The Best Hawaii Itinerary

If you’ve been following along on Instagram, you might have seen that some of our very best friends were in town visiting for the holiday. They had never been to the Hawaiian Islands before, so when they were planning their visit, it was kind of like a blank slate. They knew they wanted to see multiple islands and over the course of two weeks, we managed to check off quite a few things! In an effort to help others plan a trip, I’m sharing our best Hawaii itinerary that includes three islands over two weeks!

Best Hawaii Itinerary

Our friends flew into Honolulu and we met them at the airport with a lei, which is such a fun way to greet someone who has just flown many, many hours to the islands 🙂 The following itinerary includes exactly what we did, which included ample exploration time, as well as rest time. Let me know if you have any questions!

Hawaii Vacation Itinerary – 2 Weeks

Day 1 – Our friends flew into Honolulu and we met them at the airport with a lei, which is such a fun way to greet someone who has just flown many, many hours to the islands 🙂 We helped them with their suitcases and took them back to our house where we had food waiting. If you’re staying in a hotel, make a reservation to get food at Duke’s in Waikiki (about 10 days in advance) on your first evening and try to stay up as long as possible to combat jet lag! 

Day 2 – We woke up early, because the guys had a golf reservation at Turtle Bay’s Palmer Course. Seeing the sunrise on the North Shore was incredible and Casey and I enjoyed walking around Haleiwa Town and grabbing coffee at Island Vintage. We all at lunch at Aji Limo food truck (across from Shark’s Cove) and got a shave ice at Matsumoto’s. 

Day 3 – This was Christmas Eve for our guests, but that didn’t stop us from heading out to Kakaako to explore the colorful wall murals, stopping in at Honolulu Beerworks, and heading to Moku Kitchen for lunch. The second half of our day was spent preparing a delicious spread for a small party we hosted. If this was a normal vacation day, I would suggest heading into Honolulu and exploring Waikiki Beach!

Day 4 – This was Christmas Day and the weather was absolute junk — high wind and rain kept us inside most of the day. It’s not uncommon to experience rain in the islands, so don’t miss my full post on What To Do In Hawaii When It Rains!

Day 5 – We woke up early and hopped on a quick Hawaiian Airlines flight to the Big Island and flew into Kona, where we stayed at Sheraton Kona. We rented a car (crucial on the Big Island) and headed toward Green Sand Beach, South Point (southernmost point in the United States) and our favorite coffee farm — Ka’u Coffee Mill. We ate breakfast at Island Lava Java and lunch at Foster’s Kitchen. Honestly, the service was terrible at both and the food was just okay, but it didn’t stop our fun. 

Day 6 – We explored all of the Kona side of the island (previous trips included a stopover in Hilo which is a cute town!). We ate lunch at Merrimen’s, dinner at Island Lava Java and enjoyed dessert (Hula Pie) at On The Rock’s. The dessert was definitely a highlight since the weather took a turn and we had nothing but serious downpours. 

Day 7 – Kona was pretty rainy (spotty sun) so we laid low at the hotel and enjoyed the pool area before getting a flight back to Oahu. If the weather is nice, walk the beautiful beaches of the Big Island or visit Volcanoes National Park. The weather was really not in our favor during our trip! We took an afternoon flight back to Oahu (very short – around 35 minutes) and relaxed. 

Day 8 – The weather was finally cooperating! We started our morning hiking Kole Kole Pass, before heading up to the North Shore and enjoying some Dole Whip. We tried to squeeze in Waimea Falls, but the traffic to get up to Shark’s Cove area was INSANE. The big waves of winter attract thousands to Oahu’s North Shore, so keep that in mind 🙂 We opted for shrimp from our favorite truck right in Haleiwa Town. It’s a green truck inside the food truck roundup right across from McDonald’s. The coconut and garlic options are divine. That night, we booked the Paradise Cove Luau, because it’s in the very best location to see the sunset. The doors open at 4:30, so arrive to Ko’Olina early and swing into Monkeypod Kitchen. They have the best mai tai on the island!

Day 9 – Lots of hikes on the agenda today! We conquered Diamond Head Crater (arrive early for the best chance at parking!), enjoyed brunch at Koko Head Cafe and then headed out to Lanikai Pillboxes. 10/10 recommend doubling down on hiking to maximize time, especially if you encounter a rainy day or two. That evening, we strolled Waikiki, showing them the inside of the Royal Hawaiian hotel (be sure to go see the mini museum in the basement) and ate at Noi Thai at Royal Hawaiian Center. 

Day 10 – We woke early to drop the guys off for a tee time at Kaneohe Bay Golf Course (requires military affiliation) and I showed Casey all the adorable boutiques in Kailua. We also grabbed a coffee and avo toast at ChadLou’s (delicious!). After their round of golf, we drove the opposite way up to the North Shore so they could see the entire way around the island, passing Kualoa Ranch, Kahuku and La’ie before finally landing on Sunset Beach to watch more waves. We stopped near Kahuku for frozen yogurt then grabbed a coffee from Island Vintage (order their Island Latte, iced) before heading home. It happened to be New Year’s Eve, so we enjoyed dinner at home and watched the fireworks. 

Note: New Year’s Eve in Hawaii is insane – consider yourself warned! Fireworks start popping off as early as 2PM and carry on well into the night! 

Day 11 – We enjoyed a relaxing morning and watched a good bit of New Year’s Day football. By around 3PM, we headed out the door to enjoy some drinks and apps at Laylow in Waikiki before heading over to hike Makapuu Lighthouse Trail for sunset. It seemed like everyone had the same idea on Oahu, but the sunset was gorgeous and it was a great way to start 2020!

Day 12 – We woke up pretty early to catch a quick flight to Maui on Southwest. I definitely recommend Southwest for inter-island, because it’s cheaper and you can check bags for free! We checked into the Westin in Kaanapali, at lunch at Leilani’s and hopped on a Sea Maui Catamaran whale watching tour. It did NOT disappoint and I wouldn’t highly recommend spending a few extra bucks to go catamaran versus larger boat. 

Afterward, we hightailed it right to Monkeypod Kitchen (highly recommend a reservation) for happy hour before calling it a night. 

Day 13 – We woke up, ate breakfast at our hotel and headed straight for the Kapalua Coastal Trail. It was rainy, but we loved seeing the rugged coastline and tons of rainbows! After we drive off, we headed straight to Lahaina for lunch at Down The Hatch and shave ice at Ululani’s. We had tickets to see the PGA Tournament of Champions at Kapaulua’s Plantation Gold Course that afternoon, but other worthwhile stops in Maui include Iao Valley, Road to Hana, and the Pipiwai Trail. For dinner, we made reservations (A MUST) at The Millhouse and it did not disappoint! Owen Wilson happened to be dining a couple tables over from us 🙂

Day 14 – Early wake up to drive up to Haleakala in Maui to see the sunrise. It’s worth the drive, just make sure you have a reservation in advance! Drove back down, had breakfast in Paia at Cafe Mambo and walked around all the cute boutiques. Headed back to the airport, flew to Oahu (Southwest has cheap flights!), and got home around 5PM. Strolled around Ala Moana for a bit, which is the largest open-air shopping center in the world. 

Day 15 – Woke up at 5AM to snag will-call tickets to Pearl Harbor. Many times, this popular historical site sells out online, but all hope is not lost if you want to see it. There are a set amount of will-call tickets each morning, you just have to arrive very early. The early wake-up required a mid-morning re-charge, but after that we headed down into Waikiki to walk along the beach, grab acai bowls from Sunrise Shack, share a box of malasadas from Leonard’s and make a pit-stop at Costco for coffee and mac nuts for our guests to take home.

Dropping our friends off at the airport was…awful. We were all so sad for their epic Hawaii vacation to come to an end, but I felt confident that we had shown them a true taste of the islands as best as we could given the weather situation. There is so much to see and do across the Hawaiian Islands that you could live here for your entire life and not experience it all. Planning a trip to Hawaii? Don’t miss every post I’ve ever written about traveling to and around the Hawaiian Islands!