Dreaming of vacationing in tropical paradise? Book a trip to Kauai, Hawaii’s Garden Island. With endless miles of pristine beaches, azure waters, emerald mountains, cascading waterfalls, and charming towns, Kauai will capture your heart and soul.
Kauai’s laid-back culture and slow-paced lifestyle will immediately relax you. At the same time, Kauai has no shortage of things to do. Whether your family is into adventure, nature, watersports, shopping, dining, or wellness, Kauai’ will delight and enchant.
My husband and I last visited Kauai twenty-five years ago on our honeymoon and absolutely loved it. This time we were so excited to travel with our two daughters to see this magical island through their eyes.
I realize this itinerary is jam-packed and leaves little time for lounging at your hotel or soaking in the sun on the beach. This four-day itinerary can easily be adapted to fit your time frame, pace, and preferences.
Download Your Own Personal Guide
Before arriving, download the GuideAlong app and buy the Kauai audio tour. This app uses GPS to seamlessly narrate your journey around the island, providing detailed—and at times hokey—commentary on Kauai’s rich history, unique topography, and captivating legends. We appreciated the driving tips and suggestions of where to pull over for jaw-dropping views.
Day 1 — Toes in the Sand, Eyes Across the Canyon
Kickstart your day bright and early with a photoshoot at one of Kaua`i’s most dreamy spots, Shipwreck Beach. With the ocean mist and gorgeous cliffs behind us, we had a blast frolicking in the sand and surf as our uber-talented and experienced photographer Jason Phillips, the owner of JRP Photography, kept us laughing and smiling with his sense of humor and patient nature.
His massive volume of 5-star reviews was spot-on. Jason’s frame-worthy photos captured the Aloha spirit, and his ability to put us at ease produced authentic memories, which no doubt will become our favorite souvenirs from this trip.
With an early start to the morning, hop in your car and begin the ascent uphill to soak in the natural beauty of the miles-long Waimea Canyon. By following our trusty GuideAlong app, we easily hit all the top stops, including our favorite one—the official viewing platform lookout at mile marker ten— with expansive panoramic views right at the rim.
This should be the first lookout you visit, not only because it’s the first one you arrive at, but because it gives you the most expansive view of the canyon. No wonder Mark Twain called this colorful geological marvel “The Grand Canyon of the Pacific!”
TIP: Be careful to pull over only if it’s safe. Be respectful of locals when driving and don’t block traffic.
Continue heading north to explore Kōkeʻe State Park. Stop for lunch at the cozy Kōkeʻe Lodge, or pack a picnic to eat on the abundant green space nearby. Way up high, thousands of feet above sea level, wrapped in our windbreakers, we made two quick stops at the Kalalau and the Puʻu o Kila Lookouts. Enjoy the sweeping views of the majestic cliffs, deep valleys, and the glorious North Shore.
Once you return to sea level, head to Poʻipū Beach Park, designated America’s Best Beach by The Travel Channel. This crescent-shaped beach with golden sand delights tourists and locals alike. This beach is the ideal place to take a dip, snorkel, boogie-board, surf, picnic, and if you’re lucky, sight a monk seal!
If you time it right, shortly before sunset, you might even witness huge Hawaiian green sea turtles, honu, slowly making their way from the surf onto the sand to take a nap. Remember, the honu are a threatened species, and the law requires you stay at least ten feet away from them.
Head across the street to Brennecke’s Beach Broiler, celebrating its fortieth anniversary this year! We first dined here on our honeymoon, and we once again enjoyed the spectacular beachfront view, sitting by the expansive open windows that invite balmy breezes to compliment the tasty dishes.
The family-owned and kid-friendly Brennecke’s provides a relaxed and upbeat beachy vibe with hundreds of college-logoed hats, pennants, and shirts hanging from the walls and rafters. Brennecke’s is known for its extensive selection of shareable pupus (Hawaiian appetizers).
They inlude Ceviche Wonton Tacos and Coconut Shrimp, and loads of tasty main courses, including freshseafood options such as Wasabi Seared Ahi and Macadamia Nut Crusted Fresh Catch, as well as plenty of burgers, sandwiches, salads, and well-seasoned steaks.
Brennecke’s extensive bar offers everything you could possibly desire, ranging from our favorites, frosty tropical Lava Flows, to their world-famous Mai Tais (they have served over two million of them!). Luckily, we saved just enough room for Brennecke’s gooey chocolate lava cake topped with Lappert’s ice cream. Mmm!
Day 2 — Pick Your Passion
Spend this day exploring your crew’s favorite pastimes.
Morning
Tee Time: After playing a round at the Kukuiolono Park and Golf Course on our honeymoon, we knew we were in for a treat upon our return. This challenging public nine-hole course (with the most inexpensive greens fees on the island, as well as affordable equipment and cart rentals) serves up stunning ocean and mountain views. If time permits, check out Kukuiolono’s mini-golf, Japanese gardens, and park.
Get Wet: Kauai’s coastline is so beautiful it begs to be seen by boat. Choose from a luxury catamaran or a wet-and-wild rigid hull raft ride to tour the dramatic cliffs, spy some spinner dolphins, and snorkel among the sea life.
For the best odds of calm waters and clear snorkeling, opt for an early morning departure which includes lunch, or stay dry and set sail at sunset. Based on my research, Captain Andy’s comes highly recommended.
Afternoon
Retail Therapy: Stroll the quaint and historic Old Kōloa Town which channels a cowboy vibe, but now houses a variety of chic and kitschy souvenir shops and casual restaurants. One highlight was stopping into the barbershop-themed The Fresh Shave to sample some of the island’s best gourmet and all-natural organic shave ice.
It’s fun choosing among the menu’s flavorful fruit concoctions with punny names based on mustache styles, such as The Handlebar and the Fun Manchu. Just a few minutes away, you’ll find The Shops at Kukui‘ula, a premier shopping mall with high-end boutiques, art galleries, and upscale dining options.
Connect with Nature: Kilohana Plantation offers a kid-friendly 2.5-mile train ride touring the island’s crops and fruit orchards, coupled with a visit to feed pigs, goats, donkeys, and sheep. For those 21+, consider embarking on the plantation’s rum safari, a similar tour upgraded with sips throughout of Koloa rum in their signature Mai Tai.
After a long day of fun and sun, it’s time for dinner at a true gem consistently rated as one of the top luxe dining destinations worldwide, Tidepools, at the Grand Hyatt KauaiResort. We last dined here on our honeymoon and were wowed, once again.
A romantic, calming mood envelops you while sitting under thatched-roof bungalows perched above a koi-filled lagoon, surrounded by glowing tiki torches, with the sun setting on the nearby beach. Tidepools boasts a modern Hawaiian-inspired menu starring local ingredients and genuinely delectable dishes. Feel the relaxing vibes take over as you sip on your tropical cocktails, such as Pineapple Julep or Old Fashioned Aloha.
Kick off your meal with a bang by selecting from a wide range of starters, including Baby Lamb Chops, Hamachi Sashimi, or our favorite, the aptly named Dynamite Crabcakes. Two memorable entrees for us included the Hawaiian Catch, with its tantalizing combination platter of soy-ginger glazed fish, cold water lobster, shrimp, and scallop complemented by a lemongrass beurre blanc, and an expertly prepared juicy New York strip steak topped with Koloa Rum compound butter.
Vegetarians, like our daughter, will not be disappointed in choosing among inventive entrees such as Tofu Pad Thai, Forbidden Rice, Crispy Tofu, and Vegetable Fritters. For dessert, we couldn’t resist gobbling up every morsel of the airy Malasadas (Portuguese doughnuts) complemented by decadent salted caramel and chocolate sauces.
Tidepools plates each dish as if it were a grand work of art. The cherry on top was the exceptionally professional and welcoming service.
Day 3 — Chocolate, Waterfalls, Hanelei, and a Sunset to Remember
If you are a chocolate lover like me, then you can experience the sweetest start to your day at the Wild Kauai Chocolate’s Chocolate Bar Making Class. Owner and chocolatier Lance educated us with a brief history of chocolate and his small-batch bean-to-bar process as a confectioner—all the way from ordering high-quality beans to packaging his gourmet specialties.
During the class we delighted in taking breaks to taste various chocolate samples and tea made from cacao leaves. Then, we took turns tempering the chocolate, pouring our own mega-sized bars, and selecting among loads of gourmet mix-ins to customize our creations.
Our inventive concoctions blended flavors like pineapple and coconut or mango and coffee beans. Such a fun, family-friendly way to spend a morning, and best of all, we walked away with custom-made souvenirs to share with our family back home (that is, if you don’t eat them before then)! TIP: For those chocoholics with more time, consider signing up for the four-day in-depth chocolate experience class.
A short drive away from our chocolate class, we enjoyed quick stops at two of Kaua`i’s famous waterfalls, ʻŌpaekaʻa Falls (aka “rolling shrimp”) and Wailua Falls (aka “Fantasy Island Falls”). We then grabbed a table on the terrace at Duke’s Kauai, named for surfing legend Duke Kahanamoku.
Duke’s is a casual place to sit back and enjoy the breeze while having lunch, drinks, a towering slice of their signature Hula pie, and a gorgeous view of Kalapaki Beach and the bay.
Next up, head to the Kilauea Lighthouse at the northernmost point of the island. Book in advance for a parking permit and lighthouse tour. Don’t miss the sweeping oceanfront vista and a myriad of wildlife at this refuge which is home to birds such as albatrosses, shearwaters, boobies, and the endangered Hawaiian nene.
Keep your eyes peeled; you may even spot monk seals, spinner dolphins, whales, or turtles.
Check out hipster Hanalei Town, chock full of trendy restaurants, art galleries, surf shops, hole-in-the-wall cafés, and unique boutiques. Hanalei epitomizes the slow-paced lifestyle of Kaua`i’. Chat with locals at the indoor/outdoor Hanalei Bread Co., while sipping on your healthy smoothie or foamy cappuccino and biting into delectable egg dishes.
Then, cross the street to order a heaping bowl of rainbow-hued Hawaiian deliciousness at Jojo’s Shave Ice. Make your way to Hanalei Bay Beach and its historic pier dating from 1892, where you can bake in the sun, learn to surf, and just “live in the moment,” taking in one of the most scenic stretches of beaches framed by the towering Na Pali Cliffs.
Not far away, you’ll find one of the world’s most beautiful golf courses, the Princeville Makai Golf Course. Along the route, listen to your GuideAlong app to hear where to pull over to sneak a peek at the endless patchwork of taro fields.
We began our evening at the golf course with a casual al fresco dinner at the Makai Grill. Choose from a menu offering salads featuring local produce, pupus such as coconut shrimp and chicken wings, and entrees like island grass-fed beef burgers and organic chicken sandwiches.
The Grill also offers a full bar with its signature drink, the “Makai Tai,” a less sweet version of the original Mai Tai. Then, we joined our engaging guide, Randy, on the course’s one-of-a-kind two-hour Sunset Golf Cart Tour.
Randy provided a quick tutorial on how to operate the golf cart safely…and off we went. As you have fun cruising around the immaculate 18-hole course, Randy will entertain you with stories about the local birds, flora, topography, and history.
My jaw dropped when we reached our final stop, which Randy perfectly timed to coincide with the sunset, which cast enchanting purple hues against the majestic blue water and the green mountains. I completely get why this course was named one of the “Top 5 Great Golf Settings” by National Geographic!
Day 4 — Chill Out or Amp It Up
Time to focus on your crew’s preferred vice: thrill-seeking or relaxation! Dedicate a day (or more) to your passion.
Adrenaline junkies: Take your pick to get your heart pumping!
Into fitness? Hike the first two miles of the Kalalau Trail of the spectacular and rugged Na Pali Coast and end up on Hanakapiai Beach. Along the way, you’ll gawk at steep cliffs, sparkling ocean surf, brilliant sand beaches, and rainforest-like greenery.
TIP: Be sure you book one of the limited parking or shuttle reservations to enter Ha`ena State Park where the trailhead begins.
Love heights? Soar to a bird’s eye view from an exhilarating helicopter ride that will zip you by some of Earth’s most verdant and striking scenery. Get up close and personal with powerful cascading waterfalls, Waimea Crater’s buttes, and the awe-inspiring jagged coastline. Inaccessible by car or boat, this is the only way to experience this mind-blowing view.
Prefer to go wild? Jump on an ATV for a guided tour while taking in the Kauai scenery.
Sun Worshippers and Beach Bums (full disclosure, this was our choice for the end of our trip):
Lounge at a hotel pool or on some of the world’s best beaches. On the South Shore, consider staying at the Grand Hyatt Kauai Resort & Spa at Poipu, which offers everything imaginable to elevate your trip into a luxurious vacation.
The oceanfront Hyatt boasts oodles of activities including gorgeous pools, fabulous waterslides, nightly Hawaiian entertainment, spa services, top-rated fine dining options, and much more.
On the East Shore, look into booking at the centrally-located Sheraton KauaiCoconut Beach Resort. Located mere steps away from the beach, the Sheraton enables families to spend hours on site, whether swinging in hammocks, listening to live music in their outdoor restaurant, playing in their indoor/outdoor game room, reclining in lounges in the infinity pool, recharging at the spa, or enjoying kid-friendly activities, such as kite-making.
Down the road from the Sheraton, you’ll find the uber-popular casual waterfront Lava Lava Beach Club, with all-day-long, reasonably-priced, island-inspired cuisine.
For the ultimate ending to your Hawaiian vacation, experience the Aloha spirit at the top-rated, family-owned Smith’s Garden Luau, the island’s only luau set in a botanical garden. Arrive early to take the guided tram ride through the acres of gardens and be sure to watch the imu ceremony, where the Kalua pig is roasted in an earthen oven.
We enjoyed the extensive buffet of traditional and flavorful Hawaiian dishes at the pa‘ina (the feast), an open bar with free-flowing drinks, and live music. After dinner, you’ll settle into an impressive outdoor amphitheater.
Experience the heart of the luau, which is the show featuring the Hawaiian ancestors’ songs, chants, and dances, representing all the cultures that have called Hawaii their home. And the grand finale lives up to the hype—the Samoan fire knife dance!
Practical Tips for a 4-Day Kauai Itinerary
- The weather changes dramatically, often several times a day, and by the region on the island. Depart for each day prepared with rain gear, sunscreen, hats, water, etc.
- The roads at night are incredibly dark and twisty.
- Book your rental car in advance, since there is a limited supply on the island.
- Car rides may take much longer than they look on a map! Leave plenty of time to reach destinations accounting for many one-lane roads, circuitous routes, and traffic jams. Breathe in the Hawaiian air, remember you are on vacation, and enjoy the beautiful scenery.
- Don’t ignore warning signs! The ocean surf can be dangerous and quickly changing.
Kauai is a tropical nirvana. You will fall in love with this island’s scenery and cuisine, and the local people will leave a lasting impression. We were thrilled to learn that our rose-colored memories from our honeymoon twenty-five years before actually matched reality.
ABOUT THE AUTHOR
This guest post was written by Lisa Grabelle. Lisa, a freelance travel writer, has been traveling all her life…40 countries and loving it! Originally from the sunny skies of Miami, Lisa, a former big firm lawyer, lives near Philadelphia. Travel is her passion. As soon as one vacation ends, Lisa busily plans her next adventure for her non-stop family of adventurers. Lisa’s motto is “don’t just visit the destination…live it!” You can follow Lisa on X (formerly Twitter) or Instagram.
DISCLAIMER
The author was provided with discounted and/or complimentary tours and meals so that she could try them and review them for your information. All opinions are her own. Most images courtesy of Lisa Grabelle unless otherwise noted.
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