How to Spend FIVE DAYS in Maui, Hawaii: 5-Day Itinerary

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Ready to plan an unforgettable five days in Maui? You’ve landed on the right guide!

This island has it all—epic beaches, jaw-dropping drives, lush rainforests, and more fresh pineapple than you’ll know what to do with. But with so much to see, how do you make the most of your time without feeling rushed? That’s where we come in!

After multiple visits (and a lot of trial and error), we’ve crafted the ideal five-day itinerary to help you soak up the best of Maui, without burnout. From farm tours to snorkeling in craters and sipping drinks under string lights, we’ve got everything mapped out so you can just show up and enjoy. Let’s get to the good stuff!

Day 1

Let’s ease into paradise. Day one is all about settling in, soaking up the island vibes, and kicking things off at a relaxed pace. To make the most of your trip (and avoid sky-high taxi fares), we highly recommend renting a car. Maui is best explored on four wheels, and driving yourself is often the easiest way to reach top spots without breaking the bank.

We also suggest staying in Wailea or Kihei. These south Maui towns are not only beautiful and packed with amenities, but they’re also central, meaning almost everything on this itinerary is within an hour’s drive. Keep on reading to the end to see our top accommodation recommendations!

Morning – Tour a working pineapple farm in Hali’imaile

Nothing says “Hawaii” quite like fresh pineapple, and there’s no better place to see where they come from than on this pineapple farm tour in Hali’imaile. We signed up for the 11:45 am tour, which lasts around 1.5 hours, and it was a fun, hands-on way to start the day.

After a scenic 30-minute drive from Wailea (another reason we were glad to have a rental car), we arrived at this historic plantation and met our guide, Shiloh. He greeted us with big energy and even bigger pineapple facts. We kicked things off with a walk through the rows of Maui Gold pineapples, which were way more photogenic than we expected, so don’t forget your camera!

Shiloh guided us through Hawaii’s pineapple-growing history and explained how to tell when a pineapple is perfectly ripe (there’s more to it than you’d think). We even got to taste pineapples at different stages, which made us appreciate just how complex this fruit really is.

The tour finished with a behind-the-scenes look at the packing facility, where we saw the pineapples get sorted and boxed up for shipping. The best part? We each got to take home a whole Maui Gold pineapple!

This tour was a definite highlight—fun, informative, and family-friendly. Just check out the thousands of five-star reviews here to see why this experience is a can’t-miss in Maui!

Reserve your spot on this top-rated pineapple tour before it sells out!

Lunch – Hali’imaile General Store

Right across the street from the pineapple tour, Hali’imaile General Store was the perfect place to grab lunch without going far. The vibe is relaxed but stylish, and the menu showcases fresh Hawaiian flavors—think seared ahi, macadamia nut-crusted fish, and kalua pork tacos. We didn’t need a reservation, but it’s easy to book a table online here if you prefer to plan ahead.

The drinks here were also a highlight. Whether it’s a mai tai or something seasonal, they’re just as thoughtful as the food. With the pineapple fields still in view and the breeze coming through the open windows, it felt like the perfect continuation of our morning.

Afternoon – Explore upcountry or head back to the beach

Once you’ve had your fill of pineapple fields and Hawaiian flavors, you’ve got two great ways to spend the afternoon. Feeling curious and up for more exploring? Head just a few minutes inland to wander through one of Maui’s most charming towns. 

Prefer to kick back and take it easy? The beaches near Wailea and Kihei are calling. Either way, you’ll wrap up the day with a sunset dinner tour, so pace yourself accordingly!

Visit Makawao

Just a 15-minute drive from Hali’imaile, Makawao is a tiny paniolo (cowboy) town with serious charm. The main street is lined with wooden storefronts, colorful galleries, and locally owned shops—perfect for browsing or snapping some laid-back Maui photos. It’s a great way to get a taste of upcountry life and check out the island’s creative side.

Two standout galleries are worth checking out: Upcountry Gallery, which is open daily until 4 pm, and Jordanne Gallery, known for its stunning island landscapes (just note it’s only open on weekdays). Even if you don’t buy anything, the town itself is a vibe—low-key, artsy, and authentically local.

Or return to Wailea

If your feet are ready for a break, head back to Wailea or nearby Kihei for a relaxing afternoon in the sun. Whether you’re lounging by the pool at your resort or stretching out on the sand, this is Maui at its most mellow. We love Kamaole Beach Park I in Kihei for a soft-sand, low-key beach with lovely views, and just enough activity to people-watch without it feeling crowded.

Honestly, you can’t go wrong with any beach along the south shore here. Just keep an eye on the time, your dinner tour kicks off at 5 pm, and you won’t want to show up sandy and sun-dazed (though we wouldn’t blame you if you did).

Dinner/Evening – Celebrate your first night with a traditional Hawaiian luau

No trip to Maui is complete without a luau, and we found one of the best right in Wailea. This dinner and show is a heartfelt celebration of Polynesian culture. The whole evening felt personal and welcoming, starting with a fresh flower lei at check-in and smiles all around from the staff. 

We highly recommend booking the 5 pm option, which gives you the chance to enjoy the full experience and catch sunset views over the ocean as you eat.

The evening started with the pre-show music and entertainment before settling into a three-course, family-style dinner. The menu changes regularly, but our spread included lomi salmon, Molokai sweet potatoes, and huli huli chicken—classic Hawaiian flavors done right. 

Once dinner wrapped up, the show began, with performers telling traditional stories through music, chant, and dance. The energy built with each act until the final fire knife performance lit up the night—literally.

The whole evening lasted around 3 hours, so it’s a great way to end the day without running too late (especially with an early start tomorrow). Since dates vary, be sure to check your travel days ahead of time to lock in your reservation.

This luau was both meaningful and incredibly fun, leaving us with a deeper appreciation for Hawaiian and Polynesian culture. It was a powerful, joy-filled celebration that stays with you long after the fire fades!

Book your spot at this unforgettable luau here before it sells out!

Day 2

Morning/Afternoon – Explore Eastern Maui on a day trip

We kicked off the day bright and early for one of the most unforgettable adventures on the island: this full-day Road to Hana tour. This legendary route winds along the lush eastern coast of Maui, a side of the island known for its dramatic cliffs, tropical rainforests, hidden waterfalls, and remote villages that feel worlds away from the resort-lined beaches of the west. 

The road itself is no joke, with over 600 curves and dozens of narrow one-lane bridges, it’s not for the faint of heart (or rental cars). That’s why we were so glad we left the driving to a local pro. Our guide, Justin, was a total legend—funny, knowledgeable, and totally unfazed by the tight turns and blind corners.

Throughout the day, we stopped at all the highlights: the jet-black sands of Waiʻānapanapa State Park, the serene Keʻanae Peninsula where we watched fishermen cast lines from jagged lava rock, and the cool, green waterfall pools at Puaʻa Kaʻa State Park, where we even had time for a swim. 

Breakfast and lunch were included, but the surprise standout was the warm banana bread from Aunty Sandy’s—famous enough that even Gordon Ramsay has raved about it!

The tour lasts until around 5 pm, and we definitely recommend grabbing a light bite at your hotel beforehand so you’re not starving before the first stop. By the time we rolled back into Wailea, we were tired but completely in awe from such an incredible day!

Read the thousands of great reviews and book our favorite Maui tour here!

Dinner – Monkeypod Kitchen

After a full day on the Road to Hana, dinner at Monkeypod Kitchen in Wailea was just what we needed. This lively, open-air spot has a relaxed vibe but takes its food seriously, with a menu full of island-inspired dishes made from fresh, local ingredients. We grabbed a reservation ahead of time (which we definitely recommend, especially around sunset) and settled in for a fun, flavor-packed evening.

The wood-fired pizzas were a standout—crispy, creative, and loaded with toppings, but we also loved the fresh seafood options and pupu-style starters. And of course, no visit here is complete without their signature mai tai, topped with frothy lilikoi foam that’s as delicious as it is Insta-worthy. It was a great way to toast to an epic day in Maui!

Evening – Walk off your dinner with a stroll along the beach

After dinner, we wrapped up the day with a relaxing stroll along Keawakapu Beach, just a few minutes from most Wailea hotels. This stretch of sand is peaceful and low-key, with far fewer crowds than some of the bigger beaches nearby—perfect for walking off dinner and soaking in the soft colors of the evening sky.

There’s no need to plan anything here, just slip on your sandals, listen to the waves, and let the day settle in. After 10 hours of exploring Maui’s wild eastern coast, it was exactly the kind of quiet moment we needed at the end of an incredible day.

Day 3

Breakfast – Grandma’s Coffee House

Start day three with a slow, satisfying breakfast at Grandma’s Coffee House in Kula. This rustic upcountry café has been a local favorite since 1918, serving up Maui-roasted beans with a side of laid-back charm. The breezy lanai, tucked into the hillside, is a great place to ease into the morning while sipping strong coffee and taking in the views.

We went for the banana pancakes with coconut syrup, which were as good as they sound and just the right fuel for the day ahead. Whether you’re craving something hearty or light, their menu has plenty of home-style favorites with local flair. It opens at 7 am, but arriving around 8:30 or 9 am gives you time to enjoy a relaxed meal and still make the most of whatever you’ve got planned next.

Morning – Explore Kula

After breakfast, we stayed upcountry to enjoy one of our favorite mellow mornings in Maui. Kula, perched along the slopes of Haleakalā, offers sweeping views, crisp mountain air, and a much more laid-back vibe than the coast. You’ve got two great options depending on the day—the lavender farm or the always-open Kula Botanical Garden, just a few minutes away.

Both are scenic, unhurried, and filled with lush beauty—perfect for recharging between bigger adventures.

Visit the Lavender Fields of Kula

Just a 10-minute drive from Grandma’s Coffee House, the Ali‘i Kula Lavender Farm is a calm, floral-filled hillside retreat that offers a totally different vibe from the beaches and coastlines you’ve seen so far. It opens at 10 am, but it only operates Friday through Monday, so it’s important to check your travel dates ahead of time. 

If your visit doesn’t align, we highly recommend heading to the Kula Botanical Garden instead. But if you’re lucky enough to catch the farm on an open day, you’ll be rewarded with panoramic views over Maui’s central valley, stunning garden paths, and the gentle scent of lavender drifting through the air. 

Wander past protea blooms, sip lavender tea on a shaded bench, or take advantage of the many photo-worthy spots throughout the property. It’s peaceful, uncrowded, and feels like one of Upcountry’s best-kept secrets.

Drop by the Kula Botanical Gardens

If the lavender farm isn’t open during your visit or if you just want a different flavor of garden bliss, Kula Botanical Garden is a fantastic alternative. This 8-acre sanctuary is filled with vibrant tropical plants, native Hawaiian species, and shady walking paths lined with jacaranda trees. It’s peaceful, never crowded, and a great stop to slow the pace.

The garden has a small aviary, koi pond, and some whimsical landscaping touches that make it feel a little magical. It’s a self-guided experience, and entry is just $15 USD per adult and $5 for kids aged 6–12. Whether you’re snapping flower photos or just enjoying the cool upcountry air, it’s a lovely way to spend your morning.

Lunch – Kula Bistro

Just a few minutes down the road from the gardens or lavender farm, Kula Bistro is the perfect place to refuel. This casual, no-frills local favorite serves up generous portions of homemade comfort food that’s as satisfying as it is flavorful. The atmosphere is relaxed, with counter service and plenty of locals grabbing lunch—always a good sign.

We loved the caprese panini, stacked with fresh basil and tomatoes, and the house-made pasta was equally tempting. Whether you’re in the mood for something light or hearty, there’s plenty to choose from. It’s an easy, filling lunch stop that keeps things laid-back and local—just how we like it in Upcountry Maui.

Early afternoon – Take to the skies on a private sightseeing flight

Soaring over Maui on this private flight was one of those moments that completely took our breath away!

We’ve loved exploring by car and on foot, but seeing Maui from the sky is something else entirely. We recommend booking the 2 or 3 pm time slot, so you’re not rushed after lunch and can really savor every second of this unforgettable experience.

Our pilot, Eric, greeted us with a warm smile and made us feel totally at ease. Before we knew it, we were lifting off over Maui’s lush valleys, black lava fields, turquoise bays, and rugged coastlines.

We soared above Honolua Bay, Molokini Crater, Makena State Park, and even caught a bird’s-eye view of the Nakalele Blowhole. Eric’s commentary brought the island to life with fascinating stories about Maui’s history and geology—and since it was just us, the entire flight felt super personalized and relaxed.

This is truly one of those bucket-list activities that stays with you long after you land. Yes, it’s a bit of a splurge, but we think it’s worth every penny. Read the glowing five-star reviews here to see for yourself why so many travelers say this flight was the absolute highlight of their trip!

Check availability and book your private Maui flight here!

Late afternoon – Explore Kahului’s local side

After touching down from the scenic flight, we took advantage of being right near Kahului, Maui’s largest town, and one that most visitors don’t spend much time in. It’s not flashy or beachy, but that’s part of its charm. This is everyday Maui, and it’s a fun place to slow down and explore a more local side of the island.

We parked at Maui Mall Village, which has plenty of easy parking, and spent an hour or so browsing locally owned shops, checking out island-made crafts, and stretching our legs. For a late-afternoon pick-me-up, we stopped into Maui Coffee Roasters, a chill little spot with great cold brew and even better people-watching. It’s a mellow, low-key break between big activities, and a great reminder that Maui’s culture goes far beyond the beach.

Dinner – Tin Roof Maui

Hop back in the car for a quick drive over to Tin Roof Maui, a no-frills local spot that any foodie will love. Created by Top Chef alum Sheldon Simeon, this place serves up bold, flavor-packed Hawaiian comfort food with a modern twist that locals love and visitors quickly become obsessed with.

From mochiko chicken and garlic shrimp to ultra-fresh poke bowls, everything here is fast, affordable, and wildly delicious. It’s perfect for a casual dinner or a quick bite before heading back to Wailea. Just note: Tin Roof is closed on Sundays and Mondays, so if it doesn’t line up with your trip, Marco’s Grill & Deli nearby is a great backup for Italian-style eats.

Evening – Scenic drive back to Wailea

After dinner, it’s about a 30-minute drive back to Wailea, giving you just enough time to relax, digest, and enjoy the sunset views. This road should be quite familiar by now, offering a peaceful way to end the day after exploring so many different sides of the island.

If you’re still feeling energized when you get back, make a quick stop at Lappert’s Hawaii in Wailea for a scoop of their famous macadamia nut ice cream. It’s rich, creamy, and the perfect little nightcap. Just don’t wait too long—they close at 9 pm!

Day 4

Choose your own Maui adventure

After three days of unforgettable guided experiences, today is all about setting your own pace. Whether you’re drawn to the ocean or the jungle, you’ve got two fantastic options: head west to Lahaina for a relaxed morning of exploring and an eco-raft tour, or venture into Maui’s rainforest on a guided waterfall hike through lush valleys and hidden swimming holes.

Both options offer a slower rhythm and plenty of scenery—perfect for recharging without missing a thing. So pick what speaks to you most and enjoy this chance to experience Maui your way!

Option 1: Head west for whales (or Dolphins) and historic Lahaina

If you’re in the mood for a slower-paced day with minimal walking, this option is a great fit. Leave Wailea around 8:30 am for the 50-minute drive to West Maui, where you’ll have some time to visit nearby businesses and take in views of historic Lahaina, a town deeply shaped by its past and now in the midst of recovery following the 2023 wildfires.

Afterward, head to the harbor for a small-group eco-raft tour. Whether you’re visiting during whale season (December–April) or outside of it, you’ll enjoy a relaxed cruise with beautiful coastal views and the chance to spot wildlife with help from expert guides. It’s a peaceful, scenic way to connect with Maui’s ocean environment.

Morning – Honor Lahaina’s history

Upon arriving in Lahaina, your morning begins near a community that’s been through an incredibly difficult chapter. In August 2023, wildfires swept through much of the historic town, damaging or destroying many beloved landmarks, including the Old Lahaina Courthouse and severely scorching the iconic Banyan Tree. While the area is gradually recovering, much of the old town remains inaccessible or under restoration.

That said, visitors are still welcome in surrounding parts of West Maui, and your presence, when done respectfully, can help support the local economy and community efforts to rebuild. You can view the Lahaina Banyan Tree from a distance as it continues to recover, and nearby businesses that have reopened truly appreciate the support of thoughtful travelers. If you’d like to pick up some souvenirs or great home decor and support a local business, head to Khloella’s Garden.

Exploring here really gave us a moment to reflect on Lahaina’s deep cultural significance. It’s not the same experience it once was, but it’s still a powerful one.

Late morning – Enjoy a whale watching and dolphin eco-raft tour

Whether you’re visiting during whale season or not, this small-group eco-raft tour is a can’t-miss experience. From December to April, you’ll have the chance to see humpback whales up close—sometimes within minutes of leaving the harbor. From May to November, the tour shifts focus to dolphins and West Maui’s stunning coastline, but the experience is just as scenic and peaceful. 

We recommend booking your start time around 11:30 am to give you enough time to explore or grab a coffee beforehand. The vibe on board is relaxed and personal, with just a handful of passengers and space to move around, take photos, or simply soak it all in.

What makes this tour special is the small, low-to-the-water raft, which allows for a much more intimate wildlife experience than a crowded tour boat. The design keeps things eco-friendly and low-impact, causing less disturbance to the animals while getting you closer to the action. 

We were lucky enough to spot multiple humpbacks, including a baby calf, and even got to hear their underwater calls through an onboard hydrophone, which was seriously incredible. A marine naturalist was also on board, making the whole experience both educational and fun by helping us understand exactly what we were seeing in real time.

The entire tour felt calm, respectful of the whales, and was hands-down one of our favorite things we did in Maui. And we’re clearly not alone—just take a look at the hundreds of glowing 5-star reviews!

Check the schedule and book this once-in-a-lifetime whale tour here!

Lunch – Aloha Mixed Plate

After your morning on the water, head just north of Lahaina’s main strip to Aloha Mixed Plate, a casual oceanfront eatery that’s all about big flavors and local comfort food. The vibe is relaxed, the portions are generous, and the view of the water makes it feel like a proper vacation meal, even if you’re still drying off from your boat tour.

This is a great spot to try classic Hawaiian dishes like kalua pork, loco moco, or fresh island fish, all served plate-lunch style with rice and mac salad. The shaded patio is breezy and comfortable, perfect for kicking back and recapping your favorite moments from the tour. And if you’re craving some dessert afterwards, head over to Island Cream Co., located just outside the historic core. You’ll thank me later!

Option 2: Step off the beaten path into Maui’s rainforest

If you’re looking to stretch your legs and spend time immersed in Maui’s lush rainforest scenery, this option is a fantastic choice. With a knowledgeable local guide, you’ll explore a hidden valley, visit waterfalls, learn about native plants, and even have the chance to swim in a freshwater pool—all at a gentle, manageable pace. It’s a peaceful, off-the-beaten-path way to connect with Maui’s wild side.

Morning/Afternoon: See the wilder side of Maui on a guided hiking tour

While West Maui often gets all the attention, don’t miss the chance to experience the island’s lush eastern side. This guided rainforest hike in East Maui ended up being one of our trip highlights. 

The tour kicks off at 9:30 am and finishes around 2 pm, making it a perfect half-day adventure. It’s only a 25-minute drive from Wailea to the meeting point in Kahului, and while transfers are available, we found it simple and convenient to get there on our own.

From there, you’ll hop into a comfy minivan and head along a section of the Hāna Highway, one of the most scenic drives in the world. 

Then it’s time to hit the trail—a half-day hike through a tropical valley filled with towering greenery, hidden waterfalls, and basalt rock formations you’ll actually get to climb. We passed through bamboo groves, saw waterfalls spill down mossy cliffs, and even spotted colorful birds flitting between the branches. It felt like something out of a movie!

Our guide helped us spot native flowers, taught us about local ecology and Hawaiian legends, and led us to quiet spots where we could swim in freshwater pools beneath the falls.

Lunch is included (and delicious!), so you won’t need to worry about packing a thing. It’s a fun, refreshing adventure that shows you a whole new side of Maui—off the beaten path, but well worth the detour!

Book this top-rated hiking tour here with FREE 24-hour cancellation!

Late afternoon – Head back to your hotel to freshen up

After wrapping up your morning adventure, whether you were chasing waterfalls or cruising the coast, it’s time to head back to your hotel for a bit of downtime. This window is perfect for freshening up, taking a shower, or simply kicking back with your feet up for a little while.

Whether you squeeze in a quick nap or just sip something cold on your lanai, you’ll have time to reset and recharge before heading out for dinner and evening plans. Trust us—your future self will thank you!

Dinner – Kitoko Maui

For a change of scenery (and flavor), head to Kihei for dinner at Kitoko Maui, a locally loved spot that combines fine-dining creativity with a casual, welcoming vibe. Whether your hotel is nearby or you need to park, it’s easy to access and totally worth the short drive.

Run by a local chef with fine-dining roots, Kitoko’s menu focuses on beautifully plated, locally sourced dishes like miso-glazed butterfish, crispy pork belly, and vibrant Hawaiian-grown veggies. It’s a fantastic option if you’re in the mood for something delicious and elevated, without the formality (or price tag) of a resort restaurant. 

Just a heads-up—they often sell out early, so it’s smart to arrive on the earlier side.

Evening – Enjoy drinks at South Shore Tiki Lounge

After dinner, take a short 6-minute walk over to South Shore Tiki Lounge, a local favorite known for its tropical patio, strong drinks, and live music every night. This spot strikes the perfect balance, lively and social without being too rowdy, making it a fun way to unwind without committing to a big night out.

Grab a classic mai tai or something fruity and rum-filled, find a spot under the string lights, and enjoy the laid-back energy. Whether you stay for one drink or settle in for the evening, it’s the kind of place where you’ll feel welcome the moment you walk in.

Day 5

Morning – Snorkel two of Maui’s best spots

There’s snorkeling… and then there’s snorkeling in Molokini Crater. This 5-hour tour is the kind of Maui experience you don’t want to miss. It starts at 7 am and wraps up around noon, just in time for a relaxing afternoon. Breakfast and lunch are included, so all you really need to pack is sunscreen and a towel.

Your day starts with a ride out to Molokini, a crescent-shaped volcanic crater that’s partially submerged just off the coast. Because there’s no loose soil in the area, the water is crystal clear—we’re talking the kind of visibility that makes you feel like you’re snorkeling in a giant aquarium. We saw bright reef fish, coral formations, and more marine life than we could count.

After that, we headed to the second stop: Turtle Town. As soon as we hit the water, we were surrounded by Hawaiian green sea turtles, gliding peacefully through the reef. It was surreal! We also lucked out and spotted a few whales and dolphins on the way.

The crew was fantastic, offering fun facts, helping with gear, and serving up fresh fruit and cinnamon rolls for breakfast, plus wraps and sides for lunch. It was smooth sailing from start to finish, and with HUNDREDS of glowing reviews, we’re clearly not the only ones who thought so!

Reserve this popular snorkeling tour here before it’s too late!

Afternoon – Explore Makena and soak in one last beach day

After freshening up from your morning on the water, take a leisurely drive south to Makena, one of Maui’s most stunning and less-developed regions. Just 10–15 minutes from Wailea, this area feels a world away—wilder, more open, and framed by dramatic lava rock coastlines and uncrowded, scenic beaches.

Start with a visit to Big Beach (ʻOneloa Beach), a wide, golden stretch backed by low dunes and surrounded by natural beauty. Whether you go for a walk, take a dip, or simply lie back and soak up the views, it’s one of the most iconic spots on the island for a reason.

If you’re up for a short detour, drive a bit farther to Makena Cove (Secret Beach), a hidden gem tucked between lava rocks. It’s smaller and more secluded, often quiet, and absolutely magical in the afternoon light—the kind of place that makes Maui hard to leave.

Dinner – Humble Market Kitchin

For your final night on Maui, Humble Market Kitchin sets the stage for a dinner that’s both elegant and relaxed. Located at the Wailea Beach Resort, this ocean-facing restaurant by celebrity chef Roy Yamaguchi blends local ingredients with pan-Pacific flavors, all served in a chic, open-air setting.

The menu highlights beautifully crafted dishes like miso kampachi, wagyu short ribs, and garlic soy-glazed fish, each one as thoughtfully plated as it is flavorful. As the sun dips toward the horizon, the warm lighting and sweeping coastal views create a picture-perfect atmosphere to toast the end of an unforgettable trip.

Making reservations here is highly recommended—this spot is popular for good reason!

Related Read: Looking for even more amazing experiences? Don’t miss our full guide to the 10 best things to do in Maui here—it’s packed with can’t-miss tours, hidden gems, and local favorites to help you make the most of your time on the island.

Where to Stay in Maui

Maui is a beautiful island with lots of well-rated hotels, but honestly, we found all this choice was a bit overwhelming the first time we visited! However, we highly recommend staying in Wailea in West Maui or Kihei in South Maui, as these areas give you easy access to tours and attractions, as well as tons of great shops and restaurants.

To simplify things for you, we picked three of the island’s top hotels, with an option for every budget.

Luxury – $$$ 

If you’re looking for luxury, it doesn’t get much better than the Four Seasons Resort Maui in Wailea, West Maui. This stunning property has epic beach, ocean, and volcano views, so you’ll never forget that you’re in paradise! The rooms are sleek and modern with huge windows, and some styles even come with private pools. But honestly, we would struggle to tear ourselves away from the giant main pool! 

Rooms at the Four Seasons Resort Maui typically range from $700–$1,600+ USD per night. Check availability and book your stay on Booking.com.

Mid-range – $$ 

Aston at the Maui Banyan is a laid-back, mid-range resort in South Kihei, just steps from Kamaole Beach Park II. Perfect for families or couples, it offers spacious suites with full kitchens, two outdoor pools, hot tubs, BBQ areas, and balconies—some with ocean views. Guests love the location for its walkability to beaches, restaurants, and shops, plus the added bonus of onsite parking and tennis courts.

Nightly rates generally range from $300–$600 USD. Check your dates and book easily on Booking.com.

Budget – $ 

Days Inn by Wyndham Maui Oceanfront is a budget-friendly beachfront hotel in Wailea, just steps from Keawakapu Beach. Rooms are compact but comfortable, with mini-fridges, microwaves, and air conditioning. Guests love the quiet setting, free beach chair rentals, and on-site dining at Sarento’s on the Beach. It’s a simple, convenient option for travelers who want oceanfront access without the resort prices.

Rates typically start around $240 USD per night. Head to Booking.com to check current prices and availability.

For more options, check out all of Maui’s listed hotels here!

Renting a Car in the USA

The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.

We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.

Tips for Renting a Car in the USA

• Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
• Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
• Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
• Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.

What You Need to Rent a Car in the USA

• A valid driver’s license from your home country.
• An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
• A credit card in the driver’s name is typically required for the security deposit.
• Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.

Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!

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From sunrise to sunset, this 5-day Maui itinerary gives you the perfect mix of adventure, relaxation, and unforgettable island beauty. Whether you’re snorkeling with sea turtles, driving the Road to Hana, or simply soaking up the sun on a golden beach, Maui has a way of capturing your heart with every moment.

We hope this itinerary helps you make the most of your time on the island! If you’re planning any other Hawaiian adventures or need some trip inspiration, be sure to check out our other Hawaii blogs here for more tips—or browse some of our favorites below:

10 BEST Things to do in Oahu, Hawaii

How to Spend FIVE Days in Honolulu, Hawaii: 5-Day Itinerary

3 Best Flight Tours in Kauai, Hawaii