From volcanic summit to coral reef, you will not be disappointed by the incredible natural landscapes of Hawaii; nor the balmy tropical temperatures, fresh seafood and melodic sounds of ukuleles. Take some time to explore the islands of Oahu and Maui with this 10-day Hawaii itinerary.
Table of contents
When to visit Hawaii
There are 3 factors to consider when deciding when to visit Hawaii: climate, tourist season and experiences. Let’s tackle each of them briefly.
Climate
Hawai`i is tropical and therefore you can expect warm temperatures year-round with average summer daytime highs of 29°C (85°F) and winter 26°C (78°F) – so not a huge difference. Precipitation is the big differentiator between seasons.
May through September are relatively dry. October through February sees the highest rainfall. The wetter months also correlate with bigger surf if that is of interest to you. Check the average temperature and rainfall for your particular destination/s as they do vary by island.
Tourist season
Typically, peak tourism season runs from about mid-December through to the end of March and again in July-August. High season will mean crowds and higher prices so book early and expect to be in the company of many fellow travellers.
The low season usually starts in April and goes through to mid-June, then September to mid-December. Prices are more moderate and the crowds are thinner.
Experiences
Depending on what type of experience you are after, you may choose a particular time of year. For instance, surfers will find the biggest swells in October through April while February and March are whale watching season. Swimmers, snorkelers and divers may prefer the calmer months and higher ocean temperatures in July to September. Choose your bliss!
What do windward and leeward mean?
These terms come up a lot in Hawai`i because they are huge determinates of the kind of weather you should expect. As you probably know, the Hawaiian archipelago are volcanic islands and these variances in altitude create microclimates within islands.
This is largely due to clouds blowing in with the prevailing northeasterly trade winds and being trapped by the volcanoes. This means the north/east side of each island or “windward” side experiences more rainfall, while the south/westerly side or “leeward side” is much drier.
Getting to Hawaii
Honolulu International Airport (HNL) is not only the major airport for Oahu but also Hawaii in general. Domestic and international airlines have services to/from Oahu.
Maui’s main airport is Kahului Airport (OGG) although there is also the smaller Kapalua Airport (JHM) and Hana Airport (NHM).
How to get from one island to another
There are multiple 35-minute puddle-jumpers available each day to get between the major islands of Oahu, Maui, Hawaii(Big Island) and Kauai.
If you want to visit the smaller islands of Molokai and Lanai, ferries are available from the town of Lahaina on Maui.
Finally, cruise ships are an option if you want to see multiple islands and still unpack your suitcase. Cruises depart San Francisco, LA, San Diego and Honolulu.
Getting around Hawai`i
Since this is a Hawaii itinerary focused on Oahu and Maui itinerary, the below is advice for these 2 islands only:
Rental cars (and rental car alternatives)
This is a REALLY big deal right now with the rental car shortage. If you thought you’d just get a car for a few days, think again. Book early, I mean really early if this is the only option for you. Check availability and price for your dates before you lock in flights and accommodation if your trip is dependent on having a rental car. If you are happy to look at other options, here are a few alternatives.
Public transport
The only public transport available in Hawaii is by bus. Oahu and Maui both have bus systems that vary in regularity and island coverage. Check their websites linked above for further details.
Tours
If you can’t get a rental car and you don’t want to rely on the public bus, seek out a tour that includes hotel pick up and transport.
Peer-to-peer car sharing
On Oahu there are two car sharing apps that might help you nab a vehicle for the odd excursion here and there: Hui and Turo.
Bike sharing
Finally, Biki is a bike sharing program in place in Honolulu, Oahu if you need to go a short distance.
10-day Hawaii itinerary – Maui & Oahu
This is the itinerary that we researched and put together for our 10-days in Hawaii and first-ever visit. I have tweaked it a little based on our experience, making adjustments for places we needed more time and those we could have left off altogether.
Also note that we originally constructed this itinerary in reverse: Oahu first, then Maui. I hate to harp on about it, but the rental car shortage is a really big problem and we had to switch our itinerary again based on car availability. So, if you are stuck for transport, reversing the trip may just solve the problem for you.
Day 1 – Arrival on Oahu
This is purely an arrive and relax day. Check into your Waikiki accommodation. If you have an early flight, you might fit in an afternoon on the beach or some sightseeing.
I don’t recommend picking up your rental car until the first morning you plan to drive, as every additional night will cost an average of $30-50 for parking. We found the best value public parking garage was at the Waikiki Banyan Condominiums for $27 per 24-hour period (compared to $48 at our hotel), but it filled up early.
Spend the night in Waikiki. The Park Shore at the southern end of Waikiki strikes a good balance between comfort, service and price in this very expensive destination.
Day 2 – Honolulu and Waikiki, Oahu
This is the only full day in Honolulu and Waikiki on this Hawaii itinerary, so let’s dive right in. A walking tour is my favourite way to get oriented in a new city and learn some foundational history and culture to put the rest of the visit in context. There are various options for walking tours around Waikiki and Honolulu – below are some suggestions. We didn’t do them all, so make sure you look up reviews and judge for yourself.
Also, I recommend staying clear of Chinatown. While there are a few cool, historic things to see there, this part of town can be sketchy. Our greatest concern was our rental car, as there are a lot of car break-ins reported in this area. The handful of funky boutiques we visited, lock their doors and buzz in customers – which is a clear indication something is up.
AIA architectural walking tours – Guided tours are held on Saturdays, twice a month or you can purchase a self-guided tour booklet.
Historic Hawaii Foundation self-guided map and information can be downloaded here.
Native Hawaiian Hospitality Association (NaHHA) tours of Waikiki are also available here.
Shaka Guide offer a Historic Downtown Honolulu Audio Tour for $4.99 here.
Iolani Palace tours are available Wednesday through Saturday only.
Spend the night in Waikiki.
Day 3 – North Shore, Oahu
Get started early as today you’ll want to experience as much as you can of the famous North Shore of Oahu. We’re going to go straight up the middle of Oahu and look around the north coast, and spend tomorrow working our way down the beaches and sights of the east coast. It is possible to do a circuit in a day, but why rush and leave out any amazing sights and swims.
We’ll skip the over-crowded and Disney-ified Dole Plantation (they don’t grow any pineapples at commercial scale there anymore) and go straight out to the northwest corner of the Oahu. Here we’ll take a 5.6km (3.5mi) hike on the Ka’ena Point Trail. The Trail follows an old railroad bed and dirt road to a remote stretch of coastline and some of the last remaining sand dunes on the Island. In winter, whales are frequently spotted off the Point. I was really looking forward to this hike—the views look extraordinary—but they had closed off the area to film the reboot of Magnum P.I. the day we were there.
After the hike, mosey on east to the town of Haleiwa. Replenish with a shave ice from Matsumoto’s—a local institution since 1951. Haleiwa is also a great place to pick up lunch, as there isn’t a whole of food outlets along the northern beaches.
Explore Laniakea, Waimea, Banzai Pipeline and Ehikai Beaches as you move along the North Shore. For views of Waimea Beach, pop up to the Pu’u o Mahuka Heiau State Historic Site, a hilltop archaeological site dating back to the 17th century.
The Polynesian Cultural Center is a good place to experience a Luau if you were looking for dinner and some nighttime entertainment. Make sure you book well, well, well ahead.
If you prefer to skip the Luau, grab takeout at Ted’s Bakery and head down to Sunset Beach for a sunset picnic.
Spend the night on the North Shore. There aren’t many accommodation options on the North Shore. We were more than comfortable at the Courtyard Marriott North Shore.
Day 4 – North Shore to Honolulu, Oahu
On day 4 of our Hawai’i itinerary, we’ll work out way back to Honolulu, taking in some of the most scenic spots on Oahu, starting with Kualoa Ranch. Ever seen a little flick called Jurassic Park? Does 50 First Dates sound familiar? Maybe Jumanji rings a bell? All of them were at least partially shot around the Ranch, a 4,000-acre nature retreat. Currently, the ranch is booking up 3-months in advance and we weren’t that organized, but it is on our list for a return visit.
Following Kualoa Ranch, continue south stopping at various beaches, lookouts and short trails. Here are a few we loved and would recommend:
- Mokolii (aka Chinaman’s Hat) views from Kualoa Regional Park.
- Ho`omaluhia Botanical Garden, especially the free Kaua Kukui lookout.
- Valley of the Temples Memorial Park has wonderful scenic vistas and architecture ranging from mid-century modern chapels to the Byodo-In Temple—the replica of a historic Buddhist temple in Japan. However, I don’t think the $5 per person admission for the Temple is worth it, especially if you’ve been to Japan. Take a drive around the Valley for free and skip Byodo-In.
- Kailua, Kahana Bay, Waimanalo and Makapu’u are our picks for best beaches along the east coast of Oahu. Lanikai looks great but there is absolutely no parking. It’s a residential area that goes right up to the beach and there is no street parking. You either have to Uber, cycle or walk from nearby Kailua. There are plenty of good beaches—you don’t have to hassle with this one.
Spend the night in Waikiki.
Day 5 – Koko Crater Railway and Hanauma Bay snorkelling, Oahu
You may have heard of or seen pictures of Oahu’s Stairway to Heaven (aka Ha`iku Ladder) trail—3,922 disused steel steps to a former US Navy communication facility that has become quite the adventure-tourist drawcard. Except, it isn’t actually legal. The steps are accessed through private property and you could earn a fine or succumb to a fed-up resident’s booby trap if you try to reach them. Not to mention the poor condition of the steps themselves. Don’t worry, I have an alternative for you—the Koko Crater Railway Trail.
Koko Crater Railway is a thigh-burning 1000+ “stairs” to panoramic views from the ridgeline of an extinct volcano. From the Koko Head District Park parking lot, follow the old railroad ties that once supplied WWII pillbox bunkers to the top. Though it is heavily trafficked, this trail is a legal alternative to Ha`iku Ladder and free compared with the parking and hiking fees of Diamond Head. Just note that this is not a groomed trail, it is an old railway line that is maintained ad-hoc by volunteers. You need steady footing, a sense of adventure with plenty of sun protection and water as there is no shade.
Once you have fully exhausted yourself on Koko Crater, we’re going to cool off in the waters of Hanauma Bay, a marine life conservation area. You must book a time slot to visit Hanauma Bay Nature Preserve (HBAY) and reservations only open 2-days in advance at 7am. They sell out fast too! Passes were gone in under 3-minutes and we missed out. When checking in on the day, you must present ID (original, not a copy) at the admission window.
Hanauma Bay is open 6:45am and the beach closes at 3:15pm (latest entry is 2:00pm). https://pros8.hnl.info/hanauma-bay
You can hire a snorkel, mask and flippers through the official onsite provider, Dive Oahu, online. They also offer wetsuits, life vests, and lockers for your valuables. See their rates and book your snorkelling gear here.
Following your float around Hanuama Bay, drive over to Halona Blowhole Lookout to see the Halona Blowhole and walk through a lava tube.
Travellers tip: Skip the loooooong queues at the original Leonard’s Bakery in Waikiki and get your dose of malasada goodness from the Leonard’s Bakery Truck at the Koko Marina Center while you are out at Koko Crater and Hanauma Bay.
Spend the night in Waikiki.
Day 6 – Pearl Harbor, Oahu and Transfer to Maui
Pearl Harbor needs no introduction. The Historic Site is open 7-days from 7am-5pm except for Thanksgiving, Christmas and New Years days. There is no fee for the Pearl Harbor Visitor Center, nor the two associated museums “Road to War” and “Attack Gallery” and exhibits along the Harbor. Though you can rent an audio guide if you prefer. Parking is also free.
There are three memorials: USS Arizona, USS Utah and USS Oklahoma.
The USS Arizona involves a short boat trip, which requires a timed ticket that can be bought up to 8-weeks in advance on the NPS website. On the day of your visit, you must check in an hour before your ticket time. This hour is a good amount of time to look at the exhibits prior to your boat trip to the Memorial. The boat trip itself is 45-minutes in duration including the return journey and about 15-minutes at the actual Memorial.
USS Oklahoma and USS Utah are both on Ford Island, however at this time visitors can only access the USS Oklahoma Memorial. This can be done using the shuttle bus from the Visitor Center.
Note, this is a solemn site of remembrance, please dress and behave respectfully. Furthermore, this is a current military site so you will need to clear security. For more information, see the National Parks Service Pearl Harbor website.
Continue from Pearl Harbor to the airport for your flight to Maui.
Spend the night in Paia, Maui.
Day 7 – Haleakala National Park, Maui
Adventure alert: Today we take a leisurely bike ride… down the side of a volcano!
Of course, this kind of thrill-seeking is not for everyone. You might prefer to do some hiking in Haleakala National Park instead. Meanwhile the adrenaline junkies will get set up with some bikes, ride a shuttle most of the way up Haleakala (biking from the summit is no longer allowed) and take 3-4 hours to ride back to Paia. Fitness is not much of a concern as you will do more braking than peddling, but you do need to be confident on 2-wheels and riding in traffic.
There are various stops you can make along the way including the town of Makawao that offers various lunch options and of course, malasadas from the historic Komodo Bakery.
After your morning ride down the Volcano, drive back up again in the afternoon to take in sunset. Now sunrise on top of Haleakala gets a really big plug but there’s a couple of reasons we chose to do sunset instead. First up, it didn’t involve us getting up at 3am. Secondly, sunrise has become so popular and crowded you now need a reservation and they were all booked up for the dates we were visiting, months in advance.
I can’t give you a comparison of sunrise and sunset experiences, but I think the photos of a Haleakala sunset speak for themselves.
Make sure you take plenty of warm clothes as the summit is much cooler and often very windy. We thought we went prepared and still froze our butts off.
Spend the night in Paia.
Day 8 – Road to Hana, Maui
We have mixed feelings about the Road to Hana. It’s not that the curvaceous, coast-hugging road with its beautiful waterfalls, lush canopy and ocean scenery aren’t wonderful. It’s more to do with the lack of infrastructure and services.
I recommend starting out as early in the day as possible and going completely self-sufficient food/beverage-wise. Stock up in Paia – Kuau Store is a great place to do that. Also, make sure you have a full gas tank if you are driving yourself.
Alternatively, consider taking a tour rather than driving . A local guide is going to take care of driving/parking challenges you’ll find along the way and get you passed some of the “local roadblocks” that can make this day trip unpleasant.
Here are some of our favourite spots along the Road to Hana (hint: the best stops are just beyond Hana):
Keanae Lookout
Wailua Valley State Wayside
Lookout on the right side of the road not far passed the Wailua Valley State Wayside (look for the concrete picnic tables)
Wailua Falls
Upper Waikani Falls (aka Three Bears Falls)
The Pools at `Ohe’o (within the Kīpahulu District of Haleakala National Park)
After completing the Road to Hana, drive to Lahaina for the evening.
Spend the night in Lahaina. We enjoyed our stay at the beautiful Pioneer Inn (managed by Best Western), a historic hotel in a great location.
Day 9 – Lahaina and Lanai snorkelling
We did a lot of research into our snorkelling trip to Lanai. We chose Lanai over Molokini because the snorkelling was reported to be much better around the Lanai coast even if Molokini looks unbelievable from above the water. Taking into account windy conditions that prevented our boat from getting right out to the best Lanai spot, we still felt the snorkelling was so-so. It was fine but when compared with our experiences in the Galapagos Islands, Belize, Fiji and the Maldives, it didn’t quite measure up. We wouldn’t have minded if we didn’t pay so much to take the excursion.
After having done the trip, talking to locals and some more reading, here’s what we would recommend in stead for your 10-day Hawai’i itinerary:
- Experienced and confident snorkelers, save some money and hit the best off-beach spots in Maui. Rent or BYO your snorkelling gear and explore the waters of Honolua Bay and Mala Historic Wharf to name a couple of spots.
- Beginners or infrequent snorkelers should absolutely jump on a tour. Safety and expert knowledge of the water is worth paying for. Plus, the boat trip on its own can be quite enjoyable. One of our guides was actually a marine biologist which was a very nice bonus for our group. Just make sure you only book a morning tour. The wind picks up in the afternoon, which is often why later tours are discounted. Again, pay the extra and go in the morning.
Spend the night in Lahaina.
Day 10 – Departure
Make your way back to the airport for your departing flight. Remember when booking your flight time that you will lose at 2-hrs or more in time difference getting back to the mainland US, depending on your final destination.
Eat, drink & be merry
Obviously, the pandemic has affected lots of hospitality businesses and many are still short-staffed. Be prepared to book well in advance for restaurants and wait in long lines for take-out. Here are some of the places where we ate, drank and loved throughout our 10-day Hawai’i itinerary.
Oahu
- Basalt – Mid-range restaurant and bar for dinner in Waikiki. Good value prix fixe.
- Hideout – Trendy bar and restaurant in Waikiki with good cocktails and food. Book for happy hour to get the best value.
- Matusumoto Shave Ice – Historic shave ice spot in Haleiwa.
- Ted’s Bakery – Claim to have made the first chocolate haupia (cream pie). Their crab and bacon sandwhich is pretty darn delicious too. Terrific North Shore eatery.
- Kalapawai Market – Cool coffee and lunch spot.
- The Beet Box Cafe – Vegetarian lunch spot with awesome acai bowls, huge salads and killer sandwiches in Kailua.
- Chadlou’s Coffee – Stellar coffee, located right across from Beet Box Cafe.
- Tucker & Bevvy – Fresh picnic foods in Waikiki such as acai bowls, smoothies, avo toast and salads. Food is good but not the best value for money in terms of portion size.
- Paia Fish Market – Waikiki branch of Maui fish and chips institution.
- Kai Coffee – Best Hawaiian coffee chain we tried with terrific coffee and consistently outstanding staff across different locations. #aussiecoffeesnob tick of approval!
Maui
- Paia Bay Coffee Bar – Great coffee and breakfasts.
- Paia Fish Market – Fish and chips.
- Kuau Store – Good coffee with fresh sandwiches and salads. Great place to stock up on picnic food before the Road to Hana.
- Lahaina Sushi Ko – Best lobster sushi roll ever!
Hawaii itinerary map
Grab your copy of this map to use and customise by clicking on the top righthand corner.
I hope this 10-day Hawai’i itinerary helps you get the best out of your time on the islands of Oahu and Maui. Want more Hawaii inspiration and information, see these posts:
15 Cool Things to do on Oahu, Hawaii
What to Pack for Hawaii | A Vacation-Ready Hawaii Packing List
Peace, love & inspiring travel,
Madam ZoZo
