Ever wonder how our editors travel? In Vogue Vacations, you can take a peek at our itineraries, out-of-office style, and trip highlights to see what we wore and we where we went—and maybe bookmark some inspiration for a getaway of your own.
I have lived in the United States for six and a half years now, so when it came time to celebrate a big birthday, I wanted to take a trip to explore somewhere else in the country a little farther from the East Coast. Hawaii was a bucket list place because it felt so otherworldly compared to anywhere else I’d been; I was as curious about the landscape as I was the culture, and frankly, I wanted to wake up on my 40th birthday on a spectacular beach—and that’s exactly what I did.
The itinerary was based on the fact that I wanted to explore more than one island, and I wanted the stays to feel quite different. My husband and I made the most of our 11 days away with three destinations, each with an entirely different vibe: The Big Island, Lanai, and Maui. The transfers between the spots were a highlight, too: The flight to Lanai was in a much smaller plane, and had exceptional views. I will say many friends told me in advance that Kauai is spectacular—and while we didn’t make it there, maybe that’s my reason to go back. Ahead, everything I wore, indulged in, and snapped photos of during a relaxing trip to Hawaii.
The Destination: Hawaii.
The Airport Outfit: Travel between the islands is short, and can be an experience on its own. For the small turboprop plane to Lanai, which flew low enough to see the incredible coastline, I wore an oversized shirt (which doubles as a beach cover-up), lightweight summer denim from Mother, and slip-on suede loafers from Flattered. I wore them non-stop last summer and they’re filled with sand, but they get better the more beaten-up they are. The ferry from Lanai to Maui was an unexpected highlight of the trip: exquisite sunset views with a sky in multiple colors I’ve never seen before. It wasn’t a smooth journey (I was told to tap my feet to confuse the body and manage motion sickness) but I stayed at the back of the boat—which also had the best view. I wore my favorite fisherman pants from Matteau, and a cap from Polo Ralph Lauren to prevent myself from looking too windswept on arrival.
The Travel Bag: My Away luggage is over 10 years old now and still going strong. It likely needs an upgrade, but given how frequently I use it through fashion weeks, press trips, and personal vacations each year, it’s really stood up to the test—especially because I’m not known for packing lightly. My carry-on, carry-anywhere is a Liffner suede tote. It works just as well for a grocery trip as it does as a laptop bag in-flight and a tote for my beach essentials.
The Packing List: I’m a list-maker when I travel, which goes for a vacation as well as a fashion week trip; either way, I’m thinking about what goes together and how many different ways I can wear something. I also knew that because we would be moving around a lot, I wanted to be reasonably edited in luggage. We did a very small private transfer to Lanai, we took a ferry to Maui… the idea of lugging heavy suitcases around did not appeal at all.
My packing for the daytime tends to revolve around a lot of easy, coordinated options: maybe a white cotton skirt and an oversized men’s shirt that I can wear as a cover-up with a bikini when I’m going to the beach. Matteau makes up a high proportion of my vacation wardrobe. For me, it’s the perfect resort wear dressing because it’s true vacation wear for a minimalist, and there’s not a lot of brands out there that do that; typically vacation wear is very printed, very colorful, and that’s just not me. One of my favorite looks was the brand’s fisherman pants, which go over everything and look like they should be unflattering, but they’re really not. I also get a burnt scalp a lot, so I have a lot of headgear; I love my straw bucket hats (my favorite is from Avenue; it can get thrown around and still look perfect) and silk scarves.
The piece that I think I wore more than anything else on the entire trip was a long-sleeve top from Frankie Shop. There was a breeze in the evening, so I would wrap it around my shoulders; for early mornings on the water, it went over the top of a bikini; at the end of the day, as I started to feel like I’d had too much sun, I’d throw it on. It’s this oversized, super soft jersey fabric, and I really loved it.
The Hotels: I flew into Big Island itself to stay at the Kona Village Rosewood—honestly, I wanted to land on a beach and just flake out (it was a long trip!). There was enough variation on the property to feel like we could go somewhere different every day. (In fact, we rented a car, and I think we used it once in three or four days because the property was just so lovely.) The rooms are all individual, what they call hales, rather than it being a centralized property. Everything was beautifully done–if I could design a bedroom, I would do it like this, with the bed right in the middle of the room so you were always facing the window. My favorite thing was sitting on the deck out front at end of the day, reading a book with the fan going, overlooking the lagoon.
At Sensei Lanai, the first thing I noticed were the gardens. I don’t think I’ve ever seen color like this in my life—it was so vivid, like looking at a wild impressionist painting. I spent most of my time in and around those gardens: They have this huge lake, with paths that meander around. I think I sat and watched the carp in the pond for like 30 minutes at one point, which I’ve never slowed down enough to do in my life. That’s a testament to the feeling of that location: I’ve never had that sense of calm, and the whole experience was grounded in a thoughtful approach to wellness. When you check in, you meet with someone who puts together a straightforward program for you, grounded in the three pillars of nutrition, movement, and rest. When I travel I like to learn new things and have new experiences; and since I’d never meditated before, I chose to do a private class around meditation. To be honest, I really thought it was going to be a disaster, but it was quite transformational. I also had the best massage I’ve ever had in my life at the spa, which had a sauna, steam room, and a giant wooden tub. The food at the on-site restaurant, which is Nobu, is very much a blend of Nobu classics with locally sourced ingredients. I don’t think I’ve eaten as well or as cleanly before.
The Four Seasons Maui at Wailea was the last stop, which on the back of being in Sensei where I think I saw 20 people in four days, was a definite change of pace. Maui was lively and sociable—even being in the lobby for cocktail hour in the evening, with live music and amazing cocktails, was a really lovely vibe. That lobby has recently been renovated, with lots of texture, color, and interesting shapes—it’s very modern, but distinctive. Everything is open (there are no walls in this place) and the sea air coming in like that was such a treat. The property is a very large complex, with a large beach and an infinity pool that looks out onto the ocean, and you could spend many days here with completely different experiences. This is also where they filmed The White Lotus—and you do hear about it around the hotel, which makes the whole thing a fun experience.
The Memorable Meal: First of all, the Four Seasons app is amazing. You can book every restaurant, every beach bed, every everything on this one app. We used it to book dinner at Komo, the restaurant at Maui led by Chef Kiyo Ikeda, who had trained in Japan prior to this. The app recommended partaking in the chef’s surprise box, a series of courses that the chef puts together based on what is in season. The chef was really involved: We sat at the counter, he talked us through each course, and I appreciated everything that we ate as a result. It was an amazing sushi dinner with lots of unexpected surprises—I don’t think I’ve ever tasted fresh wasabi until I ate here. It’s the way they grate it: Normally, wasabi can be very horseradish-y and just hits you… this was so creamy and delicious and really changed my perspective on exactly what wasabi should be.
The Beach Pit Stops: My favorite beach was probably Wailea beach in Maui, which was directly accessible from the Four Seasons where we stayed. It has everything from surfing (I don’t surf, but enjoyed the people-watching) to an open, expansive landscape where the waves just roll in. I took a walk there every morning, all the way along and back, and it’s stunning. We also took a boat trip out in a waʻa (a traditional Hawaiian kayak). We went out at sunrise one morning, which was amazing—our guides on the boat brought us sea urchins and put them in our hands… it was really fun.
The other beach that I loved was also in Maui, called Koki Beach. It took an hour and a bit to reach, with a few food stands along the way: We tried a common street food dish called huli-huli chicken, and it’s amazing. The beach itself had a mix of white sand on one side and black, dramatic rocks on the other. It’s a very unique experience, because there’s nothing there. There’s a beach, six spots to park a car, a sign warning about rough water, and a huli-huli chicken stand. Someone had also tied a rope swing over the water, which I really loved.
The Outdoorsy Activities: In Lanai, a tiny island so unpopulated they don’t even have road signs, we hiked the Koloiki Ridge Trail. It was my first moment of experiencing the true landscape expectations that you have of Hawaii: Just that very dramatic, Jurassic Park-style vista, with ridges rolling down and out into the water and really deep valleys. It wasn’t a tough hike (about an hour and a half out and back), but it delivered all of the dramatic views I was looking for.
Another highlight was the Road to Hana, a road trip that’s about an hour and a half drive each way but can take up to a full day depending on how many stops you take. We’d read that there are something like 25 stops on the Road to Hana; we hit maybe three of them. There are so many things along the way, from botanical gardens to waterfalls that you can hike to. The food stands were our favorite stops. We stopped and had banana bread, and then we stopped and had that huli-huli chicken, and we stopped again and had tacos. No one needed to eat that much food; it was all local, lo-fi stands, with several farmers stands selling fruit. We did do our research beforehand (which I recommend doing): It’s very winding and does get narrow, but the scenery is mesmerizing, with incredibly luscious rainforest on one side and the ocean on the other. It felt like a controlled adventure.
