Visiting Hawaii? Keep these things in mind. A lot of thought and care needs to be put into planning a trip to Hawaii. Of course, that is why we recommend using a travel advisor (me)! There are some things to keep in mind as you go into the planning process, then during the trip.
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- Do you want to stay on one island or island hop?
- What island fits your style?
- Have a budget
- Book well in advance
- Plan activities in advance
- Knowing what to pack.
Dive into a blend of island paradise and city excitement with our Maui and Oahu itinerary. Start with four days in Maui, where you can enjoy endless sunshine, stunning beaches, and luxurious resorts. Then, switch vibes with three days in Oahu, exploring vibrant city life and adventurous outings.
But remember, it’s your vacation, and we’re here to make it uniquely yours! Want to shake things up? We’ve got you covered. Whether you’re dreaming of extending your beach days, mixing up the island sequence, or even focusing your entire getaway on just one island, we can tailor your itinerary to match your dream vacation.
Oahu, Hawaii – The Island
While hula-clad dancers, sun-kissed beaches and killer surf shape Oahu’s image, this island has all this and much more: The downtown district of Honolulu, the most populous city, features many of the island’s finest landmarks, such as the Aloha Tower and the Iolani Palace, and it is also home to some of Honolulu’s finest restaurants and cultural institutions.
Nearby, Chinatown is one of the most interesting and vibrant areas, where you will find beautiful temples, cutting-edge cultural and entertainment venues, a fine array of restaurants as well as some Chinese herbal and medicinal shops that sell a range of cure-alls.
To the North of the city, Pearl Harbor reminds of the Japanese surprise attack that led to the American intervention in World War II. To the East, the famous suburb of Waikiki awaits with its beautiful beaches, pounding surf, resort hotels, bars, and restaurants. Manoa, Hawaii’s university town, is a tranquil yet beautiful suburb tucked in between the mountains and towering above everything, while Diamond Head dominates the impressive skyline overall.
To Do & See In Oahu
The breathtaking island of Oahu offers an endless array of activities and sights. While relaxing on the beaches or braving the surf will always be Hawaiian specialties, culture and adventure should also be on the bucket-list: celebrate Polynesian culture at a luau, get a dose of modern culture in Honolulu or admire the mesmerizing natural reserve wildlife.
Dining In Oahu
The cuisine of Oahu has naturally been influenced by its surroundings – seafood, therefore, plays a large part in the local cuisine, complemented by excellent roast meats (the traditional kalua pork should not be missed), as well as by daring Asian influences. Dishes are served with a wide range of fresh fruits and vegetables including the local root vegetable taro, which is usually mashed to turn poi, a staple in the Hawaiian cuisine.
Maui, Hawaii – The Island
In Hawaiian mythology, it was demigod Māui to lift the Hawaiian Islands from the depths of the sea by lassoing the sun from the island’s highest peak, Haleakalā, bringing daylight to the islanders.
In the centuries that followed, Hawaiian culture was largely determined by the customs of Polynesian tribes until the rule of the House of Kamehameha, which lasted until the late 19th century. The island had also seen many explorers and missionaries during this extensive period, with James Cook being the first European to set foot here.
Besides being the Kingdom’s capital, Lahaina also served as the hub of the remarkably successful whaling industry. At the industry’s height between 1840 and 1865, as many as 500 ships would anchor at Lahaina’s port. The sugar industry too flourished during that time, and the installation of the first sugar mill in 1828 gave way to a massive influx of workers from China, Japan, Puerto Rico, Korea, the Philippines, Portugal, and other European nations, further increasing the cultural diversity of Hawaii, the 50th state of the U.S. today.
Apart from Lahaina, other significant places include Kahului, the commercial hub of Maui, Kihei, and Makawao. Today, tourism has become its main economic sector, and with the warm tropical climate that prevails on the island, Maui welcomes its visitors all year round.
To Do & See In Maui
Enjoy the pristine beaches with crystal clear water, roam the lush forests, and learn more about the island’s history with the plethora of activities Maui has to offer.
Dining In Maui
The eateries of Maui feature an ample lineup of international cuisine, all mixed with fresh Hawaiian flavors with the use of fresh local ingredients. Don’t miss out on Loco Moco, and the other delicious kalua and pu pu dishes.
Waikiki
The two-mile stretch of beach south of central Honolulu is the island’s main resort area and, thus, one of the biggest draws for tourists who flock here for laid-back vibes, gentle surf, dining, entertainment, nightlife and shopping. Lying in the shadow of the Diamond Head makes not only stunning views but also an easy access to one of Hawaii’s most famous landmarks.
Day 1
Fly into Honolulu on Oahu, airport code HNL. If possible, try to arrive as early in the day. It is suggested that you rent a car since you’ll be exploring other parts of the island during your time here (be sure to check out the parking rates at your hotel in advance). Make your way to your hotel, park the car, and get settled. When ready head out and spend the rest of the day exploring Waikiki. If you can, tackle on foot (it’s not too large) otherwise a hop-on/off bus is available. Grab dinner, drinks, and live music at one of the beach’s hotels to end the night!
Day 2
Fly into Honolulu on Oahu, airport code HNL. If possible, try to arrive as early in the day. It is suggested that you rent a car since you’ll be exploring other parts of the island during your time here (be sure to check out the parking rates at your hotel in advance). Make your way to your hotel, park the car, and get settled. When ready head out and spend the rest of the day exploring Waikiki. If you can, tackle on foot (it’s not too large) otherwise a hop-on/off bus is available. Grab dinner, drinks, and live music at one of the beach’s hotels to end the night!
Day 3
The morning and early afternoon will be spent at Pearl Harbor. Try to get there as early as possible – afternoons can get VERY crowded. If taking an organized tour (ensure it includes the USS Arizona), follow the instructions on where to meet and enjoy! If traveling there by car, leave ample time for the drive and traffic and to secure tickets to the Arizona. You’ll likely be there until around lunch. Return to your hotel and grab some food or a snack and spend some time on the beach or at the pool. Plan on going to a luau tonight (Germaine’s, Polynesian Cultural Center, Paradise Cove). Most include dinner and the show, and we highly recommend you book in advance. Before calling it a night, pack, and prep for departure tomorrow.
Day 4
Grab and go breakfast before heading to the airport. Ensure you leave enough time to account for the drive, rental return, and check-in. Relax and enjoy your quick island-hopper flight to Maui (OGG). Again, a car rental is recommended. Check into the hotel and spend the rest of the day getting settled and at the beach! If you’re feeling up for it, head to Lahaina in the evening – enjoy the local shops, galleries, bars, and restaurants, where you’ll grab dinner.
Day 5
Today you have options and it’ll likely be an early day, so grab breakfast quick. If you’re traveling during whale season, arrange a watching tour. If not, consider a visit to Haleakala Crater or drive the Road to Hana. Whale watching should be done in the morning and will be about two hours. That will leave time in the afternoon for the beach! If visiting Haleakala, we recommend doing so at sunrise (reservations required or afternoon is a fine back-up with no reservation needed) with plenty of beach time later in the day. The Road to Hana must be explored early as well. Allocate eight to 12 hours and incorporate stops at the many waterfalls and beaches, and snacks! Banana bread! Spend the evening in or around the hotel where you can grab dinner and drinks.
Day 6
Spend the day at leisure at your resort. Have a late breakfast, spend some time at the pool and hit the beach. If you’re up for it and would like to explore some more, incorporate one of the recommendations below or from Day 5 or 7. Spend a chill evening at or around the resort. Enjoy dinner, drinks, and local entertainment.
Day 7
Spend the day at leisure at your resort. Have a late breakfast, spend some time at the pool and hit the beach. If you’re up for it and would like to explore some more, incorporate one of the recommendations below or from Day 5 or 6. Spend a chill evening at or around the resort. Enjoy dinner, drinks, and local entertainment.
Day 8
Fly home. If time allows, grab a leisurely sit-down breakfast in or around the ho- tel before heading to the airport. Remember to leave ample time for the drive, traffic, rental return, and check-in.
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