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Hey! We are two Michiganders with adventurous souls looking to explore the beauties and wonders of this spectacular world. Our mission is to provide you with budget-friendly itineraries that inspire and encourage you to get outside, eat delicious foods, and enjoy high-quality brews. Ultimately, there are three key ingredients to any amazing trip: 

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2 Week Hawaii Itinerary: The Ultimate 14 Day Trip

Updated: Jan 19

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Maui & Kauai Travel Itinerary

Explore incredible hiking trails through lush forests, seaside cliffs, and sandy craters. Discover Hawaii's craft breweries, breathtaking beaches, local cuisines, and optimal lodging locations for a trip full of adventures.

Depending on where you are able to find an affordable round-trip flight, we would recommend starting your Hawaii trip in Maui or Kauai. We started in Maui, however, you can easily complete the below itinerary in reverse.

J&L Tip: When looking for a flight to Hawaii, use Google Flight's Explore Feature to determine the best round-trip. Within Hawaii, you can get an affordable flight to your first destination within the islands.

two week Hawaii travel itinerary

Day 1: Kihei, Maui (Arrival)

On Day 1, arrive on the paradise island of Maui. Maui is home to a lush rain forests, volcanic craters, spectacular beaches, and historic villages. It is also home to luxury resorts, shopping malls, and golf courses, however, this guide explores the unique parts of Maui and preferences excursions that cannot be easily found at home. We recommend planning five full days in Kihei in order to view the top sights, as well as, take in the beauty of this southern town on Maui.

Book your flight to Maui (Kahului Airport)

Where to stay in Kihei

Kihei is the ideal spot to stay in Maui. It rains much less frequently on the south side of Maui, is an ideal spot for day trips like Road to Hana and Haleakala, and is close to some of Maui's best beaches. We stayed at a wonderful VRBO just seconds from the beach. If our travels bring us back to Maui, we would book this VRBO again in a heartbeat.

Find great deals on lodging in Kihei


Getting around Maui

The best way to get around Maui is by car. If you are planning to visit multiple areas of the island, the best thing to do would be to rent a car. Depending on the activities you plan on doing on the island, a SUV or truck may be your preference due to less maintained roads. However, if your plan is to visit the popular attractions and parks of Maui, a sedan will suffice.

Day 2: Kihei

On Day 2, we recommend utilizing your jet lag to wake up before sunrise and head to Haleakala National Park! If traveling from the US, your body clock will be set 3-6 hours later than your 6am wake-up call, making this the perfect day to trick your body into waking up early :)

Have you ever seen the sun rise over an ocean of white, puffy clouds? Atop Haleakala's summit may be one of your only chances to witness this spectacular phenomenon. Of course, check your local weather app for the exact time of the sunrise on the day you plan on going to the Haleakala summit.

Sunrise Reservations Required for Entry: Book tickets ($1/vehicle) here 60 days prior to your scheduled trip

After admiring the breathtaking colors of the Haleakala sunrise, head down to the Haleakala Visitors Center to start the Keonehe'ehe'e Trail (more popularly known as "Sliding Sands").

In the afternoon, head to the "Hawaiian cowboy town" of Makawao. Spend some time meandering through this town and enjoy the eclectic shops & art galleries, or even grab a bite to eat at Komoda Store & Bakery, The Maui Cookie Lady, or Expresso Mafia.

Also Read: Haleakala National Park Day Trip Itinerary

Prefer a Guided Tour?

Day 3: Kihei

On Day 3, your body may be starting to adjust to the local time, however, our biggest tip is go to bed with the sun and wake-up with the sun while in Maui! Not only will this allow you to seize the day, but most beaches, hikes, and parks within Maui are best enjoyed in the mornings.

Spend the day exploring the beaches of southern Maui, such as Wailea Beach, Keawakapu Beach, Makena Beach, & Kamaole Beach Park I (our personal favorite).

Also Read: Best Beaches of Maui Hawaii

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If you are looking to break up your beach day with some activity, the perfect choice in southern Maui is the Lava Fields and Hoapili Trail. This area of Maui is a hidden gem that we consider a must-do in order to truly appreciate the vast Maui terrain.

The southern-most end of Makena Rd takes you through the Ahihi-Kinau Natural Area Reserve, which leads to the trail-head. As you wind through this beautiful terrain, admire the crashing waves, blowholes, and coral washed up along the pathway.

J&L Tip: Arrive here around 7AM for a chance to see dolphins swimming in the bay!


Day 4: Kihei

Spend Day 4 driving the famous Road to Hana. In order to see the top sites in just one day, we strongly recommend arriving at the first lookout on the Road to Hana by 7AM. Not only will this place you ahead of the traffic and crowds, it will allow you to see breathtaking lookouts, hidden beaches, spectacular waterfalls, and even allow time for the famous Pipiwai Trail's bamboo forest.

Discover all of the hidden stops, required reservations, routes, and parking tips in our Road to Hana Day Trip Itinerary.

The Road to Hana is one of the most popular things to do in Maui. Discover all of the hidden stops, required reservations, recommended routes, and parking tips in our Road to Hana Day Trip Itinerary.

J&L Tip: All of the hidden stops on the Road to Hana are pinned in our private Google Maps, FREE for all NBV readers and accessible without cellular service.

Prefer an Affordable Audio Guide?

Download these audio guides via the top-rated Shaka App for history, stories, music, and navigation. A great alternative to a guided tour!

Day 5: Kihei

On your last day in Kihei before moving to Lahaina, embark on our favorite hike in all of Maui, Waihe'e Ridge Trail. You will certainly find every moment of this 4.2 mile hike worth the effort. We have never seen such a perfect combination of vibrant green vegetation contrasting the picturesque blue waters of the ocean. On a clear day with high visibility, this hike is truly awe inspiring.

J&L Tip: Get here prior to 9AM for a spot to park and the best visibility at the summit.

hawaii travel itinerary pinterest

In the afternoon, head to the nearby Waihee Coastal Dunes and Wetlands Refuge for a peaceful walk along the coast, or head back to Maui Brewing Company in Kihei for lunch and a beer! Get $1 off beers and 50% off appetizers daily during happy hour from 3:30 to 5:30PM.

J&L Recommended Brew: Coconut Hiwa Porter 6% ABV; 30 IBU


Day 6: Kihei to Lahaina

On Day 6, we recommend moving your lodging to Lahaina. Although you could stay in Kihei for your entire duration on Maui, there are several days worth of activities available in Lahaina that make staying there more convenient.


Where to stay in Lahaina

Although Lahaina is impacted more by the island's trade winds, which leads to a higher probability of rain compared to southern Maui, it holds history and charm that allows you to immerse yourself into a more authentic Hawaiian experience. We recommend spending at least two full days in Lahaina.

Find great deals on lodging in Lahaina

Getting to Lahaina

The best way to get around Maui is by car. If you are planning to visit multiple areas of the island, the best thing to do would be to rent a car. The drive from Kihei to Lahaina is roughly 40 minutes along a paved highway. The drive is nothing short of breathtaking as you wind around the Maui coast.

J&L Tip: Stop at Papawai Point for a chance to see whales! (higher chances in January through March)

We recommend driving to Lahaina in the morning, which allows for a full day of activities once you arrive. Explore the quaint town of Lahaina, its local shops, and famous banyan tree. Grab some lunch at one of the best restaurants in Maui called Down the Hatch, which features open-air dining, daily live music, adult shaved ice, and delicious seafood items fresh off the grill. The experience only gets better once you head here between 2-5PM for their daily happy hour. Enjoy some Hawaiian cocktails like their Lava Flow, Mai Tai, or Pina Colada.

Try: Down the Hatch's Lava Lava Shrimp or Lobster and Crab Grilled Cheese.

Spend the afternoon relaxing at some of Maui's best beaches, such as Kaanapali Beach, Kahekili Beach Park, or Black Rocks Beach. Once evening hits, Black Rocks Beach offers a free evening Luau with lighted torches and cliff divers.

Also Read: Best Beaches of Maui Hawaii

Day 7: Lahaina

On your final day in Maui, get up early for some of the best snorkeling! Head 15 minutes north of Lahaina (driving) to Kapalua and the start of the Kapalua Coastal Trail. Kapalua Bay Beach was our favorite snorkel spot in Maui. From the second we put our heads under water, we saw a sea turtle swim directly in front of our eyes. Kapalua Bay Beach is in a protected bay that allows for great swimming and snorkeling alike.

Don't forget your snorkel gear!

From here, continue north on the coastal trail and wander along the many footpaths of the Ironwood Cliffs. Make your way to Oneloa Beach and admire some morning surfers catching waves. This beach is spectacular and secluded.

From Oneloa Beach, make your way to D.T. Fleming Beach. D.T. Fleming Beach is yet another gorgeous swimming beach and home to the famous Dragon's Teeth Access Trail. It is in fact open to the public, however, there are signs near the start of the trail warning of private property, which are referencing the neighboring resort/golf course. Stay on the trail leading to Dragon's Pointe and you will not be trespassing.

Make your way back to your car via the Kapalua Coastal Trail and continue exploring the nearby area! The Nakalele Blowhole is a 20 minute drive up the road and allows you to taste some of the best banana bread on Maui from Julia's Banana Bread Stand.

Also Read: Top Snorkeling Beaches on Maui

Last but not least, end your time on Maui with a truly incredible experience, a Luau! Going to a Luau in Hawaii is much more than just experiencing dinner and a show, it is experiencing a part of Hawaiian culture. Luaus date back to the early 1800s and are a feast accompanied by hula dancers and story tellers.

There are many luaus to choose from on Maui, however, we chose to experience the Old Lahaina Luau as it is the most authentic luau on the island. With an open premium bar and all-you-can-eat fresh local foods such as poi, Laulau, Lomilomi, salmon, poke, and Kalau pig, this meal is one you will never forget.

J&L Tip: Purchase tickets at least 3 months in advance. Selecting "traditional seating" provides the closest seating to the show!

Day 8: Maui to Kauai

On your eighth day on the Hawaiian island, make your journey to the luscious island of Kauai. We recommend spending at least four full days in Kauai, which is best split as two full days in the south (Koloa) and two full days in the north (Princeville).


How to get from Maui to Kauai

By Plane - Estimated $110-120 / Passenger

Book a direct train flight from Maui (Kahului Airport) to Kauai (Lihue Airport) via Hawaiian Airlines for roughly $110-120 per passenger. A non-stop flight will get you to Kauai in under an hour. While you may have heard about ferry transportation between islands in Hawaii, there are no passenger ferries that go from Maui to Kauai, so flying is the only option.

Find an affordable flight from Maui to Kauai here


Getting around Kauai

The best way to get around Kauai is by car. If you are planning to visit multiple areas of the island, the best thing to do would be to rent a car. Depending on the activities you plan on doing on the island, a SUV or truck may be your preference due to less maintained roads. However, if your plan is to visit the popular hiking trails and state parks of Kauai, a sedan will suffice.

Get an audio guide bundle for a driving tour of Kauai's top spots

Where to stay in Koloa, Kauai

We recommend spending Days 8 through 10 on the southern side of Kauai in a town called Poipu, Koloa. The benefits of staying on the south side of Kauai is that it rains much less frequently, is close to Waimea Canyon State Park and the Na Pali Coast, and has a high probability of seeing Monk Seals and Sea Turtles on the beaches.

We stayed in a wonderful Airbnb right across from great snorkeling at Lawa'i Beach. We found our location to be ideal spot to explore southern Kauai.

Find great deals on lodging in Koloa

Day 9: Koloa

On Day 9, enjoy the southern beaches of Kauai. One of the most famous beaches for snorkeling and wildlife sightings is Poipu Beach. One of our favorite beaches on Kauai for action and adventure is Shipwreck Beach. This beach has crazy waves, cliff divers, Maha'ulepu Heritage Trail along the Makawehi Bluffs, and monk seals sunbathing on the shoreline.

Don't Miss: A true hidden gem of a beach is at Kukuiula Small Boat Harbor, a local hangout with calm waters and tropical scenery.

We have two lunch and dinner favorites in the area that pair well with any beach day. The first is Da Crack, which serves affordable priced customized burritos. The second is Puka Dogs Hawaiian Style Dogs, Polish sausages that slide into a bun with a puka (hole) baked right inside and smothered with a variety of delicious condiments.

Read our full guide to Kauai for all of our suggestions


Day 10: Koloa

On Day 10, we recommend heading on a day trip to the Waimea Canyon State Park. Waimea Canyon is known as the 'Grand Canyon of the Pacific' and is home to the wettest place on earth. This leads to breathtaking views that are filled with vibrant and lush colors.

Head to this park early in the morning for the best visibility and minimal crowds. If time only allows for one hike, make sure it is this one! This trail can be challenging and muddy at parts, however, the views are incredibly rewarding! We even saw helicopter tours of the canyon happening directly at eye level.

Entry: $10/Vehicle + $5/Person (2021 Pricing). Available for purchase at parking lot kiosks.

There are many more remarkable viewpoints and hiking trails within Waimea Canyon State Park. Visit our full guide to Kauai to discover more activities along your day trip.

Prefer a Guided Tour?


If you like coffee, you certainly have to add Kauai Coffee Company to your must-visit list. The Kauai Coffee Estate is the largest coffee farm in the US and has a free self-guided tour of their coffee growing, harvesting, and roasting process. You can truly taste the difference in this tropically grown coffee.

J&L Tip: Head to the tasting room for free samples!

Day 11: Koloa to Princeville

The southern side of Kauai may have less chance of rain, but the northern side of Kauai has the most awe-inspiring tropical scenery! This is why it is best to split your time between Koloa and Princeville while on Kauai, to experience the best of both worlds. We recommend spending at least two full days in the Princeville area.

Getting to Princeville

The best way to get around Kauai is by car. If you are planning to visit multiple areas of the island, the best thing to do would be to rent a car. The drive from Koloa to Princeville is roughly one hour (40 miles) along a paved highway. You may hit traffic in Wailua during rush hour, therefore, we recommend heading to Princeville early in the morning.

J&L Tip: Drive through the Tree Tunnel to spot 100-year-old Eucalyptus trees!


Where to stay in Princeville, Kauai

We recommend spending at least two full days in the Princeville area. The weather is much less predictable on the northern side of Kauai and lodging generally more expensive. Therefore, you may choose to stay in Wailua (30 minute drive from Princeville) for more affordable lodging.

Find great deals on lodging in Princeville

Day 12: Princeville

On Day 12, wake up early to hike the famous Kalalau Trail. Kalalau was our absolute favorite hike we did while on Kauai. The views are truly surreal and it feels as though you are hiking within a postcard. Never have we witnessed such lush green and vibrant blue colors in nature.

With that being said, this hike is not for everyone and comes with a bit of prep work. Read more here about a few requirements to hike this trail, modifications you can add, and reasons you may chose to skip it all together.

Whether you decide to hike the Kalalau Trail or not, visiting Haena State Park is a worthwhile experience. Ke'e Beach is a magnificent beach, perfect for snorkeling in its protected cove, or watching the sunset along the Na Pali coast. Nearby, is another ideal snorkeling destination, Tunnels Beach. This beach has a reef so large, it can be seen from outer space!

Review the Haena State Park entry requirements here


Day 13: Princeville

On your final full day in Kauai, soak up the sun at one of Princeville's iconic beaches. We recommend spending the day in the quint town of Hanalei. This town offers one of the most magnificent beaches in Kauai, local markets, food stands, and gift shops.

Try: Hanalei Bread Company for breakfast pastries and coffee!

Discover more of Hanalei with a tour!