THE PERFECT 4 DAY MAUI ITINERARY: WHERE TO STAY, PLAY AND EAT
Just a 5 hour flight from San Francisco, Hawaii is the only state in the United States composed entirely of islands! Maui is the second-largest of the Hawaiian Islands and though it may not be as large as the Big Island, as small as Lanai, as bustling as Oahu or as quiet as Kauai, it was the perfect island to begin my Hawaiian adventure. I had the most incredible four days getting a taste of the Hawaiian culture and left no stone unturned when it came to exploring the island’s local cuisine, beach hopping and going on underwater adventures!
Planning to visit Maui soon? I’m sharing my complete guide with everything you’ll need to plan your upcoming vacation!
Know Before You Go
When to Visit — There is really no bad time to visit Maui because the weather is warm all year round! We visited at the end of June, and it was the perfect escape from the June gloom in San Francisco. “Rainy season” (which usually just means short, tropical rain showers) is from November-March, but this also happens to be the most expensive time of year due to winter holidays and spring break. They say the best times to visit Maui are April through May and September through November, since shoulder seasons provide great weather without the high rates and heavy crowds.
How Long To Stay — I would recommend at least 5-10 nights to really make the most of your time in Maui. Shahzeb and I only spent 4 nights in Maui, and though we like to think of ourselves as efficient travelers in terms of how much we are able to pack into our days, looking back, we wish we could have stayed longer to squeeze in a little more adventure and a lot more R&R!
Make Reservations — As with all travel destinations, some activities will require advanced bookings: sunrise tickets for Mt. Haleakala open up 2 months in advance, Luaus sell out early on, Mama’s dinner reservations fill up quickly and helicopter rides should account for weather / cancellations
Rent a Car — Depending on what you plan to do, in order to freely experience all that Maui has to offer, you should consider reserving a rental car in advance (see below to learn more about Getting Around Maui)
How To Get To Maui, Hawaii
We flew into into Kahului Airport (OGG), Maui’s main airport. There are also two smaller commuter airports: Kapalua Airport (JHM) in West Maui and Hana Airport (HNM) in East Maui.
Many airlines offer nonstop flights directly to Maui. Since Southwest Airlines began its service to Hawaii from Oakland earlier this year, Shahzeb and I jumped at the opportunity to use our Companion Pass to travel to Maui for the first time!
Getting Around the island of Maui
Unless you plan to relax at your resort for the entirety of your vacation (which is totally acceptable too!), you’ll want to rent a car for your daytime adventures.
And although not required, renting a Jeep or SUV is the way to go if you have plans to drive the Road to Hana — it made the ride more comfortable and was super resourceful when parking in unexpected places or off-roading a bit.
However, if you prefer not to drive the Road to Hana, you can also book tour guide / private driver and opt for Taxis / Ubers to get around the island.
What to Pack
It's always warm in Hawaii, so you'll want to pack all your summer essentials! In addition to your swimsuits and beach attire, I would recommend bringing a jacket or sweater for the early mornings and late evenings. If you plan to visit higher elevations — like Haleakala National Park for sunrise — you'll definitely want to layer up since it can get quite chilly at the summit. Overall, the dress code in Maui is pretty laid-back and casual, so anything goes! PS: I’ve linked all my outfits for you in this post!
Shop the Look: SOLD OUT | Similar striped maxi dress
Where to Stay
Most visitors stay in either West Maui (Lahaina, Kaanapali and Kapalua) or South Maui (Kihei and Wailea), since that is where most of the hotels, resorts and vacation rentals are located. We opted for Maui Beachside, a modern and stylish Airbnb in Kihei. Real talk: choosing to stay here truly made our trip that much more epic! Staying at an Airbnb also gave us a more secluded vibe and allowed us to feel like we were relaxing in our very own vacation home, away from tourists and crowds.
Falling asleep to the sound of the waves and waking up to breathtaking oceanfront views at Maui Beachside was one of the highlights of our trip. Though Shahzeb and I generally stay at hotels due to loyalty rewards and the convenience factor, there was something so special about spending our time in Maui at Royal Mauian #509. The Instagrammable decor, fully equipped kitchen and incredible view were just the beginning. We also had easy access to a heated pool, a rooftop garden and an amazingly clean beach. Our host, Stacey, provided exceptional hospitality from the moment we booked our stay all the way until our departure, and her attention to detail is fully present throughout the home. Plus, her helpful tips and recommendations made our trip one we’ll never forget. I honestly just wanted to move in forever, and I can’t imagine staying anywhere else on a return trip to Maui.
Check out the slideshow below for more photos of this beautiful vacation home!
Shop My Looks: Stripe Ruffle Dress, Linen Stripe Jumpsuit, Blue Floral Print Boho Midi Dress, Swimsuit
Planning Your Trip: The Perfect 4 Day Itinerary
If you’re visiting Maui soon, here’s a quick recap of my 4 Day Itinerary to help plan your trip:
DAY 1: ARRIVE IN MAUI
Arrival into Kahului Airport (OGG)
Pick up rental car from Avis & Drive 25 minutes to Kihei
Dinner @ Poi by the Pound: By the time we picked up our luggage and got our rental car, it was already 9pm. Shahzeb and I decided to grab a quick takeout dinner from Poi by the Pound (which ended up being some of the freshest poke I’ve ever had!) and made our way to our Airbnb, since we were planning for an early morning and a full day of driving the Road to Hana
Check in: Check into your Airbnb / Hotel and prepare for your first full day of adventure on the island of Maui
Shop the Look: Ruffle Knot Front Swing Dress
DAY 2: ROAD TO HANA
QUICK TIPS FOR DRIVING THE ROAD TO HANA
When driving the Road to Hana, leave early in the morning to make sure to give yourself enough time to stop frequently along the way. You know how they say, “It’s about the journey, not the destination”? Well, this is definitely one of those times. Stop where you can, but if you happen to miss something on your list — don’t worry, there will be plenty more to see at every turn! Take in the views, swim near the waterfalls and enjoy all the amazing eats on your way to Hana.
The best way to navigate the Road to Hana? The GPS-led, audio Shaka Guide App (Maui Road to Hana Driving Tour) made our day! It’s self-paced, informative and even humorous at times! It told us exactly where to stop, what could be skipped when we were short on time and gave us a detailed overview of all the sights throughout the drive. We downloaded the app prior to our trip and found it to be so helpful — totally worth the $10 investment!
WHERE TO STOP ALONG THE ROAD TO HANA
We stopped often along the Road to Hana for fresh fruits & juices, snacks and views! Here’s a quick list of my favorite spots along the way:
Ke’anae Peninsula: Scenic half-mile of black jagged lava rock off the Hana Highway
Huelo Lookout: This little lookout point has the cutest shack serving up coconut water & fresh smoothies
Aunty Sandy’s Banana Bread: We stopped here for the famous banana bread and I cannot stop raving about it! They sell their loaves fresh, warm and packed full of flavor.
Upper Waikani Falls: These falls are nicknamed the “Three Bears Falls”. We loved taking a quick dip and cooling off in the freshwater swimming hole here. There isn’t much parking near the viewpoint for the falls, but if you drive a minute past the falls there is more parking on your left. From here, you can walk back down to the bridge to see the falls. It’s a bit of a trek to climb down to the base of the falls, so proceed with caution — but trust me, once you get there it’s totally worth it!
Coconut Glen’s: A colorful little truck that sells the creamiest dairy-free vegan coconut ice cream you’ll ever have!
Fresh Fruit Stands: You’ll find many fruit stands along the Road to Hana (and if you’re anything like me, you’ll want to stop at them all!) cutting and selling fresh tropical fruit. One of the most unique ones we came across was an “Honesty” Fruit Stand, where you take what you like and pay by leaving your money in the box. Cool, right?!
Honokalani Black Sand Beach: Located in Wai’anapanapa State Park. If you’ve never been to a black sand beach, I highly recommend checking it out! I had the best time playing with the soft, black sand and getting some epic aerial footage of the dramatic landscape from above.
Kaihalulu Red Sand Beach: A little bit of a trek to get here, but another spot that’s totally worth it! The color of the red sand and rock contrasting against the ocean blues was just gorgeous!
Seven Sacred Pools: Since we were short on time we didn’t get a chance to stop here, but I’ve heard wonderful things about it. I definitely plan to stop here on our next trip to Maui!
Flatbread Company: Wood-fired pizzas with organic ingredients made in traditional clay ovens. We stopped here on our way back to pick up a flatbread pizza to-go and it was sooo yummy! It totally hit the spot after a long day of adventuring.
Ke’anae Peninsula - Road to Hana
Shop the Road to Hana Look: Yellow Ruffle Bell Sleeve Tunic Dress, Amerii Ata Bag
Honokalani Black Sand Beach from above - Wai’anapanapa State Park
Kaihalulu Red Sand Beach
DAY 3: HALEAKALA SUNRISE & BEACH HOPPING
Mt. Haleakala Sunrise (reservations required): One of our most memorable experiences in Maui was seeing the sunrise from 10,000 feet above sea level at Mt. Haleakala. Here are a few tips to ensure you have the best experience:
Make a reservation — If seeing the sunrise here is something you don’t want to miss, make sure to set a calendar reminder to reserve your vehicle pass 60 days in advance (if you miss the window, another batch of tickets will be released 2 days prior). You cannot enter the park before 8am without a reservation. For more information and to reserve your tickets, click here. There is a $1 fee to reserve your vehicle pass. Then, when you arrive at the park the morning of your visit, you will need to pay a separate park entrance fee (more on that here)
Dress in layers & bring a blanket — Though I layered up and brought a jacket, I made the mistake of thinking it would be enough to keep me warm. Temperatures were in the low 50’s (about 20 degrees lower than in Kihei) and I wished I had brought along a blanket to stay cozy as we waited for the sun to come up.
Pack a snack & fill up the tank — There is no food, water or gas inside the park, so plan accordingly. Fill up the gas tank the night before, bring along a warm beverage and pack some snacks for the trip.
Come early for stargazing — We left our Airbnb in Kihei at 2:45am sharp and made it to the summit a little before 5am. The stars were still out and it was the most magical feeling to have the night sky almost all to ourselves (I saw so many shooting stars!). The summit starts to fill up pretty quickly ~30 minutes before sunrise, so the earlier you arrive, the better your chances of snagging an empty seat along the rock wall.
Stay a little past sunrise — So many people make their way down as soon as the sun peeks above the horizon, but if you stay a little longer you’ll get to witness the stunning palette of colors dancing across the sky above Haleakala National Park
Sunrise from the Clouds at Mt Haleakala
Shop the Mt. Haleakala Look: Navy Stripe BR Sweater
Akamai Coffee Co: We stopped here after the drive back down from Mt. Haleakala for a little caffeine boost before waiting in line at Kihei Caffe. The coffee was good, the staff was friendly and the interior was so cute!
Kihei Caffe: Hit up Kihei Caffe for the yummiest post-sunrise breakfast. There is almost always a line out the door and for good reason! Order the famous Banana Macadamia Nut Pancakes and top them off with a little of their coconut cream syrup on the tables — thank me later :)
R&R: After an early wake up call, you’ll likely want to kick back and relax. Hit the pool or beach and work on that tan! We went back to our Airbnb to rest for a bit and shoot some content before our lunch reservations at Mama’s Fish House
Lunch @ Mama’s Fish House: Arguably one of the best restaurants on the island. Everyone recommended this place to us and it lived up to the hype. We had some of our favorite seafood dishes here — What to order: Mama’s Tahitian Fish (ceviche), Mama’s Stuffed Fish (kanapachi baked in a a Macadamia nut crust— it’s been on the menu for years), New Caledonia Prawn, Pau Hana (gin / guava cocktail with ginger sugar rim)
Beach Hopping: After lunch, we spent a lazy evening at Wailea Beach lounging and catching the sunset with our friends! You can soak up the sun here at this perfectly clean public beach even if you’re not a guest at one of the resorts.
Dinner @ Coconuts Fish Cafe: Highly recommend this spot for their amazing fish tacos, coconut shrimp and volcano fries! If you’re looking for a chill vibe with incredible food, this is your spot!
Dessert @ Maui Pie or Leoda’s Kitchen and Pie Shop: We were so full from dinner we had to skip the pie for dessert, but I’ll definitely be trying out these two places the next time I’m in Maui!
Kihei’s 4th Friday Town Party: If it’s Friday on Maui, there’s a party going on! Each Friday, Maui celebrates in a different neighborhood. We happened to visit Maui during Kihei’s 4th Friday and stopped by to check out the party. There was live entertainment, food booths, art & crafts and plenty of great local shopping. If you plan to be on Maui on a Friday, check out the schedule here!
Banana Macadamia Nut Pancakes at Kihei Caffe
Shop the Chic Beach Look: Linen Stripe Jumpsuit
Wailea Beach
Palm Trees and Ocean Breeze - Maui, Hawaii
DAY 4: UNDERWATER ADVENTURES
Scuba Dive Morning Session @ Lanai Cathedrals: We arrived in Lahaina bright and early at 6:30am and did two morning dives with Extended Horizons. We dived at Wash Rock and First Cathedral. It was such a unique experience to get a look at the Lanai Cathedrals and see the light beams shining 60 feet below! It was also my first time spotting a white tip reef shark and swimming with a sea turtle!
If scuba diving isn’t your thing, you can also go snorkeling to catch a glimpse of the marine life in Maui or book a helicopter tour to get eyes in the sky!
Wow Wow Lemonade: We came here for some post-scuba fuel — What to Order: The cold brew & acai bowls here were both wonderful!
Lunch @ Huli Huli Chicken & Ribs: Huli Huli, meaning 'turn turn' in Hawaiian, is a local street food dish. This specific food truck was recommended to us by a local for their famous Huli Huli rotisserie chicken. Funny enough, none of the locals knew the exact name of the food truck, but after pointing us in the right direction, we found it pretty easily. The Kihei location is only open Wednesdays and Saturdays from 9:30am-4:30pm. Lucky for us, it was a Wednesday!
Address: Huli Huli — 177 S Kihei Rd, Kihei, HI 96753
Ululani’s Hawaiian Shave Ice: This hot spot has the softest shave ice on the island and there are so many flavors to choose from! My order: Blue Hawaii flavored ice topped with hapui vegan coconut cream & shredded coconut (yes, coconut everything for me please!)
Afternoon Swim & Relax on the Beach: We splashed around in the pool at our Airbnb and relaxed on the beach all afternoon!
Sunset on the Lanai: We cozied up on our balcony at Maui Beachside and watched the sunset right from our Airbnb!
Dinner @ Monkeypod Kitchen: Known for their farm to table menu, Monkeypod had a great ambiance and an even better menu — What to Order: poke tacos, Chef’s Special Catch of the Day, award-winning Mai Tai & One In A Melon gin cocktail, chocolate cream pie
Luau: One of the top things to do in Maui is to attend a traditional Hawaiian luau. Here are a few of the best ones on the island:
Scuba Diving the Lanai Cathedrals — click here to see me swimming with the cutest sea turtle!
Shop the Look: Ruffle Knot Front Swing Dress, Amerii Ata Bag
Ululani’s Shave Ice - Maui, Hawaii
Shop the Look: Stripe Ruffle Dress, Amerii Ata Bag
Our Airbnb: Maui Beachside @ Royal Mauian
Shop the Look: Beige Summer Beach Midi Dress
Sunset on the Lanai @ Maui Beachside
Shop the Look: Satin Backless Maxi Dress, Flower Crown
DAY 5: SOUVENIR SHOPPING & DEPARTURE
Last Morning in Maui: Shahzeb and I took it easy our last morning in Maui. We took our time getting out of bed and really soaked up every last bit of the incredible view from the Lanai at our Airbnb. I cut up some fresh fruit and we reflected on our trip before heading out for one last adventure!
Breakfast / Brunch: We decided to revisit two of our favorite spots for our last breakfast in Maui, since they were both so close to our Airbnb. We grabbed the cold brew from Wow Wow Lemonade & got in line for breakfast at Kihei Caffe. This time around, we tried the Banana Macadamia Nut French Toast!
ABC Store: Don’t leave Hawaii without visiting an ABC Store. This is your one-stop shop for snacks, souvenirs, medicine, sunblock, etc. It’s a great idea to pop in and grab everything you need at the beginning of your trip or for souvenirs before you leave. We stopped here on our last day to pick up chocolate-covered macadamia nuts to take back home!
Pack & Check-out of Airbnb / Hotel
Lunch @ Tamura's Fine Wine & Liquors: Another local pick, Tamura’s is a total gem and is famous for its poke selection in the back of the liquor store. The poke was so fresh, it melted in my mouth!
Departure from OGG: Return your rental car and head to the airport for your flight home (and if you’re anything like me, you’ll probably be plotting ways to “miss” your flight and extend your trip!)
If Maui wasn’t on your bucket list before, I certainly hope it is now! Whether your vacation goals include rest and relaxation or ultimate adventure, there’s something for everyone in Maui. I left a piece of my heart here and I’m already dying to return as fast as possible to explore more of this incredible island!
