The Perfect 2-Week Hawaii Itinerary: Unforgettable Experiences Await!

Aloha fellow island-hoppers!

If you are lucky to have 2 weeks to travel to Hawaii, I can help you make the best out of your trip. As a bona fide Hawaii enthusiast, I’ve spent countless hours – not to mention calories – exploring the best of Maui, Lanai, and Oahu with my boyfriend. And now, I’m excited to share our tried-and-true 2-week itinerary that’ll have you soaking up paradise like a pro in no time.

You see, embarking on an unforgettable Hawaiian adventure shouldn’t be rocket science. You want to hit those must-see spots without feeling like you’re constantly battling crowds or wasting precious vacation time. That’s where I come in: after years of perfecting this journey, I can guarantee it covers all the bases – from pristine beaches to heart-pumping hikes and everything in between.

As someone clearly itching for an epic escape (and hey, who isn’t?), you deserve only the finest experiences Hawaii has to offer. My firsthand knowledge ensures that’s exactly what you’ll get on this whirlwind tour across three enchanting islands.

Warning: prepare yourself for some serious envy from family and friends as they ooh and aah over your amazing Instagram-worthy snaps!

Ready? Grab those flip-flops and let’s get started on creating memories that’ll last a lifetime!

What travel tickets will I need for this trip?

–       Arrival: Kahului Airport (OGG)

–       Ferry MAUI to LANAI: Lahaina Harbor to Manele Harbor

–       Island flight: LANAI to OAHU: Lanai City (LNY) to Honolulu (HNL)

–       Departure: from Honolulu (HNL)

Day 1: (MAUI) Arrival and exploring

Kahului Airport (OGG) offers more than 9 different car rental companies right at the airport. Make sure you booked ahead so that your car is waiting for you. Depending on your arrival time and hotel check-in time, you can go straight to the beach and then settle into your hotel.

1.    Kanaha Beach Park (close to the airport)

This beach is right by the airport and often overlooked by tourists. It’s a great local gathering spot without crowds, and there is plenty of parking. This place is gorgeous with a 2-mile-long white sand beach. There is also a nice grass area for picnics and some shade. Asides from the ocean view, this beach also has a fantastic mountain view in the background.

2.    Maui Pineapple tours

Just a short ride from the beach or airport (10 miles) is the Maui Pineapple tour at the Maui Gold Plantation. They have great tours that you can book ahead of time, online for 9:30 a.m. or 11:30 a.m. depending on your flight. Believe me, this is much more fun than it sounds, because it’s a fun 1.5-hour trip through the pineapple fields with great information, jokes, and juicy pineapple tasting. This is a good way to learn about the agriculture and traditions of the island. You also get a perfectly packed free pineapple to take home.

3.    Maui Arts & Cultural Center (live music and art exhibits)

The best way to experience all the culture and music the island has to offer is by visiting the Maui Arts & Cultural Center. If you are lucky you can book ahead a great event. They attract some of the world’s best theaters, musicians, and stand-up comedians. If not, they have two amazing outdoor venues that are usually open to the public. Visit the Community Events Lawn and Yokouchi Pavilion for amazing live music and hanging out in the open-air space as the sun goes down (bring a blanket and use their lawn chairs). On your way don’t miss Schaefer International Gallery with a huge and diverse art collection covering over 4.000 square feet.

Day 2: (MAUI) Historic road to Hana and East Maui

Driving down the Hana highway will give you the authentic feeling you have arrived in Maui. The way is full of waterfalls, short trails, and jungle-like forests. Take your time as it takes about 6 hours to get to Hana (with all the stops). Pick and choose, or visit them all.

1.    Paia Town – Cowboy culture

Start your trip with a stop in a small town, Wild West Paia. This place has held on to its authenticity and has an amazing local vibe. Here you can enjoy small shops, antiques, galleries, and local food vendors, before heading out. Try some food at Flatbread Company and Paia Fish Market. Also, we like to stop in at Mana Foods to stock up for the rest of the trip (great snacks and drinks here!).

2. Twin Falls (mile marker 2)

If you don’t want a long hike, but could use a swim at a waterfall, this is your pick. The twin falls are a sizable waterfall with a great swimming hole that’s safe and clean. It’s a safe place to cliff jump and have some fun. It’s easy to park at Wailele Farm (grab some fruit) and head out on the 1-mile round trip hike. Make sure to take some great pictures here.

3. Hookipa Beach Park – The turtle watching spot (mile marker 9)

I love this spot because there are some great professional surfers here that regularly gather. Just sitting on the beach and enjoying the show is a great activity for me. The ocean view is incredible. The bonus is that there are almost always turtles here, especially in the afternoon (usually come in between 2 pm and 4 pm). But no matter when you arrive there is something to see.

4. Upper Waikani Falls aka Three Bears (mile marker 19)

I never miss stopping by the Three Bears. This is my favorite waterfall and a great place to take photos. If you want to go down to the three waterfalls, park in the small parking up the road, then walk down the trail. Once you get to the swimming hole (never crowded), there are great opportunities to swim, jump and take pictures while standing under the waterfall. It is shallow on the edges, so you can cool off even if you are not a strong swimmer.

5. Hana Lava Tubes (mile marker 31)

This is the spot to get away from the sun (and light!). The Hana Lava Tubes are one of two lava tube spots on the Island. This is the better one. It will take you about 30 minutes to explore the large caves, and you get a flashlight with your entrance. It’s great to see these natural and unique formations carved by nature thousands of years ago.

Day 3: (MAUI) Explore the Upcountry Maui

The rolling hills and misty mountains of Upcountry provide you with the best food and drink tours, authentic towns, and the Haleakala volcano for the world-famous sunrise (or sunset). We are early birds and prefer to do the sunset, but if you love to sleep in, just flip around the itinerary.

1.    Haleakala National Park and Crater Sunrise

This infamous inactive volcano is about 10.000 feet to the summit. Asides from being part of the National Park and a true force of nature, it provides the most amazing sunrises and sunsets. Think – looking down at the sky. This is a popular location so make sure to make reservations for parking ahead of time. We also arrive 90 to 120 minutes ahead because there is usually a wait at the gate entrance. The road up is well maintained and there are restrooms available.

Note: Make sure to wear warm clothing and bring blankets. The mountain is much colder than the beaches, especially before sunrise. We prefer to bring a light breakfast and enjoy it on the mountain.

2.    O’o Farms coffee lunch tour (Best meal from Farm to Table)

They have breakfast with coffee and a lunch tour available. Both are amazing and you get a high-end fresh meal. Each tour lasts about three hours and includes a great walk through the farm grounds with information on sustainable farming, coffee growing, and native cultivation. The guides are farmers that work the land, so they are incredibly knowledgeable. Book ahead and the tour won’t be crowded. The multicourse meal is presented in a nice outdoor covered seating area and it incorporates a lot of the fresh fruits and vegetables picked from the farm.

3.    Makawao Galleries & Shopping

Clustered around Baldwin Ave. you will find at least five great art galleries to check out. Makai glass Maui is the must-see one. Not only are there remarkable pieces to look at here, but the kiln area where they make the blown glass is viewable from an upstairs seating area. If your luck some glass blowing will be going on. Viewpoints gallery and Hot Island Glass are also nice stops. Check out Maui Hands for handmade jewelry and woodwork by local artists.

Day 4: (MAUI) Relax in South Maui

South Maui has the sunniest and driest weather on the island. That’s in part why it’s known for its beautiful beaches. You are guaranteed a great swim here. Make sure to check out some unique sites also like the black sand beach and lava fields.

1.    Makena Beach or Big Beach

Only minutes from Wailea and Kihei the Big Beach is famous for its unparalleled beauty. The white sand beach is very long and over 100 feet wide. The water is a perfectly clear blue color at all times. This is a nice place to take a whim and sunbathe on a hot day. It’s spacious, so you won’t feel overcrowded. If you like you can enjoy professional surfing, but don’t try it unless you are a great swimmer. The ways can get big. But there are lifeguards.

2.    One’uli Black Sand Beach

This is a narrow long beach (with black sand) along a rugged shore. It’s not for swimming but a lovely and unique place for a picnic and stroll. There is a great green patch to the side of the beach to enjoy shade and food. If you are a good snorkeler, this is also a place for you. Overall it’s worth experiencing the unique lava-made sand and there is a scenic view of Haleakala as well.

3.    La Perouse Bay & Lava Fields

The lava fields and rugged bay were created by the lava from Haleakala. It’s a great walk with very contrasting scenery – off the beaten path for sure. Wonder the trail and feel like you are on the moon. If you are lucky some wild goats (and their babies) will be somewhere on your path. This is also a good place for skilled snorkeling. It’s not uncommon to see dolphins and turtles off the shore.

Day 5: (MAUI) Appreciate the West Maui natural beauty

This is a day to really enjoy the great things nature has to offer. They are fun, healthy, and free. Choose a long (or short) hike on the Lahaina Pali Trail and enjoy two adjacent beaches, both unique and fun.

1.    Lahaina Pali Trail Hike

This is an exciting and ancient 4.4-mile out-and-back trail near Lahaina that has many amazing stops and views. It is moderately difficult because there is a lack of shade, and some of the terrain is rocky. But you can cut the trail short and just go up to the Kaheawa wind farm. The wind farm itself is amazing to see with its size, and view of the ocean. Do this hike in the morning and wear sun protection because there isn’t much shade. It’s very worth it for someone who wants a great hike with amazing Hawaiian views to all sides.

2.    Kaanapali Beach

The most beautiful beach you will see in a while is Kaanapali Beach. It’s long, wide and not overcrowded. The sand here is fluffy, fine, and white. The water is clear, clean and a perfect shade of blue. This is a nice spot for snorkeling, especially the rocky side near the north end of the beach towards Black Rock. If you choose to watch the sunset here after your swim, you will witness the daily cliff diving ceremony off of Black Rock, which is a fun tradition and exciting to watch (if you are not scared).

3.    Black Rock Beach

While at Kaanapali Beach walk out to this unique Black Rock beach as well. This is a great snorkel spot for all skill levels where you can see octopus, eels, urchins, and much tropical fish. It is a contrast to Kaanapali beaches’ gentle white sand atmosphere, and it’s great to combine the two in one visit. This area is known for its large green turtle population, so you will see some guaranteed.

Day 6: (LANAI) The beach and a romantic resort evening

Take the morning ferry ride to Lanai to enjoy the full day of exploring the beaches. At night treat yourself to the most luxurious meal on your trip.

1.    Hulopoe Beach (one of America’s best beaches)

Don’t waste time after exiting the ferry, and make your way to this beach. It’s only about 4 minutes away from Manele Harbor. This beach is right in front of the Four Seasons Resort Lanai and is considered one of the best beaches in America. Asides from the gorgeous sandy beach there is great space for barbecues, picnic tables, showers, and everything you will need for a great day at the beach. The beach is especially great for swimming and snorkeling because the water is relatively calm.

2.    Lopa Beach (the deserted island beach)

About 25 miles from your ferry drop-off point and through Lanai City (due to limited roads on the island), is this hidden gem. The beach is pristine and tranquil, as you would imagine it on a deserted island. This is the perfect place to get away from tourists and civilization. Consider renting 4x4s and exploring the trail, or you can even camp at the beach. From the beach, there is a striking view of Maui.

3.    Luxurious dinner at Nobu (Sensei Lanai, Four Seasons Resort)

After a day of exploring, make sure to make your way to Sensei Lanai, Four Seasons Resort in Lanai City. Here you will have the best and most luxurious dinner on your trip (with an advanced booking). Nobu is an exclusive restaurant surrounded by a misty pine forest. The food is Mediterranean and Hawaiian and the chef is renowned. They have an endless wine and whiskey menu. But the best part is the high-end food prepared perfectly – just think roasted Kona lobster and yellowtail jalapeno and perfectly prepared wagyu beef. So if you don’t do anything else today, do come here.

Day 7: (LANAI) Jungle hiking and enjoying the small town

This is the smallest Hawaiian Island open to visitors. It has a lot of authenticity and charm. The best way to observe this is to spend some time in the town square exploring the shops and parks. The hikes here are full of beautiful views and lots of vegetation. So make sure to see every distinct type of atmosphere here.

1.    Dole Park

If you spent the night before dining and wining at Nobu, this is the perfect morning activity. Dole Park is a great place in the middle of the town square. It makes a great morning walk and a place to enjoy breakfast in the shade because it is covered by different types of Pine trees. The park is also surrounded by small local stores and you can see the most authentic part of the island here. Make sure to check out the nearby galleries and eateries. Also, stock up on snacks for the day.

2.    Keahiakawelo (Garden of the Gods

A drastic difference from the lush green jungles of the island is the Garden of the Gods. It gets its name from several Hawaiian legends, but it’s really an amazing red rock garden. Most will agree it’s like walking on Mars while you are here, and the area is huge to explore. Plan to spend 1 to 2 hours here, as you explore this desert-like area (you won’t run out of things to see). Also, there is an option to rent a 4×4 and just have some additional fun.

Note: Sun protection, a hat, and lots of water are a must. There is no shade here.

3.    Koloiki Ridge Trailhead

For the best panoramic view of Maui and Molokai, just follow this great trail. The hike is easy to moderate and will take you under 2 hours to complete the round trip (with a few photo stops). The trail is 4.2 miles out and back and near Lanai City. It’s the best trail on the island and can be done by almost everyone. If you don’t wish to walk it, there are 4×4 and hoarse tour options, which add to the adventure. This is a great trail to see a good portion of the island and end your adventure here.

Day 8: (OAHU) Settling in and exploring the beaches of Waikiki

Arriving from Lanai to Honolulu and Waikiki will be a big change in scenery. If you settle in Waikiki you will notice the hustle and bustle of this beautiful area, but also many things to experience and see. After checking into your hotel it’s best to check out one of the best beaches and have dinner with a view.

1. Duke Kahanamoku Beach in front of Hilton Hawaiian Village

Yes, my favorite beach in Waikiki is in front of the Hilton, and you will love it too. This is a white sand beach perfectly maintained and with a large lagoon for easy swimming. There is a nice shallow end and the water is calm. This is a place to sunbathe, read a book or just relax. If you stay longer, the beach has an amazing sunset and usually other activities. On Friday nights there is a nice long fireworks show, so try to catch it.

2.    Enjoy fine dining with a view at the restaurant Orchids at Halekulani

You won’t find a more luxurious dinner and ocean view than at the Orchids at Halekulani. Just keep in mind this is a sought out location, and you will need to book a ways ahead. I always prefer a terrace table for additional privacy and an amazing view. This restaurant serves top wines and food. Don’t miss out on trying the grilled octopus or lobster salad.

Note: If you decided to have a beachside picnic, consider visiting this restaurant for a Sunday brunch buffet or their great afternoon tea.

Day 9: (OAHU) Explore the windward coast

The windward coast provides some one-of-a-kind activities. The most efficient way to see the best of the best is to start at the temple, do a 4-hour sandbar tour and then finish with the phenomenal botanical gardens, before heading home. All three activities are close to each other but plan to be active for about 7 to 8 hours altogether.

1.    Byodo-In Temple – A beautiful Japanese Buddhist temple

Anyone can enjoy this place because the Byodo-In Temple in the Valley of the Temples Memorial Park is welcoming and open to all religions and faiths. It’s most peaceful to visit in the morning and set aside at least 1 hour to enjoy the temple and its grounds. Here you will find a large koi pond, turtles, peacocks, and swans. Also, there are several great Buddha statues and meditating areas. The most impressive sight is the 18-foot tall Lotus Buddha statue inside. And make sure to ring the several-ton peace bell before entering the temple! It brings longevity and happiness!

2.    Kaneohe Sandbar – Sand beach in the middle of the ocean

This is an exotic place where you can take some of the best pictures ever. Kaneohe Sandbar is essentially a pristine sand beach in the middle of the ocean – think deserted island. The water is crystal clear and the sand is incredibly fine and soft. The best way to get there is to take a 4-hour boat tour that organizes snorkeling and food. That way you have a boat for safety and a place to keep your stuff dry. When the tide is low the water is as shallow as your ankles, at high tide, it’s up to your waste (check for low tide times). Most tours also provide a nice burger and chips lunch. Make sure to wear a hat for shade. It’s in the middle of nowhere.

3.    Hoomaluhia Botanical Gardens

This garden stretches over 400 acres, and you will find the best plant life and wonderful jungle scenery here. Set aside 3 hours if you want to truly explore this area and bring food to have a picnic (next to the lake is a great rest stop). You can upload a map of the gardens at the visitor station and even get additional information about the trails. Many of the plants are labeled. This has become a famous place to take pictures, but you can just lay in the grass and relax.

Note: If you are not able to hike, there is a driving option to see most of the gardens. The road is paved and it takes about 20 minutes.

Day 10: (OAHU) Visit the North Shore

The North Shore is a 60-minute drive from Waikiki Beach and a well-worth day trip. The 7 miles of beach in the North are known as prime surf sports (for professional competitions) in the winter. In the summer months, it’s a good place to swim, hike, and turtle watch.

1.    Waimea Valley Trail – The cant miss waterfall hole for swimming

As you arrive at Waimea Valley there are usually workshops and crafts going on at the main entrance. There are even performances and hula shows at times. The best way to experience this trail (filming spot for Jurassic Park) is to do the 1.9-mile out-and-back trail which ends at Waimea falls. The trail is easy, kid-friendly, and mostly paved. It will take you under an hour to complete it in both directions (including stops). The hike is full of jungle vegetation and exotic wildflowers. The waterfall is over 30 feet tall and a safe comfortable place to swim. They even have lifeguards and free lifejackets. The brave souls will cliff dive.

2.    Go snorkeling at Shark’s Cove – Tidal pools and exploring in the shallow end

This is a great free place to visit with parking available. Sharks Cove is part of Pupukea Beach Park, and it’s a rocky beach made of lava. There are great shallow tidal pools to explore by walking around and observing the small animals in the shallow end. It’s also a great place for snorkeling or just soaking in the pools. They have nice facilities so you can take your time, shower, and use the bathrooms.

3.    Observe the sea turtles at Laniakea Beach

This beach is also known as Turtle Beach. This is the home to many green turtles that spend the day sunbathing here and enjoying the sand. The turtles can be seen year-round and at all different times of the day. But the best time to see them is between May and October. The beach is also very beautiful and has fine white sand. You can sunbathe, swim and snorkel here (just don’t get too close to the turtles, for their protection). I recommend this as an evening activity, but you will enjoy it any time of day. 

Day 11: (OAHU) Adventure to the Leeward coast

The leeward coast is much quieter and more peaceful than the Honolulu area. There are also fewer tourists. Spend the day enjoying some white sand lagoons, eating great fresh meals, and doing a short but powerful hike.

1.    Ko Olina Lagoons

The Ko Olina lagoons are comprised of 7 different manmade and natural lagoons. They are in front of the gorgeous resort but are free and open to the public. Enjoy a relaxing morning here and swim in the different depths the lagoons offer. This is also a good place to do beginner snorkeling and exploring in the sand. If you get hungry check out La Hiki, Noe, or Mina’s Fish House restaurants. They also have some great cocktail bars.

2.    The Maili pillbox hike – Watch an amazing sunset

The start of this trail is off of Kaukama Road and the hike is about 1.7 miles round trip. For most people, it takes about 35 minutes one way. It’s slightly steep, but generally can be done by the whole family and I consider it an easy hike. The best time to do this hike is before sunset, so you can enjoy it from the top of the trail. At the top of the trail, there are amazing panoramic views of the entire western Oahu shore. Also, the bunkers, give the trail the name –pillbox.  Bring some food and enjoy your time here, it’s really unique. Do bring a flashlight however for the trip back (just in case you need it).

Day 12: (OAHU) Get some romance and relaxation

No matter where you go, find time for romance. Honolulu has so many couple’s activities to offer that you will surely enjoy them all. Try a morning massage to get you going for the day. But if you only get to do one thing on this list, don’t miss the Maui Sunset Luau Dinner Cruise. It’s the best!

1.    Lava Massage & Day Spa couples massage

There is nothing better than getting the day going with a great couple’s massage. Lava Massage and Day Spa has an incredibly professional and highly qualified staff. The setting is relaxing and beautiful – Hawaiian style. Even here you and your partner can enjoy an amazing site view while being pampered. Everything is extremely clean. The best way to assure you get what you want is to book online and go through their offers. I personally recommend the couples massage and hot stones for 105 minutes. The COCO package is also great and includes a full body massage, a mini facial, and a Lilikoi sugar foot scrub. Whatever you choose you won’t be disappointed.

2.    Winery Oeno – Beat Island Style Wine Tasting

This pleasant winery is the only one on the island. Named after the goddess of wine it is only 15 miles from Waikiki beach. Visit in the afternoon for a great wine tasting and friendly hosts. Unlike wineries tastings you might have had on the mainland, this one is different. This is not fancy, but rather funky and fun. The wines also have interesting flavors like watermelon, pineapple, and coconut. Do the tasting and grab some dread and garlic dip while you enjoy learning about this small winery. It’s worth your time.

3.    The Maui Sunset Luau Dinner Cruise aboard the Pride of Maui

 This is the best available sunset cruise in Maui. Asides from being well priced, the tour offers a fun luau show aboard, an open bar with amazing bartenders and cocktails, a freshly made buffet dinner, and a sunset ride along the coast. I love that it doesn’t feel rushed, and there is abundant food and drink available. They really go all out. The Polynesian dancers are unique and great to watch. The staff is friendly and kind. I love it.

Day 13: (OAHU) Explore the best of Honolulu

If you haven’t yet this is the day to do the best luau and visit the reserve with the biggest collection of tropical fish. Spend the day in Honolulu and explore endless opportunities. The hike selected is on a paved road with an amazing view, so make sure you do it.

1.    Hanauma Bay Nature Preserve

The Nature Preserve’s work hours are from 6:45 am to 4 pm. So get there early. This is one of the best places you can visit in Hawaii if you want to see sea life, do amazing snorkeling or just hand out on a beautiful sandy reef with all the amenities. There are over 400 species of tropical fish living here along with many diverse corals and turtles. The water is crystal clear and blue. Since this park is limited to under 1 thousand visitors a day you need to make reservations ahead of time through the Honolulu parks & Recreation website. They do allow you to bring your own food, but only a small cooler. Inside there are showers, changing rooms, a bathroom, and a snack bar.

2.    Easy hike to Makapu’u Point Lighthouse

This is a great and easy trail with an amazing view at the top. The trail is paved and takes about 1.5 hours to do the round trip. The length of the trail is slightly over 2 miles round trip. There are many beautiful picture opportunities on the way (so no rush!) At the tip of the trail is a historic lighthouse from the early 1900s and a 600-foot sea cliff above Makapuʻu Beach. There are also great panoramic views of the open ocean and mountainside.

Note: There is very little shade on this trail so wear a hat and sun protection.

3.    Best Luau on the Island (Waikiki Starlight Luau at Hilton Hawaiian Village)

Don’t come to Hawaii and not experience a traditional lavish luau. The best one is held at Hilton Hawaiian village right in front of the lagoon with an amazing beach view. This only open-air Luau is fun, and entertaining, and lasts about 3 hours in total. At the price of admissions, you get live music, leis, hula lessons, a Tai Tai cocktail, a high-end dinner, and a show. The show has many dances for the Polynesian culture, but the best is the Fire Knife Dance. You won’t be disappointed with the Golden Circle Seating option or the Premier Seating option.

Day 14: (OAHU) Get ready for your trip home

Before heading home make sure you have bought everything, gifts, souvenirs, and maybe something for the trip. For history lovers visiting the Pearl Harbor campus will be a highlight of the trip.

1.    Visit the Pearl Harbor Museum campus

The visitor center on campus is open every day (Sundays too) from 7 am to 5 pm. The visitor center, two museums, and the USS Arizona Memorial program are free for all visitors. The USS Arizona includes a short boat ride with a guide and takes about 45 minutes. Also, don’t miss the two exhibit galleries: Road to War and Attack. You can comfortably spend 2 hours here.

2.    Ala Moana Shopping Center (largest open-air mall)

For all your shopping needs check out the biggest open-air mall in the world. There are over 350 businesses here including department stores, small local shops, and restaurants. Usually, there is even a hula show or live music while you shop. I recommend stopping by Diamond Head Chocolate Company for high-end handmade chocolate gifts for your friends. Also, grab the best smoothie at the local Blue Hawaii Lifestyle shop or Korean barbecue at Han No Daidokoro. There are so many choices.


Even though your vacation has come to an end, you can be sure that you experienced the best the islands have to offer with this itinerary. Visiting these three islands together is a great and diverse experience.

Everyone will find at least several great days on the list, so do them all or pick and choose as you wish.

Make sure to share this itinerary with your friends because it helps continue to put out quality, honest content.

Last Updated on April 6, 2023 by Brigitte