Aloha, fellow Hawaii enthusiasts!
If you’re anything like me, you’ve probably dreamt about the perfect Hawaiian vacation countless times. Trust me, I’ve been there too. But hey, guess what? My boyfriend and I have cracked the code to exploring Maui, Lanai, and Oahu in just 10 days! Yeah, that’s right – three stunning islands in one single trip.
So buckle up as I guide you through our flawless itinerary filled with breathtaking beaches, exhilarating hikes, mesmerizing waterfalls, mouth-watering restaurants, and some hidden gems we discovered along the way. After years of island-hopping and soaking in all that Hawaii has to offer (I know – tough life!), we’ve put together a plan that caters to everyone’s taste for adventure or relaxation.
Now let me be honest with you – the past few island escapades haven’t always been smooth sailing (pun intended). In fact, my boyfriend once ended up on the wrong island altogether! But hey – experience is the best teacher; am I right? And now we’re here to share our valuable insights so your tropical getaway can be nothing short of paradise.
Warning: Don’t be surprised if after trying our foolproof itinerary you catch yourself daydreaming about buying one-way tickets back to Hawaii!
Alright, folks – grab your sunblock and flip-flops because it’s time for us to embark on this unforgettable journey together!
What tickets will I need for this trip?
– One-way ticket from the continental U.S: to Kahului Airport (OGG) – MAUI
– Ferry tickets between Maui and Lanai (Lāhainā Harbor to Manele Harbor)
– One-way tickets from Lanai City (LNY) to Honolulu (HNL) – LANAI to OAHU
– One-way ticket from Honolulu (HNL) to the continental U.S.
Day 1: (MAUI) Kahului Airport (OGG), settling in and hitting the beach
After landing in Maui, make sure to pick up your rental car first. There are about 9 different rental companies available at the airport, but it’s best to book ahead. If your rooms are not ready yet, heading to the closest beach is the best option.
1. Head to the hidden gem of Kanaha Beach Park (close to the airport)
Kanaha Beach Park is a hidden gem found next to the airport. This beach is mostly visited by locals, there is plenty of parking, and is usually uncrowded on weekdays. The best part is that it’s a 2-mile-long, white sand beach with a beautiful view of the ocean and it has a green lawn area with some shade. This is a perfect spot to have your first swim or enjoy some surfing.
2. NorthShore Zipline Co (ocean views and giant eucalyptus trees)
The next best visit on your first day is the NorthShore Zipline Co. it’s about 13 miles from the beach and airport and an awesome stop for some adrenaline, authentic Hawaiian views, and time in nature. Plan to spend about 2 hours here as 7 large zip lines are going through eucalyptus trees and looking out to the ocean. Feel well taken care of and safe, because the guides are well trained, helpful, and friendly.
3. Maui Arts & Cultural Center (live music and art exhibits in an outdoor venue)
For an evening activity, the best way to get into the Hawaiian spirit and check out some local culture is to visit the MACC. If you are lucky you can book ahead a concert. World famous musicians, theaters, and comedians are often guests here. If not the Community Events Lawn and Yokouchi Pavilion host free and amazing events almost every night. There is also the Schaefer International Gallery with amazing exhibits in their 4,100 square foot gallery. Whatever the program on your visit you will love it.
Day 2: (MAUI) Historic road to Hana – 5 must-see stops
The road to Hana is a world-renowned scenic experience, only available in Hawaii. Take the day to visit all or some attractions on this famous highway. I recommend doing at least 3-4 stops and grabbing lunch before heading back. The trip to Hana with stops takes 5 to 6 hours. The drive back is under 3.
1. Paia Town
This is a famous funky town where you can experience the true local scene of Hawaii. The main street running through this small place offers local food vendors, antiques, small local shops, handmaid goods, and galleries. Stop by Mana Foods to stock up on drinks and snacks for the day, or choose a great meal at Paia Fish Market or Flatbread Company.
2. Twin Falls (mile marker 2)
This is a great spot to enjoy a short hike or take a swim and jump at the waterfall. Park at Wailele Farm and take this 1-mile round trip hike for some beautiful lush views and a great waterfall swim spot at the end of the trail. The waterfall is a nice size and a safe place to cliff jump and take some pictures under the falls.
3. Hookipa Beach Park – The turtle watching spot (mile marker 9)
Stretch your legs and take a look at some amazing views from this beach park. This is a famous spot for green turtles and you are guaranteed to see some. If you miss them in the morning, catch them on your way back. They usually come in between 2 pm and 4 pm. Hookipa Beach is also known as a surf spot for professional surfers. Take some time and watch them perform some amazing skills.
4. Upper Waikani Falls (mile marker 19)
The largest and prettiest waterfall on the drive is also known as Three Bears because three great waterfalls are flowing into one swim hole. This is my favorite place to swim and have some snacks. If you feel comfortable walking down to the falls you can do it slowly from the road ahead. But don’t park on the bridge, drive up to the off-road parking just ahead. Here you can take amazing pictures while standing under the falls because there is great footing and it is shallow enough.
5. Hana Lava Tubes (mile marker 31)
The Hana Lava tubes (Kaʻeleku Caverns) were created thousands of years ago from free lava flows. This one is the biggest on the island and definitely worth visiting. It’s also a short 30-minute stop and a great way to get cooled off in the cave. There is a fee to enter, and you can pick up a flashlight to help you explore.
Day 3: (MAUI) West and Upcountry Maui adventure
The west and upcountry of Maui have both historically and culturally great spots to visit. Every visitor should find a way to visit the infamous Haleakala Crater and Iao Valley. The beach lovers won’t want to miss Kaanapali Beach (one of the most beautiful beaches in the world). Do them in the below order and end up near Lāhainā Harbor for your trip to Lanai.
1. Haleakala National Park and Crater (world famous sunrise)
You shouldn’t visit Maui and not walk atop its famous inactive volcano. These are also world-famous places to catch a sunrise (or sunset for the sleepy tourists). It is well over 10.000 feet high providing an amazing view above the clouds. A once-in-a-lifetime experience. The road up the volcano is well kept and maintained. There are several bathrooms before the visitor center. Unfortunately, this is a popular spot, so you need to reserve your space well ahead and arrive 120 minutes before sunrise (it would be a shame to miss it).
Pro-tip: Unlike the beaches of Maui, it is very cold in the crater. Make sure to bring warm clothing, blankets, and closed-toe shoes.
2. Iao Valley State Park
This trail is not open all year round (working hours are daily from 7 am to 7 pm – but call ahead due to work being done in the park). If you are able to visit it has amazing botanical gardens, jungle forests, and Iao Needle all stretched out on 4,000 acres. Set aside 1 to 2 hours to do the short hike and enjoy the scenery. This is an ancient and sacred space for the locals, so great way to understand and learn more about the culture.
3. Kaanapali Beach
This is the beach from postcards, with soft, dust-like sand, calm clear waters, and an easy entrance for swimming. In fact, it’s one of the most beautiful beaches in the world. This is a good spot for snorkeling (north end of the beach). The beach is long and wide, making it spacious and it never feels overcrowded. If you choose to watch the sunset here after your swim, you might witness the daily cliff diving ceremony off of Black Rock.
Day 4: (LANAI) Beach and fine dining
If you took the morning ferry to Lanai, you can visit all three spots on the list in one day and enjoy incredible swimming opportunities. If not, doing a beach and dinner is still very worth it on this unique island.
1. Hulopoe Beach (one of America’s best beaches)
This beach is less than four minutes from the harbor where the ferry dropped you off, so it’s a perfect stop regardless of when you arrive. The beach is right in front of the Four Seasons Resort Lanai (not to be confused with Sensei Lanai, Four Seasons Resort). It’s a gorgeous one-of-a-kind beach and the best spot on the island for snorkeling and swimming. It also has BBQ tables and grills, showers, bathrooms, and other amenities for a great and easy time.
2. Lopa Beach
If you want to feel like you are on a deserted island this is your spot (and one of the reasons you came to Lanai). Unfortunately, the road infrastructure is minimal on the island, so you will go through Lanai City to get there (a total of 25 miles from the ferry drop point). But if you ask me, this white sand, tranquil beach with a view of Maui is so beautiful, I would be willing to walk there. One option is to rent a 4×4 and camp out on this isolated and pristine beach.
3. Diner and relaxing (Sensei Lanai, Four Seasons Resort)
After a day of exploring this wild and natural island, and swimming at some white sand deserted beaches, it’s time to get pampered resort style. Book dinner at the Sensei by Nobu for a luxury meal in a jungle setting. This is a pine-covered secluded and luxurious resort with an extensive menu and style. If you want to treat yourself, know this is the best. Personally, I love the surroundings, extensive wine card, and delicious foods such as wagyu beef, roasted Kona lobster, and yellowtail jalapeno.
Day 5: (LANAI) Wild gardens, parks, and a hike
Use the second day on Lanai to explore the unique features only found on this island. I recommend checking out downtown, some awesome rocks, and boulders specific to the area, and finishing with an amazing hike.
1. Dole Park
Enjoy breakfast in a natural setting by visiting the small but beautiful Dole Park. The park is in the middle of the town square and allows you to explore the local surroundings. It’s surrounded by great local eateries, grocery stores, and art galleries. There is a play area for children and plenty of shade created by the tall Norfolk Pines and Cook Island Pine trees. We prefer to take a short walk after eating and then head to the grocery stores to stock up on snacks and drinks for the day.
2. Keahiakawelo (Garden of the Gods）
Don’t miss out on the Garden of the Gods. This is a 35-minute drive from Lanai City and it’s an amazing rock and boulder garden. This powerful boulder-filled area displays the power of nature and is a stark contrast to the lush greenery and beaches of the island. If you enjoy playing in the red dirt (this is what Mars looks like), or want to ride a fun 4×4 pick this place. Plan to spend 1 to 2 hours here, as you explore this desert-like area. While here, you will also get to enjoy a beautiful view of Molokai on clear days. Don’t forget to bring sunscreen, water, and a hat, because there is no shade. There is ample parking and easy access.
3. Koloiki Ridge Trailhead
Explore this 4.2-mile out-and-back trail near Lanai City. It’s a perfect place for solitude and reflection as it’s not a very busy trail. Considered an easy to moderate trail, you will complete it in under 2 hours (out and back). At the end of the trail, you will be rewarded with a unique panoramic view of Molokai and Maui. Consider a horseback riding tour on this trail or 4×4. You won’t be disappointed with this experience, it’s just up to you to find the best way to see it.
Day 6: (OAHU) Settling in and exploring the beaches of Waikiki
Waikiki is my favorite part of Oahu, and since it’s close to the Honolulu airport, we use it as our central hub. After flying in from Lanai, you have the option of lounging on yet another breathtaking beach before enjoying a unique and exclusive dinner.
1. Duke Kahanamoku Beach in front of Hilton Hawaiian Village
This is a fluffy white sand beach that can be enjoyed any time of the day. Though it is in front of the Hilton, it’s open to the public and there is a great large lagoon. This is perfect for families or those wanting to enjoy the shallow end without waves. The beach is also great in the evening, for having a nice meal on the beach with an incredible sunset or taking a romantic walk. A 10-minute fireworks show goes off on this beach each Friday night, so enjoy!
2. Stock up on some local sweets (Leonard’s Bakery – Famous for malasadas)
Leonard’s Bakery is a great stop to stock up on some authentic malasadas (best on the island). You can order ahead and pick it up, or visit one of their many food trucks (less crowded than the original store). The food trucks are located at Waikele Shopping Center, Pearl Ridge Shopping Center, Windward Mall, and Koko Marina Shopping Center. I highly recommend the custard, chocolate, coconut, macadamia nut, guava, and ube malasadas. But they also have nice cookies. The malasadas without filling can stay fresh for days and are perfect to take to the beach or hiking, as a snack.
3. Enjoy fine dining with a view of Orchids at Halekulani
For your first night on Oahu, you deserve a luxurious dinner in a perfect Hawaiian beach setting. Make sure to book a terrace table ahead of time to enjoy the sunset and beautiful night sky. The restaurant offers a great Sunday brunch buffet and endless afternoon tea, but the best offer is for dinner. They have some of the best wine choices in town paired with grilled octopus, lobster salad, or Hamachi Crudo.
Day 7: (OAHU) Check out the west leeward coast
The leeward coast is well known for dolphin watching and beautiful hiking trails. Combine a sandy beach, a short hike, and snorkeling with the dolphins, for a perfect day.
1. Swim with Dolphins in the Wild
This is the best place on the island to snorkel or dive with the dolphins. Two great agencies offering affordable and safe tours, including Ko Olina Ocean Adventures boat tour agency and Oahu Dolphin Divers in Waianae. Check out their turtle and dolphin snorkeling options for a safe, half-day adventure. The tours mostly last about 4 hours and have a guided professional. Check the amenities they offer with your trip.
2. Ko Olina Lagoons
If you are a fan of shallow sandy lagoons perfect for lounging in the sun, shallow end dipping in the water, and easy swimming, this is the perfect destination for you. Ko Olina Lagoons are a combination of manmade and natural lagoons in front of a beautiful resort. They are open to the public, so relax and enjoy. Here you can also snorkel or try paddle boarding. The resort offers great food options, so you can extend your beach time and enjoy a great meal.
3. The Maili pillbox sunset hike
Finish your day with the perfect easy hike and beautiful one-of-a-kind sunset. The trail is only a 15-minute drive from Ko Olina. It’s a 2 miles round trip and takes about an hour to complete. At the end of the trail, you will find two World War 2 bunkers perfect for one-of-a-kind pictures and shade. This is a perfect place to watch the sunset because there is a beautiful ocean view and there is great room for a picnic. Make sure to bring a flashlight with you, to help you return off the trail.
Day 8: (OAHU) A day of romance
If you have been busy getting as many activities in as possible, you might have forgotten to take a break. The second half of the trip is a perfect time to take some time and enjoy time with your partner in a romantic and fun setting. The following 3 activities go perfectly together.
1. Hoomaluhia Botanical Gardens
This is one of the most stunning and exotic places to spend a morning. There is no admissions fee and you can always find parking. The botanical garden is well stretched out and covers more than 400 acres, which are protected. The views are amazing with perfect picture opportunities and jungle-like plants. Try the Hoomaluhia Lake and Stream Trails which are about 1.5 miles long, or just find a perfect place for a short picnic. It’s easy to find your way around because there is an online map with walking paths and all the park amenities.
2. Winery Oeno – Beat Island Style Wine Tasting
This funky winery is less than 15 miles from Waikiki and 7 miles from Hoomaluhia Botanical Gardens. It’s easy to book a tasting ahead of time (online) and it’s usually not crowded. The winery is situated in an industrial area in a small warehouse-type building. The tasting included six types of wine – think watermelon, pomegranate, coconut, lime, and pineapple flavors. Order some sourdough bread and garlic butter to go with your wine, and enjoy the music and friendly service.
3. Boat ride, sunset, show, and dinner all in one! (Maui Sunset Luau Dinner Cruise)
The Maui Sunset Luau Dinner Cruise aboard the Pride of Maui is the best and most worthwhile sunset cruise. The price includes a sunset ride along the coast, an open bar, freshly prepared dinner, and a luau show. They have Polynesian dancers with a wonderful but not distracting show which really adds something extra to the experience. The staff is extremely efficient and friendly. The bartenders will make just about anything you can think up and the dinner is fresh and delicious. They accommodate vegetarians and have gluten-free options as it’s a plentiful buffet setup.
Day 9: (OAHU) all the excitement of Honolulu
Even if you spent your whole vacation in Honolulu, you would not see all the sights it offers. Here is a great combination of the best snorkeling, artwork, and the top Hawaiian luau on the island. Do them in this order and you will feel refreshed and amused all day.
1. Hanauma Bay Nature Preserve – Amazing snorkeling
The preserve has more than 400 species of tropical fish along with many corals and green turtles. It is a turquoise blue oasis with tide pools suitable for children and adults. This is an amazing place to snorkel in the calm waters, or you can just swim and sunbathe. Because it’s a preserve they limit the area to 1.000 visitors per day. Make reservations ahead by visiting the Honolulu parks & Recreation website. The park hours are from 6:45 a.m. to 4 p.m. and I recommend you get there early. Feel free to bring your own food and drinks, but only a small cooler. They also have a snack bar.
2. Take an art tour at the Honolulu Museum of Art (and grab a lunch)
Make sure to plan a visit to this abundant and culturally rich art museum. There are over 50 thousand works on display and a sizable collection of Asian artwork. The time span is from ancient to modern, so everyone will find works they love. Look for a tour for additional information. Tours are free to join with general museum admission but do require registration. Also, grab a fresh lunch at the HoMA Café, which has been part of the museum for over 50 years, then continue exploring. They also have a
3. Traditional outdoor Luau (Waikiki Starlight Luau at Hilton Hawaiian Village)
The best and most extravagant Luau on the island is held at Hilton Hawaiian Village. The open-air placement of the luau is amazing and accompanies an amazing sunset and oceanfront view (held by the lagoon). The luau lasts almost 3 hours and includes live music, leis, hula lessons (if you wish), a delicious dinner, and a traditional show. The show is exciting and diverse including different traditional dances and there is even fire involved (Fire Knife Dance). The dinner is delicious and the portions are nice. Try a couple of their great Mai Tai cocktails while here! There is a Golden Circle Seating option and a Premier Seating option, but both are splendid.
Day 10: (OAHU) spend a relaxing day at the spa and shopping
On the last day of your trip, I recommend taking a short forest walk or a quick dip at your closest beach. This is also a great day to make sure everything is packed, and all the presents are bought. I like to end my vacations with some shopping and a massage, to get me ready for the trip home. These activities are not strenuous and don’t have to take up your whole day.
1. Manoa Falls Trail Hike (Easy hike to the best waterfall on Oahu)
It’s a shame not to do this short 1.6-mile round-trip hike that will take you about 45 minutes. It’s best done in the morning when it’s less crowded, and I recommend you bring some breakfast with you. Mona Falls trail is impressive and so beautiful it was used in the movie Jurassic park and the series Lost. The vegetation here is lush, exotic, and diverse. The best part is the 150-foot waterfall at the end of the trail.
2. Royal Hawaiian Shopping Center
This is a great shopping spot and it’s only a minute away from Waikiki beach. There is a huge selection of over 90 stores and 30 restaurants, ranging from luxury brands to local vendors. So grab some more gifts for your family, or treat yourself to something special. I love grabbing a meal here since they have some top food available. Check out my favorites including upscale Wolfgang’s Steakhouse, Doraku Waikiki, Il Lupino Trattoria & Wine Bar, and Pho Factory. You can spend several hours here and enjoy some great outside seating.
3. Massage package (single or couples) at Lava Massage & Day Spa
Lava Massage & Day Spa works until 9 p.m. so schedule your massage right after the sunset. This is a super professional spa with a huge offer of services for couples or individuals. The best way to enjoy your time is with a wellness package. I recommend the signature facial and body massage which last 60 minutes each. For couples try the COCO package at 100 minutes. It includes a full body massage, a mini facial, and a 10-minute Lilikoi sugar foot scrub. To secure a spot here you need to book well ahead, so do plan.
The Hawaiian Islands are a tropical paradise and well worth multiple visits.
If you are lucky to have a 10-day vacation, don’t miss out on this itinerary. It’s a great way to island hop quickly and conveniently. You will love Oahu, Maui, and Lanai, as each island offers something special.
Options here are unlimited.
If you want a garden and jungle experience on a secluded island you will love your time in Lanai.
If you love the action of a bigger city with the best tours, restaurants, and beaches, you will love Honolulu.
Don’t miss out on driving down one of the most beautiful roads in the world as you head to Hana.
Haleakala National Park and Crater will be a once-in-a-lifetime experience in Maui.
So enjoy your trip and send us suggestions for other great stops on this trip.
Last Updated on April 6, 2023 by Brigitte