Relaxing Tropical Escape: 8-Day Hawaii Itinerary from December 22-30, 2025

Day 1: Arrival and Relax

Honolulu, Oahu, Hawaii on December 22, 2025

3:00pm

Arrival at Daniel K. Inouye International Airport

Land in Honolulu and proceed to your hotel in Waikiki, the heart of Honolulu with beautiful beaches and vibrant nightlife.
USD0, 1h0m

5:00pm

Check-in at Hotel

Settle into your Waikiki beachfront hotel, offering stunning sunset views and easy access to the beach.
USD0, 1h0m

7:00pm

Dinner at Roy's Waikiki

Enjoy a delicious Hawaiian fusion dinner featuring fresh seafood and local flavors; open until 10:00pm.
USD40, 1h30m
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Day 2: Historic and Beach

Honolulu, Oahu, Hawaii on December 23, 2025

7:30am

Breakfast at Island Vintage Coffee

Start your day with fresh acai bowls and Kona coffee; open 7:00am to 5:00pm.
USD15, 1h0m

9:00am

Pearl Harbor National Memorial

Visit the historic site including USS Arizona Memorial, an important WWII landmark; open 7:00am to 5:00pm with free entry but reserve tickets in advance.
USD0, 3h0m

1:00pm

Lunch at Helena's Hawaiian Food

Savor traditional Hawaiian dishes like kalua pig and poi in a casual setting; open until 4:00pm.
USD25, 1h0m

3:00pm

Relax at Waikiki Beach

Enjoy the iconic Waikiki Beach with opportunities for surfing, swimming, or just sunbathing.
USD0, 2h0m

6:30pm

Dinner at House Without A Key

Dine al fresco with Hawaiian sunset views accompanied by live Hawaiian music; open until 9:30pm.
USD50, 1h30m
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Day 3: North Shore Adventure

Oahu, Hawaii on December 24, 2025

7:00am

Breakfast at Kono’s Northshore

Enjoy hearty breakfast burritos to fuel up for a day of exploration; open 7:00am to 4:00pm.
USD15, 1h0m

8:30am

Drive to North Shore

Experience the scenic 45-minute drive from Waikiki to Oahu’s North Shore, renowned for big wave surfing.
USD0, 0h45m

9:30am

Visit Waimea Bay and Sunset Beach

Explore these iconic surfing beaches, taking in the views and possibly spotting surfers tackling massive waves.
USD0, 2h0m

12:00pm

Lunch at Giovanni’s Shrimp Truck

Enjoy famous garlic shrimp plates from a popular food truck; open 10:00am to 5:00pm.
USD20, 1h0m

1:30pm

Explore Historic Haleiwa Town

Stroll around Haleiwa’s charming boutiques, art galleries, and local shops.
USD0, 1h30m

4:00pm

Return to Waikiki

Drive back to Waikiki to relax before dinner.
USD0, 0h45m

7:00pm

Dinner at Merriman’s Honolulu

Dine on farm-to-table dishes highlighting fresh island ingredients; open until 9:30pm.
USD60, 1h30m
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Day 4: Transfer to Maui

Maui, Hawaii on December 25, 2025

7:00am

Breakfast at Leonard’s Bakery

Try famous malasadas (Portuguese doughnuts) before leaving Oahu; open 6:00am to 5:00pm.
USD10, 0h45m

9:00am

Fly from Honolulu to Kahului, Maui

Catch a short 40-minute flight to Maui; check flight schedules with Hawaiian Airlines.
USD100, 1h30m

11:00am

Pick up rental car and check-in

Collect your rental car and check into a beachfront hotel in Wailea or Kihei area for easy beach access.
USD0, 1h0m

12:30pm

Lunch at Coconuts Fish Cafe

Enjoy fresh fish tacos and casual island flavors; open until 7:00pm.
USD20, 1h0m

2:00pm

Relax at Wailea Beach

Swim or sunbathe on Wailea Beach, known for its calm waters and soft sand.
USD0, 3h0m

6:30pm

Dinner at Monkeypod Kitchen

Dinner featuring locally sourced dishes and craft cocktails; open until 10:00pm.
USD50, 1h30m
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Day 5: Road to Hana

Maui, Hawaii on December 26, 2025

6:00am

Early Breakfast at hotel

Fuel up early with a hearty breakfast at your hotel before the Road to Hana trip.
USD20, 0h45m

7:00am

Road to Hana Day Trip

Explore the scenic drive with stops at waterfalls, botanical gardens, and black sand beaches; leave early to avoid crowds.
USD0, 10h0m

5:00pm

Return to hotel

Rest after a full day of adventure and sightseeing.
USD0, 1h0m

7:00pm

Dinner at Ka'ana Kitchen

Experience farm-to-table cuisine highlighting Hawaiian flavors in Wailea; open until 9:00pm.
USD55, 1h30m
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Day 6: Haleakalā Sunrise and Explore

Maui, Hawaii on December 27, 2025

3:30am

Haleakalā National Park Sunrise

Drive early to catch sunrise above the clouds at 10,000 feet elevation; reservation required.
USD30, 3h0m

7:00am

Breakfast in Makawao Town

Enjoy breakfast at a local café in this charming upcountry town; open from 7:00am.
USD15, 1h0m

9:00am

Explore Iao Valley State Park

Walk easy trails around the scenic valley and see the famous Iao Needle; park open 7:00am to 6:00pm.
USD5, 2h0m

12:00pm

Lunch at Tin Roof Maui

Casual spot serving delicious local-style plate lunches; open 11:00am to 2:30pm.
USD15, 1h0m

1:30pm

Free afternoon for beach or spa

Return to your hotel for some relaxation or optional spa treatments.
USD0, 3h0m

6:30pm

Dinner at The Mill House

Upscale dining with farm-fresh ingredients and stunning views; open until 9:00pm.
USD60, 1h30m
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Day 7: Snorkeling and Relax

Maui, Hawaii on December 28, 2025

7:00am

Breakfast at hotel

Enjoy a leisurely breakfast at your hotel to prepare for a day on the water.
USD20, 0h45m

8:30am

Snorkeling at Molokini Crater

Join a half-day snorkeling tour to see vibrant marine life in this crescent-shaped volcanic crater; tours typically run 8:00am to 12:00pm.
USD120, 4h0m

1:00pm

Lunch at Nalu Market

Light lunch with fresh poke bowls and smoothies; open 10:00am to 5:00pm.
USD20, 1h0m

3:00pm

Relax on Makena Beach

Spend the afternoon soaking up the sun on one of Maui’s most beautiful and less crowded beaches.
USD0, 3h0m

7:00pm

Dinner at Koiso Sushi Bar

Enjoy fresh sushi in an intimate setting; open until 9:00pm. Reservation recommended.
USD65, 1h30m
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Day 8: Departure Day

Maui, Hawaii on December 29, 2025

7:00am

Breakfast at Choice Health Bar

Healthy breakfast smoothie bowls and juices to start your last day; open 7:00am to 3:00pm.
USD15, 1h0m

9:00am

Final beach stroll or shopping in Kahului

Enjoy a relaxing morning browsing local shops or a last walk on the beach.
USD0, 2h0m

11:30am

Check out from hotel and drive to Kahului Airport

Return rental car and prepare for your departure flight.
USD0, 1h0m

1:30pm

Depart from Kahului Airport

Fly home with wonderful memories of your tropical Hawaiian vacation.
USD0, 0h0m
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