The Perfect 5-Day Maui Itinerary: Sun, Surf, and Stunning Sights

For the time-starved, and sun-depraved, Maui can still deliver an unforgettable vacation – you just need to make every moment matter. Our 5-Day Maui itinerary is designed to help you soak up the sun at the best beaches, enjoy some exciting activities, and explore the island’s most stunning sights. From breathtaking beaches to lush rainforests and volcanic landscapes, Maui offers something for every traveler. Whether you’re an adventure seeker or a beach lover, this guide will ensure you experience the best the island has to offer. Plus, with a wide range of Maui vacation rentals to choose from, you’ll find the perfect place to call home during your 5-day island getaway.

Where to Stay on Maui?

Ka‘anapali and the West Side

As Lahaina begins its journey toward recovery, some areas may still be restricted. However, nearby spots in West Maui are open and welcoming visitors. These vibrant regions feature a mix of restaurants, bars, shops, and cultural sites, blending modern attractions with rich historical charm. Ka’anapali offers stunning beaches and luxurious accommodations offering a perfect escape for those seeking a memorable Hawaiian retreat.

Kihei/Wailea (South Maui)

South Maui, including Kihei and Wailea, is known for its golden-sand beaches, beautiful snorkeling spots, and various dining and shopping options. Kihei is more budget-friendly, mostly condo accommodations, while Wailea offers upscale resorts and luxury shopping. This region’s central location makes it ideal for exploring the rest of the island.

When planning your trip, consider these areas for a balanced experience of Maui’s diverse landscapes, attractions, and community life. Remember to respect local guidelines and recovery efforts while enjoying your stay on this beautiful island.

At Maui Paradise Properties, we offer some of the best Maui vacation rentals in West and South Maui. 

5-Day Itinerary to Maui

Here we have created the perfect 5-day itinerary to Maui. We hope you find this helpful, informative, and maybe even inspired to create your own personal itinerary. Happy exploring!

Day 1: Arrival & Exploring Kihei

• Morning: Arrive on Maui and settle into your luxury vacation rental. Start your adventure off right with a visit to Kihei’s beaches like Kamaole Beach Park. Enjoy swimming, snorkeling, or just relaxing on the golden sands.
• Lunch: Head to Nalu’s South Shore Grill for fresh poke bowls and Hawaiian-inspired dishes in an open-air setting.
• Afternoon: Stroll through the charming town of Kihei. Visit local shops, grab some shave ice, and get acquainted with the area.
• Evening: Dine at Cafe O’Lei Kihei, a local favorite known for its fresh seafood and sunset views. Try the macadamia nut-crusted mahi-mahi.

Day 2: Adventure to the Road to Hana

• Morning: Hit the road early to explore the legendary Road to Hana. This scenic drive takes you through lush rainforests, past cascading waterfalls, and breathtaking coastal views. Don’t miss stops like Twin Falls, Wai‘anapanapa State Park, and the famous Seven Sacred Pools at ‘Ohe‘o Gulch.
• Afternoon: Pack a picnic to enjoy at one of the many scenic stops along the way back, making time for additional stops or a quick swim in a waterfall pool. Visit Wai‘anapanapa State Park to see the striking black sand beach and explore the lava tubes. End the drive at Hamoa Beach for a relaxing beach afternoon. 
• Evening: After an action-packed day of adventure, return to your vacation rental to unwind, and enjoy a home-cooked meal in your fully equipped kitchen.

Day 3: Sunrise at Haleakalā & Makawao Town

• Early Morning: Wake up early for a breathtaking sunrise at Haleakalā National Park. Dress warmly and head up the summit to watch the sky burst into shades of pink, orange, and gold. Local Tip: Sunrise reservations are required in advance. On your way down, stop at Kula Lodge for a hearty breakfast with panoramic views. Be sure to stop by the Kula Botanical Garden for a stroll through native Hawaiian flora.
• Afternoon: After your sunrise adventure and delicious breakfast, head to the charming town of Makawao – known for its paniolo (Hawaiian cowboy) heritage. Browse the art galleries and boutique shops, and grab some baked goods from Komoda Store & Bakery. 
• Evening: After a full day of exploring, enjoy a sunset dinner at The Restaurant at Hotel Wailea for a fine dining experience with panoramic views of the ocean.

Day 4: Snorkeling Adventures

• Morning: Head out early to Molokini Crater and Turtle Town for a snorkeling tour. This crescent-shaped, partially submerged volcanic crater is a world-famous snorkeling destination where you can encounter vibrant marine life and crystal-clear waters. Insider tip: many Molokini snorkel cruises include breakfast and snacks!
• Afternoon: After snorkeling you’ll have worked up an appetite! Enjoy a casual beachfront lunch at Monkeypod Kitchen in Wailea, where you can sip on a signature Mai Tai while soaking up the sun. After, take a scenic stroll along the Wailea Coastal Walk
• Evening: Head back to your vacation rental and take a swim in the nearby ocean or resort pool. Afterward, go to Merriman’s Kapalua for a fine dining experience, known for its farm-to-table cuisine and ocean views.

Day 5: Relax & Indulge in Pa‘ia

• Morning: Enjoy a leisurely morning at your vacation rental. Take a walk on the nearby beach, sip coffee on the lanai, and breathe in the ocean breeze. A good option is Makena Beach, also known as Big Beach – it’s the perfect spot to relax, sunbathe, or even try some stand-up paddleboarding.
• Afternoon: Drive to the charming town of Paia. Stop by Pa‘ia Fish Market for a casual lunch of fish tacos or grilled seafood. Explore the shops and art galleries in Pa‘ia before heading to Ho‘okipa Beach Park to watch surfers ride the waves or see the turtles lounging on the shore.
• Evening: End your Maui adventure with a sunset dinner at Mama’s Fish House in Pa‘ia. Savor the catch of the day in a romantic, oceanfront setting. (reservation recommended)

Navigating Maui: Tips for Getting Around

Maui’s diverse attractions are best explored with flexible transportation. Rent a car to navigate the island at your own pace or utilize public transportation for a sustainable experience that also allows you to feel like a local. 
If covering all corners of Maui is on your mind, or your stay is in a remote region, you’re better off renting a car. If you plan on staying only on the West Side, the bus is a great option since there are several routes that go through Ka‘anapali and Kihei. 
Keep in mind that Maui is not as densely populated as O‘ahu, so public transportation may not be as efficient. Plan ahead for delays and/or frequent stops. 
Remember that local buses may not go through some popular tourist attractions. Renting a car is your best bet to get around Maui if you’re short on time or are planning to explore the island extensively. 
If you find yourself somewhere in between, renting a car for only part of your trip can be a good idea too. Check out our guide to driving on Maui for more insights about driving on the island.

5 Day Getaway to Maui – When To Go?

Maui is truly a year-round destination, offering visitors an exciting vacation each season. However, in our opinion, the best time to visit Maui for a 5-day getaway is during the spring (April to May) and fall (September to November) shoulder seasons. During these months, the island enjoys pleasant weather with warm temperatures, fewer crowds, and more affordable rates on accommodations and activities. 

Spring offers vibrant blooms and calm waters perfect for snorkeling, while fall showcases mild days and stunning sunsets. This timing allows visitors to experience the island’s beauty and activities without the peak season hustle, making it ideal for a relaxing and memorable escape.

Travel Tips for Maui First-Timers

For those new to Maui, essential tips range from safety precautions to health considerations. Be informed to ensure a smooth, enjoyable, and safe Maui vacation. Here are some top tips if you are traveling to Maui for the first time:

• Peak Times to Visit: Figure out the best time to visit. Peak tourist months are Summer and Winter. If you prefer to see Maui with fewer crowds or want to see the island’s beauty for yourself, consider visiting during the shoulder months. 
• Appropriate Gear: If you plan to spend time atop Haleakala, you’ll want to bring something to keep you warm. Summer wear won’t be enough when the temperature drops low up there. 
• Whale Migration Times: Maui is the best Hawaiian island for whale watching, but keep in mind that whale watching season on Maui is only from December through mid-April. 
• Pack Light: Maui’s laid-back lifestyle calls for casual, comfortable clothing and essentials like sunscreen, slippers, and hats. Make sure only to buy reef-safe sunscreens before your flight, as regular sunscreens are banned in Hawai‘i because of their damaging effects on local coral reefs. 
• Car Rentals: A rental car is highly recommended for exploring the island at your own pace. You can opt for local car rentals on Maui like Kihei Rent-A-Car, Maui Car Rentals, Makoa Rental Car Maui, or national brands like Enterprise Rent-A-Car. Renting from local rental car companies on Maui supports local businesses. Still, a national chain may give you more peace of mind and offer loyalty points. 

5 Days in Paradise – Maui Awaits!

With this 5-Day Maui Itinerary, you’ll experience the very best of what the island has to offer, from breathtaking beaches and scenic drives to incredible snorkeling and once-in-a-lifetime sunrise views. To make your stay truly unforgettable, choosing the right accommodation is key. Maui Paradise Properties offers a range of luxurious vacation rentals that provide the perfect blend of comfort, privacy, and proximity to all of Maui’s top attractions. 
Whether you’re planning a romantic getaway or a family adventure, these premium rentals will elevate your Maui experience, ensuring your island escape is nothing short of paradise. 

Commonly Asked Questions About a 5-Day Itinerary for Maui.

What are the must-see attractions on a 5-day itinerary to Maui

A 5-day itinerary to Maui should include must-see attractions like the Road to Hana, Haleakalā National Park for sunrise, Molokini Crater for snorkeling, and popular beaches such as Wailea Beach or Makena Beach. Don’t forget to explore charming towns like Pa‘ia or Makawao and enjoy water activities like kayaking or paddleboarding.

What should I pack for a 5-day trip to Maui?

Pack light, breathable clothing, swimwear, reef-safe sunscreen, a hat, and comfortable shoes for hiking or exploring. Don’t forget a light jacket for the cooler temperatures on Haleakalā. Bring a waterproof bag for beach and water activities.

What’s the best place to stay on Maui when you only have 5 days?

The location depends on your preferences. For convenience, many visitors stay in Wailea, Kihei, or Ka‘anapali. For a premium experience, consider staying at one of the vacation rentals offered by Maui Paradise Properties, which provides luxurious amenities and convenient access to popular attractions.

Are there any family-friendly activities included in a 5-day itinerary to Maui?

Absolutely! Families can enjoy the scenic Road to Hana, visit Maui Ocean Center, snorkel at child-friendly beaches like Kapalua Bay, or explore the wildlife and hiking trails at ‘Iao Valley State Park. There are also many opportunities for kid-friendly water activities and relaxed family dining spots.

When is the best time to go on a 5-day getaway to Maui?

The best time for a 5-day getaway to Maui is in spring (April-May) or fall (September-November) when the weather is pleasant, crowds are smaller, and accommodations are more affordable. These shoulder seasons are perfect for exploring and enjoying outdoor activities.

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