Ryan's Hawaiian Vacation Guide
Updated: Jun 5
Last Updated: June 2023
Hawaii is my happy place. I have traveled to the 50th state more times than I can count. It is my favorite place on Earth, and I immediately feel less stressed and happier upon stepping foot on the islands. I have visited Oahu, Maui, the Big Island of Hawaii, and Kauai. Over the years, I have emailed friends and colleagues a few pointers and suggestions about how to make the most of their Hawaiian holidays. I decided to post it on my blog, so I can easily forward it to friends who are interested in planning their Hawaiian vacation.
I highly recommend flying Hawaiian Airlines. It feels like you've stepped foot in Hawaii the minute you board. But other airlines such as Alaska Airlines, Delta, United and now Southwest fly directly from the West Coast. The hope with Southwest is that its famous low fares will bring prices down across the board.
If you need a good, local travel agent, I recommend Bruce Fisher at Hawaii Aloha Travel. He gets good deals, and he also hosts a semi-regular podcast, The Hawaii Vacation Connection, with loads of tips and travel news.
Is there a better way to feel welcomed to Hawaii than by getting "lei'd"? To pre-book Hawaiian Lei Greetings, there are several services available. Prices are approximately $25 per lei. If you are flying via Hawaiian Airlines, you can arrange for lei greetings on their website for $21. As you exit the airport and arrive at baggage claim, a representative will be waiting for you to greet you with leis. Be sure to get the floral lei. If you are on a connecting flight to a neighboring island from Honolulu, arrange for your lei greeting to be at the final stop because they are handled as you exit the airport.
Things to do in Waikiki
I have stayed at several hotels in Waikiki, but I keep coming back to the Hilton Hawaiian Village. Yes, it's a bit like Disneyland. It's a mega-resort with huge pools, a water slide for the kids, and koi fish ponds throughout the grounds. However, it has so much to offer. It sits right on the beach for easy access. There is also a cove for standing water paddling and other activities. (Side note: I have also heard recently some great reviews of the New Otani Kaimana Beach Hotel, which is located near Diamond Head).
Next door to the Hilton Hawaiian Village is the Hale Koa hotel, which only allows military personnel to stay there. If your back is to the ocean, the Ilikai is on the left (that's where Jack Lord was seen in the opening credits of the original Hawaii Five-O on the penthouse balcony). The Hale Koa is to the right of the Hilton. The Hale Koa has a snack bar called Happy's (behind the outdoor bar) that is open to everyone (not just military personnel). Everything there is very affordable. You can get a burger for a few bucks, for example. Perhaps you might want to get a quick lunch or shave ice here?
Another good beach lunch option: Steak Shack. It's a little beachfront shack – literally – and food is packaged "to go," but their steak and salad combo has to be among the cheapest (and tastiest) Hawaiian deals going. It's not going to force Outback out of business, but it's cheap eats, and it gets almost five stars on Yelp.
One of my favorite places to dine on Oahu is Duke's Waikiki. People who go there never regret it. The first thing I tell people to do upon arrival in Honolulu is call and make a reservation for dinner at Duke's in Waikiki. If you are unable to get a reservation, I have an insider's tip that I stumbled upon accidentally: make sure to go to the hostess stand at 3:55pm and ask to be put on the other waitlist (they have two). They'll give you a pager and time to return. Don't eat in the bar (the menu is limited). You want to be seated in the restaurant at a table. The full menu is terrific, and all meals come with a delicious salad bar. Duke's is a must-do dining experience to cap off the week.
Things to do in Honolulu
Honolulu has a lot of historical landmarks that are worth seeing. A tour of the Iolani Palace is always an excellent place to start. This is the only royal palace in the United States. It was also the setting for Steve McGarrett's office in the original Hawaii Five-O. The tour is nice as docents give you the history of the palace and the royals who lived there.
Across the street from the Iolani Palace is the Kamehameha statue. It is a good picture spot. You will see that people adorn the figure with fresh flower leis. Chinatown is another favorite tourist spot. There are lots of little shops, bars, and restaurants.
The Punchbowl Crater offers impressive views of the city (and of Diamond Head). Get there by car by taking a curvy road up to the National Memorial Cemetery of the Pacific. You can snap a photo of the famous "Lady Columbia" statue there. She is said to represent all grieving mothers.
Another beautiful drive is to Diamond Head State Monument (Monsarrat and 18th Ave.). A fun morning would be to take a hike up Diamond Head for incredible views of Waikiki. It is a moderate but steep hike up (there are steps), and you will be so glad you did it when you make it to the top.
Waikiki has a lot of luxury shopping that might be out of most people's budgets. International Marketplace has become a fancy, high-end mall. All over Waikiki is the Honolulu Cookie Company, and they offer free samples.
Another cool photo spot is the Duke Kahanamoku Statue (he was the father of surfing), and it is located on Waikiki Beach.
Make your way to the Hilton Hawaiian Village's beachfront by 7pm for a free fireworks show every Friday night!
I am a big fan of Kona Brewing Company's beers (Big Wave is my personal favorite, followed by Longboard). Their brewery on Oahu serves excellent food, and all of their tasty beers are on tap. You can buy a growler and take it back to your hotel, but alcohol is not allowed on the beaches.
Attending a luau is a bit touristy, but I still recommend everyone go to one. I recommend Paradise Cove's luau, though I have also done Germaine's. There is a bit of a debate about which one is better. If you have kids, I think Paradise Cove is best because they have other activities to keep them occupied before dinner and the show. If you arranged for a bus pick-up, make sure you get to the pick-up location. If you are driving there, be sure to budget about 90 minutes to two hours to get there. Paradise Cove is only an hour away from Waikiki, but traffic can be pretty thick at that hour. There's no rush hour in Honolulu because no one is rushing! Doors open at 5pm and there's plenty for the kids to do (lei making, arts & craft demos, and canoes at the beach) before the actual luau and dinner. The entertainment is outstanding.
Elsewhere on Oahu
Hawaii's North Shore offers terrific views of the tide and waves and is a world-class surfing spot. You can drive up to Turtle Beach on the North Shore. Park your cars and explore (don't leave belongings visible in your vehicles; some people suggest leaving the windows down and the doors unlocked to avoid break-ins). Walk across the street to the beach and check out the big turtles on the beach. Matsumoto Shave Ice on the North Shore is the most famous ice spot, and you can even get ice cream at the bottom of your shave ice. Next door is a shack that serves acai bowls. If you haven't tried an acai bowl, I highly recommend it. It's a Brazilian treat, but Hawaii really popularized it, and they're everywhere. It's pureed acai (a superfood) topped with granola, fruit, and honey.
On the way there, check out the Nuuanu Pali Lookout. It is very windy but offers a great view of the Windward Coast.
Another short drive from Honolulu takes you to the Byodo-In Temple. It's tucked away in the back of a cemetery, but it is beautiful, and the kids can ring the big bell outside the temple. You will have to remove your shoes to go inside and see the big Buddha. The kids can purchase fish food bags for $1 to feed the big orange koi fish in the waters surrounding the temple.
Another option is a visit to the Dole Plantation. There's a visitor center, a train tour around a pineapple field, and a cafeteria in the back of the shopping area where they serve Dole Whips! These are served at Disneyland and the Dole Plantation.
My father is a Vietnam veteran, so it meant a lot to us to visit Pearl Harbor with him. I suggest pre-booking your ticket in advance. For a minimal fee, you can book your time and voucher for the boat excursion to the Pearl Harbor exhibit. This means you avoid a long queue to get that ticket onsite. Pearl Harbor is a meaningful monument (there's also a Navy Sub there you can explore), and there is a well-produced introductory video shown on a widescreen in a theater before you set out by boat to the USS Arizona Memorial.
While I have never done it, I hear the Aloha Stadium Swap Meet is a good way to get low-priced souvenirs. The open-air market is open Wednesdays, Saturdays, and Sundays.
So that's Honolulu. Now you want to fly to Maui, also known as the "Valley Isle." There are two airports on Maui, and you can book inter-island hops through Hawaiian Airlines. The flight between Honolulu and Maui is short. You will need to rent a car on Maui to get the most out of your trip.
I recommend staying in Kaanapali, and the Kaanapali Beach Hotel is charming. I have also stayed several times at Kahana Village, a beachfront condo community north of Kaanapali. Kahana is very quiet and only a short drive away from Lahaina, where a lot of the action is on Maui. Many of the condos here have a direct ocean view.
Lahaina is an old fishing village. It even maintains that charming look and feel. There are a lot of great shops and restaurants, including Fleetwood's on Front Street, a restaurant and bar owned by rock and roll icon Mick Fleetwood.
If you're into magic or sleight-of-hand and comedy shows, my family and I have enjoyed several shows at Warren & Annabelle's. It is a very fun show. I recommend booking in advance as the slots book up quickly. I have only visited when the owner, Warren Gibson, is performing. The website offers a schedule to see who's performing when you're there.
Road to Hana
The "Road to Hana" is one of the most scenic and picturesque road trips you'll ever take. It's a very curvy, 64.4-mile, slow-moving drive where you can see so much beauty – waterfalls, rocky beaches with black lava, sights, and much more. Budget a day to do the drive and slowly take in the sights, do a hike, or what not. There are apps you can download to your iPhone that offer narration through your stereo via Bluetooth, and that makes doing a self-guided tour easy to accomplish. By the way, be sure not to take home any black rock or lava souvenirs. People who do have found themselves cursed by Pele, and there are countless stories of rocks being shipped back to Hawaii with no return address!
One spot that is neat to see is the Hana Lava Tube, which is a massive cave with stalagmites. Apparently, there are no bats in this cave. There are self-guided tours daily, and there is even a botanical garden maze for those who do not want to traverse the lava tube.
While on the Road to Hana, stop at a roadside stand and try the homemade banana bread (you will see tons of signs for places that sell banana bread). The best ones sell it warm out of the oven, and I recommend two spots: Aunt Sandy's, which has been serving banana bread for more than 30 years, and the other is Halfway to Hana. During a recent visit to Maui, my dad and I stood in a long line for about a half hour waiting to buy banana bread, and sadly, they sold their last loaf of bread to the couple in front of us!
After your road trip, it's a good idea to stop in Paia for dinner. A family friend's daughter works at Flatbread Company, a very good local pizza place (but like most Maui spots, a tad expensive). There are other smaller, mom-and-pop shops here that are worth trying out, but they tend to fill up fast.
West Maui Coastline Tour
A drive that may rival the Road to Hana in white-knuckle riding is the West Maui Coastline loop. Some parts of the road are only one lane and it can be unnerving with cars coming around the corner. Careful, slow driving is a must, but the scenery is the payoff. Plan at least 5-6 hours if you're going to stop and check out some of the waterfalls and other scenic spots.
For another excursion, consider taking a day trip to Wailea and hanging out on the beautiful beach in front of the Four Seasons Hotel. Many of the best beaches on the island are here. It is a good idea to take a walk along the path by the beach to the beautiful Grand Wailea Maui luxury hotel. It features amazing pools and is a nice stop to people watch or take in some fresh ocean air. It is very expensive to stay there, but they may offer specials from time to time. If you want to get a preview of Wailea from your work or home computer, as you count down the days until your trip, the Grand Wailea offers a webcam where you can get a live look from the resort. During our most recent visit, we went to the Te Au Moana luau at the Wailea Beach Marriott. This may well have been our favorite luau of all time. It features dancers in front of a beautiful ocean backdrop.
Haleakala National Park
It's worth getting up super early one morning and driving to Haleakala National Park to check out a fantastic sunrise from high atop Maui. If you decide to go, make sure you dress warmly or in layers. It is a bit cold at the summit of Haleakala. It is also a popular time to go, so make sure you leave super early and arrive well ahead of sunrise.
My brother-in-law, sister, and I did a bike tour with Maui Easy Riders. We had a fun time going all down-hill in a group starting at the National Park entrance. There are several tours offered, but it wasn't a strenuous bicycle journey. We traveled single-file and stopped for breaks every so often.
Elsewhere on Maui
If you're into horseback riding, I recommend the Ironwood Ranch in Napili, just north of Kahana. We had a very scenic two-hour ride, which took us along a hillside where we had sweeping ocean views. I rode a horse named Lady Gaga. The guides are really well-informed, and they take you through pineapple fields, lush valleys, and other scenic spots.
My dad and I did a Blue Hawaiian helicopter tour over Maui and saw waterfalls, the beautiful coastline, and other scenery. It was worth it. We bought a DVD recording of the actual trip we took to show the others what they missed. It's a great way to see sights you can't get to by foot.
Maui has a Duke's restaurant, which has a beautiful oceanside location that is a bit removed from the main drag. If you're going to be in Oahu and Maui, I always recommend the Oahu one because it is the only one with a nice salad bar.
Fans of fish tacos need to take a drive to Kihei and try Coconut's Fish Cafe. Their fish tacos are unlike anything I have tried elsewhere. Fortunately, they opened a couple locations in Arizona, where my parents live. Kihei doesn't have a whole lot to do, but you can visit another beach, and the drive from Lahaina is pretty. A few other good restaurant options: Hula Grill in Ka'anapali also has excellent fish tacos, while Lahaina Fish Company serves up ono ("delicious" in Hawaiian) seafood in a delightful oceanfront setting. Try to book during sunset, if possible. If you're in the mood for Mexican food, another oceanfront restaurant is Frida's Beach House. Monkeypod Kitchen is a relatively new, trendy restaurant and bar with two locations on Maui. Their mai tai is said to be one of the best on the island and features a house-made liliko‘i (passionfruit) syrup. And I can't forget a popular breakfast spot: Slappy Cakes. Pro tip: try to be there by 7:30 a.m. to avoid a long wait and be sure to request a "griddle table." You can make your own pancakes with the toppings of your choice right at your table!
Snorkeling is always a fun activity on Hawaii, and Molokini is a crescent-shaped islet and snorkeling site. Several tour companies offer packages there.
Finally, if you didn't do this already in Wailea, grab your Hawaiian shirt and celebrate your trip in style. Nothing screams Hawaii like an evening luau. The Old Lahaina Luau is considered one of the best in Hawaii and is a great option for travelers staying on the west side. Old Lahaina has really good food and entertainment and a nice overall vibe. It is also an easy drive and parking is no problem. It sure beats taking a bus and sitting in congested Honolulu traffic for an hour.
The Big Island Tips
Hawaii Island, aka the Big Island, has a very different feel from the other islands. Given its size, you will notice how wide and open it feels. With active volcanoes, you will see plenty of black rocks throughout the island. (Remember, don't ever take lava rocks home with you; legend has it that Pele would put a curse on anyone who takes rocks home with them.) Also, interestingly, real estate is much cheaper on the Big Island than the other major Hawaiian Islands (probably, in part, due to being relatively close to active volcanoes).
Kona and Hilo
The two major towns are Kona (on the west) and Hilo (on the east) and you can fly into either location from Honolulu or the mainland. Kona has a lot of bars and shopping and feels in places like a giant tourist trap.
One great place to eat in Kailua-Kona is the Kona Brewing Company brew pub. There you can sample a lot of great beers (Big Wave is a personal favorite) and enjoy some great eats. They also have a gift shop with some great logo apparel and other souvenirs for beer lovers. Interesting fun fact: the Kona beers you drink in Hawaii are brewed in Kona, while the ones you drink on the mainland are brewed in Oregon, Washington, New Hampshire and Tennessee.
Kona is also known the world over for its delicious premium coffee. The soil and climate on the Big Island produce a very special coffee bean, which is grown in a limited supply. As such, it's a rare type of coffee and priced high. Be sure to drink 100% Kona coffee to drink the real thing; a "Kona blend" only has about 10% of Kona coffee mixed in with other cheaper grinds. Greenwell Farms offers tours of its farms and samples of its delicious coffees.
Hawaii Volcanoes National Park
Another interesting place to visit is Hawaii Volcanoes National Park. There are two activate volcanoes there, Mauna Loa and Kilauea, and both have recently been in the news with fresh eruptions. An eruption in 2018 caused widespread damage to homes and roads, and CNN broadcast live from the scene for weeks. Sometimes you will see steam vents shooting hot water vapor from the ground.
Captain Cook & Hawaii Beaches
A fun place to visit is the Captain Cook Monument, which was erected in 1874 in Kealakekua Bay to mark the area where Cook died.
If you're into the beach scene, Hawaii Island is not the most ideal spot for you. I think its beaches are not as nice, and some of them are black sand beaches.
One Place to Stay
If you're looking for an amazing resort experience, the Westin Hapuna Beach Resort is extraordinary. It is so vast it has a monorail train system to shuttle people throughout the property. The pools are magnificent, and it's located right on the beach. There was a luau on the property, which was pretty good - but like most luaus, a bit over priced for the quality of the food. One of the amazing activities here is to be able to swim with dolphins. It's expensive, probably a bit controversial, too. But it was something my nieces really enjoyed. The Westin is located in Waimea, and it's a very nice area to stay. There is a nearby shopping area that has some restaurants and bars, too.
Another great place to eat nearby is Lava Lava Beach Club, which has a gorgeous beachfront restaurant location with games and a fun (albeit slightly pricey) menu. We ate here on our last night, and it was a beautiful way to wrap up a lovely week on the Big Island.
Kauai, otherwise known as "The Garden Isle," is absolutely gorgeous and probably my favorite island besides Oahu. It is very lush and beautiful. Parts of Kauai are considered some of the wettest spots on earth.
One magical thing about Kauai: ignore the weather apps. It may lightly sprinkle or it may downpour for a bit. But in my experience, for the most part, your plans won't necessarily be ruined. Just be prepared to get a little wet here and there.
If you fly in from the mainland or from Honolulu, you will fly into Lihue. It is an easy airport to get in and out of and is well laid out. Note: if you book a Turo rental car, you'll need to take a free shuttle to an offsite parking area to pick up your car. Car rentals (either with an agency or Turo) are absolutely a must-do if you're staying on the island a few days.
Kapa'a is a great area to stay that is not too far from the airport and has some nice beachfront condo rentals. Like Hawaii Island, there is a Lava Lava Beach Club location in Kapa'a that offers great brews and food right in an oceanfront setting.
An absolute must-do on Kauai is a driving visit to Waimea Canyon, the "Grand Canyon of the Pacific." Photos just do not do it justice. I personally recommend a self-driving tour using the Shaka app (which I also recommended for the Road to Hana). The GPS tour offers a fun audio commentary that tells you spots to pull over for some great photos of the canyon and the Napali Coast (there are some great trails that you can take to snap some great photos from lookouts). There are also Napali Coast Sunset boat tours, helicopter tours and other boat adventures, but be prepared to shell out some big bucks for those. Still, the memories will last you a lifetime.
Train Ride and Safari Tour
Another popular tour, the Kilohana Plantation House in nearby Lihue, gives you a chance to ride a train through a farming plantation and have lunch at the Plantation House by Gaylords. There is also a Koloa rum safari tour where you can sample various flavors of the popular Hawaiian rum.
A one-and-done type tourist tour is of the Fern Grotto, which involves a boat ride to a lava rock grotto on the Wailua River. The grotto features ferns along the roof, and it is a sacred Native Hawaiian area. The boat ride features some Hawaiian singing and dancing and is not very expensive to do. The entire trip lasts about 2 hours.
Something fun for the whole family would be a trip to the Kauai Miniature Golf and Botanical Garden. It is a very beautiful putt putt course that teaches you about Hawaii's history and culture as you play. And I'll add - the course is quite challenging (but really fun!).
Princeville on the North Shore offers some great restaurants and beaches. Nearby, Hanalei Beach Park is probably the best beach on the island.
If you know me, a visit to Hawaii would not be proper without a trip to Duke's, and the Kauai location is a really nice one. Like the Waikiki location, it features a salad bar with the main meal (though now they're starting to uncharge it rather than include it with the entree). I highly recommend the macadamia nut crusted mahi mahi. Pro tip: book well in advance using the Open Table app. Reservations fill up quickly.
Wishing you a happy Hawaiian holiday! Aloha!