Ryan's Hawaiian Vacation Guide
Updated: May 26, 2019
Last Updated: May 2019
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 will update this post after my summer 2019 trip to Kona on the Big Island.
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 runs a Jeep touring business. 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 $16.50. 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 (and now the Sheraton Waikiki coffee shop by the circular driveway). I had Dole Whips at the Sheraton and the Dole Plantation and the latter was the most authentic and best-tasting (just like the Disney version).
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. 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 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.
Lahaina is an old fishing village. It even maintains that charming look and feel. There are a lot of great shops and restaurants (try to avoid chains such as Hard Rock Café, though).
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."
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). Also, rocker Gene Simmons' Rock & Brews chain is down the street, and it's an excellent spot to grab a beer or a bite to eat (the food is fantastic). There are other smaller, mom-and-pop shops here that are worth trying out, but they tend to fill up fast.
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.
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 near Lahaina. 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.
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, 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 on all of Hawaii (if you do only one between Oahu and Maui, this is the one to do). Having been to three different luaus, I like Old Lahaina best for food and entertainment and 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.
Wishing you a happy Hawaiian holiday! Aloha!