Not sure where to start at all? Look for flight deals. I always use Skyscanner and Google Flights when searching for airfare, and love the option to get email notifications when the price drops. Close your eyes and picture yourself in Hawaii — what do you see?
Cultural experiences? Romance and luxury? A bit of everything? Visiting Hawaii for the first time and looking for an exceptionally varied itinerary of things to do? Not scared of island hopping around Hawaii in record breaking time? On Maui, plan to wake up early to see the sunrise at Haleakala National Park, drive the curvy Road to Hana, go whale watching in the winter months , and relax at the idyllic golden-sandy beaches of Napili Bay and Kaanapali Beach.
On Kauai, your time will revolve around the rugged Na Pali coastline, with a helicopter ride to see it from above, a snorkel tour to see it from water, and hiking the first few miles of the mile Kalalau Trail no permit required for this section. Hawaii is the epitome of romance. With its abundance of spectacular sunsets, private swimming holes, lush rainforests, and exotic, tropical beaches, I can see why so many honeymooners choose Hawaii as their first trip as husband and wife.
Plan your Hawaii island hopping adventure to include lots of private beach time, hiking to secluded and not-as-popular waterfalls, splurge on private excursions sunset boat ride, anyone? Plan to avoid Oahu Honolulu and Waikiki are way over crowded with tourists , and the cities over on the Big Island. Romance on Maui: For a more beachy, less big-city vibe, be sure to add Maui to your Hawaii island hopping itinerary.
Romance on Lanai: If you want the ultimate honeymoon luxury privacy, of course , make sure to include tiny Lanai into your Hawaii itinerary. If adventures the name of your game, a 10 day Hawaii itinerary split between Kauai and the Big Island will really get your adrenaline rushing. At Hawaii Volcanoes National Park, you can hike next to active lava, explore lava tubes, and bike next to scalding hot steam vents.
Talk about adventure. Fill the rest of your days by snorkeling with manta rays, spelunking in Kula Kai Caverns, and hiking to waterfalls in Waipio Valley. We love Maui the most. We just do. And those 7 sacred pools and the Pipiwai Stream Trail through a bamboo forest towards the end of the drive is absolutely spectacular.
Large, secluded sea caves. Volcanic tubes and spouting blowholes. Coastal hiking trails. Snorkeling at Molokini and Turtle Town: If you wanna admire the underwater world of Maui , plan to do so at both Molokini a crescent-shaped partially submerged volcanic crater and Turtle Town where turtles are known to hang out. A kaleidoscope of coral awaits! Exactly my point. We loved our time at the Feast at Lele, sipping liquid aloha, scarfing down multiple plates of food, and admiring the traditional dancers.
All in all, a very worthy way to spend an evening in Oahu. Enough said. Surf Town of Paia : This funky little surf town on the North Shore is full of cute little boutiques, great restaurants, and natural food stores.
Great to wander around for an afternoon or so! Our beach of choice whenever we visit Maui. Tons of fantastic hiking through the tropical flora of Hawaii and great views of the Iao Needle and other emerald peaks. Pretty incredible if you ask me. Check out how to spend the perfect 5 days in Maui here. West Maui: Kaanapali and Lahaina : This side of the island boasts some of the most beautiful beaches on the island, in my opinion.
Wailea : Known for its massive five star resort destinations which often come with a hefty price tag , yet more laid-back than lively Lahaina and Kaanapali. The menu changes depending on what fish have been caught that day one of my favorite meals in not only all of Hawaii, but the world.
Yup, world. Oahu boasts the infamous Pearl Harbor, Waikiki Beach, and the state capital of Honolulu, making it a great escape for those wanting a good mix of city and beach break. Waikiki Beach : One of the most famous beaches in all of Hawaii, and for good reason!
Honolulu is the biggest city in all of Hawaii, and is known for the the ever-so-popular Waikiki neighborhood, historic landmarks, Diamond Head, mai tai drink, world-class surfing, Hawaiian luaus, and its location as a military fortress.
The Hawaiian Green Sea Turtles have been frequenting these sands for decades, so do your part and respect them and their land. This pristine and protected marine ecosystem former volcanic crater is full of beautiful coral reef, loads of tropical fish, and other sea life. This formation occurs due to Diamond Head being a volcanic tuff cone and dormant volcano, which has resulted in the one-of-a-kind, , year old structure.
Pillbox Hike: While not one of the longest trails, the Pillbox hike may be one of the prettiest and historic on this Hawaii itinerary. Just take my word for it and go. Lanikai Beach: If you looked up the definition of a white-sand beach, the first thing that would pop up is a photo of Lanikai!
Found on the north side of Oahu, this scenic coastline has calm, clear waves perfectly suited for beginner surfers. And hula pie. Ohhhh the hula pie. We hardly had any service on the island our carrier is T-mobile which even works internationally , which made it annoyingly difficult to get around we rely on GPS way too much, no matter where we go.
The dark sky is like no other. I thought I had seen a lot of stars in Panama particularly San Blas , Thailand , and Crater Lake , but it was out on the furthest island in Hawaii where I definitely saw the most. I have a slight suspicion that we even witnessed the Milky Way — boy oh boy did I wish I knew star photography! Java Kai Kaapa : With so many delicious-sounding breakfast options, I kinda wish we had another morning to pig out.
Lots of smoothies and blended coffees available as well. Psst: we stopped by after our helicopter tour. Little Fish Coffee Poipu : Probably one of the most popular breakfast joints in Poipu for good reason. And yes, this place is crowded and then some. I loved this little spot so much I visited two mornings in a row, lines and all! Ha Coffee Bar Lihue : We stopped in for a quick coffee before our heli flight, but wish we could have stayed longer as it was super cute and the pastries looked delish!
The line is long, but it moves fast and the portions are HUGE. Also great for breakfast burritos in the AM. A few popular menu items include the garlic shrimp and the mango chili chicken. My poke bowl was unfortunately not the greatest, so maybe order something different. I kinda wish I ordered something from Fresh Bite next door. The beach is only a few minutes away so get your food to go and head on over!
Koloa Fish Market Koloa : In full disclosure we never actually made it here too much food, too little time , but this seafood market comes highly recommended. No frills but awesome poke and bread pudding. Be sure to go early for a few drinks on the back patio before your reservation highly recommended as this place is rather popular. Al dente rigatoni with pesto, olive oil, and sausage if you were wondering. Dukes Lihue : The Mac-nut fish was a-okay, but the real star of the show is their infamous hula pie.
Just picture a huge plate filled with Oreo cookie crust, hot fudge, macadamia nut vanilla ice cream, whipped cream, a chocolate ganache topping, with extra Mac nuts on top. Lanai Poipu : This place was oh so good. Enough said. And that purple sweet potato puree cue the heart eyes. But in all seriousness — the fish was oh so fresh, and I could have eaten here every night and been happy.
Hot tip: make sure not to call it shaved ice or snow ice, as those are very different things! Crazy, right? It is your vacation after all! May as well start this mini road trip by stopping at a foot waterfall, am I right? I mean, this IS Hawaii afterall! And best of all, the Wailua Falls lookout spot requires no hiking, so you can keep your boots at home!
Time to fuel up! After a quick stop or two admiring the falls, head north a bit to Kapaa, a historic beachside town on Eastern Kauai known for its colorful, eclectic storefronts. Worth an hour stroll or so. Next stop — Kilauea Point, for the lighthouse and wildlife refuge on the Northernmost tip of Kauai. What better way to learn about a unique biodiversity of seabirds and native coastal plants than by actually observing them, right?!
And plus, the views overlooking the Pacific are quite outstanding over here from the vantage point! Psst — the lighthouse is closed on Sundays and Mondays, so if you can plan your trip on a different day, do it! And if you want to get a tour of the lighthouse, visit on either a Wednesday or Saturday, as those are the only days tours are given.
Up for a mini adventure? Why not stretch your legs at a natural tidal pool carved into a lava shelf? Sounds ridiculously Hawaiian, right?! Be cautious to the max! Normally, Queens Bath is relatively safe during the summer months swells are on the smaller side , but during the winter it can get quite treacherous. You can grab a pair on Amazon here. A rogue wave nearly washed away 40 people here in January ! The road here occasionally washes out with winter rains and stays that way for awhile.
Princeville makes the perfect base to minimize drive time for beach time here. Oceanfront Luxury Penthouse Pua Pua. Enjoy one of the most iconic views on Kauai of the legendary Bali Hai coastline from this top floor penthouse. Listen to the birds sing and the waves crash below from the privacy of your lanai. Check price and availability on the oceanfront luxe penthouse here. The Westin Princeville Ocean Resort Villas is nestled on a cliff with all the amenities, including three swimming pools, Nanea Restaurant, and a shuttle service to golf courses and shopping.
Very friendly staff. And the very best way to fully appreciate this beauty—complete with rushing waterfalls—is to get out on the water! The best snorkeling cruises are small catamarans for a more intimate and personalized experience. Expect to see spinner dolphins and Hawaiian green sea turtles. Stay fueled with breakfast and a buffet lunch on board. Check price and availability on the Napali Coast snorkel tour here. There are so many incredible beaches to enjoy here that I recommend adding any extra days in your itinerary for more time here.
The others are easy to access. Features include golden sand, a shallow reef with plentiful tropical fish, and plenty of sea turtles. Anini Beach —Perhaps slightly lesser known than Tunnels, waves break farther out at Anini Beach due to the wide reef, making it also a great spot for snorkeling and turtle spotting.
Public restrooms are also available here. Families like the shallow water protected from the wind. Secret Beach —Possibly my favorite Kauai beach! This is a beautiful soft sand beach and it was deserted on the day we visited. Be prepared to scamper down a steep and muddy trail for this reward though. And the cute wooden pier makes for a great sunset photo. This beach backs up to the little town of Hanalei, which is a great spot for lunch or a meal.
And on your way here, be sure to stop by the Hanalei Valley Lookout. Just be sure to wear good shoes. I always take my Keens with me to Hawaii and highly recommend them. You can get them on Amazon here. Also, do not get into the tide pool! Be smarter. People have been swept away taking photos here. So do your due diligence and make sure conditions are safe.
Kilauea Lighthouse —The Kilauea Lighthouse is located on Kilauea Point in the wildlife refuge here and makes a great photo stop with the deep blue ocean beyond. Are you all packed for Kauai? Look for red-footed boobyes, albatross, and others here.
I particularly loved exploring the canoe gardens here. They showcase the plants that Native Hawaiians brought with them originally from French Polynesia as they thought about how best to make life on a new island. If you have five days in Kauai, day 4 is the day to move your base to Poipu.
If the north shore is wild and adventurous, the south shore is more flat and accessible. Visit Waimea Canyon for epic views and beach time on the south end of the island.
Stay oceanfront at Kuhio Shores in a corner condo with unsurpassed sunset views. Floor to ceiling windows, a glass balcony, and elevated views from the third floor give you an up-close view of parakeets that visit here…not to mention surfers, dolphins, turtles, and whales. Check price and availability of the Kuhio Shores condo here.
Location is perfect with snorkeling and activities near by. Very clean and modern feel with a lot of amenities.
The stunning penthouse at the Villas at Poipu Kai offers a luxury residence with resort amenities. These include a beachfront restaurant, heated pool, and hot tub with a waterfall. Plus, you can walk through the manicured grounds to the white sand of Shipwreck Beach and Poipu Beach.
Check price and availability at Villas at Poipu Kai here. Keep going past Poipu and wind your way clockwise back around towards the top of the island. If the road went all the way through, it would be easy to zip over here from the north shore.
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