Destination Spotlight: Maui, Hawaii

Maui, Hawaii was always more difficult to go to than Oahu, so we grew up vacationing on Waikiki. Since nonstop flights to Maui now leave from several major airports such as Seattle, San Diego, Los Angeles, and Portland, we were excited to explore Maui again! Immediately upon landing, we could feel the laid back peace of Maui. While Oahu offers glimmers of the peaceful Hawaiian culture, Maui lives it day in and day out. We could sense the relaxed feeling of vacation setting in!

Note: All of the experiences discussed in this post relate to our trip to Maui in late Spring 2021. Because of this, some COVID restrictions altered services. (For example, certain activities at our hotel were by appointment only, and our photos of the hotel may vary from the current layouts, since furniture was moved to allow for social distancing.) Please consider how these rules affected our experience as you plan your own vacation!

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Where to Stay in Maui, Hawaii: The Four Seasons

When we first started researching our travel plans for Maui, we choked at the hotel prices (especially since COVID-era travel made Hawaii one of the only destinations for U.S. travelers). We ultimately decided to splurge and stay at our bucket-list location: the Four Seasons Resort Maui at Wailea. From the moment we stepped on the property, we were glad we made this decision.

Situated at the far end of Wailea Beach, the hotel offers all of the amenities of Wailea while also feeling secluded. Guests are lavishly cared for throughout their stay, with twice daily housekeeping, complimentary water bottles, and impeccable pool-side assistance (including towels, water, and food/drink ordering). 

The resort offers three pools: a main pool, family pool, and adults-only pool. Plus, guests can dine at three ocean view restaurants, work out in a large gym, relax at the spa, and use the kids club services. Plus, you can join in on fun complimentary activities such as lei making, outrigger canoe trips, or nightly music and hula performances in the lobby.

Where to Eat in Maui, Hawaii

Around the Four Season’s Hotel

The hotel offers three high-end restaurants, each with their own specialties. Ferraro’s is an Italian restaurant that offers several different dishes including pizzas and pastas. If you go to Ferraro’s, make sure to try the house specialty dessert: Milk Chocolate Budino. This is an amazing concoction of caramel gelato, chocolate pudding, and hot fudge (all served in a fancy glass)!

Duo is the hotel’s primary restaurant. This steak house offers a buffet brunch, poolside lunch service, and dinner. The dinner menu includes fish, steaks, tasty sides (try the truffle mac and cheese!), and chocolate soufflé. Plus, we loved Duo’s grand breakfast buffet. Because the hotel was following COVID-19 rules, some buffet items were offered on a menu (i.e. eggs, pancakes, and waffles). Plus, several items were still offered on a buffet in separate packaging or served by employees. Even with these limitations, we still got a full experience thanks to a mix of menu and buffet options.

The final restaurant at the Four Seasons is Spago, a Wolfgang Puck restaurant. While we never ate here during our stay, we took note of the fantastic ocean view from the hotel’s second floor.

Waikiki Brewing Company

Outdoor Restaurant with covered patio in Wailea, Maui

Located at The Shops at Wailea, less than a mile from the hotel, The Waikiki Brewing Company is fun for lunch and Happy Hour! This restaurant offers a mix of food, including smoked meats and burgers. During Happy Hour (2pm-5pm as of May 2021), all appetizers were 25% off, including coconut shrimp and huge pretzels.

Lappert’s Ice Cream

Ice cream shop in Hawaii

Also located in the Shops at Wailea, Lappert’s Ice Cream is a Hawaii based ice cream shop. Waffle cones are a classic here, and the smell often wafts throughout the shopping center. Plus, fun flavors such as chocolate Oreo makes every ice cream combination seem fun!

Around the Island

Hula Grill Sign and Barefoot Beach Bar in Kaanapali, Maui

While Wailea offers a ton of great restaurants, we suggest eating lunch around the island. We especially recommend eating near Kaanapali (go to Hula Grill’s barefoot bar!), Lahaina, or Paia. Make sure to check out local favorites (or even food trucks for a Hawaiian plate lunch).

Things to Do on Maui

Maui has a ton of activities! Honestly, it is best to understand that you won’t fit everything into one vacation (save the rest for your next visit). That being said, we consciously skipped famous activities, such as boat tours or sunrise vistas from mountaintops, to maximize our top priority activities. Here are the activities we most recommend!

Day Trip to Kaanapali and Lahaina

Center of Lahaina's town, on the oceanfront shopping street.

Maui, Hawaii’s two primary resort areas are Wailea and Kaanapali. While we recommend staying in Wailea because the resorts are newer, Kaanapali is worth visiting during your trip. Kaanapali is located less than an hour from Wailea, making it an easy day trip. Check out Whalers Village for shopping and lunch at Hula Grill. Wander along the beach at Kaanapali. While on this side of Maui, also make sure to visit Lahaina, a historic ocean-front town. While Lahaina is touristy, we still loved walking through the Hawaiian souvenir stores and seeing the historic buildings.

Day Trip to Paia and Makawao

shop fronts line the main road through Makawao

We visited Upcountry rather than driving the famous “road to Hana” since we could visit cute towns without the curvy roads. Paia was our first of two stops. Paia is an adorable surfers town just past Kahului. Cute restaurants such as Mama’s Fish House and the Paia Fish Market make for great lunch spots.

After exploring the stores in Paia, drive up the country roads to Makawao. This small artist community is one of Upcontry’s largest towns. The shops in Makawao are filled with various items, including clothing and art (such as paintings and sculptures). 

Note: for this day trip, try to avoid Sundays. We visited on a Sunday, and while some shops in Makawao were open, many were closed (open Monday-Saturday).

Lei Making and Hawaiian Cultural Events at the Four Seasons

One of our favorite parts of the Four Seasons was the Hawaiian Cultural events. Auntie Wendy is Hawaiian Cultural Ambassador for the Four Seasons Maui, and is the brainchild behind these events. Auntie Wendy served as a Concierge for several years before her promotion. Since then, Aunty Wendy has introduced Hawaiian cultural events to the resort, including lei making classes, conch shell horns at sunset, palm frond weaving, and several other activities. The best part? These activities are complimentary to hotel guests. (Note: call the concierge a couple months before your stay to ensure you don’t need reservations for these events.)

supplies for our lei making class at the Four Seasons Resort, Maui.

While we were at the resort, we had the luck of attending a lei making class taught by Auntie Wendy. She taught us how to string the different flowers and plants correctly, and told us the history of leis in Hawaii’s culture while we worked on our own leis. The picture to the right shows our supplies at the beginning of the class!

In addition to Aunty Wendy’s new programs, the Four Seasons offers a low-key Hawaiian music and Hula dancing show nightly in the lobby of the resort. Make sure to stop in before dinner to enjoy the music and watch the dancing!

Kayaking, Paddleboarding, and Outrigger Canoe Trips at the Four Seasons Hotel

Our family outrigger adventure at the Four Seasons Maui

When staying at the Four Seasons, you can enjoy a complimentary outrigger canoe trip during your stay! (NOTE: call the concierge a couple of months before your stay to ensure you get a reservation in time.) This awesome tour lasts roughly an hour, and allows you to learn how to row an outrigger. Plus, the knowledgable guides will teach you about Hawaiian outrigger practices, and some of the history and cultural influence of the outrigger in Hawaii. When we got to go out, our guides also pointed out the coral reefs and helped us look for wildlife such as fish and sea turtles.

For those who would prefer to go alone, you can rent snorkels, kayaks and paddle boards from the hotel. We would suggest going in the morning when the wind and current is calm, although depending on weather, you can go throughout the day. If you aren’t staying at the Four Seasons, other hotels and companies offer rentals too!