Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.
I was a kid when I first saw photographs of Kauai in National Geographic. The magazine had listed kayaking the island’s Na Pali coast — a range of high, sloping cliffs on its north shore — as one of the “best American adventures.” I vowed to one day make the trek (which has since been described as the “the longest and roughest ocean kayak trip in the world”) but had mostly forgotten about it until this summer, when my grandmother passed away. Born just after World War I in a small English town, she spent much of her adult life traveling the world (often by boat, or bouncy, unpressurized commercial airplanes). When she died she left my sister and I some money to be spent — strictly — on travel.
I made a case for Kauai. What could be more thrilling than an island that is 80 percent uninhabited? My sister (more of a yoga/gardening kind of girl) shot me down. When I mentioned kayaking, she told me point blank she was “terrified of the ocean.” Eventually she caved and we booked a trip two weeks in advance. Kauai is a smallish island with one main highway and is well-suited for relaxed exploration. I didn’t have to think hard about where to stay; I knew we’d be on the north shore because of kayaking, and I’d read that it was more remote than the south and east sides of the islands where families tend to stay because they are more developed, resort-y, and closer to the airport.
Our timing also worked out: Early fall is a good time to visit since the summer crowds have thinned and the weather is good — high 70s. The water is also ideal for swimming; warm, with few swells. Just remember to wear reef-safe sunscreen, pee in the bathrooms (not the sea), and step on sand, not the reef. The island is small so three days felt sufficient, but next time I would add a day to volunteer (Kauai has a lot of voluntourism options — from beach cleanups to farm work through one of its many community organizations).
Day 1
10 a.m.: Pick up your Jeep Wrangler
We flew into Honolulu and took a 30-minute jumper to Kauai, both on Hawaiian Airlines (Honolulu’s main airport is small, and flights to neighboring islands leave every couple of hours, so don’t stress about catching a transfer.) After landing at the island’s tiny airport we rented a car. Ubers are hard to come by in Kauai, and taxis are scarce. There’s a car-rental stand at the airport that shuttles you to a variety of nearby services. Book in advance to skip lines.
There’s no offroading in Kauai but remote beach roads can get bumpy, and the main road that hugs the coastline can flood. We got a Rubicon because it has a removable roof, so you feel like you’re in Jurassic Park (which was filmed in Kauai). We started the beautiful coastal drive up the east side of the island.
11 a.m.: Check into your Princeville rental
Formerly the site of sugar plantations and a cattle ranch, Princeville is now a resort community full of condos, golf courses, and tennis courts. It’s too manicured for my taste but has lovely views of the sea and mountains, and is considered the north shore’s designated tourist area. Many of the condos are rentable for $100-$300 a night.
They are all pretty dated and simple — a bed, tiny balcony, kitchenette — but you’re well-located: a ten-minute drive to the north shore’s main town, Hanalei, and a short drive to some of the island’s best beaches. We rented with VRBO because I’ve dealt with too many roach-infested Airbnbs.
After dropping our luggage we grabbed breakfast and Kona coffee at Hanalei Bread Co. (5-5161 Kuhio Hwy #4), an organic bread shop in the Hanalei Community Center, where we watched the center’s charming ward of wild kittens frolic peacefully amongst a pack of feral chickens (Kauai is replete with chickens, be careful of them when you drive).
Noon: Head to Waimea Canyon
Waimea Canyon is on the west side of the island, about a two-hour drive from the north shore (there are no roads going through Kauai, so getting around can take some time). As we drove the environment began to change; the island has distinct biomes due to trade winds: While the north point tends to be wet and tropical, the west side is arid and desert-like — I even saw some cacti.
A surfer we met in Hanalei glibly described Waimea as a “mini-Grand Canyon” and told me to lower my expectations, so I was shocked when we pulled up. Waimea, it turns out, is still the second largest canyon in the U.S. — 14 miles long and at points 4,000 feet deep. You can do a scenic drive but we opted for a moderate, half-mile hike/walk with views of the canyon’s sheer, colorful rock faces and gorges. (There’s a popular two-mile hike that makes a 2,000-foot elevation drop to the canyon floor, but sis vetoed it.)
3 p.m.: Eat a late farmers’ market lunch
Throughout the weekend we mostly ate at food trucks, fruit stands, and one of Kauai’s rotating farmers’ markets, which dot the main road. They’re great, fresh alternatives to the touristy western fare served at restaurants, and you help support local businesses. We stopped at the Waimea Town farmer’s market (Parker School campus at 65-1224 Lindsey Road) for Caribbean food, fresh coconut water, and Dole Whip (pineapple soft serve).
6 p.m.: Catch the sunset at Hanalei Beach
Hanalei Beach is a two-mile-long crescent-shaped beach near Hanalei town that Tripadvisor recently named one of the country’s best beaches. It’s huge and was a bit too wavy for swimming, but we saw surfers hit the swells as the sun went down.
Day 2
6 a.m.: Arrive for the kayak tour
After pounding oatmeal and Dramamine for breakfast we drove to Napali Kayak in Hanalei where we met up with the rest of the team and our guides. I found three or four companies that offered day trips up the coast, but I picked Napali Kayak for its excellent reviews on Tripadvisor and Google, and the fact that their coastal day trip was one of a handful of their offerings. (In comparison to other services, which had dozens of tours to choose from. I figured Napali went for quality over quantity, and I was right.)
Our guide, Mitch, a biologist who seemed to know everything about local wildlife, informed us that ocean conditions were okay (e.g. we probably wouldn’t flip) but that we would be doing “a half marathon” with our arms today. Did he mention the Na Pali coast faces the biggest storm-producing expanse of the Pacific? He had already canceled the rest of the week’s tours due to swells. My sister, at this point, was looking green.
7 a.m.: Cast off at Haena Beach
We hit the ocean as the sun rose and a massive rainbow dipped into the sea. I felt pretty good, but I was also doing most of the work — I was on the rudder, and my sister froze up whenever a big wave hit. She got the hang of it eventually, but the next six hours were grueling. A few groups fell behind; some guy got seasick, a girl dropped her phone into the sea. Mitch’s group drove on; we paddled through sea caves and beneath waterfalls and stopped to swim in a cave open to the sky.
An hour later, back on the open ocean, we saw a bunch of rubbery dorsal fins. The sea was bouncy and I remember thinking sharks, and we’re toast, but it turned out to be a pod of affable dolphins. Shortly after, we hit very rough water; to make things worse the sea was teeming with little purple bubbles. It was a swarm of venomous jellyfish — Portuguese man-o’-war, whose tentacles can stretch over 30 feet. My sister was stung after she mistook a tendril wrapped around her paddle for a fishing line. She was a champ about it, though, and Mitch provided some mysterious green goop that helped with the pain. We kept paddling.
3 p.m. Stop for lunch at Miloli‘I Beach
Miloli’i is one of the most remote beaches in Hawaii, only accessible in the summer by boat. We stopped for an hour to eat a picnic lunch at the base of a cliff that was over 4,000 feet high. Several seals were napping on the beach. I followed suit, sleeping on a pillow made of a rock.
6 p.m. End at Polihale Beach
Polihale is the longest stretch of beach in Hawaii. It’s backed by huge yellow cliffs, has fine, golden sand, and the clearest water I’d ever seen. At this point I couldn’t feel my ass, my face was burnt raw, and my hands were cramped and blistered, but I swam a bit, relieved to be alive and no longer on a kayak.
Day 3
10 a.m.: Check in to 1 Hotel Hanalei Bay
This is a new hotel (5520 Ka Haku Rd, Princeville) on the north shore and possibly the most luxurious stay on the island (it was formerly a St. Regis, and came recommended by a friend of mine who’d gone for a glamorous-looking wedding.) It has two huge pools, a spa, and several fancy gyms. There’s even a med spa if you want fillers. The crowd was very White Lotus — coastal elites on vacation and wealthy Europeans I overheard talking about $20,000 yacht rentals.
Service was excellent and attentive — they let us check in early into our room, which had a beautiful view of Pu’u Poa beach. First thing was a sitdown breakfast at 1 Kitchen, the hotel’s main restaurant. We ordered croissants, cold-pressed juice, and Kona coffee, of course.
11 a.m.: Book massages at the Bamford Wellness Spa
The spa was beautiful, and had everything from hyperbaric chambers to meditation pods to $800 facials that were fully booked up by what seemed to be a troupe of LA influencers. Sis and I opted for Hawaiian-style Lomi Lomi massages since neither of us could move after yesterday’s journey.
1 p.m.: Beach hop along the north shore
As well as kayaking, we picked the north shore because of its remote, beautiful beaches. We’d read about a few of the famous ones — Hanalei, Tunnels — but for the most part we asked locals for suggestions, or drove along the coast until we saw a beach sign. There were even viewpoints along the main road where you could park and hit up an undesignated beach (we called these “road beaches.”) Though many north-shore beaches have lifeguards and bathrooms, these aren’t ritzy beaches (no chair rentals or snack bars) which is probably why they’re so stunning and clean.
After a reef swim at Pu’u Poa, the public beach attached to 1 Hotel, we got back in the Rubicon. Our first stop was Anini, which we saw signs for as we drove towards Kilauea, a town on the northeast coast; it’s a pretty white sand beach protected by Hawaii’s largest coral reef. After that, we stopped at Kalihiwai Beach, which was recommended by one of our kayak guides — it was practically empty and had a calm, cool river leading to the sea that was good for swimming.
Before heading back to Hanalei we grabbed lunch at Big Nick’s (4000 Kilauea Road, Kilauea), a food truck with delectable hamburgers, and made a quick stop at Hideaway Beach, which required us to descend a cliffside trail (there’s rope and some steps, but don’t go when it rains, apparently it’s a mudslide.)
6 p.m.: Watch one last sunset at Tunnels Beach
With a dramatic backdrop of soaring green cliffs, Tunnels is one of the most photographed beaches in Hawaii. It’s also a favorite resting place for the endangered Hawaiian Monk Seal. There are roughly 1,600 of them left, and we saw two — each over six feet long — resting on the beach that day. When they come to the beach people (the good ones) make a kind of driftwood fence around them. (There’s a lot of wildlife in Kauai, and the rule of thumb is to stay 100 to 200 feet away.)
Sangeeta’s Kauai packing list
The best toiletry kit in the world. After endless broken zippers from cheap dopp brands I splurged on what I would argue is the world’s best toiletry kit. I’ve now had it for seven years. It’s my most prized travel possession, and packs down nicely into a backpack or cabin luggage.
My Baggu sunhat is a must have for every beach vacation, especially in Hawaii where the sun is fierce, even in September. Not only does it pack into the size of a slim paperback, it has a chin tie so it doesn’t blow away. Also, the brim is so wide it practically doubles as a beach umbrella.
I’ve been gatekeeping this Australian swimwear brand that makes the most perfectly cut triangle bikinis. They look beautiful and are also quite sturdy (like they didn’t fly right off when I was being whacked around by ocean waves).
I don’t like snorkeling (I’m always swallowing buckets of water) but I take my Arena goggles with me everywhere; they’re super light and were perfect for exploring the reefs.
I’m a big destination reader and this book is, I think, required reading for any trip to Hawaii. It details the overthrow of the Hawaiian monarchy by Europeans and Americans and Hawaii’s annexation by the United States in 1893. Told from the perspective of Hawaii’s last monarch.
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