a-listed travel: hawaii travel guide

Chris and I have made a tradition of going on a vacation to a new-to-us destination at the end of each summer. It’s the perfect time to get away before the fall season sets in. This year, we admittedly wanted to go to Tokyo and Kyoto, but as we started to research that trip we quickly realized that it would be *really* expensive. We tabled that idea (for now) and researched other locations that are equal parts adventurous and luxurious.

We love starting off a trip with something adventurous, like our safari in Africa for our honeymoon, and then ending on a relaxing note. We landed on Hawaii for this very reason. As we researched the islands, we loved that Maui offers fun activities, like the famous Road to Hana, helicopter tours, surfing and ATV riding. The neighboring island of Lanai is the epitome of relaxing and luxurious. Here, I’m sharing the highlights of what we loved most on our trip to Hawaii.

Maui

Stay

When I started to research where to stay, Hotel Wailea caught my eye because it had recently been voted the best hotel on Maui by Conde Nast Traveler, plus it’s adults only. We’d heard that some of the other hotels on the island feel can like Disneyland, which is great if you’re with kids, but not so great if you’re looking to really relax and unwind.

The property lived up to it’s reputation in every way. The rooms are plush and clean with amazing bathtubs, luxe living areas and outdoor balcony areas. The pool is absolutely stunning and has a very entertaining bar tender, who hosts biweekly mixology classes. There are fun happy hours and cooking classes, the food is delicious and the service is impeccable. In short, there’s really nothing not to love.

Eat

Mama’s Fish Camp – Everyone and their mom recommended this place to us before we went on this trip. It’s situated on an idyllic stretch of beach (pictured below), and serves seafood that actually lives up to the hype. Make sure you get a reservation well in advance, and order the Mama’s Stuffed Fish. Everything is over priced, but, hey, it’s vacation!

The Restaurant at Hotel Wailea – When we first landed in Maui after our 15 hour journey, we wandered over to the hotel restaurant after settling into our room. We were so happy that the food was absolutely delicious, and we kept hearing the same reviews about the restaurant from locals and tourists alike. Put this on your list whether you’re staying at the hotel or not, and don’t miss the torched ahi appetizer.

Do

Poolside Poké Class  – Hotel Wailea offers a poké making class by the pool, and we had so much fun learning how to make one of our favorite dishes alongside other hotel guests. Well, actually, at least I liked that last part. On vacation, I always love meeting and chatting with other vacationers, while Chris doesn’t love putting in effort with people he “knows we won’t ever see again.” Which person are you?

Road to Hana – The Road to Hana is a day long road trip that travels through state parks, stops off at waterfalls and beaches and has amazing places along the way to stop for food. It’s a full day adventure on really curvy roads, so rent a car, get an early start and download the Gypsy Guide app for a guided tour. Our favorite pit stops were the black sand beach at Waianapanapa, Wailua Falls and Koki Beach. As for snacks, make sure to stop at Aunty Sandy’s Banana Bread (literally you must stop for this treat!) and Coconut Glens for ice cream. The winding road on the drive can be a bit scary at times, so take your time and make lots of stops to make the day a fun adventure.

Luau at the Andaz Hotel – A luau is a must-do while you’re in Hawaii. What’s not to love about a dance performance and dinner at sunset? We did the one at the Andaz Hotel in Wailea, and absolutely loved it. The family style dinner was a fun way to meet other vacationers, and the set up is like a beautiful outdoor wedding.

Palauea Beach – On our second morning on the island, we were in desperate need of a bit of exercise. We went on a jog near the hotel, and happened upon a path in the middle of a neighborhood with huge, celebrity-status homes that led us to this secluded stretch of beach. It was the most perfect place to start the morning, so we ran there a few more times throughout the trip and returned for sunset to snap the photos below.

Lanai

We knew when we booked Hawaii that we wanted to explore a couple of islands on the trip, but neither of us had heard of Lanai until we stumbled upon it during our research. It’s Hawaii’s smallest inhabited island and has such an off-the-beaten-path feeling. We took a tiny plane over to the island, but there’s also a ferry option that just takes a couple of hours. No matter how you get there, you’re going to love this island.

Stay

The Four Seasons is one of the only operating hotels on the island, so twist my arm, we stayed there. The property is definitely a splurge, so we visited for three quick, but luxurious, nights. We were so excited to spend the end of the trip relaxing by the pool, sipping cocktails and practicing the art of doing nothing for a few days. The hotel has a stunning pool, where the staff circulates with popsicles and mini smoothies every hour (nothing better than a frozen treat by the pool!), and a tiny private beach in walking distance from the property.

Eat

Nobu – The hotel has a Nobu on the property, so we ate here two of the three nights we were on the island. I know this may sound ridiculous since we have it in New York, but we never go when we’re home for some reason. I’m obsessed with the yellowtail crudo and the black miso cod, but you really can’t go wrong.

Malibu Farm – The hotel also has this Malibu favorite on the property, and they serve their food by the pool. I loved the Kale Caesar Salad with the local fish on top, and proceeded to have this almost every day. I’m a creature of habit when it comes to eating, sue me.

Do

Sunset Cruise – We absolutely loved taking a cruise at sunset on a catamaran. We booked ours through the hotel, and the route took us around the island and stopped right in front of Sweetheart Rock. You may have seen on my Instagram Stories that we got pretty lucky with the fishing while we were cruising too. Chris has never fished in his life and caught a huge blue marlin and a couple of tuna during the boat ride. I’m calling it beginner’s luck, but we shall see.

Sweetheart Rock – Sweetheart Rock is just a 20 minute walk from the hotel, so wake up early and walk up to the top for sunrise. The story goes that a warrior fell in love with a beautiful princess from Maui and brought her to a cave in the rock so we could marry her when he returned from fighting. A storm came, and he rushed back to save her from drowning in the sea cave, but he was too late. He buried her at the top, and then jumped off the rock to his death. Luckily, we had a far less dramatic visit to this beautiful place.