2 Week Hawaii Itinerary - Oahu, Maui, & the Big Island

Written By Romie Robertson

A view of Waikiki from the top of Diamond Head crater.

Rugged mountains, volcanoes, fresh fruit, beaches with the perfect surf. Hawaii is truly paradise on Earth. Abraham and I recently completed a two week trip where we island hopped and visited Oahu, Maui, and the Big Island. Want to plan for your 2022 trip to Hawaii? Read on to see everything that’s possible, even during the Covid-19 pandemic!

Oahu

DAY 1: Arrival Day

  • Land at Daniel K. Inouye International Airport. Show Safe Travels Hawaii QR code to airport personnel and get wristband.

  • Take bus to Waikiki (Bus #20 or #41). Rideshares, taxis, and shuttles are also available. Check into Airbnb/hotel.

  • Walk around Waikiki and eat.

Note: We landed at 5:30 pm, so it was already pretty late for our first day. Since we live in the Eastern time zone, we were exhausted early and just went to bed after grabbing food.

Abraham at the top of Diamond Head Crater.

DAY 2: Waikiki, Diamond Head, & Surf Lesson

  • 8:30 am: Wake up and get dressed. Grab smoothie or bagel for breakfast.

  • 10 am: Head to Diamond Head and hike to the top.

  • Noon: Return to Waikiki and grab lunch (Oahu Mexican Grill is right on the main Kalakaua Ave and has affordable, yummy options [including vegan]).

  • 2 pm: Stop back at Airbnb/Hotel to rest and change into swimsuit (if your accommodation is far from Waikiki, you can skip this).

  • 3 pm: Relax at Waikiki Beach.

  • 4:30 pm: Surf Lesson (click here for the experience we booked).

  • 6:30 pm: Head to accommodation to shower and change for dinner (or just grab food straightaway). Barefoot Beach Cafe is a lovely outdoor restaurant on the beach and is super affordable and has a separate vegan menu!

Romie and Abraham at the summit of Haleakalā.

Romie at the summit of Haleakalā.

Maui

DAY 3: Fly to Maui and Catch Haleakalā Sunset

  • Mid-morning: Fly to Kahului Airport (the main airport in Maui).

  • 1 pm: Arrive in Kahului and pick up car rental.

  • 2 pm: Grab lunch at the food truck park by the airport (adjacent to the Costco).

  • 3 pm: Check into Airbnb and settle in (we stayed in the town of Paia).

  • 3:45 pm: Start drive to Haleakalā National Park ($30 USD per vehicle - valid for 3 days)

    • The time you depart depends on where you’re staying on the island. Factor in travel time in advance so you arrive on time for the sunset. A google map search will tell you how long the ride is.

  • 5 pm: Arrive at park and enjoy the sunset.

  • 7 pm: Dinner (in your respective town of accommodation).

DAY 4: Road to Hana Pt. I

Note: We decided to split the Road to Hana into two days instead of one day, which is what most visitors do. This turned out to be a great idea because it allowed us to start the day later and get more time at each stop (and visit even more stops) than what most people are afforded. If you are able to secure accommodation in Hana (which is scarce), then I highly recommend staying one night in Hana. For Day 4 and Day 5, I will list the stops we made. The timing is your discretion.

  • Ho’okipa Lookout Point

  • Twin Falls (we actually didn’t get to visit because the parking lot was full, but this is a popular stop)

  • Huelo Lookout and Fruit Stand

  • Lava Cave

  • Wai’anapanapa State Park & Honokalani Black Sand Beach (reservations are required)

  • Arrive in Hana and grab food from the food truck park

  • Check into accommodation and relax in the sleepy town of Hana

Ho’okipa Lookout Point in Paia, Maui.

Romie at the Wai’Anapanapa black sand beach.

Romie at the Wai’Anapanapa black sand beach.

DAY 5: Road to Hana Pt. II

  • Pipiwai Trail Hike (back at Haleakala National Park, so you can re-use your previous ticket)

  • Seven Sacred Pools (also at Haleakala National Park)

  • Any other stops that you didn’t get to see the day before

  • Drive back to your accommodation

“Pro Tip: Purchase the $15 USD Road to Hana guide on the Shaka Guide App. It’s worth every penny!”

DAY 6: Snorkel with Turtles and Luau

  • 9 am: Head to Honokeana Bay to snorkel with turtles

  • 12 pm: Lunch in Lahaina

  • 1 pm: Drive back to accommodation to shower and change

  • 4:30 pm: Luau (click here for the one we booked…it was the most affordable one on the island and family-owned)

Snorkeling with sea turtles at Honokeana Bay.

Garden of Eden Botanical Garden in Maui.

Pīpīwai Trail at Haleakala National Park.

Big Island

DAY 7: Relaxation Day

Note: This day was Abraham’s birthday. I planned it as a mini “stay-cation” in a really nice cottage that I booked for the day. For your own planning, you can also use Day 7 as a “rest day” of sorts. We stayed in a cottage in the town of Volcano, which is where I recommend booking a stay for this part of the trip. It’s really close to the entrance of Hawai’i Volcanoes National Park, which is where you’ll visit the next day).

  • Mid morning: Depart from Kahului Airport.

  • Mid Morning: Arrive at Kona Airport on the Big Island. Get car rental (we opted for a jeep because we needed 4-wheel drive for one of the activities)

  • Noon: Drive to the town of Volcano, HI (you can stop in the city of Hilo for greater variety of food options)

  • 3 pm: Check into hotel and relax rest of day. It’s been a busy week!

DAY 8: Hawai’i Volcanoes National Park

  • 11 am: Check out of hotel and grab lunch (the time you depart your accommodation depends on how far you are from the park)

  • Noon: Arrive at Hawai’i Volcanoes National Park ($30 USD per vehicle - valid for 7 days)

    • Stop by Visitor Center to use restroom and get park maps (there is also a park ranger who gives out helpful and interesting information)

    • Optional: Rent bike to ride along trails (we ended up just walking the trails to save money)

    • Go through lava tubes

    • Visit the crater and get a glimpse of the lava from the 2018 eruption

  • Optional: Stay to watch the stars and see the lava glow at night (we ended up driving to Hilo while it was still light outside)

  • Drive to Hilo and check into your accommodation.

Fresh fruit at the Hilo Farmers Market.

DAY 9: Hilo Day

  • 9 am: Check out of accommodation. Visit Rainbow falls and the Wailuku River State Park

  • 10:30 am Breakfast at Ken’s House of Pancakes

  • 11:30 am: Head to downtown Hilo (park at 301 Kamamehama Ave at the parking lot)

  • 11:45 am: Walk the shops along Downtown Hilo and explore what they have to offer (there are a lot of pretty cool ones!)

  • 1 pm: Visit the Hilo Farmers Market.

  • 2 pm: A few options:

    • (If sunny) Coconut Island to enjoy the beaches and gardens

    • [If raining - and Hilo is known for its rain] Lyman Museum and Mission House (excellent for history buffs) or ‘Imiloa Astronomy Center (for the more scientific kind)

      • We visited the Lyman Museum and Mission House and absolutely loved it!

  • 4 pm: Grab an early dinner in Hilo

  • 5 pm: Drive up to Waipio Valley to check into Airbnb

DAY 10: Waipi’o Valley

  • Grab breakfast in the town of Honoka’a

    • There’s a Drive-In in Honoka’a that opens at 10 am that has a ton of affordable food. For my vegans and tea-lovers, you have to stop at The Cardinal Herbs shop for you breakfast.

    • Even if you don’t get hungry in the morning (like myself), still get food to go because there’s no places to get food in Waipi’o Valley.

  • Drive to Waipi’o Valley

    • You will need 4-wheel drive if you plan on driving down the valley. If you don’t have a vehicle with it, there’s a small lot for parking at the top of the valley and you’re able to hike down (but just know that it will be a steep hike up).

    • Relax at the beach.

    • Walk into the community and see the wild horses and the epic waterfall!

  • Drive back up before dark and drive to Kona.

A surfer at the beach in Waipi’o Valley.

Hi’iliwale Falls in Waipi’o Valley.

The reddish black sand beach at Waipi’o Valley.

DAY 11: Kailua-Kona Day

Note: This day can also be used for some rest. This was more of a laid-back day for us, especially since we flew back to Honolulu in the late afternoon.

  • Late morning: Check out of accommodation.

  • Explore/beach/snorkel in Kailua-Kona for first half of day.

    • We snorkeled at

    • Captain Cook (which is farther away from Kona) is also wildly popular for snorkeling and diving.

  • 3 pm: Arrive at airport. Drop off rental.

  • 5 pm: Flight to Honolulu.

  • 6 pm: Land at airport and head to accommodation.

Oahu

DAY 12: Pearl Harbor and China Town

  • 9:00 am: Head to Pearl Harbor

    • Visitor Center

    • Choice of Museums (they’re ticketed separately or you can purchase a combo pack ticket)

      • USS Missouri Battleship

      • Aviation Museum

      • USS Bowfin Submarine

    • USS Arizona Memorial — MUST do (reservations are required)

    • Grab Lunch on the grounds

  • 4:15 pm: Head home to change and rest

  • 6:45 pm: Walk around China Town

  • 7:30 pm: Dinner reservations at The Pig and the Lady

DAY 13 : Dole Plantation

  • 10 am: Grab breakfast/smoothies/juice

  • 10:30 am: head to Dole Plantation

  • 11:30 am: Arrive at Dole Plantation and explore (make sure to get some Dole Whip)

  • 1:30 pm: Get lunch nearby (or at the cafe at the Dole Plantation)

  • 2 pm: Head back to Honolulu and relax on Waikiki beach

    • Alternatively, head up to the North Shore and check out some world-class surfers do their thing

Abraham on the way up to the Haleakalā summit.

DAY 14 : Head Home

  • Check out of your Airbnb/Hotel

  • Catch bus/taxi/shuttle to Honolulu Airport

  • Board your flight, get cozy, and safe travels home!

What did you think of this itinerary? Would you be willing to take on 2 weeks island-hopping around Hawaii? Drop any questions or comments in the comments!

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Romie Robertson

Hi there, I’m Romie! I’m an avid traveler, educator, and lover of learning. I write blogs that have a focus on budget travel, culture, and history. When I’m not traveling, I enjoy spending time with my husband and dog, reading, cooking, and visiting museums. I also love Pad Thai, astrology, anime, and exploring my home of Atlanta.

Connect with me on my Instagram.

https://roamingwiththerobertsons.com
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