Welcome to Hawaii! Whether this is your first time to Hawaii or your tenth, you want to have a great time with the perfect itinerary. We’ve got you covered. This 10-day itinerary includes seven days on Oahu and three days on Maui, giving you a taste of some truly unique experiences on each island.

Why Oahu and Maui? According to the Hawaii Tourism Authority, these are the two most visited islands in Hawaii.

Day 1: Arrive and Enjoy Waikiki Sunset

Aloha and welcome! You’ve probably had a long journey to Oahu and you’re most likely arriving mid-day or later. So today, don’t plan on doing too much other than getting settled and soaking in the scenery. You’ve been planning this trip and dreaming of it for a long time — take a minute to slow down and enjoy it after a hectic travel day.

Once you’ve grabbed your rental car and checked into your hotel or vacation rental, change into those vacation clothes and hit the street. You can stroll Waikiki’s main drag, Kalakaua Avenue and take in the vibrant atmosphere. Once you’ve explored and oriented yourself, head to the Moana Surfrider. It’s a Marriott resort now, but it first opened in 1901 as the first hotel in Waikiki. The original building still has historic charm that will set the mood for your first night.

Head to the beach bar for live music, cocktails, and a front row seat for the famous Waikiki sunset.

After sunset, there are plenty of places to grab dinner, but we recommend something quick. Try Marugame Udon or Paia Fish Market for a quick, but delicious bite.

Oahu and Maui Itinerary Haleiwa

Day 2: North Shore Beach Day

Good morning jet lag! You’re probably up early today and while you could spend the day enjoying the beaches in Waikiki, we recommend hopping in your car and heading north. You might as well take advantage of your early start and enjoy the day exploring the north shore.

You’re going to head up to Kuilima Cove at the Turtle Bay Resort for a day of snorkeling and beach going. Fun fact: all beaches in Hawaii are public, so even though you’re not staying at the resort, you’re welcome to use the beach.

Before you get to Turtle Bay, make a quick stop at the Sunrise Shack for breakfast. You can grab acai bowls, smoothies, or bulletproof coffee. It’s a great place to start your morning right.

After a day at the beach, head to Haleiwa to explore the town. Here you’ll find plenty of restaurants for lunch or dinner, charming shops, and the famous Matsumoto Shave Ice.

pearl harbor guided tour from waikiki

Day 3: Spend a Day at Pearl Harbor

Pearl Harbor is one of the most visited sites on Oahu, with thousands of people visiting every year to pay their respects at the USS Arizona Memorial and learn more about the history and the US entry into WWII.

There is so much to see and learn at Pearl Harbor, that we recommend spending a day here. Entry is free, but to visit the USS Arizona Memorial, you will need to make a reservation online for $1.

Once you’ve visited the memorial, don’t leave yet. There is so much more to explore. Check out the other nonprofit museums including the USS Bowfin Submarine, the USS Battleship Missouri, and the Pearl Harbor Aviation Museum.

Each museum has its own entrance fee, so you’ll need to buy tickets to each, but those can be purchased upon arrival.

If you want to book a guided tour for the day and have them handle everything for you: from picking you up at your hotel to taking you to each museum, we highly recommend this tour we enjoyed with Hawaii Tours. You can read our full review and watch a video of our day at Pearl Harbor with Hawaii Tours.

Day 4: Enjoy a Waikiki Beach Day

You’ve been out and about so now it’s time to enjoy a Waikiki beach day. But you have choices! Did you know there are actually eight beaches in Waikiki? Here are some suggestions for where to spend your day:

  • If you have kids with you, head to either Duke Kahanamoku Beach at the Hilton Hawaiian Village and play in the lagoon or Prince Kuhio Beach.
  • If you want learn to surf, head to Queens Beach
  • If you’re looking for a beach in the center of it all, head to Waikiki Beach Center

When you’re in Waikiki, you might be inspired to try your hand at surfing. You can rent a board from one of the beach vendors near the Duke Kahanamoku statue. Or, you can hone your skills with a surf lesson. There are plenty of options to choose from, but we enjoyed our experience with Ohana Surf Project. You can see our video, full review, and booking options with Ohana Surf Project.

When you get tired of the beach, head to Kalakaua Avenue for some shopping and dining. For casual dining options, you can head to the Kūhiō Ave Food Hall in the International Marketplace. Or enjoy the Waikiki Food Hall across the street in the Royal Hawaiian Shopping Center.

trip to hawaii cost estimate 2022

Our family enjoying a tour of the Iolani Palace in historic downtown Honolulu.

Day 5: Learn About Hawaiian History

While you’re on Oahu, this is the perfect place to learn about Hawaiian history. There are plenty of museums, exhibits, and historical sites to learn from. Today, you’ll head to Iolani Palace, which was built in 1882 by King Kalakaua. The palace was home to Hawaii’s last reigning monarchs until the overthrow of the monarchy in 1893. This is the only official royal residence in the US.

The palace has been meticulously restored and you can spend time touring both the palace and the sprawling grounds in downtown Honolulu.

After touring the palace, don’t rush out of downtown Honolulu just yet. Take a stroll through Chinatown and grab lunch at one of the many great restaurants in the area. Check out farm to table restaurant, Fete, or a plate lunch at Ohana Dish.

oahu best beaches waimanalo beach

Day 6: Explore East Oahu

Today you can either hop in a rental car or hop on the Waikiki Trolley Blue line to explore some of the sights on the east, windward side of Oahu. Some of the places you can stop include:

  • Diamond Head (Lē’ahi): take a hike up Hawaii’s most recognized landmark, a crater that was formed 300,000 years ago from a single volcanic explosion. Note that parking here is challenging, so if you plan to hike here, be sure to get up early to get a spot. Otherwise, you may prefer to hike at Koko Head Crater.
  • Halona Blowhole and Cove: enjoy the coastal views at the Halona Blowhole and beach cove.
  • Hanauma Bay: Plan ahead and get tickets to the Hanauma Bay Nature Preserve for great snorkeling.
  • Waimanalo Beach: If you have a car, you can continue on the journey and spend time at Waimanalo Beach, a beautiful white sand beach that is usually very quiet.

And don’t forget to stop for some delicious Malasadas at Leonard’s Bakery Food Truck, The Malasada Mobile.

There is so much to discover and when you’re coming to Hawaii for a limited time, you want to make sure you see the best without wasting time or money. That’s where our island itineraries come in. They take you step by step on the best excursion days filled with great stops, restaurants, activities, and tips. All on a time efficient pre-planned route (with links to directions!).

“Just want to say thank y’all for putting together the Oahu & Maui itineraries. Our family had a great trip to Hawaii due to having those itineraries handy anytime during the day and we all had an amazing time.” – Tony R.

Day 7: Island hop to Maui

Your final three days are going to be spent on Maui. And while this is nowhere near long enough to explore everything the Valley Isle has to offer, you are going to have a great time mixing exploration with relaxation.

But first, you need to get there. To make the most of your time on Maui, we recommend getting an early flight from Oahu. While the flight is short (30 minutes) island hopping can still take up a surprising amount of time.

Related read: What to Know Before Island Hopping in Hawaii

Once you land on Maui, you’ll head down to your hotel in south Maui. You’re staying in South Maui strategically, for close proximity to your activity tomorrow. Check out our Where to Stay on Maui guide for hotel recommendations.

When you’re checked in, you can head out to explore the area. Go soak up the sun and enjoy the scenery at one of Maui’s best beaches, Wailea Beach.

After you’ve enjoyed your time on the beach, head to Monkeypod Kitchen for happy hour and an early dinner. You can enjoy their live music as well as their mai tai’s made with lilikoi foam. Delicious!

Then tuck yourself into bed early because you’re going to get an early start to the day tomorrow.

Related read: Check Out the 17 Best Beaches on Maui

Kai Kanani Molokini morning snorkel tour

Day 8: Maui Snorkeling Day

Today you’re going to head out on one of our favorite tours: the sunrise Molokini snorkel with Kai Kanani. We love this tour because thanks to the beach loading in Wailea, you’re the first boat to the crater. You’ll get to go in the water and enjoy some of the best snorkeling on the island before the rest of the crowds arrive. Also, thanks to the early start time, you’re able to get back to land mid-morning, which gives you enough time to explore another part of the island.

For the remainder of the day, you’re going to head 45 minutes north to Lahaina, a historic whaling village and former royal capital.

You have the remainder of the day to explore the town, shop, enjoy the restaurants and shave ice options, and more.

Check out our complete Lahaina Visitors Guide with information on how to get there, what to do, and where to eat.

Haleakala Kids Things to Do

Day 9: Upcountry Maui and Haleakala Sunset

For your final full day on Maui, you’re going to end it in a memorable way. But first, you’re going to take the afternoon to explore upcountry Maui.

When you head up the hill to upcountry, you’ll be met with green rolling scenery, cooler weather, and beautiful farmland. You’re making your way up the slope of the volcano Haleakala, making plenty of stops to enjoy the scenery along the way.

While you’re in upcountry, consider taking a farm tour, stopping at a farm stand, and enjoying some great places to eat like the Ulupalakua Ranch Store (their burgers are the BEST).

Related read: check out our favorite farm tours on Maui

Once you’ve experienced the beauty of upcountry, it’s time to head into Haleakalā National Park. While most people wake up at 2:30 to experience the sunrise, we think the sunset is an underrated activity. So that’s what you’re here to do today. Get here with enough time left in the day to enjoy a little hiking, explore the park, and then settle in to take in the views as the sun sets.

Pro tip: be sure to bring VERY warm clothes because it gets cold on top of the mountain.

Day 10: Stop at Maui Tropical Plantation and Say Aloha to Maui

It’s your last morning here and while I’m sure you’re sad to leave, you can start planning your next trip back.

Before you get on the plane, it’s time to enjoy one final stop at Maui Tropical Plantation. Depending on how much time you have, you can enjoy a coffee from the cafe, walk around the grounds, shop for souvenirs at the farm store, or do the plantation train ride. Our son loves getting the duck and fish food and spending 10 minutes feeding the ducks in the pond. And if you’re hungry and want a full meal before flying, Cafe O’Lei at the Mill House is an excellent restaurant choice.

Your Perfect Hawaii Itinerary

If you’re planning a trip to Hawaii, we’ve got you covered. Our island itineraries help you navigate the planning process and make your trip smooth once you’re on-island. Thousands of customers have loved them, whether they were planning for a trip that was a year away or a trip that was a day away.

“I just wanted you to know that my family and I purchased the Maui itinerary and we are wrapping up 12 days on the island. We did so much of what you recommended and it was awesome for everyone. We have three college-age kids and everybody enjoyed the things you suggested, including the restaurants. Thanks for all of the work that you put into this. Mahalo.” – Gunnar A.

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