towering emerald cliffs, mossy rocks, and the iconic ʻĪao Needle rising through the mist like a monument. The trails are easy, the air is cool and crisp, and the drizzle that came and went only added to the atmosphere, it felt like walking through an ancient temple garden.
Lunch: Local Flavor at a Hidden Food Truck Court
By noon, we were hungry and ready for something special. We stopped at a food truck court tucked behind a gas station in Kahului, a little red Thai food truck caught our eye. Their green curry was creamy, bold, and comforting, and the owner chatted with us like we were old friends.
Late Afternoon: Last Swim & Souvenir Stops
With just a few hours left on the island, we knew exactly how we wanted to spend them, floating in the ocean one last time. We returned to our go-to beach in Kihei, laid out our towels, and waded into the turquoise water. Afterward, we made a quick stop for souvenirs: locally made soaps, macadamia nuts, and a tiny framed photo of Haleakalā sunrise to take home with us.
Evening: A Farewell Dinner at Mama’s Fish House
For our final night, we dressed up just a little and drove to Mama’s Fish House. Yes, it’s a splurge. But it’s also the kind of place where time slows down. With ocean waves just steps away and tiki torches lighting up the sky, we clinked glasses and let ourselves truly soak in the moment.
Related Read: Still wondering how Maui compares to the rest?
Here’s our Maui vs. Kauai post to help you choose.
Where to Stay in Maui
Finding the right home base for your Maui adventure is more than just choosing a hotel, it’s about setting the tone for your whole trip. Do you want to wake up steps from a quiet beach? Be close to bustling food trucks? Have room for the kids to roam? Here’s what we’ve learned from staying in different parts of the island and why it matters.
Wailea – Luxury & Romance
If your dream Maui trip includes spa mornings, oceanfront pools, and sipping cocktails with your feet in the sand, Wailea is your place. We splurged on a couple of nights here and still daydream about those epic sunsets and outdoor bathtubs. The resorts are top-tier (think, Four Seasons and Andaz), the beaches are calm and picture-perfect, and there’s a romantic, peaceful energy throughout. Ideal for honeymoons or couples celebrating something special.
Kihei – Budget-Friendly & Balanced
Kihei was our home base for two different trips, and we’d go back in a heartbeat. It’s laid-back, sunny almost year-round, and offers great value. You’re close to fantastic beaches, local eateries, and food trucks (including the best Thai curry we’ve had). Accommodations here range from affordable condos to family-run inns. It’s perfect for travelers who want the full Maui experience without blowing the budget.
Lahaina/Kaanapali – Family-Friendly & Lively
If you’re visiting with kids or love having everything within walking distance, Lahaina and Kaanapali are great picks. We recommended this to friends traveling with little ones, and they loved being close to restaurants, snorkeling tours, and shops. The beaches are wide and great for beginner swimmers, and resorts often include kid-friendly amenities like pools with slides or cultural activities.
Paia/Haiku – Offbeat & Creative
This area of North Shore Maui is for travelers who want to slow down and connect with the quirky, creative spirit of the island. We loved staying here during a slower-paced trip, it felt like living inside a yoga retreat. Think art galleries, organic cafés, and jungle vibes. Plus, it’s the perfect starting point for the Road to Hana. Just be prepared for some rain and a more rustic feel.
Hana – Remote & Magical
If you’re up for an overnight stop on the Road to Hana, Hana is peaceful, lush, and unlike anywhere else in Maui. No crowds, no rush, just waterfalls, starlit skies, and the sound of waves lulling you to sleep. Our stay here felt like a deep exhale from the busyness of everyday life. Perfect for nature lovers or anyone needing true disconnection.
Quick Recommendations:
- Luxury & Romance: Wailea (Four Seasons, Westin)
- Budget or Solo Travelers: Kihei (affordable condos, Airbnbs)
- Kid-Friendly: Kaanapali (Westin Maui, Hyatt Regency, Sheraton Maui)
- Boho/Nature Lovers: Paia or Hana (charming cottages, boutique retreats)
Tips for Booking Your Stay:
- Check out hotel deals on Costco, we have managed to grab a great deals for our Hawaii vacation through them!
- Book early, especially in winter and summer.
- For longer stays, condos with kitchens are great for saving money and making smoothies after beach days.
- Always check if parking is included, resort fees and parking costs can sneak up on you.
- Want to mix it up? Stay in two different locations to get a varied experience, like three nights in Kihei and two in Hana or Wailea.
Bottom line: Maui isn’t just one experience, it’s a collection of vibes. Where you stay shapes how you experience it. So choose the one that matches the story you want to tell when you get back.
Related Read: If you’re still weighing whether Maui is the island for you, check out our post on Which is the Best Hawaiian Island for You.
FAQs About Visiting Maui
What is the best month to go to Maui?
March to May and September to November offer the best combo of great weather and smaller crowds.
Is 5 days enough for Maui?
Absolutely. You can hit all the highlights while still having time to unwind. Our 5 day itinerary Maui is proof!
Should I rent a car in Maui?
Yes, 100%. Public transport is very limited, and you’ll want flexibility.
What should I pack for Maui?
Layers, reef-safe sunscreen, water shoes, reusable water bottle, and light rain jacket (especially for Hana).
What are the best beaches for swimming?
Wailea Beach, Big Beach and Baby Beach in Lahaina are all great options.
Are there vegetarian options in Maui?
So many! We even wrote a guide to Best Vegetarian and Vegan Restaurants in Hawaii.
Is the Road to Hana worth it?
Definitely. It’s more about the journey than the destination.
Final Thoughts: Our Personal Takeaway
Maui is where some of our most cherished memories have been made. Whether it’s the silence atop Haleakalā at dawn or eating banana bread on the side of a jungle road, this island has a way of slowing you down and soaking you in wonder.
We hope this 5 day itinerary Maui helps you plan an unforgettable trip. Use it as a framework but leave space for spontaneous magic because Maui always delivers.
