The Perfect 5-Day Oahu, Hawaii Itinerary for Couples



Turquoise blue waters, white and black sand beaches, fruity tropical drinks and vibrant printed shirts – the islands of Hawaii are a destination of choice for many travelers. Five days on Oahu is perfect, one day to explore each of the island’s distinct and diverse regions, each with its own flavor and personality.

Five days to explore the entire island will allow you to see most of the best spots, but really absorb the relaxing vibe, you might like to stick around for another beautiful Hawaiian sunset. This Pacific Ocean paradise has it all: gorgeous beaches, surfing, kayaking, hiking, waterfalls, lush tropical gardens, whale watching, and more.

Oahu is the perfect place to explore the aloha spirit, relax, and enjoy a restful vacation.

Diamond Head Lighthouse, Oahu

Photo credit: Hawaii Tourism Authority (HTA)

Day 1: South Shore – Honolulu

Buzzing with a bustling city, Honolulu is packed with all the history and drama you’d expect to see in a state capital. With trendy Waikiki and the infamous Diamond Head, you’ll easily spend the whole day (or more) exploring this part of your Oahu itinerary.

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Waikiki Beach

Waikiki Beach is a beautiful, long stretch of sandy beaches perfect for seeing and being seen. The Waikiki Beach area is the quintessential beach day in the Hawaiian Islands. Beautiful people combined with lots of glitz and glamour.

Hanauma Bay

Hanauma Bay State Park is a nature preserve specifically designed for the protection of marine life. The underwater park is perfect for snorkeling; the showy display of colorful fish will be on your list of best snorkeling experiences – ever.

Pro tip: Hanauma Bay is closed on Mondays and Tuesdays. There is an entrance fee of $25 per person.

diamond head

The iconic Diamond Head State Monument is a must-see photo opportunity on any Oahu itinerary. The easy out-and-back hike takes you along a paved path and several steps for the steep 1.8-mile climb; high High high.

Pro tip: Diamond Head charges nominal entry and parking fees for non-residents. Advance reservations are required.

Iolani Palace

Former official royal residence of King Kalakaua and his sister Queen Liliuokalani, Iolani Palace offers visitors a glimpse into the world of Hawaii’s kings and queens. the original Five-O’s from Hawaii fans will recognize this downtown Honolulu landmark as the show’s base.

Statue of King Kamehameha I

Dominating the entrance to the Hawaii State Supreme Court is the statue of King Kamehameha I. The statue honors the man, the king, who changed Hawaii’s history by uniting the four islands hawaiian. The statue sits across from Iolani Palace, making it an easy stop on your Oahu itinerary.

Ho'omaluhia Botanical Gardens in Hawaii

Ho’omaluhia Botanical Garden

Photo credit: Kelly Headrick /

Day 2: Windward Coast

Traversing the Windward Coast of Oahu offers guests sweeping scenic vistas filled with beaches, lush valleys, and Hawaiian history. As you drive along the rich coastline surrounded by the Ko’olau Mountain Range, you have the privilege of exploring Oahu’s magnificent natural gifts.

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Kailua Beach Park

Kailua Beach is known for its wonderful warm waters and offshore trade winds. It is one of the best spots on the island for water sports like windsurfing, kitesurfing, kayaking and stand-up paddleboarding. Kailua Beach Adventures offers a 2-hour guided kayak tour through a sea turtle feeding ground. It is a perfect kayak paddle for beginners. Adventure seekers will love Kailua Beach Adventures kayak surf experience.

Lanikai Beach

Lanikai Beach is the quintessential Hawaiian beach. Also known as Kaʻōhao Beach, you will fall in love with the soft blue waters surrounding the island views. This is the best place to sit and soak up the island lifestyle and sunshine.

Kualoa Ranch

Kualoa Ranch is beyond beautiful. The 4,000-acre private nature reserve is home to thrilling off-road tours including a Jurassic Adventure Tour, UTV Raptor Tour, Jurassic Valley Zipline Tour and many more thrilling adventures for the island daredevil experience .

Polynesian Luau Cultural Center

The Polynesian Cultural Center is a living history museum. It is well known for entertaining and educating visitors about Hawaiian tradition. The center offers several traditional luau packages that include a flower lei welcome and buffet at the Alii Luau.

Ho’omaluhia Botanical Garden

The Ho’omaluhia Botanical Garden is a 400-acre natural conservatory where visitors can relax and simply enjoy the fruits and flowers of Hawaii’s tropical landscape.

Byodoin Temple

The non-practicing Byodo-in Buddhist Temple is located in the Valley of the Temples Memorial Park. It was dedicated to the commemoration of the 100th anniversary of the arrival of the first Japanese immigrants in Hawaii. It is a peaceful place for a quiet moment of reflection and meditation.

North Shore of Oahu

North Shore of Oahu

Photo credit: Hawaii Tourism Authority (HTA)

Day 3: North Shore

The laid-back surfer vibe enlivens North Shore culture, creating a joyful beach-life attitude on Oahu’s North Shore.

Shave the ice in Oahu

Shave the ice in Oahu

Photo credit: Sandi Barrett

Hawaiian Shave Ice

Savoring a refreshing Hawaiian shaved ice at Matsumoto Shave Ice is a must when traversing the North Shore of Oahu. Lychee, yuzu and many more are delicious frozen treats.

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Turtle Bay

Turtle Bay is a beautiful North Shore beach and all beaches in Hawaii are public. If you want to make this North Shore paradise your home for the week, Turtle Bay Resort is a luxurious option. Golf, surfing, horseback riding, even a helicopter ride await your arrival.

Waimea Bay

When you think of surfers tackling giant waves, you think of Waimea Bay. In winter, giant 30-foot waves test surfers’ limits and inner strength. Grab your binoculars, find a great vantage point and admire these daring athletes as they ride huge waves.

Waimea Ahupu’a

The Waimea Valley is a ahupu’a, one of the wedge-shaped sections of land stretching from the mountains to the sea that divide the island. Historically, the land was divided so that each section had access to the important resources it needed to survive. Each Ahupua’a had access to water, trees, plants, etc. The Waimea Valley is a lush and bountiful ahupua’a., a nice place for a scenic drive.


One of the most famous snorkeling beaches on the north coast is Shark’s Cove in Pupukea. Underwater marine life moves in and out of small ledges and caves, playing in the water for your viewing pleasure.

Pro tip: Be sure to buy reef-safe sunscreen before you go snorkeling – it’s mandatory in Hawaii.

Kahana Bay Beach Park, Oahu

Kahana Bay Beach Park, Oahu

Photo credit: Heather Goodman / @hbgoodie

Hawaii Tourism Authority (HTA)

Surfing lessons

The Côte-Nord is the ideal place to take surf lessons. Join the crowds and grab a board in the laid-back surf town of Haleiwa. North Shore Oahu Surf School offers 2 hour lessons for beginners and experienced surfers.

USS Arizona Memorial, Pearl Harbor National Monument, Oahu

USS Arizona Memorial, Pearl Harbor National Monument, Oahu

Photo credit: Sandi Barrett

Day 4: Central Oahu

Pearl Harbor National Memorial

The Pearl Harbor National Memorial is an emotional stop for many visitors to Oahu. Walking the grounds, reading names and exploring memorial sites is an intensely personal moment.

USS Arizona Memorial

Tickets to visit the USS Arizona The memorial is free but reservations are required. Reservation slots open 8 weeks in advance for this unmissable visit.

Battleship USS Missouri Memorial

Tickets are available online to visit the Battleship USS Missouri Memorial.

Dole Plantation

The famous Dole Plantation is a must on the Oahu itinerary. Enjoy the Pineapple Express train or the Plantation Garden Tour while learning about the history of the Dole Plantation and its sweet and juicy harvest.

Wahiawa Botanical Garden

When you’re in search of some cooling shade, the Wahiawa Botanical Garden offers 27 acres of tropical rainforest habitat. It’s perfect for an immersive stroll through Oahu’s greenery.

Marriott's Ko Olina Beach Club, Ko Olina, Oahu

Marriott’s Ko Olina Beach Club, Ko Olina, Oahu

Photo credit: Sandi Barrett

Day 5: Leeward Coast

The Leeward Coast is a popular tourist destination with wonderful resorts, beaches and golf.

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Koh Olina Resort

Tiki-lit walks along white-sand beaches, poolside piña coladas, and blooming colorful tropical flowers aim to put you in a relaxing, I’m on Vacation mode.

The Ko Olina Resort area is home to some of the biggest names in luxury resort vacations: the Four Seasons Resort Oahu at Ko Olina; Aulani, a Disney Resort & Spa; Marriott’s Ko Olina Beach Club; and the Beach Villas at Ko Olina.

Makaha Beach

Known for its world famous surf waves, Makaha Beach regularly has waves of up to 25 feet during the winter surf season. Not ready to hook 10 with the pros, watching them hit the waves on the beach will put any sports fan on their feet.

Extra day island hopping

If you have a few more days and want to go island hopping, there are plenty of islands just a short flight away. In 30 minutes without luggage, you can be at Lihue Airport in Kauai, Kahului Airport or Kapalua-West Maui Airport in Maui. Lanai airport is only 25 minutes away and Molokai airport is only 20 minutes from a puddle.

Play like an islander and take a day trip to another beach, golf resort, or stroll to another island. Imagine skipping a flight to try a new restaurant and a walk on the beach – very romantic.

Beach Safety

Hawaii’s ocean conditions change regularly. Visit for up-to-the-minute surf, wind and public safety on Hawaiian beaches.

This comprehensive Oahu itinerary covers many classic tourist attractions and once-in-a-lifetime experiences. No matter how you visit Oahu, you’ll love every beautiful minute.

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