Ultimate Hawaii Travel Guide
Aloha! 🤙 One of my favorite places to visit on the planet is Hawaii! I haven’t figured out how to live there yet but we have been lucky to work there and visit many times and it is the travel destination I get asked about most often. Most recently I surprised my brother Finn with an amazing island hopping adventure to Kauai, Oahu and Maui, and of course to film some great content for my YouTube channel. I'm going to share some of my favorite things to do in Hawaii and general advice I have when visiting this magical part of the world.
Getting There (with points!)
It is no secret that Hawaii is an expensive place to visit. The first way to save money on a trip to Hawaii is to book your flights with points and you’ll only have to pay about $6 in tax per flight. For economy class anything up to 30k points one way is a pretty good deal, but you can find flights from 22.5k miles on United. My favorite redemption to Hawaii if you can find it is Hawaiian Airlines first class flatbeds which can sometimes be found for 40k miles from Boston, New York, Austin, and several west coast cities as well. You can also book island hopper flights from 4k points one way, but I would avoid Southwest due to delays and stick with Hawaiian for more reliable service between the islands. If you’re paying cash for your flights you’ll usually find the best prices between 3 weeks to 2 months before your flight.
Jet Lag
You won't have much jet lag going there, you'll just want to go to sleep early every night but traveling east is much worse because you're losing time instead of gaining it. Try and stay up until at least 9pm Hawaiian time the first day you arrive if possible, and always a great excuse to watch the sunrise if you wake up too early there. I always plan a day of jet lag recovery anytime I fly east, so flying home to the mainland is not going to be as easy as going there.
Timeshares
You will encounter a lot of people selling timeshares in Hawaii, we own a small number of timeshare points through one of the big brands but I would not recommend you purchase a timeshare. A timeshare is a bad investment where the fees will likely go up every year, you can’t really sell it (many people end up giving them back to the timeshare companies, often paying a fee to do so) and availability is pretty awful in my experience.
However you can save a lot of money on tours and accommodations by enduring one of their 2-3 hours sales presentations. Often times when you say no they’ll give you a really great deal to come back again, and this can be a great way to make your next visit to Hawaii more affordable. Just be prepared to say no repeatedly!
Oahu
Oahu is the most populated and most visited island, famous for Waikiki beach which has welcomed tourists to the historic Moana Hotel starting in the early 1900s. The north shore is famous for incredible surfing and that is my favorite part of the island. Look for the beautiful Waimea Bay Beach which features a large rock you’ll see people jumping from all day.
Turtle Bay Resort is amazing if you’re looking for a place to stay. The Polynesian cultural center is worth a stop as well as the Dole plantation - definitely ride the train there! Pearl Harbor is somewhere you’ll want to spend a good half a day if you’d like to do the USS Arizona memorial and the Bowfin submarine. Waikiki is very touristy, worth a visit for sure but I wouldn’t spend my whole vacation here. Ko Olina has some really nice newer resorts like the Four Seasons and Aulani so everything is quite a bit more modern, but not so Hawaiian if that makes sense.
I think the biggest mistake that people make when visiting Oahu is not visiting the other islands. If my only impression was Waikiki beach vs. the beauty of Maui or Kauai I might be a bit let down. Take advantage of the ability to island hop and go somewhere else while you’re there!
Maui
Maui is where we have spent the most time, I could probably spend forever there and be perfectly happy. Unfortunately the real estate prices disagree with this plan of mine! OK I know everyone says this but splurge on a dinner at Mama’s fish house if you can, it is my favorite restaurant on the planet. They book up 5-6 months in advance but I have always been lucky last minute if you set an alert on opentable for availability or check the app repeatedly. The food, the service and the atmosphere are an experience you don’t want to miss.
Spend a day driving the road to Hana, it is one of the best road trips you’ll ever take. It’s not a fast ride, most of the road is around 20 mph with lots of hairpin turns and single lane bridges. You need reservations for the black sand beach as well as sunrise at the top of Haleakala if you plan on doing that which is worth getting up early for. I wouldn’t do the sunrise and Road to Hana on the same day, they’re both a lot of driving and I’d pick the road to Hana if you only have time for one. We bought an app called GyPSy Guide and you can buy tours for each of the islands, I would do them wherever you’re doing but it is especially helpful along the Road to Hana.
You can book a helicopter tour of West Maui and Molokai to see the worlds tallest sea cliffs, always book helicopters with no doors if you want good photos!
If you want to snorkel you can do it on your own in Honolua Bay or there’s another bay right next to it, rent or purchase gear from one of the local shops. We did the Molokini crater snorkel tour from Lahaina and I wouldn’t recommend it, it may be better if you go from a closer port like in the Waimea area, but we found the snorkeling was actually better in the other places I mentioned. There is great zip lining on Maui, the ATVs are better on Kauai. \
Kauai
Kauai is the oldest of the major islands and I think it is the most beautiful. Don’t expect a party atmosphere, it is very quiet and things shut down a bit earlier here. Our favorite resort on Kauai is the Grand Hyatt Kauai which features several incredible pools and a lazy river. The old St Regis overlooking Hanalei Bay was the only 5 star hotel on Kauai but it is now closed for renovations so hopefully something exciting is coming soon to that property.
You should really consider a helicopter tour of Kauai, it is arguably the best place to do it because of the island’s beauty and the fact that you can’t see most of the island from the roads. In fact the road does not do a full loop around the island so to experience the majestic Na Pali Coast you’ll need to go by helicopter, boat tour, or a long hike which requires a reservation. However Waimea Canyon State Park is definitely worth driving through, it’s like Hawaii’s Grand Canyon and a stark contrast to the rainforest on the opposite side of the island.
Kauai ATV tours features the most fun I’ve ever had in an ATV. They have newer model Polaris vehicles and these things go fast, like over 50mph on bumpy dirt roads. Prepare to get muddy so bring some clothes you can ruin. They’ll provide a gator to reduce the amount of dust you inhale.
If you have time I would drive the entire length of the highway, from the canyon all the way around past Hanelei Bay on the other side. The whole ride will take maybe 2 hours plus any stops you make along the way.
The Big Island (Hawaii)
I haven’t spent as much time on the big island as I’d like, it is definitely someplace I need to get back to again. We have stayed in the Kona area and really enjoyed it. Without a doubt the highlight was night snorkeling with Manta Rays. These majestic creatures can be as large as 15’ wide and will swim so close to you that you may feel them brush up against you. This was one of the most incredible things we’ve ever done and we’ll absolutely do it again next time. I would love to hear any tips you have for visiting the island of Hawaii!
Molokai & Lanai
Most of Lanai is privately owned, however there are two amazing Four Seasons resorts located on the island, and a stay there is definitely on my bucket list. You will also get great views of the island from Maui and especially flying from Oahu to Maui if you’re seated on the right side of the plane, or left side heading the other way.
Molokai is not a touristy island but it does feature the world’s largest sea cliffs which you can view on a helicopter tour from Maui. There are also day tours you can book, most conveniently from Maui which is nearby. I have done the helicopter tour which was amazing but I have not set foot on this island yet.
Luaus
A luau can be a pricey evening so be sure to take advantage of that open bar! OK even if you don’t enjoy adult beverages you will enjoy a delicious feast featuring staples like Kalua pork, fried rice and poi (you’ve got to try poi, I like it best when you mix it with the pork!) The luau is a beautiful way to experience not just Hawaiian but other Polynesian cultures as well. We haven’t been to enough luaus to tell you where the best ones are, but we really loved the Luau Kalamaku along with the train ride, and on Maui the Royal Lahaina Luau was also really great.
Helicopters
A helicopter ride isn’t without risk as there have been a few accidents in Hawaii’s history, however these accidents are very rare and hundreds of tourists take helicopter rides throughout the islands every day. There are several highly rated companies offering helicopter tours but in my experience the best tours are on Kauai and I imagine the volcano tour of the big island would be quite spectacular as well. If you’re brave enough to book a helicopter with no doors you’ll get much better photos and videos, and I think its a lot more fun too. Be sure to check the rules on what cameras you can bring and clothing you should wear, even though you’re in Hawaii it gets a bit chilly up there!
Dining
Everyone who has been to Mama’s Fish House is going to tell you to go there, but getting a reservation can be a challenge. Don’t count on the AmEx concierge to help with this one, because they can’t. What you can do is try to book about 5-6 months in advance if possible, but I’ve had luck setting alerts on OpenTable and finding a last minute reservation. Another favorite of ours on Maui is Fleetwood’s on Front Street.
Some Hawaiian staples you’ll find throughout the islands are Spam Masubi which is found in most convenient and grocery stores, Saimin noodles which are absolutely delicious any time of day, and Shave Ice which is well worth trying and maybe a bit different then other frozen ice desserts you may have tried back home. If you like fish always go for the local catch, you won’t be disappointed. My best recommendation is to eat local and avoid the chains & hotel restaurants as much as you can.
There is a great food truck scene throughout the islands and this can be a more affordable way to eat great food on a budget and also support some of the local businesses. You’ll find many types of cuisines from Thai to Mexican, local fish shacks, and some of my favorite are the shrimp shacks on Oahu’s north shore. Don’t drive by without stopping by, if you don’t want a full meal share one with your traveling companion!
Getting Around
Although rideshare services are available throughout most of the islands this is someplace where you’re going to want to rent a car. We typically rent through Hertz when visiting the islands but recently had a great experience with Sixt, and I would consider renting through Turo as well as you’ll often find more unique vehicles and better deals there. The driving is a bit more laid back and slower than you might expect with some occasional traffic in busy spots, so I try and leave my Massachusetts driving style behind and be polite on the roads.
Plants, Fruits & Vegetables
It is extremely important that you don’t bring an plants, fruits or vegetables, or anything that could upset the ecosystem in Hawaii. Foreign plants and animals have done terrible things to the islands in recent years and there are stiff penalties and fines for those who don’t comply. This may be a good reminder to respect the land you are visiting and not leave trash behind or take anything from the land that you aren’t supposed to take such as the ocean sand or water.
Snorkeling
Since all of Hawaii’s beaches are public you don’t need to take a tour do find some great snorkeling. A quick google search will help you find the snorkeling hotspots near where you’re staying, and you can rent gear from local snorkel shops at very reasonable prices. That being said the snorkeling tours we have taken have been a lot fun so go with whatever option you prefer.
Sunsets & Rainbows
Some of the best sunsets and sunrises I’ve ever seen have been in Hawaii, and you’ll typically see a lot of rainbows here too. Plan some time to enjoy these moments at the beginning and end of your day, and you’ll get your best photos shortly after sunrise and shortly before sunset on a clear or partly cloudy day. There have been trips where we have seen rainbows every day, but this also means Hawaii gets a lot of rain but fortunately it usually passes through quickly. Some of the wettest places on the planet can be found in the middle of Maui and Kauai with as much as 600 inches of rainfall a year! Luckily the coastal areas where you’ll probably be staying are much dryer. Make time to enjoy the beautiful scenery each day, that’s probably why you traveled so far!
I’ll keep this updated with more info as I continue to explore more of Hawaii in the future, and I hope you have a chance to explore these amazing islands as well!
Aloha & Happy Travels!
-Jeff
