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Oahu and Kauai Itinerary

How long was your stay?

10 days

How did you travel?

As a family

Tell us why you traveled to this destination.

My husband and I spent our honeymoon here 20 years ago and wanted to share our love for Hawaii with our kids.

What was your itinerary?

Day 1: Arrived in Oahu, The Sheraton Waikiki, visited Waikiki Beach, dinner at Sheraton’s RumFire
Day 2: Explored Pearl Harbor National Memorial, shopped in Honolulu and  traveled to Kauai’s Hanalei Bay Resort
Day 3: Visited Hanalei Bay Beach, dinner at Happy Talk
Day 4: Went to Puu Poa beach, Hanalei Bay Beach, dinner at Dolphin Sushi
Day 5: Hiked the Kalalau Trail along the Na Pali coastline to Hanakapi’ai Falls
Day 6: Day in  Hanalei, dinner at Ama Restaurant
Day 7: Left for Poipu,  stopped for breakfast at the Olympic Cafe in Kapa’a, headed to the Grand Hyatt
Day 8: Breakfast at the hotel’s IlimaTerrace, Na Pali Experience ocean charter, dinner at Stevenson’s Library
Day 9: Pool-time at the Grand Hyatt, dinner at Tidepools restaurant
Day 10: Took a shelter dog on a field trip in Koloa, visited Poipu Beach, dinner at Keoki’s Paradise

Give us all the details! Tell us where you went and what you did on your trip.

Day 1: We arrived in Oahu at 2:30 in the afternoon and made it to our beautiful hotel, The Sheraton Waikiki in time for some late afternoon sun at the famed Waikiki Beach. Dinner: Sheraton’s RumFire at sunset – a perfect way to end the day!

Day 2: Pearl Harbor National Memorial – early! I reserved our spot 30 days in advance on recreation.gov. There is so much to see at this incredible site. If you want to enjoy all there is to offer, I’d recommend 4 hours at least. We spent 90 minutes at the memorial and were able to enjoy the museum and take the US Navy boat shuttle and board the USS Arizona Memorial. It was a moving experience I’d recommend to all. After, we headed back to Honolulu for shopping before hopping on a Hawaiian Airlines flight to Kauai. We arrived at our Hanalei Bay Resort condo after dark (and a quick stop for groceries).

Day 3: Waking up at our condo in Kauai was incredible! We had an obstructed view of Hanalei Bay, and enjoyed coffee and sunrise. We headed to our resort pool for a morning swim, had a quick, fresh rice bowl at the food trucks in Hanalei for lunch and drove further north to check out some of the beaches at the end of the road near Ha’ena State Park. You cannot park here (like you could 20 years ago), instead you must reserve a parking spot or a seat on the shuttle bus. Getting the lay of the land was nice, and we ended up at our favorite beach for all in our family, Hanalei Bay Beach. We boogie-boarded, got a lot of sun, and had a great dinner at our condo resort, Happy Talk. They offer live entertainment every night of the week–we loved it!

Day 4: After enjoying another sunrise, we walked down the resort path toward the beautiful Puu Poa beach and the base of the remodeled Princeville hotel, now the Hanalei 1 hotel, where we would enjoy a delicious breakfast. We ventured up the steep flight of stairs alongside the hotel to get a bit of a pre-meal workout. Breakfast was a beautiful experience! Loved the freshly squeezed guava juice, one of the things I most look forward to when visiting Hawaii. This hotel is stunning–all with sustainability as a mission and carbon neutrality goals; its facelift was done keeping this in mind. I would put this in the “luxury” category, for sure. Afterward, we rented boogie boards for $5 dollars a piece at a surf shop and spent a perfect day at Hanalei Bay Beach. Dinner at Dolphin Sushi in Hanalei…OMG. GO!!!

Day 5: We awoke early, hoping to grab some Holey Grail Doughnuts on the way to the Kalalau Trail to hike up to Hanakapi’ai Falls along the Na Pali coast. Unfortunately, they are closed Monday and Tuesday, and we never got our doughnuts! We hear they are the best! After grabbing a bag of hostess doughnuts from the local grocer, we made it to the shuttle pick-up outside of town. To take this hike, you must make a reservation at least one month in advance for reserve space! The hike was moderate to difficult at times and took us around 6 hours total. The waterfall itself was breathtaking and worth the hike swim under the falls! We grabbed some food to grill on the way home and cooked out next to the tennis courts (Dad was the chef and tennis-ref) at our resort that evening. So great to be able to run to our condo for sunset-cocktail hour. It was the perfect ending to an unforgettable day.

Day 6: Our final day in Hanalei–we decided to mill around Hanalei again and find the perfect beach spot. I went on a quest for the ideal bikini (I found a pretty good one, great bikini boutiques!) while everyone chilled at the beach. When I returned, it was raining, and the kids were playing in the ocean. Because our excellent condo had every supply we needed, we could hide comfortably under the umbrellas they provided! Dinner: Ama Restaurant in Hanalei, all locally sourced–delicious ramen, steamed buns, and unique cocktails in the most beautiful setting!

Day 7: We woke to a downpour as we gathered our things to head to the island’s south end, Poipu. We stopped in Kapa’a for breakfast at the Olympic Cafe–loved this traditional breakfast with open views of the rain. Next stop: The Grand Hyatt in Poipu, with completely different vibes from our situation on the north shore! We stayed here for our honeymoon 20 years prior, and our kids had never experienced a resort before. We usually stay in homes or condos when we travel, and I could see they were interested in the hotel shops as we waited for our room to be ready! I was impressed with the awesome reusable water bottles they gave us and the filling stations. We are still using these! We took shelter from the rain, enjoyed complimentary cocktails and snacks, and unpacked in our new home for the rest of our trip. Dinner: room service–the food was fresh and delicious!

Day 8: After a superb breakfast at the IlimaTerrace (we ate here daily–beyond expectations!! Wonderful!!) we chartered a boat to see the Na Pali coastline from the ocean. We booked with Na Pali Experience and couldn’t have been happier! Our captain was JD, born and raised in Kauai-his breadth of knowledge was so impressive! He was also a talented captain–the ocean was very rough as the storm lingered, and he surfed the huge waves with our small boat until we made it to the calmer side near Na Pali. We navigated caves–one of the most incredible experiences we have ever had!!! Dinner: Stevenson’s Library for sushi at our hotel–great food, views and service.
Day 9: Today was a pool day. We had been so excited to enjoy this impressive pool–voted the best on Kauai–and spent the day going down waterslides and dunking each other in the lazy river! Dinner: Tidepools at the Grand Hyatt–OUTSTANDING food and service !!!

Day 10: Woke up to rain and storms. The guys were satisfied to watch the Women’s Final Four, so we ladies decided to take advantage of a volunteer opportunity (in our “Ultimate Kauai Guidebook” and in the lobby of our hotel) on the island–“take a shelter pet on a field trip” through the Kauai Humane Society. We had the absolute pleasure of spending a rainy and wet day with Johnny Quest–we went on a hike, a walk on the beach, and out for lunch. There were tears saying goodbye, and he is still on our minds. We stopped at Poipu Beach and saw the nesting sea turtles on the way to dinner. Dinner: Keoki’s Paradise–in Poipu, great atmosphere and food.

Day 11: Wrap it up–one final breakfast at Ilima, a little sunshine, and last-minute sunbathing. Heading home with Aloha in our hearts. Want to keep it that way ♥️

Would you recommend this trip to a friend?


What was the highlight of your trip?

Our condo in Hanalei!! Highly recommend!! email me, apezza@mypinerary.com for details
Our beautiful family hike along the Na Pali coast. Wear hiking sandals with good tread!
Shaved Ice, Dinner in the rain at Dolphin Sushi Hanalei, Dinner at Tidepools!!, Grand Hyatt pool, seeing the “lava” face on our Na Pali charter, the pineapple JD prepared for us on the boat sprinkled with Li Hing Mui, watching my family boogie board, swimming with them for hours in Hanalei Bay, our servers at Ilima Terrace, no plastic straws anywhere, and last but not least, our day with Johnny Quest at the Kauai Humane Society.

If you were to take this trip again, is there anything you would add or do differently?

Make restaurant and attraction reservations when booking your trip!
Spend an extra day in Oahu and see more of the island.
The rooms on the “left side” (facing the ocean) of the Grand Hyatt are located above a parking lot, fyi! 
Don’t bring any work with you to Hawaii–leave it all behind!!
Be patient–remember island time and try not to stress about things taking longer.

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