Trip Report | Maui, Hawaii

Happy Friday, friends, and cheers to the weekend! I know many of you sent your babes back to school this week… how did that go? Are you enjoying a peaceful house or mourning the end of Summer Break?

We have a few more days until reality kicks back in, and I’m hanging on to it by my fingertips! Our time together as a family of four is fewer and further between these days, which mad our Summer trip to Maui that much more special. It truly was one of the best family vacations we’ve ever had, and we loved every second of it!

So grab your coffee, because this Trip Report is photo overload!

Maui, Hawaii //

aboard the Lani’i Coastal Snorkel Sail on Sail Trilogy

Wailea Beach Path

Maui Tips //

  • Maui is the second largest Hawaiian island, and from what we saw, the most visited! But while all the hot-spots are packed with tourists, you can easily venture out and discover countless peaceful areas. It also 100% lives up to the hype and truly looks like a postcard at every turn.
  • There are five regions of Maui, and all worth exploring, but it does require quite a bit of time in the car (up to an hour-plus depending on where you’re starting and where you’re going). In a perfect world, if we were to go again, I’d spend a week in West Maui and a week in South Maui, with two nights in Hana in the middle! That way you could explore each of the areas more thoroughly with less drive time each day.
  • There are a million and one things to do in Maui, and there’s no way you’ll cover them all in a single trip… so just relax and enjoy what you can. You literally can’t go wrong! And even if you don’t eat at Mama’s Fish House (we didn’t, as they’re booked out six months in advance!), I promise you’ll still have the best time!
  • Maui is expensive. Like absurdly expensive. The only thing to do is make peace with it and understand it costs a lot to import to the middle of the Pacific Ocean! To save in some areas, we ate at mostly small local spots, cooked for ourselves, and packed a lot of picnics. Also, the beaches, parks, and hikes are all free and absolutely stunning, so don’t feel like you need to book all the fancy excursions and activities. Honestly, some of our most magical moments were those we stumbled upon ourselves.
  • You’ll need a rental car, but 4×4 isn’t necessary, and I wouldn’t go any larger than a small SUV (some of the roads are narrow).
  • Rent boogie boards and snorkel gear for the duration of your stay, and just keep them in the car… you never know when you’ll stumble on the perfect spot. We used Auntie Snorkel and had a great experience.
  • Take a cooler with you in the car every day, you never know when you’ll stumble on a Farmers Market or roadside stand that sells yummy snacks and lunches.

Ohai Trail

Road to Hana

snorkeling Lanai’i with Sail Trilogy / They have a photographer on-board for boat and water shots!

What We Did in Maui //

The first thing you want to do is pick up this book… it truly is an incredible guide to everything on the island! I read it on the flight over, making notes of all the things we wanted to do. Once we arrived, I used the island map provided by the rental company and plotted out each of the spots… from there, we just tackled a specific area each day.

So since we stayed in South Maui, that meant a lot of driving on days we explored West Maui… hence why splitting up your stay would be a fun idea for making the most of your time. But fortunately the views are jaw-dropping everywhere you go, so the driving didn’t bother us at all.

We loved every moment we were there, whether it was lounging on our resort’s beach, reading on our patio, hiking trails, or swimming waterfalls… but these are some of the highlights:

  • Snorkeling in Honoloa Bay // Go later in the day and you’ll have the place to yourself. It’s a large bay with calm waters and a beautiful reef!
  • Boat Day with Sail Trilogy // If you like getting out on the water, and seeing the island from a new perspective, Sail Trilogy has the nicest boats in the marina! The crews are beyond nice and fun, they serve amazing food and drinks, and snap cool underwater photos while you snorkel!
  • Road to Hana // Yes it’s a long day in the car, and the road is a little narrow and windy, but it was our favorite day of the trip! Several of our top spots were discovered along this drive, so I’ll share a full Road to Hana post soon!
  • Farmers Markets // We caught the Napili and Hana Farmers Markets, and both had the yummiest food and artisan crafts.
  • Nakalele Blowhole // A short, rocky hike with beautiful, cliffside views, and a powerful blowhole.
  • Hike, Hike, Hike! // We like to explore off the beaten path, and had many of the trails all to ourselves! And these shoes were absolutely clutch for everything we did!!
  • Maui Ocean Center // An impressive indoor/outdoor aquarium on the beach, with some really cool exhibits. It’s a great place to burn an hour or so if you’re waiting for your flight or checking in to your condo.
  • Lava Fields // If you’re in the West Maui area, it’s definitely worth driving to the end of the road to see these rolling fields of lava rock! At first glance, it looks like tilled soil, but it’s actually mounds of black lava rock. Follow the road to the end to see La Perouse Bay, a great spot for turtle and dolphin sightings.
  • Wailea Beach Path // Mr. Sugarplum and I loved grabbing an early morning coffee, and walking Wailea Beach and the Wailea Beach Path. The waters and winds are calm in the morning, and it’s fun to watch all the water sports and soak in the views before the resorts come to life.
  • Dragon’s Teeth Point // A breezy path leading out to a cool lava formation, with cliffside views, it’s great for turtle-spotting. DT Fleming Beach is a short path away, and a great spot to swim away from crowds!
  • Iao Valley Monument // An easy, paved trail leads you to the heart of this lush valley… you can also venture off the main trail to swim in the pools, or hike up to the peak.
  • Paia Town // A quirky town with fun shops and food. A great place to explore before a late-afternoon flight, or upon arrival when waiting to check in to your hotel/resort.
  • Kahekili Highway (West Maui’s North Shore Drive) // This one-lane drive from Kapalua to Wailuku is not for the faint of heart, but so fun with incredible views and tiny towns.

Lava Fields

Nakalele Blowhole
on Mr. SP: Long Sleeved Tee | Kore Shorts | Similar Waterproof Shoes
on me: Button Up Shirt | One Piece Swimsuit | Smocked Pull-On Shorts | Teva Sandals

Nakalele Blowhole

Ohai Loop Trail

Road to Hana

snorkeling Lanai’i with Sail Trilogy // They have a photographer on-board for boat and water shots!

Our Favorite Beaches in Maui //

  • Red Sand Beach // Definitely a highlight from our Road to Hana day! The narrow path hike to the beach hugs the edge of the mountain before descending down to a dramatic, hidden cove. The beach is made of soft, tiny red pebbles, with clear, cold water. It’s protected by a line of lava rocks, giving it a lagoon calmness, and fun cliffs for jumping.
  • Po’olenalena Beach // Next door to our resort, we spent more time on this wide, sandy beach than any other. It was calm in the morning, and great waves in the afternoon, with gorgeous sunsets. We set up camp for hours, and rarely saw more than a few people.
  • Slaughterhouse Beach // This beach looks straight out of a movie set! It’s a protected cove fully-surrounded by towering cliffs. The parking lot is small, so you won’t find a lot of people there.
  • Big Beach // A long, wide stretch of beach with a big surf break, there’s plenty of space to spread out. Hike over the cliff to Little Beach, but you might see some boobs!
  • DT Fleming Beach // Follow the trail from Dragon’s Teeth to this wide beach, then hike out via the Ritz Hotel for a little cafe and beautiful amenities.
  • Napili Beach // A gorgeous, white sand beach…but it was shoulder-to-shoulder with people, so we didn’t stay long.
  • Ka’anapali Beach // This beach is huge and wide, and packed with people! But you can walk to the end and jump off the 20-foot black rocks.

Makena Surf Resort / We saw more turtles snorkeling this bay than anywhere else!

Kahekili Highway (West Maui’s North Shore Drive)

Honolulunui Bay

Honolulunui Bay

Lahaina Harbor / Fun spot and town, but super crowded!


Red Sand Beach / My outfit HERE

Makaluapuna Point (Dragon’s Teeth) with DT Fleming Beach in the distance

Turtle-Spotting in Makaluapuna Point

The Ritz Kapalua Hotel / We accessed it from DT Fleming beach, and ate in the ocean-side cafe

Makena Surf Resort

Iao Valley Monument

Iao Valley Monument / Sunrise Crop Tank | Halo Performance Short | Teva Sandals | Aviators

Iao Valley Monument

H.A. Baldwin Beach Park to Paia Secret Beach


Where We Stayed in Maui //

Makena Surf Resort C-102 // We got so lucky finding this spot, and the beautiful rental and resort is a big part of what made our Maui experience so incredible! We didn’t book our July trip until May, so by that time, there were very few options on-island available for our dates! So while this unit is more than we’d budgeted, it was worth every penny!

It’s a 2-bedroom/2-bath unit with a fully renovated and well-stocked kitchen, comfy beds and couches, and incredible patio view. The resort itself is very quiet and just outside of the busy Wailea hotel zone, with multiple pools, tennis courts, and a short path to the beach. Some of our favorite snorkeling on-island was in the cove by the resort, and we spent more time on the Po’olenalena Beach beach next door than any other.

All of the units are privately owned, with many of them not in a rental pool, so we saw very few people, which was so peaceful to come home to. Parking is steps from the building, which was great for hauling beach gear everyday!

Ali’i Resorts handles the booking, and it was one of the best rental experiences we’ve ever had! They provide all the household necessities (detergent, paper towels, trash bags, etc.), and even refresh your towels every third day and provide full housekeeping every sixth day! Everything is done electronically (including check-in and out), and it was seamless.

Car Rental & Groceries //

We booked our rental car with Wiki Wiki Car Rental through Ali’i Resorts, and the car was waiting for us at the airport upon arrival, and we simply left it in the departure lot when we left! So easy!

Ali’i Resorts also connected us with a local grocery delivery service, and while it was pricey, it was worth it to arrive to a stocked fridge!

Makena Surf Resort / These are the beach-front buildings, which are considerably more expensive

View from Makena Surf C-102 / Short path to the beach

Makena Surf Resort is like a lush garden!

Where We Ate in Maui //

Okay, if you ask anyone where to eat in Maui… they’re all going to say ‘Mama’s Fish House,’ ‘Star Noodle,’ and ‘Monkeypod,’ (to name a few!). The problem is, every tourist on the island is trying to eat there, too… which means unless you snag a reservation months out, or you’re willing to wait for hours, you likely won’t get to see them for yourself!

We don’t really plan our meals or restaurants in advance, so we stuck to local spots and cooking at home. Our favorite thing was actually to pack the cooler with wraps or Farmer’s Market finds, and picnic on the beach, parks, or along the cliffs with a view of the sunset. Here are the places that stood out for us:

  • Paia Fish Market // Fresh fish platters, fish tacos, and steaming bowls of pasta, this popular spot has a fast line and is delicious!
  • a’a Roots Health Cafe // Our top two place on-island for a casual breakfast or lunch. The most beautiful açaí bowls, burritos, and incredible curries and baked goods.
  • Cafe O’Lei Kihei // A nice setting and favorite for locals, they have a big menu of Thai, sushi, and seafood.
  • AE’s Thai Kitchen // A permanent food truck in Hana, it’s heaping portions of delicious Thai food.
  • Paia Bay Coffee // Great stop before starting out for the Road to Hana. Darling setting with top-notch coffee drinks and snacks.
  • Peggy Sue’s Diner // Nothing overly special, but a kitchy spot that’s easy to get in to for old-fashioned burgers and shakes.
  • Hamsa Exotic Kitchen // Catch Eden at Hamsa at either the Napili or Wailea Farmer’s Market, for the best breads, olives, hummus, and more. She’ll suggest the best treats for an incredible picnic! We ate ours at nearby Napili Park.
  • Monkeypod // We happened to be out and hungry one day around 3, and managed to snag a table here. The mai tai was my favorite in Maui, but it’s packed and loud.
  • Pita Paradise // Our last night dinner, it was full of locals and was so yummy! The owner goes out every morning at 5am to fish for that day’s menu!
  • Ululani’s Shave Ice // Several locations around the island, we never drove by without stopping!
  • Coconuts // Yummy fish tacos and sandwiches… go for a late lunch to skip the line.
  • Island Gourmet Market // Near our condo, it has a great selection of pre-made wraps and fruit, perfect for stocking a picnic cooler.
  • Banana Bread & Fresh Pineapple // Pick these up anytime you see them… it may not be ‘the best on the island,’ but I guarantee it’s better than any you’ve had in the States!

Picnic dinner after snorkeling Honoloa Bay

What I Packed & Wore in Maui //

Swimsuits, shorts, and a couple of sundresses was all I needed… and these shoes, of course!

My Teva Sandals | Men’s Teva Sandals

Racerback Tank | Floral Skirt | Cut-Out Sandals (Also HERE) | Aviators

Paradise Smocked Waist Dress (code SUGARPLUM10 to save 10%) | Cut-Out Sandals (Also HERE) | Rattan Circle Bag | Woven Headband | Aviators

Button Romper | Oversized Straw HatAviators

Ribbed Swimsuit | Tie-Waist Skirt (code SUGARPLUM10 to save 10%) | Oversized Straw Hat | Straw Tote Bag | Removable TasselAviators

Halo Performance Crop | Halo Performance Short | Teva Sandals | Baseball Cap

Cabana Dress (code SUGARPLUM10 to save 10%) | Cut-Out Sandals (Also HERE) | Straw Hat (A01: Beige) | All-Weather Bangles | Gold Hoop Earrings | Aviators

Boca Chica Halter Bodysuit (code SUGARPLUM10 to save 10%) | Jean Shorts | Cut-Out Sandals (Also HERE) | Rattan Circle Bag | All-Weather Bangles

Tie One-Piece Swimsuit | Oversized Straw Hat | All-Weather Bangles | Gold Hoop Earrings | Aviators


Oh Maui, we loved you!! I hope this Trip Report is helpful for your future trips, or at least brightened your Friday! Feel free to leave any other questions in the comments, and I’d love to hear what we need to add to our list for next time! Happy weekend, lovebugs!



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