When it comes to planning the perfect holiday, there aren’t many locations that can surpass the allure and quality of the Hawaiian Islands. With practically year-round warm weather, an abundance of delicious restaurants to choose from, and activities for any preference and budget, Hawaii pretty much has it all when it comes to vacationing.
Seeing the best parts of the state in one week is tricky, but it isn’t impossible. While you shouldn’t expect to experience everything Hawaii has to offer in a mere seven days, a week is certainly enough time to fit in some amazing highlights.
Day 1: Oahu (Honolulu)
Starting your trip off on Oahu (aka: “the gathering place”) is a no brainer. The Daniel K. Inouye Airport in Honolulu is the largest and most convenient gateway to the islands by far, with 50,000 passengers coming through every day and the most flights options for both international and domestic.
Waikiki is typically the most advantageous area to stay in if you’re just visiting Oahu for a few days. There are plenty of great accommodations to choose from for almost every budget, and no shortage of things to do. Spend today getting to know Waikiki and the surrounding beaches. If you’re looking for a more social experience close to the hustle and bustle and near the best oceanside bars, stay closer to the main Waikiki Beach in front of the legendary Moana Surfrider. If you’re looking for a quieter area with more space, head either west to Kahanamoku Beach, Fort Derussy, and Ala Moana, or southeast to Kaimana Beach near the Waikiki Aquarium and Honolulu Zoo.
Have lunch somewhere in town, or if you haven’t had enough beach time, then opt for a meal to-go at Tucker & Bevvy. The grab-and-go spot is known for their healthy picnic-friendly sandwiches, salads, acai bowls, and smoothies, perfect for the beach. Be sure to hang out to catch the sunset on the beach before dinner.
Day 2: Oahu (Roadtrip to North Shore)
Hit the road for an island road trip on your second day in Hawaii. Start in Waikiki and head east on the H1 Highway (this will turn into Kalanianaole Highway) past Aina Haina and Hawaii Kai. Stop at Hanauma Bay for some snorkeling or simply to take in the view; just a bit further down you can check out the Halona Blowhole from the lookout off the highway as well. Continue up past Sandy’s Beach, Makapuu, and Waimanalo, stopping along the way if you want to get in the water. Follow the signs to the HI-83 North to beautiful Kualoa Ranch where you can take a tour of the grounds on horseback or by jeep.
With the towering green cliffs to your left and the turquoise ocean water to your right, the drive from Kualoa Ranch to the northernmost tip of the island is simply breathtaking. Stop in Kahuku for some of the area’s famous garlic shrimp from Romy’s or Fumi’s, or curb your sweet tooth at Ted’s Bakery. Continue towards Waimea Valley for a quick hike among the historic botanical gardens and Haleiwa Town for a bit of shopping, before heading back down through the center of the island past the Dole Pineapple Plantation and Pearl Harbor.
Day 3: Oahu (Pearl Harbor & Luau)
Your third day on Oahu is best spent experiencing some of the history and culture that this exciting island has to offer. There’s a reason why Pearl Harbor is the number one most-visited attraction in the state of Hawaii; the area is steeped with events that bore great significance to the history of the islands. Because of its popularity, there are plenty of ways to get there. Choose from a number of highly-rated organized tours if you want to get the most out of your visit to Pearl Harbor, or simply take the Waikiki Trolly and even the public bus to visit on a budget. While the larger attractions within Pearl Harbor such as the USS Missouri Battleship and the USS Bowfin Submarine will cost extra to enter, the USS Arizona, the visitor center, and parking are all free.
In the evening, take your pick from one of Oahu’s many different luaus. If you’re driving, consider one near the west side of the island such as Chief’s or Paradise Cove. If you’re sticking close to Waikiki, the Diamond Head Luau (on the grounds of the Waikiki Aquarium) and Waikiki Starlight are excellent choices as well. Don’t forget to book tickets in advance, as some of the more popular luaus have been known to sell out on the weekends during the busy season.
Day 4: Maui (Paia)
Just a few short miles from Kahului Airport, the artsy surfing town of Paia is the perfect introduction to Maui. Catch an early flight to Kahului (about 30-45 minutes in the air from Honolulu) and grab a rental car from there. There are a couple of options for accommodations in Paia, from vacation rentals to the chic Paia Inn. Check out Baldwin Beach Park—one of the largest and most gorgeous beaches in the region—or Lower Paia Park for some surfing or turtle watching (tip: Baldwin’s is great for romantic, evening sunset strolls). Paia has a truly relaxed vibe around it, with cute boutique shops and casual eateries that take full advantage of the area’s incredible access to seafood. This is also the location of one of the most iconic restaurants in the state, Mama’s Fish House.
If you’re up for it, drive south from Paia to visit Upcountry Maui. Go wine tasting at Maui Wines or explore the famous lavender fields in Kula. The tropical botanical gardens in this region are located on the slopes of the dormant volcano Haleakala, and contain hundreds of different special native plants.
Day 5: Maui (Road to Hana)
Wake up early to set out on one of Maui’s most famous and notorious-windy roads. Along the Hana Highway on the Road to Hana you can stop at some of the island’s most beautiful highlights such as Twin Falls, Garden of Eden, Upper Waikani Falls, and the black sand beaches as Waianapanapa State Park.
Don’t feel pressured to drive all the way to Hana, this trip is about the journey not the destination. If you’re strapped for time, just pick one or two highlights to see and spend a little extra time at each one before heading back. Keep in mind that although the map says the distance to Hana is just over 50 miles, the drive itself is full of twists, turns, and switchbacks (not to mention the time it will take to pull over and see the sights along the way), so try to allot much more time than you’d expect to complete the trip.
After you’ve made it back to Paia or Kahului, head west towards Lahaina. This part of the island is great for travelers as it contains a wide variety of accommodations and restaurants for any type of budget. If you’re not too tired from all the driving, take a walk down Front Street in Lahaina once the sun goes down, you’ll find all the best restaurants and shops there.
Day 6: Lanai Day Trip
Today you’ll be getting a taste of old Hawaii with a day trip to Lanai, nicknamed the “Pineapple Isle.” Take the ferry from Lahaina Harbor (don’t forget a return ticket) in the morning, the company can even help you rent a jeep once you reach the Lanai harbor to take you around the small island to see the highlights. If you don’t want to shell out the extra cash for a rental, there is a fantastic beach right within walking distance from the boat harbor once you arrive. Hulopoʻe Beach Park is hardly ever crowded and has some of the best snorkeling on the island thanks to the calm surf and protected reef. Bring a pack lunch to enjoy on the beach or get fancy with a snack at the nearby Four Seasons. Either way, make sure to take the short hike up to Sweetheart Rock on the left side of the beach to access the spectacular views, or spend some time exploring the pristine tidepools instead.
If you do decide to rent a car, drive towards Lanai City, the largest town on the island and home to most of the approximately 3,000 residents who live there. There are a couple of local shops and small cafes to choose from (we recommend family-owned Blue Ginger Cafe) if you want to grab a bite. Take some time to drive around the island and explore its highlights, including Shipwreck Beach where you can see an abandoned WWII ship floating nearby, the unique rock formations at Keahiakawelo (Garden of the Gods), or the Lanai Cat Sanctuary.
Once it's time to head back to Maui with your return ticket, be on the lookout for migrating Humpback Whales during the Winter mating season—the channel between the two islands is one of their favorite places.
Day 7: Maui (Lahaina)
Take advantage of your last chance to relax and enjoy the island on your final day in Hawaii. Start the morning with a hike up the Kapalua Coastal Trail, where the volcanic rock formations meet the sea just about 20-minutes from Lahaina. Spend the rest of the day lounging at the beach and wandering around Whalers Village.
Rent some snorkels at one of the beachside resorts and head to Black Rock Beach in Kaanapali — it has some of the best snorkeling on the island with frequent visits by Hawaiian Green Sea Turtles as well. Have lunch at Leilani’s on the Beach overlooking the ocean or grab one of Monekypod’s famous Mai Tais.
In the evening, why not cap the trip off with a night on the water? A sunset dinner cruise on the Trilogy catamaran, departing Wednesday-Mondays, comes with a four-course meal and a beautiful view.