Hawaii Family Vacation Travel Agency - Sunset-Travel.com

There are only a few family vacation spots in the world quite like Hawaii. Between the history, unique cuisine, welcoming culture, and, of course, the wildly varied landscape there is a little something for everyone to enjoy—especially families.

Every island has its unique flare and draw, but Oahu and The Big Island (formally known as Hawaii), specifically, hold countless activities and sights for families to experience together.

Combining these two unique islands into one ten day itinerary offers travelers the opportunity to experience historical sights such as Pearl Harbor, the unparalleled geological marvel of Volcanos National Park, the sparkling beaches of the North Shore, and countless memories along the way.

Our Hawaii Family Vacation Itinerary

Waikiki Beach Hawaii Family Vacation - Sunset Travel Agency, Chicago IL

Day 1: Arrival into Honolulu

Welcome to the Aloha State! Chances are, you will be arriving mid-afternoon after a very long day of travel. After grabbing your bags and picking up your car, head to the hotel to check-in and unwind. Jetlag will most likely have you ready for an early bedtime, but before you turn in too early be sure to have a stroll around downtown Honolulu and maybe a sunset walk on Waikiki Beach.

Where to eat in Honolulu:

Duke’s Waikiki: Start out your stay by having dinner at the famous Duke’s Waikiki located in the Outrigger Waikiki Resort. As a Waikiki staple, this iconic restaurant will give you a perfect introduction to classic Hawaiian cuisine and if you’re tired from jetlag, the live music will surely perk you up.

Where to stay in Honolulu:

Outrigger Waikiki Beach Resort: Located directly on the famed hotel zone of Waikiki Beach, this family-friendly hotel offers activities, cultural programs, entertainment, live music, and excellent cuisine at the famous Duke’s Waikiki located in the lobby. The smell of the ocean is right outside your door and the beach only steps away. Everyone in the family will love all that the Outrigger Waikiki has to offer!

Hyatt Regency Waikiki Beach: Also located on Waikiki Beach, the Hyatt Regency boasts a central location to the hotspots in downtown Honolulu, Diamond Head, and the relaxing beaches. With modern amenities, delectable on-site dining, a pool with a perfect view of the ocean, and large, fully-equipped rooms, this hotel is perfect for those looking to stay in the heart of Honolulu.

 

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Day 2: Pearl Harbor and Honolulu Sightseeing

Jet lag will mostly likely have you rising very early this morning so be sure to take advantage of it by watching the sun rise over Waikiki Beach. Depending on the time of year, Diamond Head may block the view of the sun, but the quickly changing colors of the morning Hawaiian sky will make the early morning beach walk well worth it. Today is a big day of sightseeing so after breakfast, get ready to head out for the day! If you’re a coffee drinker, be sure to start your day with a big cup of Kona coffee—Hawaii’s best!

What to do in Honolulu:

Pearl Harbor: Easily one of the biggest draws of Oahu is a visit to Pearl Harbor and the surrounding museums, memorials, and exhibits. Visiting the USS Arizona Memorial is a sobering experience for everyone and a good opportunity for the entire family to learn more about the sacrifices made during World War II. There is no fee to enter Pearl Harbor, however tickets are required to visit the USS Arizona memorial so be sure to book those ahead of time as there are time slots. Other sights at Pearl Harbor include the Battleship Missouri Memorial, USS Bowfin Submarine Museum, and Pearl Harbor Aviation Museum. Pearl Harbor is located approximately 45 minutes from downtown Honolulu so it is easily accessible with your rental car.

Bishop Museum: Learn about Hawaii’s colorful culture at this leading cultural and natural history museum. Spend some time browsing the exhibits showcasing environment, history, artifacts, and culture to get a better understanding of Hawaii’s past, present, and future.

Hanauma Bay Nature Reserve: To experience a pristine ocean ecosystem like no other, look no further than the Hanauma Bay Nature Reserve located just a half hour from Waikiki. As a nature reserve that has gone through extensive restoration efforts in recent years, this area is strictly enforced with only a limited amount of visitors allowed each day. Visitors must bring their own snorkeling gear (which can be rented from the hotel or other locations around Waikiki). Visitors can expect to see diverse tropical fish, sea turtles, and other marine life.

Iolani Palace: This beautifully restored summer vacation palace of King Kalakaua, Hawaii’s last reigning monarch, will give visitors a glimpse into life on the islands before becoming a US State. As the only official royal residence in the United State, this is a unique opportunity to learn more about the island’s dynasties and culture.

Best places to eat in Honolulu:
  • Ono Seafood
  • Hula Grill Waikiki
  • Helen’s Hawaiian Food
  • Waiola Shaved Ice (A trip to Hawaii is not complete without one or two shaved ice stops!)
Suggested Tours in Honolulu:

Catamaran Sail and Snorkel

Salute to Pearl Harbor Tour

Waterfall Hike & Nature Walk

Pearl Harbor, Arizona, Missouri & City Tour

 

 

Day 3: Hawaii’s North Shore

It’s another early start to the day so stock up on some Kona coffee (for the adults) and hit the road as you prepare to drive to the famous North Shore of Oahu. Watch the surfers take on the waves of Waimea Bay, live the foodie dream by stopping at each food truck along the way, and soak in the art and history at the Polynesian Cultural Center.

What to do in North Shore:

Dole Pineapple Plantation: A trip to Hawaii would not be complete without a pineapple planation tour. As the largest and, of course, most recognized pineapple plantation on the islands, it is the best place to try the freshest pineapple you will ever taste, have some fun in their pineapple maze, and snack on some pineapple ice cream!

Historic Haleiwa: This small town is a perfect stop to pick up some gifts, enjoy the local art gallery, or grab some shaved ice at the famous Shaved Ice by Matsumoto. If this is your first stop, be sure to grab a fresh acai bowl from Haleiwa Bowls for breakfast!

Lanikea Beach (Turtle Beach): The name says it all. Known for a popular resting spot for weary sea turtles, this beach is a perfect viewing spot for a first glimpse of the hard-shelled sunbathers.

Waimea Beach, Valley & Falls: With huge waves (depending on the time of year), fit for the world’s top surfers, the views are truly spectacular. Enjoy a picnic on the beach or get some swimming in during the summer months when the waves have died down. Also be sure to check out Waimea Valley and Waimea Falls if there is time for some added beautiful scenery.

Polynesian Cultural Center: The Polynesian Cultural Center is a must-stop for families looking to educate themselves on the island culture that came to Hawaii. With regular activities, shows, and events this cultural center has something for everyone in the family to enjoy!

Kualoa Ranch: Located in what is known as “Jurassic Valley”, thanks to its silver screen representation in the movies, the Kualoa Ranch is a fun stop for a classic touristy thrill. Boasting various activities, including horseback riding and movie site tours, this site has a lot to offer. For those short on time though, a quick stop for some roadside pictures is plenty.

Where to eat in Hawaii’s North Shore:

Any food truck: The North Shore is famous for their roadside food trucks so be sure to stop at at least one. From exceptionally fresh seafood (especially shrimp) to Korean BBQ there is a little something for everyone. Why not have so fun with it a sample the offerings of two or three trucks along the way!

  • Haleiwa Bowls
  • Shave Ice by Matsumoto
  • Kono’s
  • The Elephant Shack
  • Ted’s Bakery
Suggested Tours in Hawaii’s North Shore:

Tour of North Shore and Hanauma Bay

Oahu Cage Shark Dive

Kualoa Ranch Zipline Tour

Kualoa Ranch Movie Set Tour

Kualoa Ranch Horseback Riding Tour

Oahu Grand Circle Tour with Snorkeling

 

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Day 4: Beach Relaxing and Diamond Head

With two busy sightseeing days and major jetlag behind you, enjoy the morning with either some early activity or some simple relaxing. Visit Diamond Head for some incredible views and then take the rest of the day to enjoy the beach—Waikiki or some other recommended beaches around Honolulu. If you didn’t get to Hanauma Nature Reserve, consider venturing there for some beach and snorkel time.

Diamond Head State Park: To get the most stunning views of the city below, head up to Diamond Head for a beautiful hike. The main trail, while only about 2 miles, can be challenging because it is quite steep so keep that in mind if you are traveling with little ones. Starting out at Diamond Head first thing in the morning is advisable to avoid the scorching afternoon sun.

Ala Moana Regional Park: Notable for its calmer waters thanks to the protecting reef, this beach is ideal for visitors looking to get away from the crowds of Waikiki and enjoy some pleasantly quiet time under the sun. With the Magic Island Lagoon extending out from this beach, it makes for the perfect swimming conditions for children to also experience the calm Pacific waters.

Suggested Tours in Diamond Head:

Snorkeling with Dolphins and Sea Turtles

Oahu Helicopter Tour

Magic Island Snorkeling Tour

Diamond Head Crater Shuttle and Self-Guided Hike

 

Hilo Hawaii Family Vacation Travel Agency - Sunset Travel in Chicago IL

 

Day 5: Off to the Big Island

Today begins with a morning at leisure or catching up on any last minute things you may have missed in Honolulu from previous days. While flights to Hilo depart many times a day, it is advisable to catch one that leaves early afternoon so that you will be able to check into your hotel straight away. Flight time is about 45 minutes so it’s a quick jump over to the Big Island.

Upon arrival head over to your hotel to check-in, drop off the luggage, and head straight back out to do some walking and a late lunch around Hilo. The day is yours to explore this north-eastern, authentic Hawaii Island town or simply relax at your resort.

Where to stay on Hawaii’s Big Island:

Hilo Hawaiian Hotel: Boasting authentic Hawaiian charm with a contemporary upgrade, the Hilo Hawaiian Hotel is the perfect backdrop for your stay. With a beautiful oceanfront location and central to many of north-eastern Hawaii’s great attractions, it’s sure to be a wonderful stay for the whole family.

Grand Naniloa Resort: Translated to mean “very beautiful”, Naniloa is a perfect description of this oceanfront resort. Experience the true essence of Hawaii while you watch the dancers of Hula practice their traditional moves on the resort grounds every Monday. As a Hilton property, this resort is held to the highest standards while still holding onto it’s Hawaiian identity.

What to do on the Big Island:

Hilo Farmers Market: This farmers market is an absolute must. It is open everyday, but has more vendors on Wednesdays and Saturdays. With over 200 local farmers and artists selling their goods and crafts, you are sure to find the best souvenirs and freshest foods.

Rainbow Falls: Located directly in Hilo, Rainbow Falls is a quick nature stop to take while you explore town. Stop in the afternoon to enjoy a nice picnic while you listen to the falls cascading over a natural lava cave.

Botanical Gardens: The lush landscape of this part of the Big Island makes it a perfect place for plenty of botanical gardens to thrive. Featuring tropical flowers and rainforest foliage, there are a few gardens to choose from around Hilo. The Hawaii Tropical Bioreserve & Garden is the most popular located just a few minutes drive outside town.

Liliuokalani Gardens: This is the largest authentic ornamental Japanese garden outside of Japan so it’s a perfect place to take the kids to experience a different culture that is still very familiar to the islands of Hawaii. This peaceful setting is beautifully landscaped with fishponds, rock gardens, Japanese stone lanterns, and even a teahouse.

Where to eat:

  • Pineapples Island Fresh Cuisine
  • Hawaiian Style Café
  • Hilo Bay Cafe
  • Hilo Bay Pesto Coffee

 

 

Day 6: Volcano National Park

Enjoy breakfast and, of course, some Kona coffee at your hotel this morning before hitting the road for Hawaii’s crown jewel, Volcanoes National Park. With two of the world’s most active volcanoes, Kilauea and Mauna Loa, this sacred land has unique geology, culture, and landscape.

What to do in Volcano National Park:

Kilauea Visitor Center: Start your day off with a stop at the visitor center. Featuring a 25-minute introduction to the park film and some background on the history and culture of the area, this is definitely the best place to start. Guided ranger tours and talks can be booked here. Once you are educated and ready to go, grab and map and get ready to be amazed!

Halema’uma’u Crater Overlook Points: There are many place to “see the glow” of the lava lake in the middle of the active crater of Kilauea volcano. The most popular museum and outlook in the park, the Jaggar Museum, has been closed since the 2018 LERZ eruption so the next best overlook is the Kilauea overlook point. Other good areas include, Wahinekapu (Steaming Bluff), the Volcano House, Waldron Ledge, and Old Crater Rim Drive.

Kilauea Iki Crater: A short hike takes you across the crater floor of an eruption that only happened about 50 years ago. Take your time to marvel at the force that is mother nature and see just what a volcano can do.

Thurston Lava Tube: A trip to Volcanoes National Park wouldn’t be complete without a journey through a lava tube. Naturally created when air is trapped in a lava flow, the Thurston lava tube is easily accessible and a fun experience to walk through the cave-like tube.

Junior Ranger Program: Children up to 12 years old can become junior rangers by completing a few activities throughout the park. This is a free and engaging opportunity to get the whole family involved in learning more about Volcanoes National Park. Information for this can be found online or at the visitor center.

Drive the Chain of Craters Road: Chances are, you will already be on this road if you are heading to any of the major attractions in the park. You’ll know when you are on it from its stunning ocean and lava flow views.

Where to eat:

  • Kilauea Lodge & Restaurant
  • Eagles Lighthouse Café
  • Café Ono
  • Lava Rock Café
  • The Rim

 

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Day 7: Relax and Akaka Falls State Park

Today is the day to make sure to see any things in and around Hilo that you may have missed over the last couple of days. Spend some time on the beach and then venture off to the Akaka Falls State Park to see two beautiful waterfalls in one easy hike. Take your time and soak in the surrounding area filled with enchanting rainforests and tropical flowers. The day is yours to take it easy, eat some good food, and enjoy the rest of your time in Hilo.

Suggested Tours in Akaka Falls:

 

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Day 8: Waipi’o Valley, drive to Kona

Today you will depart early on a road trip adventure along the north coast of the Big Island, ending at your resort in or around Kona. Along the way you will visit scenic treasures such as the Waipi’o Valley, indulge in some amazing Hawaiian cuisine, and enjoy the ride as you make your way south to Kona.

What to do in Waipi’o Valley:

Waipi’o Valley: This area is knowns for its incredible views and the black sand beach at the bottom on the valley. The overlook is easily accessible from the parking area, but if you want to venture to the beach it’ll be a 6.5 mile round trip journey. Even if you just stay up top, the views of the valley, beach, and ocean beyond are not to be missed. Note that rental cars should not be driven into the valley thanks to the rough terrain.

Pololu Valley: Another beautiful ocean and valley viewpoint can be found at Pololu Valley on the northern tip of the island. The view from the overlook is perfect, but an easy 1.2 mile walk down to the beach is unmissable.

Waimea: Stop into Waimea for some lunch at the Hawaiian Style Café and a Kona coffee fill-up at the Waimea Coffee Co.

Where to stay:

Fairmont Orchid Hawaii: As a leading luxury, up-scale resort on the Kohala Coast, the Fairmont Orchid is the perfect place to stay for those looking to indulge in the serenity and comfort of this resort. Guests can return to ultimate relaxation in their luxury ocean front room after busy days of sightseeing. Children are welcome at this resort with plenty of activities to keep the whole family entertained.

Sheraton Kona Resort: Sitting atop rugged, iconic lava rocks, this ocean front resort is located in a perfect spot for those looking for some seclusion on the Big Islands Keauhou Bay. Combining adventure, culture, good eats, and top notch hospitality, this resort has it all. Families are encouraged to join in on the traditional luau to get the true essence of Hawaii history and culture.

Where to eat:

  • Hawaiian Style Café (Waimea)
  • Waimea Coffee Co.
  • Basik Café (Kona)
  • Broke Da Mouth Grindz
  • Kona Brewing Company
  • Jackie Rey’s Ohana Grill

 

 

Day 9: Snorkeling, Drive to Southern Point

Today can be as relaxing or as packed as you make it. There is a lot to see in and around Kona so we suggest making the most of your morning before the sun really starts to scorch. Today, if it’s your thing, a Kona Coffee plantation tour is a definite must.

Get in some great snorkeling along the southern shores and head down to the Southernmost Point for some beautiful ocean views.

What to do:

Green Sand Beaches: The Papakoela Green Sand Beach Mahana Bay in the southern point of the Big Island is an amazing spectacle to behold. The hike out to the beach is about 2-3 miles, but you can really call in your adventurous side with one of the tours hosted by locals of the area. Many of these tours are just roadside set-ups without any prebooking so some luck is often involved. You will pile into one of their pick-up and take a ride through rough and bumpy terrain. It’s a fun, yet harrowing ride to the beach. Don’t worry though, most drivers have been catering to tourists for years.

Kona Coffee Tour: A trip to Hawaii is not complete without a Kona coffee plantation tour. While the adults will be doing most of the tasting, it is still an educational experience for the kids as well. The Heavenly Hawaiian Coffee Farm tour comes highly recommended and is a fun experience for everyone.

Pu’uhonua O Honaunau National Historical Park: This will most likely be a quick stop on the itinerary today, but it is well worth it to learn more about Hawaiian tradition and history.

Evening Luau: Enjoy your last night at your resort with a lovely sunset luau. Most resorts offer their own event for guests, but if yours doesn’t, feel free to check at another resort for outside reservations. They are usually welcome. Enjoy traditional music, performances, food, and dancing as you watch the sun set on your final evening in paradise.

Where to eat:
  • Kaaloa’s Super Js Authentic Hawaiian
  • Shaka Tacoz
Suggested tours:

 

Day 10: Relax before Late Flight Home

This last day is meant to be total relaxation as you reminisce about the amazing trip you’ve just had. Spend some quality time at your resort by the pool or on the beach, try out any last minute food that you wanted to taste, and enjoy your last hours under the Hawaiian sun.

You’ve got a long evening flight ahead of you, so take it easy today and enjoy the true essence of Aloha.

 

Now, Let us Make it All Easy for You!

The expert travel agents at Sunset Travel & Cruise in Chicago can plan your family vacation to Hawaii, so you have more time to relax!!! Contact us today for a free consultation to talk about your ideas and let us make them reality.

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