Aloha, fellow Hawaii lovers!
A Hawaiian vacation has something for everybody. If you are limited to 7 days in this tropical paradise, you can get the most out of your vacation by visiting Oahu and Maui together.
As someone who’s been fortunate enough to visit the beautiful islands of Oahu and Maui multiple times with my boyfriend, I’m here to share a fantastic itinerary that’ll help you experience the best of what these two islands have to offer, all within just seven days. Trust me, this trip will be filled with breathtaking beaches, exhilarating hikes, and unforgettable memories – it truly is paradise on Earth!
Now let me tell you: planning a perfect Hawaiian vacation can be overwhelming. There are so many gorgeous spots to see and thrilling activities to try that it’s hard not to fear missing out on something amazing. But worry no more! After countless hours spent exploring every corner of these enchanting islands and chatting up locals for their insider tips, I’ve curated a foolproof plan that’ll guide you through an incredible week in Hawaii.
My passion for Oahu and Maui stems from years of firsthand experience: lounging on pristine sands under swaying palm trees; swimming alongside vibrant marine life in crystal-clear waters; trekking through lush rainforests towards cascading waterfalls… The list goes on! So take it from someone who knows – by following this itinerary, you’re guaranteed nothing short of an authentic island adventure.
As you dive into this guide, picture yourself as a free-spirited explorer eager for new experiences or perhaps as a couple seeking romance amidst some of nature’s most awe-inspiring landscapes – whichever feels closer to your heart. My aim is for you to thoroughly enjoy every moment spent discovering the captivating beauty and warm spirit of our beloved hula land.
Warning: Don’t be surprised if upon returning home from your Hawaiian getaway, life becomes riddled with daydreams about majestic sunsets over turquoise waters… But hey – there are worse things than being lovesick for paradise! Now let’s embark on our 7-day island-hopping journey together. Aloha ‘oe!
Day 1: (Oahu) Settling in and hitting the beaches of Waikiki
After landing in Honolulu make sure to pick up your rental. There are over 10 rental vendors at the Honolulu airport and they are located across terminal no. 2. There is a rental car shuttle pick up if you are at a far terminal. You can start your activities after checking into your hotel, or just get right to the beach.
1. Duke Kahanamoku Beach in front of Hilton Hawaiian Village
This is a beautiful sandy beach and lagoon entirely open to the public even if you’re not staying at the Hilton resort. If you haven’t checked into your hotel yet, don’t worry, there is plenty of parking. This area is generally not crowded and there is a nice shallow end, so start slowly. The view is beautiful toward the open ocean and a great place to watch the sunset.
2. Kuhio Beach or (The Ponds)
Kuhio Beach is part of Waikiki Beach and starts at the Sheraton Moana Surfrider Hotel, It also has a great shallow end and easy entrance into the water. The beach is made of white sand and the water is calm. This is a perfect place to try out snorkeling or another water activity. The beach is generally safe and you can stay till late or have some dinner right on the beach.
Tip: If you plan on renting snorkeling equipment, you’ll get the best deal by renting for the whole week. In Waikiki try Snorkel Bob’s Oahu, 1 800 Snorkel, or Surf in the City Waikiki. Feel free to contact them ahead of time.
3. Enjoy fine dining with a view at the Beachhouse at the Moana
Indulge in high-end Hawaiian cuisine and relax on your first night in Hawaii. The Beachhouse has an amazing view and the terrace is right on the beach. Make sure to reserve a table outside. Try the 4-course tasting menu with 2 appetizers, one entrée, and a dessert. I guarantee that’s more food than you can eat. My personal favorite appetizer is the crab cake and butternut squash curry. Try it!
Tip: Other dining options with a great view and menu include: Michel’s at the Colony Surf, DECK, and La Vie.
Day 2: (Oahu) Check out the west leeward coast
This is the quiet and authentic Hawaii, largely undiscovered by tourists and filled with small off-the-beaten-path activities. Enjoy the beaches, jungle-like forests, and great hiking trails.
1. Ko Olina Lagoons (2 miles of lagoons with white-sand beaches)
Just 17 miles outside of Honolulu you will find peace and serenity in the sandy lagoons of Ko Olina. This is a publicly available beach with 7 lagoons both natural and manmade. This is a perfect and calm place to sunbathe, swim, snorkel and just enjoy the sand. Try canoeing or stand-up paddling in these calm waters. For those wanting more excitement visit the aqua park Wet and Wild which has some thrill rides and private cabana rentals.
2. Kaena Point Trail (bird sanctuary and hike with a lava shore)
Hike through Kaena Point Natural Area Reserve and enjoy wildlife, rugged scenery, and amazing views. Challenge yourselves with the amazing 3.5 Miles Round Trip hike. The hike is relatively easy, but lacks shade and takes about 2 hours to complete at a leisurely rate. The trail is coastal with plenty of opportunities for great pictures.
3. The Maili pillbox sunset hike
If you skipped the longer hike, you definitely want to do this one. It’s a 2-mile round trip easy hike (only 15 minutes away from the Ko Olina beach). This hike is famous for the World War 2 bunkers at the top of the trail which make a great resting spot and gives a perfect sunset view. The hike will take you an hour to complete and plan some time at the top. When hiking at dusk or dawn, bring a flashlight just in case.
Day 3: (Oahu) all the excitement of Honolulu
1. Manoa Falls Trail Hike (Short hike to the most beautiful waterfall)
This area is so beautiful it was featured in the series Lost and the movie Jurassic Park. The vegetation is lush and rich and the waterfall is the best one on the island. I recommend doing this hike in the morning. It’s an easy hike at 1.6 miles round-trip and about 45 minutes each way (with stops to enjoy the surroundings). At the end of the trail is a 150-foot waterfall, and it makes an impressive place for breakfast or snacks.
2. Pearl Harbor National Memorial
While in Hawaii, buff up on history and visit the amazing Pearl Harbor Memorial. The visitor center is open every day from 7:00 a.m. to 5:00 p.m. The visitor center, two museums, and the USS Arizona Memorial program are free for all visitors. Make sure to check out the two exhibit galleries: Road to War and Attack. Arizona memorial program takes about 45 minutes and includes a boat ride. Altogether, plan a 2 to 3-hour trip here. Well worth it!
3. Traditional outdoor Luau (Waikiki Starlight Luau at Hilton Hawaiian Village)
Finish your day off with the best and most exciting Luau. In Hilton style, this is an extravagant open-air luau with an amazing sunset ocean view and highly skilled entertainers located off of the Duke Kahanamoku Lagoon. The luau starts at 5:30 pm and lasts about 3 hours. Tickets include leis, a hula lesson, live music, dinner, and a show with fire. The food is high quality and so are the Mai Tais. I recommend the Golden Circle Seating.
Day 4: (Maui) Historic road to Hana (first day in Maui with a Bang!)
After picking up your rental, don’t delay towards Hana. The road to Hana is one of the most beautiful drives in the world. Make sure to set the whole day aside and enjoy the views and sites. Check out all the sites on this list, or pick and choose. Either way, expect to travel about 6 to 7 hours to Hana. The trip back (if you choose not to sleep in Hana) is under 3 hours without stops.
Tip: Make your way across the island from Kahului to Hana. Then move to the South side and through Upcountry Maui, making your way back towards the airport. This trip should take 3 days.
1. Twin Falls (mile marker 2)
If you’re looking to jump into a swimming hole with a nice waterfall this is the best first stop. There is plenty of parking provided by Wailele Farm, so park and head out. The hike is an easy 1-mile round trip and very quick. There is still lots to see along the way including beautiful lush trees and flowers. Take some great pictures here and cool off by cliff jumping.
2. Hookipa Beach Park – The turtle watching spot (mile marker 9)
Stopping at Hookipa Beach Park almost guarantees that you will see some large green turtles lounging and swimming. This is also a famous surfing spot (for watching professionals). So grab a blanket out of the car and enjoy sitting at the beach. This is a well-known local spot and a bit off the beaten path.
3. Waikamoi Ridge Trail (mile marker 9.5)
This is a good resting spot in the forest. After a short hike, you get to a nice picnic area. This place is not commonly visited, so it’s great for alone time and peaceful rest. If you want a longer walk, continue forward and you will reach the water.
4. Upper Waikani Falls (mile marker 19)
Upper Waikani Falls (aka Three Bears) is my favorite stop on the road. The three waterfalls are clean, clear, and altogether impressive. Drive past the falls and park in the small off-the-road parking. It’s a short walk down the side of the falls down to the swimming hole. You can stand under the waterfalls for a great photo because it is shallow on the edges. Really one of a kind photo! Just be careful making your way down to the falls. Don’t attempt if you are not sure or if it’s a slippery day.
5. Hana Lava Tubes (mile marker 31)
The Hana Lava Tube (Kaʻeleku Caverns) is one of two lava tubes on the island and the largest cave you will see. It takes about 25 minutes to do the walkthrough. At the entrance, there is a fee and you can pick up a flashlight. This is a great one-of-a-kind activity and the best way to escape the heat for a while. It’s interesting to think the tubes were formed thousands of years ago.
Day 5: (Maui) South Side (Most beautiful beaches in the world)
The South Side of Maui is the one with the sunniest and driest weather. This makes the conditions perfect for visiting beaches, swimming, and snorkeling. Whichever beach you choose there will be plenty to see and do, but don’t miss the ones on this list.
1. Makena Beach aka Big Beach
This is a huge sandy beach that is over 2/3 of a mile long and more than 100 yards wide, It’s one of the prettiest beaches on the island with powder-white sand and crystalline water. This beach is great for swimming, snorkeling, body surfing, and other water activities. Sometimes the waves can get big, so be careful. However, there are multiple lifeguards on duty here. The beach is so big you will have plenty of space, and it’s almost impossible to feel crowded.
You might also like: Oahu Activities for Couples
2. One’uli Black Sand Beach
Don’t miss taking a walk on this beautiful beach and enjoying the one-of-a-kind black sand only found in Hawaii. The sand here is black because it’s made of lava rock. Because the ocean floor here is generally lava rock, it’s not for swimming, but it’s rich in marine life. Take some time to walk around and enjoy the uniqueness of this area.
3. One-of-a-kind snorkeling and diving at Molokini Crater
This is a great activity for adventure seekers and a one-of-a-kind experience at a crater. I recommend the Molokini and Turtle Town snorkeling aboard the Malolo Power-Catamaran. This tour costs about $150.00 and lasts between 4 and 5 hours. The groups are small and all the gear and flotation devices are included. There is even a waterslide and freshwater showers. No need to bring food because it’s included. Altogether a great and memorable experience.
Day 6: Haleakala & Upcountry Maui
Coming to Maui and not experiencing the powerful and impressive Haleakala Crater would be a shame. It has one of the most beautiful sunrises in the world (the sunset is just as glorious). Start your day early at the crater so you have plenty of time for more activities on your way back to the airport.
1. Haleakala National Park (sunrise) – Most romantic view, above the sky’s
Haleakala means “house of the sun” and the peak is well over 10.000 feet high. Making it one of the most beautiful spots in the world to witness a sunrise. Visit the dormant volcano’s crater by creating a reservation for your vehicle. Arrive 120 minutes earlier and bring warm clothing and blankets. I recommend some warm drinks and a snack too. The road is in good shape and there isn’t too much traffic. There are some facilities on the way but prepare for pure nature. If you just can’t make a sunrise, consider coming up for the sunset.
2. Ocean Vodka Organic Farm Tour – A funky and fun couple’s activity
Book an online guided tour and take the additional drinks as well! Everything here is extremely beautiful, tasty, and well done. The value for your money is well beyond and it’s not an expensive activity. You will enjoy a great 1-hour tour and information on cultivating sugarcane and all the varieties used (many sorts are grown right at the farm). Afterward, there is a tasting of vodka, gin, and rum. There are different options. The farm has an amazing restaurant with lawn chairs, so after the tour spread out and enjoy the views with delicious food.
3. Maui Pineapple tours – A great and fun tour by people who love pineapple
Maui Gold pineapple plantation tour will pleasantly surprise you! It’s a 1.5-hour tour with interesting tour guides and great information. In addition, you get to taste some amazing fresh pineapples right off the farm, walk through the pineapple fields and packing facility and learn about the Hawaiian culture. They even give you an airport-ready pineapple at the end. Choose one of 3 available times of the day.
On your last day on the trip, you are probably getting ready for your flight home. That’s why it’s easiest to do a few activities close to the airport. Also, visit a shopping mall and buy the souvenirs and presents you might have forgotten.
1. Kapiolani Park and Queen Kapiolani Garden
This is a beautiful small botanical garden filled with blooming exotic flowers. It’s a perfect stop for an hour easy walk before or after breakfast. It covers 200 acres and it’s about 150 years old. They have the best collection of hibiscus on the island. The garden is also right next to the Zoo and aquarium, so if you are looking for more great content, it’s adjacent. After 11 am you can grab an amazing plate lunch at Diamond Head Grill, I recommend the Mushroom Garlic Herb Chicken Plate.
2. Check out the Art at the Honolulu Museum of Art
This is another culturally rich and interesting visit, perfect to get away from the sun for a few hours or use as an activity on a rainy day. The Art Museum has over 50,000 pieces on display including paintings, sculptures, graphics, and cloth work. Here you can see some well-known painters on display, so enjoy. It has something everyone will love and the artwork spans from ancient to modern times.
3. Royal Hawaiian Shopping Center
It’s only on the last day of the trip we remember, that we forgot a gift for someone. Don’t worry! The Royal Hawaiian shopping center has everything you need and some great food. They offer world-brand shops, as well as local businesses, antiques, and handmade items. This is a perfect place to grab a meal. For food, I recommend upscale Wolfgang’s Steakhouse, Wicked Maine Lobster, or Pho Factory (healthy Vietnamese).
Hawaii is one of the most beautiful places on earth. There are so many things to see and experience, and each island offers a unique and exciting adventure. What better way to spend your limited time than visiting Oahu and Maui?
This itinerary truly has something for everyone and includes diverse and important activities to do and see on your vacation.
Pick and choose, or do them all, you won’t be disappointed.
Have a safe trip and enjoy.
Last Updated on May 24, 2023 by Brigitte