Annual Birthday Trip: Maui

Every year, I travel for my birthday. I started this tradition in 2018 because I just didn’t feel like hosting dinners anymore. Not that there’s anything wrong with hosting dinners, but it was starting to feel awkward as I got older because of combining different friend groups who don’t really mesh and not wanting to leave anyone out. In those situations, it’s difficult as a guest to mingle when you’re seated at a big table, stuck talking to the stranger sitting next to you. I always feel weird having my friends pay for me. My new tradition has been more fun because I get to pick a different destination every year. I’ve done a few yoga retreats on my birthday, and some of those have been enjoyable, but those are a week long and don’t give you as much flexibility for exploring, so I’ve stopped doing them. Sometimes friends have joined me on my trips, sometimes I’m solo. Either way, I’m exploring somewhere new and that’s always a great way to spend a birthday. This year, I chose Maui.

In the past, my birthday trips have been a week long. But I had just come back from traveling to Europe in Sept for a week, and didn’t feel like another week long commitment. I wanted a short relaxing escape. I decided on Maui because it’s not too far from LA. I could do a short, easy, low-planning 3-day trip. Plus, I had been before and had done all the touristy things. This time, I wouldn’t feel the pressure to see the whole island. I could spend more time relaxing. I knew that I wanted to base myself in Wailea this time because I hadn’t really explored that area before. It’s known for it’s luxury resorts. I am always hesitant to commit to a locations or hotel I’m unfamiliar with. Usually, when I travel, I’ll split my stay up at one budget-friendly area and then splurge on a nicer hotel. It makes staying at the nicer hotel that much sweeter.

For my first 2 nights, I stayed at Maui Coast Hotel in S. Kihei, which neighbors Wailea. This area is the more budget friendly for those who want to spend time in Wailea. It was decently priced and spacious. They have a pool, but I didn’t use it at all because I was out exploring. The room was the first one closest to the entrance on the first floor, so it was a bit loud. The back patio was a view of the parking lot. Not the best room! But I guess, you get what you pay for! Make sure you request an upper floor that doesn’t have a view of the parking lot or pay a little more for a better room. The receptionist made it sound like she gave me a complimentary upgrade because I was in the newer building, but the room location did not feel like an upgrade at all. However, this would not deter me from staying here again. Overall, the room was nice, clean, spacious, and comfortable. The room also had a fridge and a microwave. The hotel is located across the street from the beach and within walking distance of local restaurants. In addition, they offer free shuttle service and pick up within a 5 mile radius of the hotel. That was a nice benefit that I took full advantage of because I went to Wailea everyday. I didn’t spend much time at the hotel, which is why I’m glad I chose to stay at a budget friendly spot for the first two nights.

Straight from the airport, I headed to Sugar Beach Bake Shop because I wanted to try their famous malasadas, particularly the ube and coconut filled ones. Sadly, they sold out by the time I got there around 12:30pm. They say that I need to come before 10am, but I didn’t want to Uber/Lyft specifically there for a donut later because the donut would end up costing $30-$40 with the roundtrip car ride. The reason I had chosen to go straight from the airport was because it was on the way to the hotel, but too far out of the shuttle radius to go from the hotel on another day. I was disappointed, and instead went next door to the famous Ululani’s Hawaiian Shaved Ice and it was fantastic. I now get the hype of shaved ice. I didn’t understand what was so exciting about ice before. It’s so finely shaved that it tastes like ice cream with the house-made flavoring/syrup! I like the coconut and mango flavors with the snow cap (condensed milk) and mochi topping.

After checking into Maui Coast Hotel and freshening up, I took their shuttle to South Maui Gardens. I had never been before, but saw images of it on Tiktok and really wanted to try it out. It’s so cute! A zen garden with lots of buddha statues, giant life-size games, a tortoise sanctuary, live entertainment (including hula shows), picnic tables, play area, and a variety of food trucks. I specifically wanted to try Kitoko’s because of the images I had seen on Instagram and it did not disappoint! It’s a fancy food truck with creative flavors and beautiful presentation. I enjoyed their crispy pork belly with Japanese sweet potato gnocchi and their grilled shrimp with papaya salad. I wish I could have tried more of their menu because everything sounded appetizing and interesting. I loved the garden seating. It was such a relaxing and peaceful vibe. I definitely recommend checking out South Maui Gardens. Because they have hula shows and live entertainment, I think it’s a great affordable alternative to going to a luau.

Next, I decided to have drinks at The Andaz Hotel. I had read that it has a great view from their Lehua Lounge. While it does have a great view, Lehua Lounge is just a poolside bar. Very casual and very average drinks. Great unobstructed panoramic view though! You could also get a great view from Miromoto’s at The Andaz if you dined there and got a table outside. But I didn’t want to eat there and the bar area of the restaurant does not face the view. Instead, I decided to go to Monkeypod for dinner and sat at the bar, and wow, was it packed and lively at 6:30pm! It was so fun though! A man sitting next to me was celebrating his birthday solo that night so we bonded over our shared November birthday week and both got free pie for dessert. I would recommend Monkeypod for dinner one night and skip out on Lehua Lounge. Monkeypod doesn’t have a view though, but it would be a fun casual dinner spot for after sunset. The food and cocktails were pretty good.

On day two, I woke up early and took the shuttle to Island Gourmet Market at The Shops at Wailea. It’s right behind The Marriott hotel. Picked up an iced matcha latte and walked the Wailea Beach coastal path by cutting through The Marriott Hotel. It’s such a beautiful walk and you pass by all the luxury resorts. I walked through some of hotels and they are quite overwhelming. You could get lost. I made it onto the beach and the water was so warm and calming. I live in Los Angeles, but I never go to the beach. I don’t consider myself a beach person, but a beach on vacay just hits differently, ya know? I didn’t think about work once. I didn’t think about anything stressful. I felt so at peace. Afterwards, I walked back to The Shops at Wailea. I wanted to get another iced matcha at the Maui Matcha stand, but didn’t feel like waiting in line. I had expected more places to carry good matcha options because Hawaii is closer to Japan, but it wasn’t on a lot of menus. I went back to Island Gourmet Market because my sister wanted me to pick up Piaca Pineapple Shortbread Cookie with fruit filling. I love grocery stores and this place has so many goodies! You can pick up pre-made packaged food (salads, sushi, rice bowls) or made-to-order food, as well as charcuterie and fresh fruit for a picnic on the beach or to bring back to your hotel. They also carry souvenirs and alcohol.

That second night, I went on the most magical Sunset Dinner Cruise with Kai Kanani Sailing. They do hotel pick up from most hotels in Wailea or can pick you up from their office in Wailea. This tour group is a great option for those staying in Wailea. If you’re staying in West Maui, it’s better to look for a different tour group so you don’t have to drive far. TKai Kanani provides van transportation for everyone to Maluaka Beach close by, where we board a catamaran. It’s a 2 hour cruise where they serve you cocktails and dinner. On our cruise, we were surrounded by at least a dozen whales swimming around us. It was a bit early for whale season and this wasn’t even a whale watching tour, so this was the best surprise! On the last supermoon of the year too! I don’t think I’ve ever been a whale person, but I was probably the most excited person on the boat! It was so beautiful to see these large creatures swimming as the sun was setting over the water. What an unforgettable experience! You’ll have to watch my videos on Instagram of the whales and of my whole trip. I have a dedicated highlight for Maui in my Instagram bio.

After the cruise, I stopped at The Birdcage for drinks. It’s located in Hotel Wailea and is basically their lobby lounge. It is shaped as a birdcage and lovebirds (actual birds) do come into the open-air bar and sing. But since I got there closer to 6:30pm after the sun had just set, most of them had gone to bed. This bar would have been the perfect option to watch the sunset. The view is not as unobstructed as The Andaz, but definitely a better vibe with better cocktails. I just loved the idea of sitting with lovebirds singing around you as you watch the sunset.

On my 3rd day, my last day and my birthday, I treated myself to a stay at The Four Seasons Hotel. Because I’ve heard of so many people going to Maui and staying at The Four Seasons, I had to try it for myself. They offer complimentary activities and shuttle service as well. I intentionally checked into the hotel super early at 7:30am so that I could join their beach yoga class. My room wasn’t ready, but that was okay because I wanted to take full advantage of their amenities. I got lei-d as soon as I arrived. After yoga, I changed into my swimsuit, picked up an iced matcha latte, and headed back to the beach. The Four Seasons offer beach chairs to their guests. Though I didn’t really need a chair because I spent the entire time in the ocean! It was so lovely! Then at the last minute, there was a cancellation for their last outrigger canoe tour of the day. I just happened to run into them getting ready to embark. This complimentary activity was listed on their schedule, but it mistakenly said Mon-Fri only. I was lucky to catch them when I did! It was so fun! We rowed around the coast, saw some sea turtles swim by us, and then stopped to snorkel. One of the guides, played ukulele and sang to us. I love ukulele. It’s so romantic.

My room was still not ready by noon, so I got a cabana by the pool and ordered lunch. My server was so lovely and accommodating. I wanted to try everything, but it would be too much food. So he got me half portions. I wanted wings and their signature salad, but was also pondering their Wagyu Yasoba noodles with bok choy and shiitake mushrooms. My server said he can make anything half portion for me to try and he comped my whole meal because it was my birthday! I thought he meant he was going to comp one cocktail, but he comped the entire bill! What a sweetie! And there I was eating buffalo wings with my hands—probably the most unrefined thing to eat at a luxury resort! But that was what my belly wanted on my birthday: good bad food, if that makes any sense. With pina coladas, which were amazing! I was living the life! I have never been a resort girl, but staying at The Four Seasons resort in Maui is an entirely different experience than probably most resorts. Although I’m sure it’s on par with it’s neighbors like The Andaz, The Grand Wailea, and The Fairmont, but I felt it was more manageable and not as overwhelmingly huge. That day, I decided I do like resorts and I love when cute men wait on me, ready to accommodate my every need. I could do this more often. I should do this more often.

My room was not ready until 2pm, and by then, I was so exhausted from, you know, relaxing all morning. I just wanted to shower and curl up in bed. The Four Seasons gave me a complimentary upgrade from their Mountainside room to their Deluxe Garden-view. There was Hawaiian music playing in the bathroom when I entered. The room was spacious with a couch area and a balcony. I wish I could have stayed in the room longer, lounging in my robe, sitting on the balcony, but I only had enough time to shower and then had to get ready for a sunset cocktail pre-dinner.

I ordered an espresso martini at the bar at Ferraro’s (on their lower floor, closer to the beach) and it was probably one of the best I’ve had! I think because they topped it with cinnamon. I loved that they served olives and crispy chickpeas with their cocktails. The bar is facing away from the beach, so you have to turn to watch the sunset or eat dinner on their patio. I had debated having my birthday dinner at Ferraro’s, but had decided on Spago’s instead because I have enjoyed Wolfgang Puck’s other restaurants. I’m sure Ferraro’s is good, but I’m so particular about Italian food and I didn’t see anything on the menu that I felt drawn to. But then I enjoyed their cocktail and snacks so much that it made me second-guess my decision. I guess I’ll have to come back next time!

Spago’s is located on their lobby level, which is technically their 2nd floor up from the beach. The bar area does not have a view. I think there could be a nice view at sunset if you dine al fresco and are seated on the right side of the restaurant. But the sun sets so early now at 5pm-5:30pm that it’s really hard to catch the sunset without eating dinner early because most bars are indoors and not facing the view. They sat me on the side of the patio that faces the pool. The sun had set by that time anyway. The vibe didn’t feel as social as Ferraro’s. I got a lychee martini and the martini didn’t even have a lychee in it! I was bit disappointed by the cocktail. I got a Lobster Ceviche with papaya salad, ahi tuna cones, and tagliatelle with local mushrooms. The lobster dish was my favorite. The cones were a bit sweet and the tagliatelle could have used more salt. It was good and I enjoyed my meal, but it wasn’t amazing. I prefer Wolfgang’s Merois in Los Angeles.

On my last morning in Maui, I woke up early to take full advantage of the beach. I wanted to get my toes wet and walk on the sand one last time. I had breakfast at Duo’s, which is a seafood and steakhouse at The Four Seasons. They offer a breakfast buffet for $57, but I ordered a la carte. It’s worth it to do buffet if you want to order coffee, juice, or pastries because one entree is already $34 before you add on extras so you might as well pay $57 and get everything. I am not really a breakfast girl, but because I was flying out that afternoon, I needed to eat before heading to the airport. FYI. Maui airport is small and there’s no Delta Sky Club Lounge, so do not get there earlier than an hour. My flight was at 1:30pm and I got to the airport before 12pm and it felt like I was too early. Spend every last minute soaking in the beach vibes before you leave!

I think a short trip to Maui is a great weekend escape. However, if you’ve never been before, you’d probably want to spend at least 5 days there, rent a car, and book an AirBnB. It can be a lot of driving, but there is so much beauty on the island. You’d want to dedicate a day to driving the road to Hana yourself or doing a tour, stopping at the bamboo forest, black sanded beach, and waterfalls along the way. I would also recommend going on a boat tour, either a day snorkeling tour or a sunset tour. Some people drive to the top of the volcano to watch the sunset, but it is a bit of an early drive so I have yet to experience it. Another day option would be to explore Paia town and beach. I remember it being beautiful because of it’s white sand, but the waves were strong and there was a dip from the sand into the water. It was quiet though and not as touristy, which was nice. I think experiencing a traditional luau is a must. It’s a little pricey, but it is a lovely Hawaiian experience with a buffet dinner, roasted pig, hula show, live music, and dancing. The one I attended years ago seated you at communal tables with strangers. As I mentioned earlier, South Maui Gardens is a great (budget friendly and commitment friendly) alternative to a luau because you can dine at the food trucks and still get a show.

I really loved my Maui trip. It was such a nice treat to give myself. Wish I could have stayed their longer. It was such a nice indulgence! Now, where should I go next?