Hawaii is no doubt on most people’s bucket list. Warm sandy beaches, clear turquoise ocean waters, and breathtaking peachy sunsets insistently lure you into booking that ticket, but it’s low-key the pineapple juice that will keep you coming back for more! lol. I’m excited to share with you our exact itinerary for the trip so you can visit all the yummy foodie spots, the best beaches and lots of hidden gems!

Flights + Island Hopping

We visited Hawaii for 14 days and had enough time to island hop. (Oahu, Maui, and The Big Island) We flew into Honolulu with Delta (who I fly with exclusively) and then caught inter-island flights on Hawaiian Air. Depending on the time of year you chose to visit, the flight cost will vary. During low season, if you are flexible, you can find flights (from the east coast) for $400-500! On average with Delta I’d say they sit around $800 to fly into Honolulu. The flights we purchased on Hawaiian Air were very inexpensive. Under $40/each, Kevin and I combined paid $175 for 2 flights each, and the flight times were all under 45 minutes. We did have the additional costs for our bags once we checked in, so keep that in mind! ($30 checked each way)

I previously had heard of taking a ferry for inter-island travel as opposed to flying, but I did some research and found that it had been shut down! So the only way to get between islands as of this writing is by plane. I didn’t mind one bit because of how quick it was!

Getting Around

We chose to rent a car at the airport for each island we visited. I would always do this in advance so you can get the best rates and secure your preferred car type! We use Avis to rent while we travel, so we paid around $50 a day for a sedan and around $70/day for a Jeep (while we were in Maui). In Oahu there is definitely limited parking, so keep in mind you may have to pay to park in some areas. If you stay in Waikiki, I felt it was extremely walkable, but if you plan to explore other areas of the island you’ll want your own car. Either way, our hotel had a private parking garage with valet, so we could come and go as we pleased. We did have to pay a daily parking fee (in addition to our total rate for our hotel), which seemed to be pretty standard. In Maui and on the Big Island, there’s a lot more space and availability for parking, so it wasn’t an issue by any means.

The Itinerary:

*Budgeting for restaurants and food: $ great value, $$ delicious + the price reflects, $$$ on the pricier side.

*Everything was pre-mapped for efficiency while driving around the island. If you decide to go in the same order we did, you won’t have to do hardly any backtracking, as each place is on it’s way to the next!

Day 1

• Check into our hotel: Vive Hotel Waikiki. I absolutely loved the vibe here. There seemed to be a lot of people our age, everything was beautiful, bright and welcoming, and they offered such an impressive free breakfast. It was located in a great spot in Waikiki, so we were able to walk to a ton of places right out of our front doors!
• Dinner at Hawaii’s Favorite Kitchens ($)
• Tantalus Lookout for sunset. Amazing views of Honolulu, where you can also see the crater clearly. It’s a touristy spot, but there seemed to be a lot of kids hanging out too. Bring a snack or some wine and watch the sunset here!

Day 2

• Ho’omaluhia Botanical Garden. 400 acres of jaw dropping greenery. You might recognize those huge, iconic mountains on the way there! The entrance is also very well known for being grand and gorgeous, but due to so many tourists stopping traffic to take photos, they are EXTREMELY strict. We were turned away a long with a dozen other people before the park eve opened. Don’t be discouraged though! There’s a ton of places inside you can capture some beautiful memories! Here you can drive around, park and walk to explore, and even have lunch on the picnic tables.
• Lunch at Maui Mike’s Fire Roasted Chicken ($$)
• or try lunch at The Beet Box Cafe ($$ – vegan friendly!)
• After lunch, head to Makapu’u Lighthouse where you can find some secret tide pools. The lighthouse is a great lookout spot, but if you’re feeling adventurous you’ll want to hike down to the pools. WARNING: MAKE SURE YOU CHECK THE TIDE TIMES PRIOR! (Simply google “tide times”) We made sure to time this well, because you cannot get into the pools during high tide or any other time- it’s extremely dangerous and manyyyy people have been killed from wave surges that can drag you out to sea. Only go during low tide. Seriously. After parking, start on the paved road for the lighthouse trail and when you get to the whale watching sign, you will walk down from there. It is STEEP and can be dangerous! I wore tevas- I was slipping on the rocks a bit, but if you’re careful, its doable. Also look out for any white/pink marked rocks as they’re telling you which direction to walk. The walk back up was much quicker and less scary (if you’re afraid of heights!).
• Halona Beach Cove and Blowhole. (also known as Cockroach Cove, but I can guarantee we saw no bugs or I never would have gone LOL) This little gem is so freaking cool to me! There was a decent amount of people, but it’s a beautiful little cove tucked right off the road. We spent a few hours here catching some sun and watching the waves crash. Right nearby you can also see the Halona Blowhole!
• Dinner at Marukame Udon Waikiki ($)

Day 3

• On the way to Haleiwa Town, grab some fresh lemonade at one of my favorite places, Wow Wow Hawaiian Lemonade!
• Check out Sunrise Shack ($$) for their famous Bullet Coffee and enjoy an açaí bowl for breakfast/brunch! This is one of my favorite places in Hawaii, hands down.
• After fueling up, grab your hiking boots and head to the Peace Pillbox Hike (Ehukai pillbox). There’s multiple pillboxes and hikes on the island, so double check where you’re going!

• Waimea Bay Beach Park is a great place for cliff jumping, if you dare!
• Shark’s Cove is right nearby, but don’t be fooled by the name, there are zero sharks! It’s actually an amazing place to snorkel! Rent some gear and hop in the water to see all kinds of fishies.
• Across the street from Shark’s Cove there were a handful of food trucks. I tried North Shore Fish Tacos, ($$) and although I’m not a fan of seafood, they did have yummy chicken tacos.
• If instead you fancy an açaí bowl after swimming in the sea, try out Hale’iwa Bowls! ($$)
• Sunset Beach to watch the sun set on the beautiful island.
• Kono’s North Shore for dinner ($$)

Day 4

• Start your day off with a hike to the Pink Pillbox (Ma’ili). I loved this hike, but there’s little to no shade, so try to make it here while its still early and bring lots of water!

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• Lunch at L&L Hawaiian Barbecue. ($) I have to admit, its not my favorite. But its cheap eats and was my first time trying it!
• Visit the Kaneana Cave (aka Makua Cave). It’s a super cool cave with a lot of interesting history, but I will tell you I chickened out about 15 steps in because it was so dark and there was no one else there!
• Makua Beach is where we spent most of our day. It’s super chill with tons of locals, so its a great place if you want to get away from the crowds in Waikiki.
• After that we took a trip to the Mermaid Caves. Be very careful here and also would recommend going at low tide, but you can actually hop down into the small caves if the waves allow it and let the sun beam through on top of you!
• Splitting Cave / China Walls is where we spent our sunset. This is located against the ocean behind a neighborhood, so just be respectful! Park and walk back following a chain link fence and you’ll come out on top of the cliff. It’s one of my favorite places we saw the sunset, and even got to witness someone cliff jumping into the splitting cave here!
• Dinner at Tlacuaches 808 ($$)

Day 5

• After our hotel breakfast, we hung out for awhile at Arvo Cafe, one of the cutest outdoor coffee shops with tons of fun variations and snacks. Try a to-go lemonade too!
• Sandy Beach is where we spent most of our day.
• While walking around, we wandered into Spitfire Rotisserie & Flatbread ($$) for dinner, and were not disappointed!

BONUS ADVENTURE 1: Hike Stairway to Heaven. This is basically an all day hike if you want to go to the top so we weren’t able to commit the time, but if you’re physically able, it looks unreal! Would recommend finding a local guide via airbnb experiences, instagram or all trails to take you for safety reasons and because it is technically closed off to the public (aka it’s illegal) due to damage on the stairway.

BONUS ADVENTURE 2: Hike Koko Crater Trail. Another intense hike, but a lot shorter. A great way to start your day with a workout!

Day 6

• Head to the airport because today you’re going to MAUI!
• Pickup your rental- you’re gonna need it here. We got a Jeep for this island since we planned to be doing a lot more driving (specifically the Road to Hana) and really appreciated the extra space!
• Lunch at Zippy’s ($)
• Akamai Coffee ($) Might be the best coffee I’ve ever had, no joke. We came here every single day for coffee!
• Check into your hotel or airbnb. We stayed in Kihei, located on the southwest shore, which is a less touristy, more relaxed, and significantly less expensive than other areas. We were right on the water with a good amount of local restaurants and spots surrounding us. Deff would recommend staying here!

Day 7

• Start early to visit the Olivine Pools and be sure to check the tide times before you go. Swing by Nakalele Blowhole right after, which is super close by!
• Dragon’s Teeth is next- not the most swoon worthy views, but definitely a unique stop on your day’s trip.
• Fancy some shaved ice? It’s a must try in Hawaii! Ululani’s Hawaiian Shaved Ice is a favorite among locals and tourists! There’s so many fun flavors (like calamansi) to choose from, and I recommend sprinkling some li hing hui on top!
• Kapalua Bay Beach to chill in the sun for a bit, then head to…
• Lahaina Old Town. So many cool places to shop around and explore. We watched the sunset here and it was the most breathtaking view I’ve seen in my life!
• Maui Brewing Co. for dinner ($$)

Day 8

• Fork & Salad ($$) for an early lunch- definitely one of the yummiest healthiest options I had on Maui! I went back twice!
• Spend today at Makena Beach or head to MauiWine for a wine tour!
• Watch the sunset from Wailea Beach.

Day 9

• Today is the day for Road to Hana! I 10/10 recommend downloading the Shaka app (while you have wifi) and listening to the guided tour during your drive. There’s so much interesting information and history, and there’s no better way to pass the time!
• We made an unsuccessful attempt to visit Wai’anapanapa State Park where you’ll see the famous Black Sand Beach. It’s required to purchase tickets in advance, and they are only for an allotted window of time. Since most were sold out, our only option was 7-10am (apparently meaning you have to leave by 10am, not enter by 10am) Our mistake was attempting to start the road trip here and work backwards. I’d learn from my mistake and save yourself some time by doing RTH west to east. PACK FOOD! There are some local stands on the road, but its no guarantee they’ll be open. Plan for this to be an all day adventure.
• Stop at the Red Sand Beach or Kaihalulu Beach for a break from your long car ride. It’s a quick hike down to the cove, but totally worthwhile!

Day 10

• After breakfast, head to Ali’i Kula Lavender Farm. It’s such a great place, especially if you’re a lavender lover like me. The views are amazing and I walked out with lavender lemonade, lavender tea, chocolate, pepperjam, a latte… you get the point.
• Visit Haleakala National Park to watch the sunset. ($30 per vehicle) There are some restrictions and capacity due to covid, and you’ll need tickets in advance!
• Coconut’s Fish Cafe ($$) for dinner.

Day 11

• Drop off your rental and head to the airport- you’re going to The Big Island!
• After landing, head to Vibe Cafe($$) for lunch.
• Take a stroll around Hawaii Tropical Bioreserve & Garden. You probably only need 1-2 hours here!
• Tetsumen Ramen for dinner ($$)

Day 12

• Due to rainy weather, we spent the morning at a local escape room and played laser tag– it was SO much fun!
• Lunch at Hawaiian Style Cafe Hilo ($$)
• Dinner at Sweet Cane Cafe ($$)

Day 13

• Wake up extra early, put on your warmest clothes, and take a drive up Mauna Kea, Hawaii’s highest elevation atop a dormant volcano and home to one of the most epic places to stargaze! You’ll want to be there for sunrise, so plan ahead and allow an extra 3o minutes to stop and acclimate to the altitude at the Visitor Center (half way up). The Visitor Center views are also incredible…but trust me, you’ll want to get to the top! You’ll also need a 4×4 vehicle for the last portion of roadway. (free)
• Check out Rainbow Falls once you’ve made it back down from the volcano. (free)
• Head to Kaumana Caves where you can walk through a lava tube formed in 1881. (free)
• Lunch at Hilo Bay Cafe ($$)
• Akaka Falls State Park is next up, where you can quickly venture through the park to see a 442 ft waterfall and all its glory! ($5 entry fee)
• Daiichi Ramen for dinner ($)

Day 14

• Start your day off at Volcano’e National Park -the only national park in Hawaii (and you can use that National Parks pass here!) Otherwise $30/vehicle.
• Next up is the Nahuku Thurston Lava Tube (inside the park) – this lava tube is lighted and you can walk all the way through!
• Kilauea Ski Crater Trail (inside the park) is a great way to see an overview of the massive crater.
• Once you leave, head over to Punalu’u Beach Park, a free and beautiful black sand beach (easily my favorite part of The Big Island!)
• If you’re up for it after a day of walking, visit South Point Cliff Dive & Trail for some more great views!

That’s it! Our trip was a great balance of exploring, adventuring and relaxing. 2 weeks felt perfect, but you could easily spend 1 full week on any island and enjoy all it had to offer. Let me know if you use this itinerary and find it helpful!!! Below is the map with each exact location. Enjoy!