I had never been to Hawaii before. When you grow up on the East coast, it’s quite the long journey to get there. So when I moved to Los Angeles several years ago, Hawaii was on my must-do list (along with becoming a sitcom writer and owning a baller convertible…so, checking off the list at a glacial pace). Months ago, I received a promotional letter from the Westin Ka’anapali Ocean Resort Villas for a deal on their hotel that even I could afford! Is this real life?! I called the Westin to investigate. Am I going to have to spend half my time inside, listening to a timeshare presentation? “No,” they told me. “This is just a thank you for being a Starwood Preferred Guest.” Amazing. Especially since I’m definitely not a Starwood member. Trip booked.

The one problem I had with booking a trip so far in advance was that it became the only thing people associated with my life. For the eight months leading up to the trip, I was constantly asked if I was excited for Maui. As if that answer would fluctuate from month to month. In October I was psyched but in February I was kinda “meh” about the whole thing. Yes, I was excited!

And now, we’re back. Thrown into the real world with only my burnt & peeling skin to show for it. But, so is life. And to keep the good times rollin’, I wanted to share my top tips, experiences, and advice for any fellow Maui-travelers. Number one piece of advice: just go! And live it up while you’re there. It’s a pricey place, for sure. But as I said multiple times in Maui (and my boyfriend told me multiple times isn’t necessarily true), you gotta live it up, because YOMO: You Only Maui Once.

The Westin Ka’anapali Ocean Resort Villas

Do you have kids? Then, definitely consider staying here. The resort was rampant with tiny tots (cute) and menacing middle-schoolers (so unattractive at that age). There were several pools, the beach was right on the property, and there were activities that you could partake in all day long. If you don’t have kids, like me, maybe consider staying elsewhere. I’ve heard that Wailea has some snazzy hotels, but we didn’t make it to that part of the island.

When we arrived at the hotel, we were pushed to sign up for the 90-minute property tour. It wasn’t mandatory, but highly encouraged. I knew it was too good to be true… (FYI we signed up and didn’t show, and it was no big deal). Then, we got to the room and I went to sit on the balcony. But alas, I could not. What is this, a balcony for ants? Because only ants would be able to sit out there, set up their tiny chairs, and indulge in a tiny version of Liane Moriarty’s book, Truly, Madly, GuiltyThen, I tried the jacuzzi. Because while I think it’s disgusting to take a jacuzzi in my own apartment, I like to assume (please don’t correct me) that hotel ones are definitely more sanitary and not gross at all. The warm bath relaxed me until I turned on the jets and the bath was filled with black specks of I-don’t-wanna-know. Back to the reception desk we went.

It was a struggle to get moved to a new room. At first we were told the only one available with a balcony was right in front of the children’s pirate ship play zone. They eventually were able to switch us to another room after the first night. It did have a balcony, yet it was a concrete wall that was higher than every other balcony, so when sitting, you couldn’t see out. But hey, at least this room had a laundry machine, which for anyone living without one in their apartment knows, is some pretty exciting shit.

We only ate once at the resort because hello, only total tourist eat all their meals at the hotel. Tourist who like to waste money on sub-par food. We went to the breakfast buffet at Auntie’s Kitchen; if you call the night before and say you’ll forgo housekeeping for the following day, you can receive one free breakfast voucher! A few towels on the floor seemed like an easy price to pay for free brunch. Like I said, sub-par. The iced coffee was just hot coffee with ice thrown in, the eggs were an odd consistency, and the pastries reminded me of ones you could pick up in a 50-pack from Costco.

My birthday was during the trip so we decided to splurge and get massages from the hotel spa. My boyfriend and I were both surprised when two male middle-aged masseurs came to grab us. While I can’t speak for the boyfriend (because you know how guys can get weird about that stuff), I thought my masseur was great. He told me I had super tight shoulders, but he liked the challenge. When the massage was over, he thanked me for letting him just “do his thing,” since so many people try and instruct him on what to do. Of course! I would never talk during a massage, even when on the brink of pain, for fear that this could open up conversation. Don’t you agree, the phrase “silence is golden,” must be referring to getting a massage?

The Road to Hana

This is a day trip that I highly recommend doing if you have the time and a car. We rented my high-school-dream-car, a red Jeep Wrangler, for the journey. If I knew then, what I know now, I would have dreamed bigger. But, it was totally fun to put the roof down (could not figure out full plastic removal) and feel the breeze while we took about a billion sharp twists and turns. For about 60 miles, it was a rough ride. If you are someone who gets car sick, this may not be for you. Also, leave super early in the morning because this is an all day event. We left at 7:30AM and could have used one more hour.

If there is an award for apps, let me know, because I would like to nominate the Maui Road to Hana Gypsy Guide. It was like having a personal tour guide along with us; he told us where to stop along the road, where to park, history throughout the drive, and by the end, the mysterious man from the Gypsy Guide felt like a friend I was going to miss.

Our first stop was at Twin Falls. There is an intimidating sign on a gate that tries to scare you off, saying that hiking past it is only for experienced hikers and anyone with heart conditions, anxiety, one-leg, gluten-allergies (something along those lines) should turn back. Well, my advice is to open that gate and keep going. It was only about a 20-minute “hike” that was less strenuous than the easy side of Runyon Canyon to get to the natural pool and waterfall at the top. Luckily, we had purchased these super dorky, but totally worth it, water shoes, which made it easy to walk along the rocks and get into the pool. When others shriek from the pain of their bare feet on the rocks and you feel fine, you’ll thank me.

We then stopped at the Garden of Eden, a 15-dollar admission park. We saw trees like the rainbow eucalyptus and tons of exotic flowers, but the free arboretum a mile past the garden probably would have sufficed. My advice? Skip it. We then drove to a lookout called the Keanae point, which was beautiful. But really, everything along the entire ride, was beautiful. It was all beauty, no beast. The best part of stopping at Keanae point was finding Aunt Sandy’s Banana Bread. We made the mistake of buying only one amazingly delicious mini loaf. Don’t be like us; stock up, buy her out (and then bring me back one, please?!). Continue your drive to Waianapanapa State Park, where you can see the black sand beaches. Right before you get there, there is a small area with some food trucks/stands. Get the Pad Thai. It’s good. When you get to the state park, check it out but don’t spend too long there. Because you’ll want to keep going to hit the Seven Sacred Pools. We made it to the entrance, but ran out of time. Sundown was in t-minus 2 hours, and we did not want to be stuck on the Road to Hana when it gets dark out. We drove into the town of Hana, which it’s important to note, is really no big deal! So as our good friend from the Gypsy Guide told us, it’s about the journey, not the destination, when you’re on the Road to Hana.


This is the big dormant volcano on Maui. Prior to this trip, my perception of what a volcano was, was embarrassingly that of a 5th grade science fair project. That steep mound with lava that spews out the top… I learned is NOT what a volcano is like at all! We woke up at 1AM (FYI I’d advise not eating a huge dinner a few hours prior) to meet up with our group for our Maui Mountain Cruisers tour. They picked us up at 2AM and took us to the top of the volcano. Yeah, even though you’re in Maui, it’s cold AF up there at night. We got to the top at around 4:30AM and got our spots for “the show.” We watched a star-filled sky slowly disappear as the most magical display of colors filled the sky. The sky continued to change until the sun officially made its debut. Pictures don’t do it justice. You have to see if for yourself.

Once the sun was up, it was time to go down. Our guides gave us enormous helmets, a bit much for the not-so-dangerous activity, and bikes that are only meant for downhill. Seriously, they were like four notches past no resistance on a Soul Cycle bike. But, the ride was all downhill, so that worked out. I was shocked to find that there were woodsy areas and homes on the volcano. People live on volcanos, who knew?! If you’re in Maui, you’ve gotta check this out!

Sail with Trilogy to Lanai

We spent our last full day in Maui on a Trilogy catamaran sailing to a private beach on the island of Lanai. The ride out was smooth and filled with tons of things to stuff in your mouth. The crew came around, like cocktail waiters, serving cinnamon buns, pineapple juice, coffee, fruit, and later on, sandwich wraps. When we arrived to Lanai, we were greeted by about 15 spinner dolphins, jumping in and out of the water. Nice touch. We got to the beach and they had all the things we would need ready: snorkel gear, chairs, beach mats, and snacks. We did some good snorkeling, saw tons of florescent-colored fish among the coral, and explored the island. The cliffs overlooked the bluest water I’ve ever seen. Once we built up an appetite, the company served a lunch of BBQ chicken and stir-fry noodles (Maui loves noodles).

The trip back was a bit (re: extremely) bumpy, which paired nicely with the ice cream sundaes followed by Moscow mules they gave us. I didn’t vomit, so I loved it. When we returned to Lahaina Harbor, we walked around the area. We hadn’t seen this part of Maui yet and it’s a cute place to check out. A bit touristy, with a Burger in Paradise and a restaurant owned by Mick Fleetwood, but it’s worth a visit; it’s full of cute shops, galleries, and restaurants. And we caught a magnificent sunset from a grassy park in town.

Maui Dining

I think a huge part of travel is food! But for once, the scenery/ambience of a restaurant outshone even the food (which was also great). I’m talking about Mama’s Fish House. This restaurant was recommended to me at least a dozen times, and I could see why. We sat at a table that faced a glass-less window, which faced their beautiful private beach. Get the macadamia-crusted, crab-stuffed mahi-mahi for dinner. There’s no appetizer you’ll be disappointed by. The cocktails are also on point.

Our first stop in Maui was for linner (lunch/dinner) at this roadside restaurant, Leoda’s Kitchen and Pie Shop. I had their seared ahi sandwich, which along with the ahi had avocado, Jarlsberg cheese, pesto, and garlic aioli. It was really good, and probably tasted even better since I hadn’t had carbs in over a month (Hello, bikini diet!). Neither of us tried a pie, but I’d have  to imagine they were good, since it’s in their name. The guy at the car rental place also recommended the chicken ‘n waffles sandwich, and he seemed like he knew what’s up.

We had my birthday dinner at Lahina Grill. The menu was filled with fresh seafood and other beautifully crafted dishes. It was good, but to be honest, I forgot what I ate which is telling. I’m a bit of a food snob so to me, it was a very nice meal, but not fully worth it for the $40 – $50 main dishes. I’m not usually big on dessert, but the standout dish was the triple berry pie that came with my birthday candle. It was filled with fresh berries and it was damn good. And they also gave me a birthday card signed by the entire staff which was an adorable touch.

Our last meal before we left the island was at Top Chef alumni, Sheldon Simeon’s casual eatery, Tin Roof. It looks like a nothing place, hidden away in a strip mall near the airport, but the inexpensive dishes were so flavorful. It may have been my favorite meal all vacation! We had the popular Mochiko Chicken, which was chicken thighs marinated overnight and then fried twice (vacation = no diet), topped with a creamy mayo-y sauce, and the Pork Belly, also fried, atop rice and garnished with tons of Asian-inspired goodies.

Overall it was a fabulous trip. Have any more Maui questions? Feel free to ask me! Want to see the 800+ photos we took? I can share those too! Come over and I’ll set up a slideshow. Mahalo, Maui.

Leave a Reply

Your email address will not be published. Required fields are marked *