This itinerary blends outdoor adventure, cultural experiences, and relaxation, giving you a taste of Oahu’s diverse beauty!

Day 1: Arrival and Sunset Sips in Waikiki

After landing in Honolulu, head to Waikiki to get settled. Unpack, unwind, and ease into island life with a relaxing evening. Enjoy your first mai tai and local, live music at one of Waikiki’s iconic spots: House Without a Key (oceanfront at Halekulani) or Monkeypod Kitchen (oceanfront at the Outrigger).

Soak in the sunset vibes and views of Diamond Head as you kick off your Hawaiian adventure.

Day 2: City Highlights & Beach Time

Start your day with a Hawaiian staple: a cup of locally brewed coffee and a fresh acai bowl from a popular café like Island Vintage Coffee. Then, take a leisurely stroll along Kalakaua Avenue, exploring shops and landmarks such as the Duke Kahanamoku Statue and the pink Royal Hawaiian Hotel.

For beach lovers, spend the afternoon at Kaimana Beach—a local favorite with soft sand, calm waters, and a chance to spot a Hawaiian monk seal. Alternatively, head to Fort DeRussy Beach Park, where you can rent water toys or catch a friendly volleyball game.

In the mood for more walking? Take an urban stroll around Kapiʻolani Regional Park, the largest park in Hawaii.

For happy hour, drop by Arnold’s Beach Bar, a Waikiki gem hidden among the hustle and bustle, or enjoy the views at Monkey Pod Kitchen. End your day with a relaxed dinner and sunset Tiki’s Grill & Bar or Duke’s OR splurge on oceanfront dining at Azure or the Kaimana Hotel.

Day 3: East Oahu Adventure

If you’re ready to work up a sweat, tackle Koko Head Crater for a sunrise climb—over 1,000 steps with breathtaking panoramic views. Afterward, stop by Sandy Beach to watch some of the best bodyboarders ride the waves.

Continue your scenic drive and stop at Makapu’u Lighthouse Trail for more stunning views. Feeling daring? Descend to the Makapu’u Tidepools for an adventurous swim.

Make your way to Waimanalo (my favorite place on Earth) and relax at Bellows Beach Park, known for its powdery soft sand and great bodyboarding waves.

Waimanalo Beach — *Waimanalo. My favorite place on Earth.*

For dinner, consider stopping at Kona Brewing for a heaping plate of nachos and Marina views. Or hit up one of my favorites— Beastside Kitchen. Known for hit’s heaping, affordable plates of umami fried rice and guava fried chicken, you may even catch some amazing live music . If you see Tavana on the schedule, make sure to reserve a table. He’s amazing and very, very popular!

Day 4: Into the Jungle

Today, it’s all about hiking! After a healty breakfast at Heavenly Island Lifestyle, choose a trail based on your skill level:

Beginner: Head to Manoa Falls, a gentle jungle trail that leads to a pi! cturesque waterfall.
Intermediate: Take on the Kuliouou Ridge Trail a more challenging hike with switchbacks and rewarding summit views.
Advanced: Conquer Ka’au Crater Trail (or KA OWE as we fondly call it) for an epic adventure through dense jungle, waterfalls, and a hidden crater.

After all that hard work, head to Kaimuki where there’s plethora of great local, restaurants and Food Purveyors, from fresh meats and sweets at the Local General Store and acai bowls at Jewel or Juice to malasadas and ice cream at Pipeline Bakery and the BIGGEST burger I’ve ever put in my mouth at the The Surfing Pig.

Day 5: Culture & Beach Day

Slow things down and soak up the sun. If you’re tired of the Waikiki crows, head to nearby Ala Moana Beach Park or Kahala Beach.

In the evening, enjoy a whale-watching boat ride (from approximately October-March) or immerse yourself in Hawaiian culture at a traditional lu’au. Both will likely provide an island feast. No, it will NOT be the best meal you’ve ever had, but it will give you a taste of the diversity of island cuisine, from mac salad to sashimi.

Day 6: Pillbox Hikes & North Shore Adventures

Rise early to hike the famous Lanikai Pillboxes for unbeatable views of Kailua and the Mokulua Islands. If you’re tired of the car, Kailua is never a terrible place to spend the day. Rent a SUP or kayak and get out on the water or just hang lazily on the beach watching local kiteboarders. Make sure to stop by Foodland first, to grab some poke and cold beverages to keep your stomach satisifed. PRO hint: The most popular poke flavors, especially for more mainland tastes, are spicy and shoyu.

Kailua also has a plethora of botiques for those who are inclined to shop.

And if you get bored of all the beaching, the Hoʻomaluhia Botanical Garden is nearby and has some epic views.

For those who aren’t tired of the car, instead of hanging in Kailua, drive up the Windward Coast making small pit stops along the way to enjoy the beauty and local culture. You’ll see Chinaman’s Hat (another climbing opportunity), the Kualoa Ranch (fancy a horseback or ATV ride?), Lion’s Head (yet another short, steep climb with spectacular views), and Kahana Bay (perfect spot to watch paragliders while having a picnic). Now is a good time to turn around, unless you have another 30-40 minutes in you and want to head up to the famous shrimp trucks just past Turtle Bay Resort.

Day 7: West Side or North Shore Finale

For your last full day, choose your own adventure:

Take it easy in Waikiki and cap your evening with dinner at The Pig and the Lady in Chinatown. Everything here is delicious, but I highly recommend the Tea Salad and the papparadelle ragu, and any of creative desserts. Sit at the counter to watch the amazing staff pull together some of the most creative dishes.
Head West to Yokohama Bay where things don’t get much more beautiful or local. Here you can take the relatively 6 mile out-and-back Kaena Trail hike along the coast to the Western most tip of the United States. Beware: there’s very little shade and hit can get HOT. But depending on the time of year, you may see the amazing Albatross birds nesting, Hawaiian Monk Seals basking on the shore, and whales breaching in the distance. The beach here is also great for swimming when it’s calm. And when it’s NOT, it can be exciting to watch the barrels roll in.
Head to the North Shore for the ultimate waves. If you like big surf and it’s winter time, you won’t want to the North Shore from Haleiwa to Sunset Beach and Waimea Bay. This is where ti BIG kids come to play. Home of the popular Eddie Would Go competition, and dozens of others, this is where big wave surfing started. And it won’t disappoint. Halewia is fantasic little town filled with good eats and shops, but when it’s busy, it’s very busy. You’ve been warned.
For the daredevils: SKYDIVING! Head out to Waialua for an epic jump.

Day 8: A Houi Hou!

Enjoy a leisurely morning before heading to the airport. Say goodbye to Oahu with one last beach stroll, coffee, or quick souvenir stop before your flight home.

Oahu Favorites: Adventurer's 7-Day Itinerary