If you have a special occasion to celebrate like a birthday or anniversary and want to go all out, the Four Seasons Maui is THE place to go. From the lei necklaces, drinks, and snacks we received upon arrival to the incredible amenities like the adult only infinity pool, this place impressed me every day. I’ll give you specifics about why I enjoyed our stay at this particular hotel but will also list activities in this area (southern Maui) even if you choose to stay somewhere else. There are several other hotel and Airbnb options in south Maui, so check them out to see what’s best for you.

1. Go on a run/walk on the Pathway by Wailea Beach

There is a pathway along Wailea beach in front of the hotels with gorgeous views. We ran on this beach pathway almost every day! Grab a cup of free coffee from your hotel and get out there early as it becomes more crowded the later you wait. In total, the pathway is about 2 or 3 miles. If you are staying at the Four Seasons and wake up too late, you can always use the outdoor treadmills at the hotel. They have virtual runs, a great view of the hotel outdoor area, cold fruit-infused water, towels, and everything you could imagine to enhance your workout.

If you walk out of the hotel and choose to start your run or walk to the left on the Wailea Beach Pathway, it’s a little less crowded and stops at a dead end after about a mile. We continued through the dead end into the parking lot and then straight into a neighborhood to discover a private beach down the way, full of chickens!

If you walk out of your hotel and go to the right, the pathway is a little more crowded and you’ll pass by lots of major hotels plus the Wailea Shops. There’s also a cute beach bar along this way called The Whale’s Tale where you can grab breakfast, lunch, or dinner and coffee or cocktails. We stopped here for a drink and ended up seeing a huge turtle lounging on some rocks in the ocean right in front of us!

2. Spend the day on Wailea Beach

The resort provides towels, chairs, and umbrellas, but if you’re not staying at the hotel, bring your own! The beach is public and therefore free for everyone and is also one of the most beautiful beaches in Maui. You can rent snorkeling gear if you’re feeling adventurous or simply lounge on the sand all day. We ended up seeing a huge rainbow on the day we went out! One thing to keep in mind is that drinking alcohol is prohibited on the beach.

3. Spend the day at the Serenity Pool

If you do decide to stay at the Four Seasons, the Serenity Pool is the Adults Only pool with views that will blow your mind! It is open until 7-sunset, has a swim-up bar (opens at 9am), and starts serving food at 11:30. Servers will let you pick a chair and deliver your food and drink from there, or you can choose to swim up to the bar to order. There are a couple of hot tubs in addition to the long infinity pool. The food and drink at this pool and at every restaurant at the hotel ain’t cheap, but they are quality and worth it!

4. Visit Maui Brewing Company

We’re from Asheville, NC (Beer City USA), so beer is a big deal for us. We had to make the short 10 minute drive to Maui Brewing, especially since we had rented a car. It was raining this particular morning (apparently we visited Maui during a weird weather week) and thought “this is our opportunity!” Just when we arrived to the brewery, the sun came out and we were able to sit at an inside table next to the huge open doors to the front yard of the brewery. The beer was very tasty (we both ordered flights to find our favorite one), and we also ordered the house cut fries with kurikake and sriracha. They were DIVINE!

5. Eat at Monkeypod Kitchen

Just up the road about a mile from the hotel is a restaurant, Monkeypod, that we heard multiple people rave about. The staff as well as some travelers who had visited Maui before said we MUST try Monkeypod… so we did. Twice. We first stopped there on our way back from Maui Brewing. Stuffed from fries, we weren’t really that hungry so we just tried a drink and an appetizer. We were so impressed that we made reservations for dinner for the next day (Friday) and we’re glad we did, because it was packed! Their Mai Tai was the. best. Mai. Tai. I’ve. ever. had. It’s made with silver rum, dark rum, lime, house-made macadamia nut orgeat, orange curacao, and topped with a dairy-free honey-lilikoi foam. Our bartender, and then our server, said the best thing on the menu was (hands-down) the grilled Ahi, so I went for it. It came with jalapeño mashed potatoes and bok choy, and was —dare I say— better than the Mai Tai.

6. Have Breakfast in Bed (or Breakfast on Balcony hehe)

Enjoy the spectacular views from your hotel room by ordering room service for breakfast. The resort has something for everyone including gluten and dairy free items. I ordered the gluten and dairy free pancakes, and my husband got the Breakfast Quesadilla. YUM!

7. Go on a Whale Watch

Whale Season in Hawaii is between November and April, so if you find yourself here during these months, book a whale watch! We went through Alii Nui ($149 each), and I can’t say enough about them and their employees. They picked us up at our hotel, provided all you can eat drinks (alocholic and non) and appetizers. The staff was enthusiastic, friendly, and helpful throughout the boat ride. Plus, we saw a bunch of whales! One even swam right under our boat! It was amazing.

8. Eat dinner at Ferraro’s beachfront restaurant

Even if you’re not staying at the Four Seasons, go eat at Ferraro’s! Make a reservation 15-30 minutes before sunset (make this days or weeks in advance if you can and note that you’d like to sit beachfront), and watch the sun go down while eating pasta and drinking red wine. It’s magical.

9. Eat lunch at Tommy Bahama’s

Isn’t that a store, you ask? Yes, but it’s also a restaurant! It’s located in The Shops at Wailea so is only a short walk away. I ordered the Lump Blue Crab & Avocado Salad. In addition to the delicious food, they gave us a postcard and pen at the end of our meal, so we could write to our family and then mailed it for us. How nice is that?

I feel like most of the activities I recommended involve food and drinks, but hey, isn’t that what a vacation is? A few things we didn’t get to this time around that are on my list: The Road to Hana, Mama’s Fish House, paddle boarding, helicopter tour, and a hike (we had planned one, but the weather was unusually bad that day). Have you been to Hawaii? Which island? What were your favorite spots? What else should I add to my list?

Four Seasons Resort Maui at Wailea (Things to do in South Maui)