When one of my best girlfriends called to invite me to her wedding in Hawaii, I had two clear reactions. One, I was overjoyed for her. I’d known both her and her fiancé for years and couldn’t wait to watch the two of them start this new chapter of their lives together. Two, HAWAII!! With the wedding as a catalyst, Ben and I started our tropical escape in Maui.
Top: Sunrise at Haleakala Crater; Bottom: Black Rock at Kaanapali Beach
Whether you are looking for some destination inspiration, are planning a trip to Maui yourself, or simply want to join me for a virtual tropical escape, this post has everything you need to plan your own four-day Maui itinerary. I’ve included what we did each day, along with our favorite Maui restaurants, beaches, activities, and a stellar hotel recommendation too.
If you have more than four days in Maui, you could easily add more activities or simply take what I have included here at a more leisurely pace.
MAUI IN FOUR DAYS: Seeing, Eating, and Staying in Paradise
The Basics: How to Plan Your Time in Maui
Maui is shaped like a lopsided figure-eight, mostly mountainous, and only one main road circles the island.
As a result, even though its square mileage is small, getting from one part of the island to another can take hours, so where you chose your home base can greatly impact the amount of time you spend in the car.
You will need to rent a car to properly explore Maui. I recommend picking one up as soon as you land at the airport. Parking can be challenging, so I recommend selecting a hotel where parking is included in your resort fee.
(Resort Fee <— Most hotels in Hawaii charge something called a “resort fee.” It’s mandatory, and the amount and what it includes varies by hotel. Typically, you’ll find it covers amenities such as access to a fitness center. We also looked for hotels where the fee included parking so we didn’t need to worry about where to leave our car.)
Maui Four-Day Itinerary
We landed late afternoon Friday and flew out on a Wednesday morning, giving us four full days.
Our priorities were a mix of a few select top Maui activities (which we packed in at the beginning), time for relaxing on the beach, and of course eating! We sought to minimize our time in the car, so you’ll see the order is grouped by part of the island. We also weren’t afraid to stay up late, especially if it meant scoring a meal at a restaurant we’d really been wanting to visit!
Here is how our time translated. I’ve included more detail on each activity and restaurant below. Overall, even though the first few days were beyond packed, we both would not have changed the order, as it was quite efficient.
- Arrive: Stay in Wailea. Casual dinner in Wailea town at Monkeypod Kitchen.
- Maui Day 1: Sunrise at Haleakala + Road to Hana. Breakfast at Kula Lodge. Dinner at The Restaurant at Hotel Wailea. Stay in Wailea.
- Maui Day 2: Molokini Snorkel and Turtle Tour (includes lunch). Relax at Wailea Beach. Cocktails at hotel at Sunset. Late dinner at Mama’s Fish House. Drive to the west side of the island. Stay near Kaanapali Beach in Lahaina.
- Maui Day 3: Morning at Kaanapali Beach (our favorite)! Lunch at Paia Fish Market in Lahaina. Afternoon on Black Rock Beach. Dinner at Merriman’s. Stay in Lahaina.
- Maui Day 4: Morning at XYZ Beach. Lunch at Monkeypod Lahaina (yes, again! We LOVED it for dinner in Wailea and decided to go back for lunch in Laihaina. No regrets.) Afternoon at Kaanapali Beach. Dinner at Frida’s. Stay in Lahaina.
Where to Stay in Maui: Hotel Recommendations
We elected to spend the first part of our stay at the luxurious adults-only Hotel Wailea on the southern, central part of the island. It was PARADISE. If you are looking for a romantic Maui escape, I can’t recommend it enough.
Hotel Wailea is near some of Maui’s best beaches, was ideally positioned for of our top activities, and happens to be absolutely fabulous.
The grounds are lushly landscaped, and the service is exceptional. Waterfalls, beautiful flowers, and soaring trees surrounded us everywhere we went. Anytime I needed something, a member of the hotel staff was eager to help me with my request, and staff members even went above and beyond to make our stay memorable.
The pools were serene with plenty of seating (we never had to worry about finding a chair). While you are lounging, you MUST order the truffle fries (thanks to a reader for giving me this tip!), and go ahead and pair them with a cocktail too.
I could happily have moved into our hotel suite for months. The room was spacious and airy, and we even had our own porch with an ocean view.
Hotel Wailea also knocks it out of the park with dining. The Restaurant at Hotel Wailea overlooks the sunset. You can catch an ocean breeze, glass of champagne in hand, and eat your fill of the freshest seafood. Each course was beautifully presented, and like the rest of our hotel experience, the service was sublime.
I also loved how many little places to escape and relax the hotel offered. From the lobby to chairs and tables scattered throughout, it’s the perfect place to recharge.
Whenever you are ready to peel yourself away from the hotel, as an included service, a member of the staff will drive you anywhere in Wailea in one of the hotel’s luxury vehicles.
What to Do in Maui: Top Activities
Sunrise at Haleakala Crater
On top of the world at Haleakala Crater
The #1 must-do activity in Maui. This was easily one of the most memorable experiences of my life and more than worth the 3:30 am wake up call. Be sure to:
- Book your reservation in advance. There are a limited number of cars allowed entry. The reservation costs around $1. When you arrive, there will be an additional park entrance fee (around $25).
- Arrive well before sunrise. The pre-sunrise light display is the best part.
- DRESS WARMLY. The temps before sunrise can be below 40 degrees F.
- Bring a camera, settle in, and watch Mother Nature in her glory.
Haleakala Crater. Worth the early AM wake up!
Road to Hana
Road to Hana pitstop
The Road to Hana isn’t so much a destination as a journey. A long stretch of beautiful highway that extends from the central town of Paia to the western town of Hana, it’s lined with a scenic route driver’s dream collection of stops. From waterfalls to short hikes to stands selling fruit and banana bread, you’ll find dozens and dozens of tempting turn offs.
Traffic is slow, so don’t be in a hurry. You’ll miss the point.
The Road to Hana doesn’t need a specific itinerary. I’d recommend doing a bit of research (there are dozens of stops and no way to fit them all in), picking your top five, then seeing how far you care to go.
Road to Hana waterfall hike
Hana is not a destination round trip—you essentially drive as far as you care to or time allows and then turn around.
As far as how to determine which stops to make, we used Maui Revealed: The Ultimate Guidebook. It was spot on for the Road to Hana (and led us to the neat waterfall hike pictured above) but otherwise fairly useless and poorly organized. You could try using online options first, but be sure to print them off to carry with you. Cell reception along many points of the road is nonexistent.
Snorkeling at the Molokini Crater
Maui has some of the best snorkeling in all of Hawaii, and Molokini is THE primo spot.
To reach the crater, you’ll need to book a tour. We selected the Molokini Crater and Turtle Arches Tour with the Pacific Whale Foundation and could not have been happier. The staff was friendly, the gear was clean and fit well, and the included lunch, while nothing fancy, hit the spot.
If you want to be a conscious tourist, the PacWhale is also an excellent organization to support. It’s a nonprofit, and proceeds go towards education and conservation efforts.
Molokini snorkel trip
The tour stopped at two locations. I was dazzled by the rainbows of fish that allowed us to come up ultra close to them, and we saw several large turtles too.
The Best Maui Beaches
Maui is treasure box of beautiful beaches. We visited several, and these were our opinions on the gems.
- Kaanapali Beach. When you hear the word “Maui,” Kaanapali Beach is what you are picturing. A wide, open expanse with plenty of room for lounging; serene, blue waters; and sparkling sands, this was our very favorite.
- Kaanapali is bordered by major hotels, but no matter where you are staying, you are welcome to bring your own chair and find a spot, as all Maui beaches are public. We stayed within walking distance, so I’m not sure about parking. I’d suggest doing a bit of research and arriving early to make sure you have a spot.
- Black Rock Beach. Located on the north end of Kaanapali, it’s a short walk to visit. Black Rock is a popular jumping point, but we elected to observe from our chairs.
- Wailea Beach. Our second favorite. Very spacious. Bring a decent shirt and stop by the Four Seasons (located on this beach) for a fabulous sunset cocktail.
- Kapalula Beach. This is the beach I was most excited to visit…and by which I was the most disappointed. It was shorter and narrower than I anticipated; the angle of the beach into the water is quite steep, and if you aren’t staying within walking distance or arrive after 9 am or so, parking is a nightmare. I’m glad I saw it for myself, but I would not make it a priority.
- Waianapanapa Black Sand Beach. This was our final stop on the Road to Hana and….we probably could have skipped it. If you’ve always wanted to see a black sand beach, by all means, go for it. That said, it’s small and not ideal for lounging, so unless you are staying nearby or already making the drive, I’d say it’s not a priority.
- Makena Beach (a.k.a. Big Beach). This is the one that got away. We ran out of time to visit, but every local we asked named this one as their favorite. Next trip back, it will be a priority!
Where to Eat in Maui: The Best Maui Restaurants
Catch of the day at Paia Fish Market, Lahaina
- Mama’s Fish House. Make your reservations MONTHS in advance. I would have loved to be here for sunset, but we found out about it too late and didn’t end up sitting down until after dark. That said, it was absolutely worth it and one of my favorite meals we’ve ever had. Come prepared to spend and to stay for hours. The experience will be absolutely worth it.
- The Restaurant at Hotel Wailea. Whether or not you stay at the hotel as a guest, the sunset views and 5-star service make this restaurant a worthy stop. Reservations recommended in off season and essential in peak season.
- Merriman’s. Another one of my absolute top recommendations. From the food to the airy atmosphere to the live music, Merriman’s is a top spot for locals and tourists alike. Again, we missed the sunset view (goals for next time), but I still would re-live our experience again and again. Merriman’s is known for having a stellar happy hour, so if that timing works for your schedule, that is definitely worth checking out too! Reservations are important and helpful.
Fabulous fish and Mai Tais at Monkeypod Kitchen
- Monkeypod Kitchen: We ate dinner here in Wailea and loved it so much that we hit up their new location right on Kaanapali Beach in Lahaina. Amongst a lineup of more touristy spots along Kaanapali Beach, this spot is a treasure. Be sure to order the Mai Tai. It’s a signature drink of Hawaii, and although usually too sweet for my taste, Monkeypod’s was absolutely dreamy. Lunch reservations are not necessary. Dinner reservations are helpful if you don’t want to wait.
- Paia Fish Market. The freshest fish, simply and deliciously prepared. Our lunch (two plates of blacked snapper with fries) was good but didn’t blow us away. Lahaina offers many similar market spots, and I got the feeling this could be interchanged for any one of them. No reservations necessary.
French toast with the most and Kula Lodge
- Kula Lodge. After your sunrise trip to Haleakala, you’re only a short stop from the Kula Lodge. Offering stick-to-your ribs lazy breakfast fare with a lovely mountain valley view, it’s a nice way to fill up and reward yourself for your early morning. You won’t find earth-shattering cuisine, but it’s homey, the food is decent, and you really are paying for the view. Reservations necessary if you care about having a table with the best possible view.
A stroll down Kaanapali, our favorite Maui beach
PHEW. There you have it. Four sun-, fun-, and food-packed days in Maui. From here, we traveled on to Kauai. I’ll be sharing a similar trip guide of our time there soon.
Have you been to Maui? Any top restaurants or activities we missed?
We left Hawaii determined to return, so I’d love to hear your tips in the comments section below!
Thank you Hotel Wailea for hosting us for our 2-night stay and hotel dinner and to the Pacific Whale Foundation for our tour. As always, all opinions are 100% my own. Thanks for reliving my trip with me! I hope this information will be valuable as you plan your own vacation.