One Week Itinerary: Rest and Relaxation in Maui

From left: views on the Wailea Beach Walk, sunset at the Hotel Wailea

After a year spent staring into screens and reminiscing on past trips, my husband and I were more than ready for an escape. Maui seemed like the ideal destination: warm temperatures, great food, beautiful beaches, and lots of adventures. And with the uncertainty surrounding travel and COVID-19, we figured a US-based destination was a safe bet.

With just a bit of planning and research, we enjoyed a relaxing trip, choosing to lounge by the pool or at the beach most days. Here’s my guide to Maui if you’re looking for a relaxing time.

At a Glance

Best Time to Visit - April to May, or September to October. The summer months can get crowded, since it’s a popular destination for families. When we visited in mid-August 2021, the crowds were manageable.

Currency - USD. Note that many places do not carry cash due to the COVID-19 pandemic. Most places we visited accepted Apple Pay.

Getting Around - Renting a car is the easiest way to get around the island. There are several major rental car companies (Thifty, Alamo, National) at the Kahului airport.

Getting There

Kahului airport offers direct and connecting flights to and from the U.S. mainland. From the Kahului airport, most resort areas are a short driving distance. For example, Wailea is a half an hour away from the Kahlului airport.

A note on the Hawaii Safe Travels Program as of August 2021: We participated in the COVID-19 Vaccine Exemption program in order to gain entry into Hawaii. As part of the program, travelers could upload their vaccination card to a government portal and the skip COVID-19 testing and quarantine requirements to enter the state.

Several airlines allow you to skip the line at your Hawaii destination airport and offer “pre-clear” services at your departure airport. However, we ran into a bit of an issue at the airport. Our vaccination card images weren’t appearing in the Southwest agent’s computer right before we were boarding the plane. We ended up having to re-upload and re-submit all of our documentation, which was a nail-biting task as we were counting down the minutes until our plane was about to board. If you’re participating in the program, be prepared and ready to log in to your account and re-submit your documents if needed.

Finally, if you’re planning a trip to Hawaii, please keep an eye on the Hawaii COVID-19 website because the situation there is ever-changing.

From left: the pool at the Hotel Wailea, lush grounds at the Hotel Wailea

Where to Stay

From vacation rentals to 5-star resorts, to Airbnbs and cottages, there are all sorts of accommodations on Maui.

Hotel Wailea

We stayed at the Hotel Wailea, the only luxury adults-only resort in Hawaii. We were blown away by the romantic atmosphere and incredible service. From check in to check out, I felt like every detail was taken care of, from the complimentary sunscreen by the pool, to the Tesla shuttle that took us to and from anywhere in the Wailea area upon request.

There are just 72 suites on the property, so we never felt like it was too crowded. One caveat is that the Hotel Wailea is not located directly on the beach. We took advantage of the complimentary shuttle to the beach several times without issue or complaint.

From left: the grounds at the Hotel Wailea, one of the cabanas at the Hotel Wailea

Wailea

Many of Maui’s sprawling, romantic resorts are located in Wailea, along with restaurants, shopping and great beaches. We loved how close by everything was in Wailea. Not having to take a train or bus really helped make for a relaxing trip, and we left the area just a handful of times. I will say that it is very pricey to stay here and the beaches can get crowded during the day since several resorts share beachfronts.

Kaanapali

This is another popular area located in West Maui, home to the famous Black Rock beach and Whaler’s Village. We visited on a day trip and thought it was equally as gorgeous, with lots of shopping, activities and restaurants. However, the Kaanapali area gets more rain than Wailea, so keep that in mind as you plan out where you want to stay.

From left: the bar at the Lineage Maui, the bar at Akamai Coffee

Where to Eat

Oh boy. I was so excited for all the food in Maui, and it did not disappoint!

Fine Dining

Mama’s Fish House - one of the most anticipated meals on our trip and it blew our high expectations away! This is the one restaurant you must try if you visit Maui! But make reservations as soon as you book your trip since they book up months in advance. Mama’s is set in a palm grove on a private beach and has fantastic sunset views. I highly, highly recommend Mama’s to celebrate an anniversary, honeymoon, birthday, or another special occasion.
The Restaurant at Hotel Wailea - we dined here with our friends on our first night in Maui and it was a great start to our trip. Each of us tried a few dishes from their spectacular tasting menu as the sun was going down. It was definitely one of those pinch me moments and the food helped make it magical.

From left: poke at the Costco Food Truck lot, Mama’s Fish House decor, and avocado toast at the Restaurant at the Hotel Wailea

Casual Dining

Kahului Airport Costco Food Trucks - where the locals go for amazing food. I love that everyone can get exactly what their heart desires. We tried both food truck parks and got poke each time. It was out of this world!
The Birdcage Maui - also located at the Hotel Wailea, we had sunset drinks and dinner here one night. Great service and you have the sweeping views of the ocean and nearby islands.
Monkeypod Kitchen by Merriman - this place is so good! They are known for their mai tais, pizzas, and burgers. We had to wait about an hour but you are allowed to roam around the area after you put your name in, so it was a painless experience.
Lineage Maui - Hawaiian meets Asian fusion, and they have both small plates and big shareable entrees. We tried some delicious dishes like Korean fried chicken and black pepper crab fried rice.
Island Gourmet Market - another unexpected culinary treasure located in Wailea, we found ourselves at this spot for breakfast, lunch or dinner on many days. The market is a grab n’ go convenience shop with cut-up fruit, sushi, snacks, booze, and other items, but they also have two separate bars where you can order coffee or takeout. An awesome spot to get food before or after a busy day of exploring.
Coconuts Fish Cafe - THE place to go for fish tacos on Maui. My husband and I tried them and they were delicious, and they offer big portions, too. With several locations across the island, this is a great spot for a quick lunch, casual dinner, or takeout any time of the day.
Kimo’s Maui - we stumbled across this waterfront Lahaina spot and were so happy we did! This place has been open since 1977 and serves up classic casual beach food like fish tacos, burgers and fish sandwiches. I was impressed that they had a gluten free bun! And don’t miss out on the Hula Pie - Kimo’s is famous for theirs.

From left: Ululani’s Shave Ice, iced lattes at Island Vintage Coffee

Coffee/Snacks

Island Vintage Coffee - another spot with a long line, but there’s a reason why. They have locally grown coffee and some unique flavored drinks like macadamia nut lattes and honey nut lattes.

Akamai Coffee Co - a third wave coffee shop located in Wailea with 100% locally grown coffee.
Olowalu Juice Truck - this colorful truck on the side of the Honoapiilani Highway offers slushes made from fresh fruit. Refreshing on a hot Maui day.
Ululani’s Gourmet Shave Ice - serving up the most delicious shave ice! Ululani’s was like nothing like I’ve ever tasted before - the ice is ground in a special way that makes it taste almost creamy. The lines are long but the wait is worth it!

From left: Hula Pie at Kimo’s, meats at Lineage Maui, and acai bowl at the Costco Food Truck Lot

What to Do

Go on a Snorkel Tour - I’ve never been much of a morning person, but I had a huge smile on my face the entire time on our sunrise snorkel tour with Kai Kanani sailing. By 6:30 am we were cruising on a catamaran to Molokini crater, where we saw tropical reefs and colorful fish. From there, we headed to Turtle Town, a spot known as a hideout for the Hawaiian Green Sea Turtle. En route, they served us great coffee, food and drinks and after our last snorkel there was an open bar. I highly recommend doing this tour on one of your first few days in Maui before you get fully adjusted to Hawaii time, since you’ll naturally be waking up earlier. Also, a sun shirt or rash guard is a must - you will get sunburnt snorkeling due to the reflection of the sun in the water.
Go Beach Hopping - Maui is known for having the best beaches in the world, so take advantage and see as many as you can. Our favorite was Makena Beach/Big Beach, known for its powerful waves and expansive sands. But we also checked out Wailea Beach since it was the spot reserved for our resort, and another beach in Kihei called Maalea Beach that I wouldn’t recommend since it was so windy on the day we went.
Shop ‘Til You Drop - if you’re in the mood to shop, Maui’s many stores and shops are there for you! At the Shops at Wailea, there are luxury good stores like Prada, Gucci, and Louis Vuitton along with small boutiques and surf brands like Volcom, RipCurl and Quicksilver. We also browsed the home goods stores, locally owned boutiques and surf shops in Lahaina Town and Whaler’s Village in Kaanapali.
Visit a Spa - Many hotels have a spa so if you’d like to check out another property it’s a great way to do so!I had a relaxing facial at the Maui Four Seasons Spa. I opted for their most basic package, since I wanted to check out the steam room and sauna. Sadly both were closed due to COVID-19. I still had a great experience and was so wonderfully relaxed after my facial. The Hotel Wailea also offers in-room spa services, which our friends took advantage of before their long flight home.
Walk the Wailea Beach Path - I spent a couple mornings walking this path that takes you along Wailea’s beaches. The views are beautiful and it’s a great way to get some steps in before a lazy day at the beach or pool. You can access the path from any of the beaches, or park at the free lot for Polo Beach.

The one big omission here is the Road to Hana. We opted not to partake in the journey since we were in the mood to relax. The idea of sitting in a car for 7+ hours on windy roads was not appealing for the type of trip we were on. Next time!