So, You Want to Go to Hawaii...?
Greetings, friend! I’m writing this post two years after spending a winter in Maui. I’ve found that my time on the island, even if it was just six months, has made me a go-to source (and I daresay expert) for friends & family looking to plan a trip to Hawaii. This post is meant to address some of the most common questions I’ve heard, and some of the recommendations I consistently make.
A Quick Recap of My Time on Maui
I worked for Trilogy Excursions (below, right), a sailing company operating out of Lahaina Harbor and Maalaea Harbor. I crewed sailing trips, sunset cocktail trips, two-hour whale watches, all-day snorkeling trips, and day-trips to the island of Lanai. I also worked as a scuba-diver for Reefdancer (below, left), the yellow submarine docked in Lahaina Harbor that explores the reefs (only take if you have kids).
I lived in Lahaina, which is on the west side of Maui, and spent most of my working days in this area, though I adventured around the island every chance I could get. That’ll give you a sense of how I spent my time, and the lens through which you should read this post.
As such, pretty much all of the recommendations I have relate to exploring the natural features of the islands. I can’t give any advice on bars, clubs, restaurants, resorts.
What Island Should You Visit?
There are eight islands in the State of Hawaii: Hawaii (also known as the Big Island), Oahu, Maui, Kaho’olawe, Lanai, Molokai, Nihau, and Kauai. Here’s a brief rundown if you’re interested in learning more about them, but my advice has typically been to visit either Maui or the Big Island.
Maui: I lived on Maui, so I know the most about it. Maui is good for whales (in winter), snorkeling (from shore and a boat), surf spots (including Peahi/Jaws), rainforests, golf courses, mega-resorts, and Haleakala, a 10,023-foot dormant volcano from which you can see the sunset/sunrise, the night sky unlike any other, rare birds, and hike among eucalyptus and redwood trees.
The Big Island: I’ve never been to the Big Island, but for what it’s worth this is the island I want to visit most. It’s by far the biggest Hawaiian Island and things are farther apart, meaning you should research your itinerary in more detail. It has beaches, rainforests, waterfalls, snorkel spots, dive spots, golfing, and Mauna Kea and Mauna Loa, two 13,000-foot+ volcanos from which you can see sunrise/sunset, hike, and check out the stars (and lava flows, if you’re lucky/unlucky).
Oahu: Oahu has the largest population, by a wide margin. There you’ll find Pearl Harbor, the “North Shore”/Pipeline of surfing fame, Honolulu (a surprising monstrosity of a city), Waikiki Beach, Diamond Head, and a large military presence. It’s the best-known island, and extremely overcrowded. I would recommend avoiding going Oahu unless you have a specific reason for visiting.
Kauai: Kauai has fewer people, is more rural, and more laid back. Consequently, while there are still resorts, there are also are many timeshares and smaller bed and breakfasts. It has great white-sand beaches, rainforests, and the epic Na Pali Coast.
Lana’i: Lana’i is sparsely populated and has few services. The primary tourist destination is the Four Seasons, where Bill and Melinda Gates were married. It’s $1000/night, and there are few other options for lodging, so I wouldn’t recommend going to Lanai unless you have a specific agenda in mind. Axis deer were introduced to the island in the 1800s, so sport hunting is relatively popular (I have a guy if you’re actually interested in this). Lanai is a short boat ride from Maui, so if you want to visit your best bet is to take the ferry and rent a car, or take Trilogy’s Discover Lanai trip (you’ll snorkel at the beach by the Four Seasons, have lunch, have an option for a short tour of Lanai city, and sail back).
Molokai: Molokai is a relatively small island with a relatively small population, though has a high concentration of Native Hawaiians. While you can visit if you’re really set on it, casual, large-scale tourism is generally discouraged on Molokai.
Nihau: Nihau’s nickname is the “The Forbidden Isle”—it is privately owned, and most tourists aren’t welcome.
Kaho’olawe: Kaho’olawe lacks a consistent source of freshwater, and was used for target practice by the US Navy until 1990. It has no permanent residents.
My advice for the average traveler that has never been to the islands, but is seeking sun, sand, ocean, smaller crowds, and is up for other adventures is to visit Maui or the Big Island.
Maui Recommendations
Where to Stay
This depends on a number of factors, including what you want to spend your time doing (resort pool, surf, adventure exploration, spend time on boats), and how much you want to be pampered.
The two main resort destinations are located in Kaanapali and Wailea-Makena. There are AirBnBs and hotels located in both places. There are also a lot of lodging options in Kihei and Lahaina. It’s helpful to understand what you want to spend most of your time doing before booking lodging.
Things to Do
In terms of land-based adventures, you can take a day trip to Hana, along the curvy, rocky, wet, and winding Road to Hana. It's an absolutely amazing drive and is super cool to see some of the diverse biomes along the coast of Maui. There are a ton of secluded beaches of the rocky and sandy variety to enjoy, but you will spend a lot of time in the car if you do this. It is not a relaxed destination to get to, and once you’re there, it’s a chill, laid-back surfer town with not much going on. It’s a nice way to see the island, but I’d probably take a pass if you have limited time.
Waihee Ridge Trail in the early morning. It’s a beautiful hike, close to Kahului, the main city-center on Maui.
If you're looking for a hike, then I'd recommend doing the Waihee Ridge Trail (early in the morning, if you can). It'll give you beautiful views of the coast, the valley in between the two sides of Maui, and the jungly interior. It's pretty easy and can be done in a morning, especially if you find yourself in the area.
Cool towns to visit are Paia, a small, artsy surfing town on the north shore known for wind-surfing, and Makawao and Kula, bout of which “upcountry”, aka located up Haleakala, and are cool towns. Dress warmly, because they are at elevation.
Haleakala
Haleakala is a 10,023-foot dormant volcano (to be more specific, the entire east end side of Maui is a dormant volcano; Haleakala is what rises above sea level). You absolutely must visit Haleakala.
Stars from the summit of Haleakala
Don’t fall for the tourist trap of going to see the sunrise; rather, go for sunset. You’ll have a whole afternoon/day to explore the mountain. You can check out Hosmer Grove, where you can see native/invasive trees, and endemic Hawaiian birds, such as the ʻIʻiwi. At upper elevations, you can see silversword plants, a rare plant growing in an unlikely environment.
Poli Poli Spring State Park has great hiking trails and even redwood trees. It’s great perspective to look down on the island from up here.
You can also hike into Haleakala crater, starting at the summit, but beware that you’ll have to hike back out.
Check out sunset from the summit. The view is absolutely magical; you feel like you're floating on the edge of the world. After sunset, get back in your car and wait for literally everyone else to leave, and, assuming it’s clear, you'll have the place to yourself to see one of the most amazing night skies anywhere in the world. There's a reason some of the most advanced telescopes on earth are placed on top of the mountains in the Hawaiian Islands (lack of light pollution, close to the stars), and the experience is surreal. It can be extremely cold and windy up top, so be sure to bring warm clothes for this adventure. Also, pack snacks/drinks to have in the car while you wait.
Above photos: Hiking in Poli Poli, Silversword plant, Haleakala Crater, Sunset from Haleakala summit
The Ocean
There are a ton of options for getting in the water: surfing, snorkeling, scuba diving, sailing, sunset cruises, and whale watches. If you’re looking to get on any sort of boat, there are two main commercial harbors: Maalaaea (smaller, most trips run in the morning due to the wind picking up in the afternoon) and Lahaina (bigger, more protected, many more trips). I’m biased because I worked for them, but if you’re looking to take a boat trip, consider going with Trilogy Excursions. They’ll be the most expensive option, but I guarantee you that they will deliver an amazing experience, regardless of the trip you book. They’re absolute rockstars and have been for 45+ years.
The snorkeling on Maui is good, not great, but still worth checking out. If you take a boat trip, you’ll be able to access a more diverse range of snorkeling spots, but you’ll be at the mercy of where the captain decides to go that day, based on weather conditions, tides, and visibility. Unless you’re a keen swimmer/snorkeler, it’s probably best to just book a trip.
A boat will take you to some cool places, but a lot of them are accessible by land. Most will go to Honolua Bay or Olowalu, however, in the winter Honolua is a big surf spot and they don't go snorkeling there. Olowalu is accessible by land, so I wouldn't go on a boat trip to snorkel there. You can access it by car; it’s right off the highway and accessible by a small strip of beach.
Molokini, an island crater, off the coast of Maui, is another option for snorkeling trip. It's a great spot since there's little runoff to muddy the water, so it's usually incredibly clear snorkeling. You’ll have to take a boat from Maalaea to get there.
There are also sailing trips: sunset sails and dinner sails are great options to dress up in all white, drink some mai tais, watch the sunset, and listen to Hawaiian music. There are definitely worth doing if you're keen to get on the water, but not spend your time snorkeling on a boat during the day.
In terms of diving, there are places to go, but honestly, there isn't all that much that you can't see by snorkeling. I dove some of the shallow reefs there for work, but I didn’t go on any dive trips, so I’m not in a position to recommend anything.
If you’re looking to go whale watching, make sure that you book your trip in the wintertime. Humpback whales migrate to the Maui Nui channel (between Maui, Lanai, Molokai, and Kaho’olawe) to breed, so if you go in February/March, you will absolutely see whales. If you’re looking to drink cocktails on a sailboat and see whales, book with Trilogy, if you’re in it for the wildlife as opposed to the whole experience, book with Ultimate Whale Watch.
The surf is usually pretty big in winter, and you'll want to hit the north side of the island for that. I didn’t surf much on Maui, so there’s not a ton of expertise I can provide on this one.
Below photos: Molokini Crater seen from Kihei, Whale watching, Trilogy snorkel trip at Olowalu, Turtle
FAQs
Should I go island-hopping?
It’s tempting! Inter-island flights are typically quite cheap, and scenically beautiful. But unless you are spending at least 5 days on each island, or have a specific itinerary that requires visiting another island, I’d avoid island-hopping. The hassle of checking out, getting to the airport, traveling, checking in to a new place will be better spent staying in one place.
Should I rent a car?
Yes. There are many cheap options, including Kimo’s Rent-a-Car. Being mobile will greatly increase the places you can see and the adventures you can have.
Any reading recommendations before visiting?
In the Begninning: Archipelago is a fantastic book with great visuals about the natural history of Hawaii. It will help put everything you see into wonderful context.