Ultimate Family Friendly Relaxation Itinerary in Hawaii – April 2026

Day 1: Arrival in Kauai

Kauai, Hawaii

11:00AM

Check-in at The Westin Princeville Resort & Spa

Settle into your luxurious accommodations with stunning ocean views and family-friendly amenities.
From Lihue Airport, take the rental car via HI-56 northbound to Princeville, approximately a 30-minute drive.
USD 450, 2 hours

1:00PM

Lunch at Nalu Health Bar & Cafe

Enjoy a fresh and healthy meal with options for the whole family, right by the beach.
A short drive from the resort, approximately 5 minutes.
USD 80, 1 hour

2:30PM

Anini Beach Relaxation

Spend the afternoon unwinding on the sandy shores of Anini Beach, perfect for family enjoyment with minimal waves.
Drive to Anini Beach, around 15 minutes from the cafe.
USD 0, 3 hours

6:00PM

Dinner at The Hanalei Gourmet

Savor delightful Hawaiian dishes and kid-friendly options in a casual atmosphere.
Quick drive back to Hanalei, approximately 10 minutes.
USD 120, 1.5 hours
View Hotel Availability

Day 2: Exploring Kauai

Kauai, Hawaii

8:30AM

Breakfast at The Westin Princeville

Feast on a delicious buffet breakfast featuring tropical fruits and Hawaiian specialties.
On-site.
USD 100, 1 hour

9:30AM

Waimea Canyon Drive

Take a scenic drive through Waimea Canyon, also known as the Grand Canyon of the Pacific, enjoying spectacular views.
Start from Princeville, approximately a 1-hour drive.
USD 0, 3 hours

12:30PM

Lunch at Pizzetta

Grab a pizza or salad made with fresh local ingredients at this casual eatery.
Close to Waimea Canyon, 15 minutes.
USD 70, 1 hour

2:00PM

Visit Poipu Beach

Spend the afternoon swimming in the sun or building sandcastles at family-friendly Poipu Beach.
Drive to Poipu Beach, about 30 minutes from the restaurant.
USD 0, 4 hours

6:30PM

Dinner at Keoki's Paradise

Experience a delightful outdoor dining setting with Hawaiian cuisine and entertainment.
Drive back to Poipu, around 10 minutes.
USD 150, 1.5 hours
View Hotel Availability

Day 3: Travel to Maui

Maui, Hawaii

7:00AM

Breakfast at The Westin Princeville

Fuel up with their breakfast buffet to prepare for the transition to Maui.
On-site.
USD 100, 1 hour

8:00AM

Check-out & Flight to Maui

Check-out and head to the airport for a quick inter-island flight to Maui.
Drive to Lihue Airport, about 30 minutes, and take a short 30-minute flight to Kahului Airport.
USD 300 (for the family), 2 hours

11:00AM

Check-in at Hyatt Regency Maui

Settle into your beautiful family-friendly resort with pools and beaches.
Drive to the resort, about 10 minutes from the airport.
USD 400, 1 hour

12:30PM

Lunch at Pulehu, an Italian Grill

Enjoy authentic Italian fare with a Hawaiian twist in a relaxed setting at your resort.
On-site.
USD 90, 1 hour

2:00PM

Relax by the Pool

Spend a leisurely afternoon lazing by the pool, taking a dip, and sipping on tropical drinks.
Right outside your room.
USD 0, 3 hours

5:30PM

Dinner at The Cliff Dive Grill

As the sun sets, enjoy a laid-back dinner with ocean views and live music.
On-site.
USD 120, 1.5 hours
View Hotel Availability

Day 4: Exploring Maui

Maui, Hawaii

8:00AM

Breakfast at the hotel

Indulge in a hearty breakfast to kickstart your explorations around Maui.
On-site.
USD 100, 1 hour

9:00AM

Visit Haleakalā National Park

Marvel at the sunrise (or hike) in this stunning national park, home to the largest dormant volcano in the world.
Drive approximately 1.5 hours from the hotel.
USD 30, 4 hours

1:00PM

Lunch at Kula Lodge

Stop for lunch with spectacular views of the island and delicious local food.
On-site in Kula, about 10 minutes from the park.
USD 80, 1 hour

2:30PM

Explore Lahaina Town

Wander through this historic town, visiting unique shops and galleries.
Drive to Lahaina, about 1 hour.
USD 0, 2.5 hours

5:00PM

Dinner at Lahaina Fish Co.

Savor fresh seafood while enjoying ocean views in a family-friendly atmosphere.
On Front Street in Lahaina, about 5 minutes from the history tour.
USD 140, 2 hours
View Hotel Availability

Day 5: Travel to Oahu

Oahu, Hawaii

7:00AM

Breakfast at the hotel

Refuel before another island hop adventure.
On-site.
USD 100, 1 hour

8:00AM

Check-out & Flight to Oahu

Check-out and get ready to explore yet another beautiful island.
Drive to Kahului Airport, about 10 minutes, and take a short flight to Honolulu.
USD 300 (for the family), 2 hours

10:30AM

Check-in at Hilton Hawaiian Village

Arrive at your luxurious resort with direct beach access and family facilities.
Drive to the resort, about 25 minutes from Honolulu Airport.
USD 450, 1 hour

1:00PM

Lunch at Tropics Bar & Grill

Get a taste of local flavors with beachside dining.
On-site.
USD 100, 1 hour

2:30PM

Relax on Waikiki Beach

Spend the afternoon soaking up the sun at one of the most famous beaches in the world.
Access is direct from the resort.
USD 0, 4 hours

6:30PM

Dinner at Roy's Waikiki

Indulge in an exceptional Hawaiian fusion meal at this upscale restaurant.
Drive about 10 minutes from the hotel.
USD 200, 2 hours
View Hotel Availability

Day 6: Exploring Oahu

Oahu, Hawaii

8:00AM

Breakfast at Hilton Hawaiian Village

Enjoy a lavish breakfast buffet with options for all ages.
On-site.
USD 120, 1 hour

9:30AM

Visit Pearl Harbor

Take a historical tour of Pearl Harbor and learn about its significance during WWII.
Drive to Pearl Harbor, around 30 minutes.
USD 0, 3 hours

12:30PM

Lunch at Aloha Mixed Plate

Try some casual Hawaiian plate lunch with traditional flavors and gigantic portions.
Drive to nearby beachside eatery, about 15 minutes.
USD 60, 1 hour

2:00PM

Hike Diamond Head

Take a family-friendly hike up Diamond Head Crater for stunning views of Honolulu.
Around a 20-minute drive from the restaurant.
USD 1 (per adult), 2 hours

5:00PM

Dinner at Duke's Waikiki

Experience Hawaiian hospitality and fantastic sunset views while dining beachside.
Return to Waikiki, about 20 minutes.
USD 150, 2 hours
View Hotel Availability