May 25, 2024

Happy Travel & Tour

Specialists Travel & Tours

The Perfect 5-Day Oahu, Hawaii Itinerary For Couples

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 top bucket list destination for many travelers. Five days on Oahu is perfect, a day to explore each of the island’s distinct and diverse regions, each with their own flavor and personality.

Five days to explore the entire island will let you see most of the top spots, but really absorb the chill vibe, you might love staying for one more gorgeous Hawaiian sunset. This Pacific Ocean paradise has everything you need: gorgeous beaches, surfing, kayaking, hiking, waterfalls, lush tropical gardens, whale watching, and more.

Oahu is the perfect spot to explore the aloha spirit, kick back, and enjoy a relaxing vacation.

Aerial view of Diamond Head Lighthouse, Oahu

Diamond Head Lighthouse, Oahu

Photo credit: Hawaii Tourism Authority (HTA)

Day 1: South Shore – Honolulu

Humming with a busy city buzz, Honolulu is filled with all the history and drama you would expect to see in a state capital. With the hip Waikiki neighborhood and the infamous Diamond Head, you will easily spend the entire day (or more) exploring this part of your Oahu itinerary.

Beach Hopping

Waikiki Beach

Waikiki Beach is a beautiful, long stretch of sandy beaches perfect for the see and be seen crowd. The Waikiki Beach area is the quintessential Hawaiian islands beach day. Beautiful people paired with lots of glitz and glamor.

Hanauma Bay

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

Pro Tip: Hanauma Bay is closed Monday and Tuesday. There is a $25 per person entrance fee.

Diamond Head

The iconic Diamond Head State Monument is a photo opportunity not to be missed on any Oahu itinerary. The easy out and back hike takes you along a paved path and more than a few stairs for the steep, 1.8-mile climb; up, up, up.

Pro Tip: Diamond Head requires nominal entrance and parking fees for non-residents. Advanced reservations are required.

Iolani Palace

Formerly the official royal residence of King Kalakaua and his sister Queen Liliuokalani, Iolani Palace offers visitors a glimpse inside the world of Hawaii Kings and Queens. The original Hawaii Five-O fans will recognize this downtown Honolulu landmark as the show’s home base.

Statue Of King Kamehameha I

Towering over the entrance of the Hawaii State Supreme Court is the Statue of King Kamehameha I. The statue honors the man, the king, who changed Hawaiian history by unifying the four Hawaiian Islands. The statue is across the street from Iolani Palace making it an easy stop on your Oahu itinerary.

Ho'omaluhia Botanical Gardens in Hawaii

Ho’omaluhia Botanical Gardens

Photo credit: Kelly Headrick /

Day 2: Windward Coast

Traversing along Oahu’s Windward Coast offers guests panoramic scenic vistas filled with beaches, lush valleys, and Hawaiian history. As you drive along the rich coastline hemmed in by the Ko’olau Mountain Range, you are privileged to explore Oahu’s gorgeous natural gifts.

Beach Hopping

Kailua Beach Park

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

Lanikai Beach

Lanikai Beach is the quintessentially gorgeous Hawaii beach. Also known as Kaʻōhao Beach, you will fall in love with the soft blue water surrounding island views. This is the best spot to sit and soak up the island lifestyle and sunshine.

Kualoa Ranch

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

Polynesian Cultural Center Luau

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

Ho’omaluhia Botanical Garden

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

Byodo-in Temple

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

North Shore Oahu

North Shore of Oahu

Photo credit: Hawaii Tourism Authority (HTA)

Day 3: North Shore

The laid-back surfer vibe drives the North Shore culture casting a happy, beach life attitude across Oahu’s northern coastline.

Shave ice in Oahu

Shave ice in Oahu

Photo credit: Sandi Barrett

Hawaiian Shave Ice

Enjoying a refreshing Hawaiian shave ice at Matsumoto Shave Ice is a must-do as you traverse Oahu’s North Shore. Lychee, Yuzu, and many others are tasty frozen treats.

Beach Hopping

Turtle Bay

Turtle Bay is a beautiful North Shore beach and all the 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. Golfing, surfing, horseback riding, even a helicopter tour are waiting for your arrival.

Waimea Bay

When you think of surfers tackling giant waves, you are thinking of Waimea Bay. In the winter, giant 30-foot waves test surfers’ limits and internal fortitude. Grab your binoculars, find a great viewing spot, and admire these daring athletes while they ride huge waves.

Waimea Ahupua’a

Waimea Valley is an ahupua‘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 each section had access to important resources they needed to survive. Each ahupua‘a had access to water, trees, plants, etc. Waimea Valley is a lush and abundant ahupua‘a, a beautiful spot for a scenic drive.


One of the most famous snorkeling beaches on the North Shore is Shark’s Cove at Pupukea. The underwater marine life darts in and out of the small ledges and caves, playing in the water for your viewing enjoyment.

Pro Tip: Be sure to purchase reef-safe sunscreen before you head out to snorkel — it is required in Hawaii.

Kahana Bay Beach Park, Oahu

Kahana Bay Beach Park, Oahu

Photo credit: Heather Goodman / @hbgoodie

Hawaii Tourism Authority (HTA)

Surfing Lessons

The North Shore is the place to take surfing lessons. Join the crowd and grab a board in the laid-back surf town of Haleiwa. North Shore Oahu Surf School offers 2-hour classes for newbie wave runners 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 Oahu visitors. Walking the grounds, reading the names, and exploring the memorial sites is an intensely personal moment.

USS Arizona Memorial

Tickets to visit the USS Arizona Memorial are free but reservations are required. Reservation slots open 8 weeks in advance for this bucket-list visit.

USS Battleship Missouri Memorial

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

Dole Plantation

The famous Dole Plantation is a staple on the Oahu itinerary. Enjoy the Pineapple Express Train or Plantation Garden Tour while you learn about the history of the Dole Plantation and its sweet and juicy crop.

Wahiawa Botanical Garden

When you are in search of some cooling shade, the Wahiawa Botanical Garden offers 27 acres of tropical rainforest habitat. It is 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 gorgeous resorts, beaches, and golf.

Beach Hopping

Ko Olina Resort

Tiki-lit strolls along white sand beaches, piña coladas poolside, and colorful tropical flowers in bloom aim to get you in a relaxing I-am-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 surfing waves, Makaha Beach regularly has up to 25-foot waves during the winter surfing season. Not ready to hang 10 with the professionals, watching them tackle the waves on the beach will get any sports fan on their feet.

Extra Day Island Hopping

If you have a few extra days and want to spend one island hopping, many of the islands are just a short flight away. In 30 baggage-free minutes, you can be at Lihue Airport on Kauai, Kahului Airport or Kapalua-West Maui Airport on Maui. Lanai Airport is only 25 minutes, and Molokai Airport is a mere 20-minute puddle jump.

Play like an islander and day trip to another beach, golf resort, or ride around on a different island. Imagine hopping 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 at the Hawaiian Beaches.

This full Oahu itinerary touches on many of the classic tourist attractions and unique experiences. No matter how you visit Oahu, you will love every beautiful minute.

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